Demon (Knight of Hell) (cured)
Horseman (Death) (temporarily)
Incomplete Vampire (cured)
Jefferson Starship (briefly)
Honorary Dog (temporarily)
|Title/Alias|| Michael Sword |
Soldier of Heaven
Squirrel (by Crowley)
Not Moose (by Crowley)
Dean-O (by Cole, Rudy, Gabriel, and Meg)
Rocket (by Dark Charlie)
Hoss (by The Colonel)
Hasselhoff (by Claire)
Buffy (by David)
Ken Doll (by a waiter)
Chief (by Benny)
True Vessel of Michael(currently unused)
Man of Letters
Bearer of the Mark of Cain (formerly)
True vessel of Michael (unused)
Knight of Hell (formerly)
Construction Worker (formerly)
Soldier of Heaven (formerly)
|Affiliation:|| Himself |
Men of Letters
Anna Milton (formerly)
|Family|| Cain (ancestor) †|
Abel (ancestor) †
John Winchester (father) †
Mary Winchester (mother) †
Henry Winchester (paternal grandfather) †
Millie Winchester (paternal grandmother)
Samuel Campbell (maternal grandfather) †
Deanna Campbell (maternal grandmother) †
Sam Winchester (brother)
Emma (daughter) †
Adam Milligan (half-brother)
Bobby Singer (surrogate dad) †
Christian Campbell (fourth cousin) †
Gwen Campbell (third cousin) †
|Portrayed by:|| Jensen Ackles |
Hunter Brochu (Toddler)
Ridge Canipe (Child)
Nicolai Guistra (Memory of Bobby Singer) (Death's Door)
Brock Kelly (Teenager)
Dylan Everett (Teenager)
Chad Everett (Elderly)
"We track evil and kill it, the family business, is that it? Look at the tape, Sam. Evil tracks us. It nukes everything in our vicinity, our family, our friends, it’s time we put a proper name to what we really are and we deal with it."
– Dean, Brother's Keeper
Dean Winchester is a human and hunter as well as a member of the Men of Letters with his younger brother Sam. He and his brother are members of the Winchester and Campbell families, and Dean is also the destined vessel of the archangel Michael. He and Sam are also the surrogate sons of Bobby Singer. Dean is best friends with the angel Castiel, close friend to the late prophet Kevin Tran, and reluctant ally of Crowley. Dean has an ex-girlfriend, Lisa Braeden who he lived with for a year when he thought Sam was in Hell. She has a child named Ben, who Dean acted as a father for. Dean is also the former apprentice of Alastair. Both Dean and Sam were raised in the hunting life by their father, after the demon Azazel killed their mother. Dean's main role in the series is being the self-appointed guardian of Sam and often going to extreme lengths to protect him regardless of personal cost. Often in these occurrences Dean finds himself the center of a much larger picture. When he was killed by Metatron whilst using the Mark of Cain, Dean returned as a demon and a Knight of Hell loyal only to himself. He was then cured by his brother using purified blood. Eventually, the Mark was removed, but the price was that the Darkness has now been released into the world, something Dean tried to avoid.
Dean was born on January 24, 1979 in Lawrence, Kansas. Mary Winchester, Dean's mother, was killed by a yellow eyed demon when she interrupted him while he was feeding demon blood to Sam. Azazel pinned Mary to the ceiling, where she suffered a bleeding stomach and was consumed in flames. Upon witnessing this, John, the boys' father, handed the infant Sam to Dean as the nursery burned and told him to "Take your brother outside as fast as you can! Don’t look back! Now, Dean, go!" John left their home in Lawrence with Dean and Sam before Dean's fifth birthday.
When Dean was 6 or 7, John took Dean out shooting for the first time, using bottles as target practice. According to Dean, he bulls-eyed every one of them. Dean has cited this story as one of his fonder memories of his father.
On an occasion when John was hunting a Shtriga in Wisconsin and left Sam and Dean alone in a hotel room, Dean got bored and went out. When he came back, he found the Shtriga feeding on Sam. John returned in time to scare the Shtriga off. For a long time Dean was haunted by his failure to defend his brother. In 1991, when Dean was in sixth grade, he made his first sawed-off shotgun.
Once when 12 year-old Dean was left to babysit Sam (8 years old) while John was on a hunt, Sam began to interrogate Dean about what it was that their dad actually did. Dean responded with "You know that. He sells stuff." When Sam moved on to ask about their mother, Dean got angry and stormed out after yelling, "Shut up! Don't you ever talk about mom! Ever!" Upon his return, Sam revealed to Dean that he had found and read their dad's journal, and demanded to know if monsters are real. Dean finally resigned himself to telling Sam the truth.
Dean: "I swear, if you ever tell dad I told you any of this, I will end you."
Dean: "First thing you have to know is...we have the coolest dad in the world. He's a superhero."
Sam: "He is?"
Dean: "Yeah. Monsters are real. Dad fights em. He's fighting them right now."
– Dean and Sam, A Very Supernatural Christmas
Dean continually excused his father's flaws while the tension between Sam and John was clearly starting to take root. Disappointed with John's lying and absence, Sam gave Dean a Christmas present intended for his father: an amulet. Dean wears the amulet from this time on.In 1995, Dean lost all of his and Sam's food money in a poker game and was caught stealing food. As a result, he was sent to a reform school run by a man named Sonny who is an ex-con who turned his life around and eventually got the charges against Dean dropped. While living at the home, Dean flourished, he became a high school wrestling champion, made friends and was doing well in school. Dean met a girl named Robin who gave him his first kiss and shared his desire not to go into the "family business". Dean's dreams at the time were to become a rockstar or a mechanic and he was supposed to go to a dance with Robin, but his father returned the night of the dance to pick him up and refused to delay even for one night. Sonny offered Dean the chance to stay permanently, but Dean reluctantly left because he couldn't leave Sam..
Sometime later in 1995, Dean goes on a hunt with his father and burns the monster they were hunting in the nearby woods. As it burns, Dean thinks to himself he's only sixteen and he's seeing things normal teenagers would never even know of. From that point, Dean chooses to forget being regular and embraces the hunting life. 
- "Sammy's waiting in the car and me and my dad take the thing into the woods, burn it to a crisp. I'm sitting there and looking into the fire and thinking to myself, 'I'm sixteen-years old. Most kids my age are worried about pimples, prom dates. I'm seeing things they'll never even know. Never even dream of'."
- —Dean on when he embraced the hunting life[src]
During the summer of 1997 John, Dean, and Sam were hunting a werewolf. In November 1997, John "parked" the kids in a small town in Indiana where they attended Truman High School. While Sam was having trouble with a bully named Dirk, Dean got a girlfriend, Amanda. He became uncomfortable when she asked him to meet her parents. When she caught Dean cheating on her with another girl, she challenged him, charging that his "cool", persona was just a cover for his pathetically sad loneliness.
Amanda: "I thought maybe ... under your whole "I could give a crap", bad boy thing that there was something more going on. Like the way you are with you brother. But I was wrong. You spent so much time trying to convince people that you're cool, but it's just an act. We both know that you're just a sad, lonely little kid and I feel sorry for you, Dean."
Dean: "You feel sorry for me, huh? Don't feel sorry for me. You don't know anything about me. I save lives. I'm a hero. A hero!"
– Dean, After School Special
Dean never graduated high school, but did manage to get his GED.  Around 1998, Dean and John left Sam alone to go hunt a Kitsune. At this time, Dean also gave Sam advice over the phone on how to talk to girls.
In 1998 or 1999, Dean went on a road trip that was supposed to be "5 states, 5 days" while Sam was "in Orlando with dad, wrapping up that banshee thing". However, he spent most of his time in Lisa Braeden's loft.
Sometime between 2001-2005, Sam left for Stanford. While there, he became estranged from Dean and his father and didn't speak to them for at least a couple of years. During this time, Dean met Cassie Robinson while he and John were in Athens, Ohio, for a hunt. She and Dean dated for a couple of weeks. Before Dean left, he told Cassie the 'big family secret' about hunting. It was then that Cassie promptly called him 'nuts' and dumped him. During this time, Dean has also tracked down Edward Trenton, a monster and father to Cole Trenton, who would later pledge to hunt Dean down in revenge. Dean also hunted a Vetala by himself during this period.
When Dean was four years old, his mother Mary was killed in his younger brother Sam's bedroom. Twenty-two years later, the demon responsible for their mother's death kills Sam's girlfriend, Jessica Moore. Together, Dean and Sam go on a road trip to fend off supernatural creatures and search for their father, John, who occasionally leaves new missions for them to complete.Early in the season (Skin), Dean and Sam battle a shape-shifter responsible for a string of brutal murders in the St. Louis, MO area. During the course of the episode, the shape-shifter assumes Dean's form, causing police to believe that Dean is responsible for the murders. The shapeshifter also gains insight on Dean's inner conflict, partially revealing his secret self-loathing and resentment of his father being gone and Sam leaving them to go off to college. However, Dean kills the shape-shifter while it is still in his form, and the authorities officially declare him dead.
- "He's sure got issues with you. You got to go to college. He had to stay home. I mean, I had to stay home. With Dad. You don't think I had dreams of my own? But Dad needed me. Where the hell where you? [...] See, deep down, I'm just jealous. You got friends. You could have a life. Me? I know I'm a freak. And sooner or later, everybody's gonna leave me."
- —Shapeshifter channeling Dean's hidden insecurities and frustration[src]
In Home, Dean first becomes aware of Sam's psychic abilities when Sam has a vision of trouble at their old home in Lawrence, Kansas. In Asylum, while influenced by the spirit of Doctor Ellicott, Sam tries to shoot Dean in a spirit-induced rage over Dean's insistence in obeying John's orders rather than going to California to find their father. In the following episode, Sam actually does leave Dean, insisting he and John are both selfish because all they care about is revenge. Later, Dean tells Sam he was always proud of how he pursued what he wanted. Sam eventually goes looking for Dean when he can't reach his brother on his cell phone.
In Faith, Dean acquires a fatal heart condition when he is electrocuted during a hunt. Later, he is saved by a faith healer, Roy Le Grange, whose wife is controlling a Reaper. When Dean asks why he was saved, Roy Le Grange says he looked into Dean's heart and saw "A young man with an important purpose. A job to do. And it isn't finished."
In Shadow, as they prepare to battle Meg, Sam confesses to Dean that he will return to Stanford after they kill Azazel, the demon who killed their mother and Sam's girlfriend, Jessica Moore. Dean becomes upset with Sam and insists that they keep fighting together.
- "Don't say just in case something happens to you, I don't want to hear that freaking speech, man. Nobody's dying tonight, not us, not that family, nobody. Except that demon. That evil son of a bitch ain't getting any older than tonight, understand me?"
In the last episode of Season One, Azazel possesses Dean's father in an attempt to get The Colt for his own. After Dean realizes this, The Yellow-Eyed Demon pins him and Sam to a wall and reveals that John favors Sam over Dean. The demon also tells Dean that he was responsible for sending the demon's children back to Hell. After Dean makes a sarcastic remark about the situation, the demon tortures him and Dean pleads for his father's help before losing consciousness.
The season finale concludes with Sam, Dean, and John escaping from a clash with The Yellow-Eyed Demon in Salvation, Iowa. While Sam is driving to the hospital after Dean and John were injured, a demon-possessed driver drives his truck into the Impala, causing massive damage to the car and the Winchesters inside.
- "Back at the hospital, I made a full recovery. It was miracle. Five minutes later Dad's dead and The Colt's gone. You can't tell me there's not a connection there. I don't know how the demon was involved, I don't know how it went down exactly, but Dad's dead because of me and that much I do know.[...] You and Dad ... you're the most important people in my life. And now ... I never should've came back. I was dead. And I should've stayed dead."
- —Dean's spiraling depression[src]
All three of the Winchesters survived the wreck, although Dean was more severely injured than his father or brother. In the first episode of Season 2, In My Time of Dying, Dean is in a coma and a reaper, Tessa, tries to convince him to cross over. In an effort to save Dean, John makes a deal with Azazel, trading his life for Dean's. Before John dies, he tells Dean that someday Dean may have to kill Sam.
Over the course of the second season, Dean struggles with the death of his father and the resulting guilt that he should have died instead. This, however, Dean's hides under hunting and at first brushing off every attempt Sam did to make him talk about his feelings. Dean became more reckless and harsh, particularly in hunting until Sam finally made him get more of a handle on it.
- "You're lucky this turned out to be a real case. Because if it wasn't, you would've just found something else to kill.[...] You're on edge, you're erratic. Except when you're hunting because then you're downright scary. You're tailspinning, man. And you refuse to talk about it and you won't let me help you."
- —Sam describing Dean's reckless behavior[src]
During an investigation in Baltimore, MD, (The Usual Suspects), Dean is arrested in connection with another series of murders. It is revealed that Dean has a rather impressive police record with charges including credit card fraud, breaking and entering, and grave desecration. Although Sam and Dean are able to prove that the murders were actually committed by one of the detectives on the case, it is unclear whether or not the charges against Dean were ever officially dropped. However, the problem still remains that the authorities have realized that Dean is not dead as they had previously believed.
Shortly afterward, while doing a case revolving around deals with the crossroads demon and trying to save a man named Evan, Dean learns from the demon John went to Hell when he exchanged his soul for Dean's life. Dean's self-loathing and guilt increases, believing John should've went out fighting against the yellow-eyed demon, not bargaining and getting tortured for his sake. While Sam believes it's enough to save people and keep up his memory, Dean remains unconvinced.
Dean becomes more and more pressured under John's final order-- to kill Sam if he couldn't "save" him---after knowledge of Sam's destiny to turn evil and side with the Yellow-eyed demon in coming war. He continues to draw in on himself, tormented between obeying his father and his love for Sam. Dean begins to consider quitting hunting, chalking the "job" as nothing more than a catalyst for all the bad luck they ever had.
During this time, after hunting cases and misunderstandings in Baltimore and Milwaukee, Sam and Dean gain attention from the cops. Dean, in particular, is described as a wanted criminal and charged for "murder" and several different crimes. Both brothers are tailed by the relentless Special Agent Henriksen and forced to cover their tracks more persistently. Sam and Dean allow themselves to be arrested once while doing a case for an old friend of John's, but soon break out of prison.
Later, Dean is caught by a djinn and cast in an alternate reality where their mother never died and he and Sam never became hunters. He has a girlfriend and a normal life. John is still dead and the brothers were no longer close since they never hunted together, though in real life Dean is slowly dying from the monster. Dean is happier in this life, but suffers the guilt of realizing every one they saved died. Ultimately Dean was forced to sacrifice his happiness for his life and the lives of everyone he saved, but the experience left him more disillusioned and tired of the hunting life.
- "All of them. Everyone you saved, every one Sammy and I saved. They're all dead. [...] It's like my old life is coming after me or something. Like it doesn't want me to be happy. [...] Why? Why is it my job to save these people? Why do I have to be some kind of hero? What about us, huh? Mom's not allowed to live her life, Sammy's not allowed to get married. Why do we have to sacrifice everything, Dad?!"
- —Dean talking to John's gravestone in an alternate reality[src]
- "Look at me, Sam. It's not even that bad. It's not even that bad, alright? Sammy? Sam! Listen to me. We're going to patch you up, okay? You'll be as good as new. I'm gonna take care of you, okay? I'm going to take care of you. I've got you, because that's my job, right? Watching after my pain in the ass little brother? (realizes Sam is already dead) Sam? Sam? Sam?! Sammy?! No. No, no, no, no. Oh no come on. Oh God. (pulls Sam's body against his and yells) SAM!"
- —Dean while Sam dies[src]
Inconsolable, Dean lapses into anger and self-loathing. He brushes off the incoming threat and outright refuses when Bobby Singer suggests they burn Sam's body, prompting Bobby to leave the cabin. After his monologue with Sam, during which he confesses his failure as an older brother, Dean storms out of the cabin in a furious rage. At his wits end, he travels to a crossroads to recklessly make a deal with a "crossroads demon" for Sam's life in exchange for his soul. In the end, Dean is allowed one year to live and Sam is resurrected.
- "You know, when we were little, you couldn't have been more than five, you'd just started asking questions. How come we didn't have a mom; Why do we always have to move around; Where'd Dad go.. when he'd take off for days at a time. I remember I begged you, quit askin' Sammy. Man, you don't wanna know. I just wanted you to be a kid. Just for a little while longer. I always tried to protect you, keep you safe. Dad didn't even have to tell me. This was always my responsibility, you know. It's like, I had one job. I had one job. And I screwed it up. I blew it. And for that I'm sorry. I guess, that's what I do. I let down the people I love. I let Dad down, and now I guess I'm supposed to let you down too. How can I? Am I supposed to live with that? What am I supposed to do? Sammy... God.. What am I supposed to do? WHAT AM I SUPPOSED TO DO?!"
- —Dean to Sam[src]
Sam quickly comes to life, but with no memory of anything past Jake stabbing him. Dean is overjoyed to see his brother alive, but hides the fact he died and that he made a deal. Bobby is the only one to figure it out immediately and furiously yells at Dean for his impulsiveness and sending himself to Hell. Dean explains everything to him, even admitting he felt like this deal made his life mean something again, and pleads for him to not tell Sam as he knows it will upset him.
Soon after, along with Sam, Bobby, and Ellen, Dean arrives at a Devil's Gate that had been sealed off from other demons thanks a huge devil's trap made by Samuel Colt. Jake, however, manages to open it with the Colt, releasing hundreds of demons from Hell. Dean is visibly disturbed when he sees Sam brutally kill Jake without hesitation afterwards, nursed further nursed when the Yellow-eyed Demon mocks if he truly believes what he brought back was "pure Sam". John's spirit, which escaped from Hell, suddenly appeared and distracted Azazel just long enough for Dean to kill him with the Colt's last bullet, avenging his parents' death. John makes peace with both of them, then flickers out.
Sam soon figures out Dean's deal, realizing he only has one year, and is angry and hurt over his decision. Dean pleads that his job was to protect him and he couldn't let him die like that. Sam vows to find a way to get him out of the deal and the two brothers set out to exterminate the freed demons.
- "I've got nothing to lose now, right? [...] Dad brought me back, Bobby. I'm not even supposed to be here. At least this way, something good can come of it, y'know? It's like my life can mean something. [...] I couldn't let him die, Bobby. I couldn't. He's my brother."
- —Dean to Bobby on his deal[src]
- "Yeah, you're right. It was selfish. But I'm okay with that. [...] After everything I've done for this family, I think I'm entitled. Truth is, I'm tired, Sam. I don't know, it's like there's a light at the end of the tunnel [...] You're alive. I feel good, for the first time in a long time. I got a year to live, Sam. I'd like to make the most of it. So what do you say we kill some evil sons of bitches and raise a little hell, huh?"
- —Dean on going to Hell[src]
Dean decides to make the best of his final year, indulging in various acts of hedonism while Sam tries desperately to find a loophole in the crossroads demon's deal. Dean accepts his deal to Hell with unnerving calm, telling Sam there was no way out of this without Sam himself dying again and that he should give up on saving him. Dean seems to have lost will for life and just wants to save as many people as he can before he goes. Against his brother's wishes, Sam continues to look for loopholes anyway.
While doing a case, Dean drops by an old girlfriend Lisa Braeden that hasn't seen in almost nine years. She has a son named Ben that's just turned eight and bears striking resemblance to Dean. Dean believes him to be his son. After saving them from changelings, Lisa insists Ben isn't his and she did a blood test long ago just to be sure. Dean is disappointed, admitting that since he was going to Hell he was starting to wonder what he would leave behind.
After hearing the female demon Ruby's proposition to Sam, Dean is angry at his brother's lenience with her and believes Ruby to be lying about getting him out of Hell. He refuses to trust her, though Sam wants to use her. Dean learns from a surprisingly amicable demon named Casey the chaos surrounding the demon word with Sam's refusal to lead them and how many are after his brother. After Sam kills two demons--including Casey who wanted to spare Dean-- with the remade Colt thanks to Ruby and Bobby, Dean is shocked at his brother's ruthlessness and starts worrying Sam truly came back "different".
Early in the season, the brothers meet up with another beautiful woman, Bela Talbot. Bela acquires magical objects and sells them for a large profit, is unscrupulous and seemingly amoral. Meanwhile, Dean continues to bar Sam's attempts to break his deal of going to Hell, not still not to wanting Sam to risk dying. Dean tries to tell him he'll be fine with him and he's sorry for the pressure he put on him, but Sam only grows angrier and insists he care more about the fact he's dying, not how he feels.
After being pitted against Gordon Walker once again, Dean is show to be increasingly more reckless in his hunting, knowing he was going to die soon anyways. Sam is furious over this and calls out Dean's cavalier behavior on going to Hell being only a front to hide how scared he truly was. Dean denies this, but nonetheless decides to hold back on his recklessness in hunting for Sam's sake. He still seems resigned to his death, teaching Sam a "thing or two" on working on his Impala and even celebrating Christmas since it's his "last year".
Dean finally comes face to face to Ruby during a witch case, who warns them to stay away considering the powerful demon they're worshipping. Dean immediately points the Colt at her, accusing her of manipulating Sam. The two argue and Dean shoots at her, only for Sam to make him miss. He is angry at his brother defending Ruby and demands they kill her before she betrays them, but Sam is adamant on using her. Dean also confronts Sam on his growing ruthless and learns Sam is trying to "change" for this war to be "more like Dean", worrying him.
After Dean is about to die from the powerful demon's spell, Ruby suddenly swoops in and saves him with witchcraft. Dean begins to soften towards her, particularly after she fought against the head demon of the witches, but realizes she lied about being able to break his deal. The brothers also learn from her that all demons used to be human but had their humanity burned away in the fires of Hell. Dean realizes this will eventually happen to him when he goes to Hell and begins to show real fear of dying for the first time.
Ruby shares with them a knife that can kill demons. Dean begins to train Sam to fight demons alone for after Dean's contract is up.
In Dream a Little Dream of Me, when Bobby falls into a coma, Sam and Dean investigate the murder of a scientist. While viewing Dean's dreams it becomes clear that Dean believes Sam was their father's favorite but only thought of Dean as a tool. It confirms that Dean is so resigned to death out of self-loathing and his belief that he is worthless. Dean also encounters a future, demonic version of himself in a nightmare, which shocks him into starting to fight for his life. After waking up, Dean admits to Sam that he doesn't want to die. Meanwhile, Bela steals the Colt, meaning they won't have it when the hellhounds come for Dean.
- "My father was an obsessed bastard! All that crap he put on me about protecting Sam, that was his crap. He was the one who couldn't protect his family. He's the one who let Mom die! He wasn't there for Sam, I always was! He wasn't fair! I didn't deserve what he put on me! And I don't deserve to go to Hell!"
- —Dean to himself[src]
In Mystery Spot, Sam is forced to relive the same day, a Tuesday, over and over again. On each new day, Dean dies a different way despite Sam's frantic efforts to save him. Sam later discovers that the culprit is the Trickster, a villain from Season 2. It finally becomes Wednesday, but this time, Dean dies and doesn't come back. Sam spends months trying to hunt down the Trickster, who reveals that he has been trying to get Sam to understand that he and Dean can't keep making sacrifices for each other, and that Dean is going to die no matter what Sam does. The Trickster then sends Sam back to Wednesday, despite Sam failing to learn the Trickster's lesson. Sam is warned by Ruby that Dean might not make it back from hell.
In Jus In Bello, the FBI and Agent Henriksen capture Sam and Dean, thanks to a tip from Bela. While Sam and Dean are in jail, a host of demons come to kill them. Ruby comes to help them, but is furious to learn that they have lost the Colt. She says that she knows of a spell that will destroy all the demons nearby, including herself, and that she is willing to die in order to help Sam. However, they will need the heart of a virgin. Sam and the virgin, Nancy, agree to the plan, but Dean refuses to let her die. Dean's plan to exorcise the demons works, but one demon manages to escape and tells Lilith who, taking the form of a little girl, blows the police station up, killing everyone inside.
Lilith, it turns out, wants to kill Sam, as she sees him as a rival. According to Azazel's plan, Sam was supposed to lead the demon army, and Ruby was ready to follow Sam. Now, Lilith has become their main enemy.
Dean and Sam do a case of people committing suicide because of phone calls from their dead loved ones'. Dean gets a call from John, who tells him the demon is holding his contract is in town and there's an exorcism that can kill it. Despite the suspicious timing, Dean obeys the phone calls unquestionably in hopes he could be saved. In actuality, the calls were a Crocotta. Lured to a house, Dean nearly kills a man until he realizes it was a human and not a demon. After killing the monster, Dean apologizes to Sam and admits he just wanted to believe there was a chance he could've been saved.
- "I wanted to believe so badly there was a way outta this. I mean, I'm staring down the barrel at this thing. Y'know, Hell, for real, forever and I just ...[...] I'm scared Sam. I really, really scared. I guess I was willing to believe anything.[...] Hope doesn't get you jack squat. I can't expect Dad to show up with some miracle at the last minute. I can't expect anyone to, y'know? I mean, the only person that can get me out of this thing is me."
- —Dean to Sam[src]
Dean continues to search for a means to save himself from his fate, though knows there is likely no way out of it. Shortly before Dean's contract comes due, he learns from Bela that Lilith, the demon pursuing Sam, holds his contract; Bela had also made a deal with a demon. Bela pleads with Dean that she needs help and explains everything. Dean is unsympathetic, telling they might've helped her if she told them sooner and leaves Bela to die by Hellhounds and dragged to Hell.
As the brothers search for Lilith with Bobby's help, Dean begins suffering nightmares and hallucinations of his hellish fate. When Lilith is located, the three head to New Harmony, Indiana, and Dean discovers that he now has the ability to see the faces of demons underneath their human hosts.
Dean, with 30 hours left, still desperately tries to free himself. However, Dean outright refuses to summon Ruby when Sam suggests to and reiterates he still sees her as nothing more than a liar and a manipulator. Knowing Sam would summon her anyway, Dean challenges her and uses the opportunity to steal her demon-killing knife. With help from Bobby, he discovers Lilith is in Indiana. While the trio head to Indiana, Dean discovers he can see who is possessed and can see demons, such as hellhounds. After a quick struggle with Ruby, the four manage to escape a mob of demons using Holy Water. Now inside the house where Lilith was hiding, the three quickly manage to locate her.However, Dean discovers that Lilith has switched bodies as Sam is about to kill the little girl. As the clock strikes midnight, Dean smiles and tells Sam to be brave and to continue what he's doing. The brothers and Ruby run from the hellhounds and place a salt barrier to protect themselves. However, Dean realizes Lilith is in Ruby.
Sam: "I'm not gonna let you go to Hell, Dean!"
Dean: "YES, YOU ARE! Yes, you are ... I'm sorry. I mean, this is all my fault. I know that. But what you're doing, it's not gonna save me. It's only gonna kill you. [...] Keep fighting. Take care of my wheels. Sam, remember what Dad taught you ... okay? And remember what I taught you."
– Dean shortly before he dies, No Rest for the Wicked
Too late. The demon uses her powers to subdue the two, opening the door for the hellhounds. Sam watches as his brother is mauled to death by the hellhounds, pleading that Lilith stop. As Lilith leaves an unconscious Ruby, Sam holds the dying Dean in his hands, frantically yelling out to him.
Now in Hell, Dean is desperately yelling for help, calling out for Sam.
Dean was in Hell for a total of four months, which he later tells Sam "felt like 40 years", as in Hell, time is different from the mortal world. He was tortured by Alastair every day, and was even offered the option to torture other souls instead. Dean refused his offer for thirty years until finally giving in, triggering the first seal to Lucifer's Cage. Dean spent his last 10 years in Hell torturing other souls until Castiel pulls him out and declares that Dean is the only one who can stop Lilith from freeing Lucifer from Hell.
- " Do you even know how far off the reservation you've gone? How far from normal? From human?[...] Slippery slope, brother. Just wait and see. Because it's gonna get darker and darker and god knows where it ends.[..] It's already gone too far, Sam. If I didn't know you ... I would want to hunt you."
- —Dean to Sam[src]
The fourth season premiere, Lazarus Rising, begins four months after the third season finale. Dean awakes to find himself in a coffin and manages to dig himself out. He then breaks into a nearby gas station where he gets some water, food and cash. Before leaving the store, Dean sees the television and radio flicker on and a powerful whine that shatters the gas station's windows. Dean calls Sam but learns that Sam's number has been disconnected. He calls Bobby who hangs up on him. As a last resort, he hot-wires a parked car and goes to Bobby's house. A fight ensues until Dean is able to prove to Bobby that it is really him. Dean and Bobby then find Sam in a town right near where Dean was buried—he's in a hotel with a girl, but claims he is in town searching for a demon.
The Winchesters soon attempt to track down the force that ripped Dean from Hell. Dean is functional, albeit dazed, from his experience in Hell. He claims he has no memory of it, but it's clear it's a lie as he continues to get flashes of the torture. At first Dean believes Sam made a deal to save him and is furious, but Sam insists while he tried, it wasn't him. By the end of the episode, it is revealed that an angel named Castiel pulled Dean from Hell on God's command; Castiel tells Dean that God has work for him. The girl in Sam's room, it turns out, is Ruby in a new vessel, and it becomes clear that Sam lied to Dean when he told him he didn't know where Ruby was. T
In Are You There God? It's Me, Dean Winchester, Dean is unwilling to believe angels exist and is unnerved that God ordered himself ordered him to be brought back. He becomes further disillusioned, showing contempt for God allowing all these horrible things to happen to people and not absolutely anything to stop it. During this time, the brothers are haunted by the spirits of Meg Masters, Henriksen and Ronald Reznick who want to kill them for not saving them. Bobby figures out they're witnesses and the appearance of them is meant to be the first sign of the apocalypse. Dean, with guidance from Bobby, ultimately lays their souls to rest.
- "See, this is why I can't get behind God. [...] If he doesn't exist, fine. Bad things happen to good people. That's how it is. There's no rhyme or reason. Just random, horrible evil. I get it, okay? I can roll with that. But if he is out there, what's wrong with him? Where the hell is he while all these decent people are getting torn to shreds? How does he live with himself? You know, why doesn't he help?"
- —Dean's disgust with God[src]
Bobby's suspicions are later confirmed by Castiel, who visits Dean in the middle of the night. He reveals the angels are trying to stop Lilith breaking the 66 Seals for if she does, Lucifer will be freed from his cage and walk the Earth. Dean believes that Lucifer is a fairy tale told in "Demon Sunday School," but Castiel is serious and confirms Lucifer is all too real.
In In The Beginning, it takes us to 1973 where Dean learns about the Winchester history. He meets his parents, John Winchester and Mary Campbell, before he is born. Although tempted to stop Azazel from killing his mother, he realizes that he and Sam will no longer be hunters and all the people they saved will die. Dean learns that his mother was a hunter from a long line of hunters. Teaming up with his future mother and grandfather, they plan to take out Azazel with a borrowed Colt. Azazel, however, is one step ahead and possesses Samuel, Dean's grandfather. Dean fails to stop him and the possessed elder finds John about to propose to Mary. Samuel kills John. A heartbroken Mary confirms a deal with Azazel, allowing him "permission" in 10 years. Dean arrives home shortly and realizes he can't change destiny. Castiel warns Dean of Sam's dark actions behind his back and they must stop before the angels have to kill him.
in Metamorphosis, Dean catches Sam exorcising a demon with his mind and discovers Ruby is still working with him. He is furious with Sam for lying and using his demon-given powers, but Sam explains he's using it to help people. Dean is unconvinced, knowing it was only going to get darker from her. The brothers argue, but after a case of a Rougarou, Dean acknowledges he was too judgmental, though stands by his uneasiness over his psychic ability. Sam suddenly tells him he was right and that he wasn't going to use his powers anymore.
Dean continues hunting with Sam, but still suffers from flashes of his torment in Hell. It's revealed time flows differently in Hell and he was there for "forty years" rather than four months. Despite this, he still hides this from his brother. Dean also begins to feel the weight of the angels' special interest in him and feels more responsible for people's lives. in Monster Movie, Dean admits while he recently resented the cost of hunting, ever since he came back from Hell he sees it as more as a "mission from God".
In It's the Great Pumpkin, Sam Winchester, Dean and Sam work to stop the rise of a powerful demon called Samhain, who's presence would break one of the 66 seals. Uriel and Castiel are prepared to wipe out an entire town to stop it from happening, but both brothers refuse. The angels back down under Dean's orders, who forces them to give them more time to stop it. Unfortunately they fail and the seal breaks, letting Samhain roam free. Sam manages to use his psychic ability to exorcise the demon, which Dean witnesses in secret.
- "So I failed your test, huh? I get it. But y'know what? If you waved that time-travelling magic wand of yours and we had to do it all over again, I'd make the same call. 'Cause see, I don't know what's gonna happen when these seals are broken. Hell, I don't even know what's gonna happen tomorrow. But what I do know is that this, here? These kids, the swings, the trees ... all of it is still here because of my brother and me."
- —Dean to Castiel[src]
In the aftermath, Castiel visits Dean and the two talk. Castiel reveals he's not as black-and-white as the other angels and their "true" orders is to follow whatever Dean says. The choice with the town had been a test. Castiel informs Dean that a seal is still broken nonetheless and he doesn't envy his importance in the upcoming battles.
Dean starts to become overwhelmed by all his memories of Hell, using alcohol and work as a crutch. Sam, who was told by Uriel he remembers Hell, is suspicious of his excessive drinking and tries to get Dean to tell him the truth. Eventually, Dean at last admits he remembers Hell, but refuses to open up about it, telling Sam there's nothing he could say to make him feel better.
In I Know What You Did Last Summer, Dean and Sam hearing a young woman in a mental ward named Anna Milton who hears angels and has suspiciously accurate knowledge about the apocalypse. Sam and Dean warily protect her, knowing she didn't seem like a bad person. However, they're attacked by a powerful demon named Alastair, Hell's grand torturer who Dean has a history with "downstairs". Sam and Dean are badly wounded, but manage to get Anna to safety and escape. During this time, Dean finally learns what Sam did during the four months he was in Hell and why he suddenly trusts Ruby so much. Dean still doesn't trust Ruby fully, but is grateful she was there for Sam. Just then, Castiel and Uriel demand for Anna to kill her.
In Heaven and Hell, both brothers refuse to hand Anna over. Anna then activates a angel banishing sigil with her blood, though doesn't know how she knew. Sam and Dean take her to psychic Pamela Barnes to retrieve her memory and it's revealed Anna was once an angel who "fell" for becoming too human (catching human emotions). The group tracks down Anna's grace which will turn her into an angel again and grant protection, but the time they arrive at the location it's already gone. During this time, Dean develops a soft spot for Anna, intrigued that she'd rather be human than a angel and relates to her unease of taking orders from a absent father.
Sam, Dean, and Ruby continue to protect Anna, but the angels raise the stakes and demand her or they'll send Dean back to Hell. Still they refuse. Anna and Dean have a moment and have sex in the backseat of The Impala, but Uriel invades Dean's dreams and now threaten to kill Sam. Dean reluctantly gives up their location, but demons appear too and a battle between both sides take place. With them distracted, Anna takes her grace and becomes an angel again, disappearing in a white light.In the aftermath Dean, finally reveals to Sam what happened to him in Hell: Time flows differently there, so four months on Earth was forty years in Hell. During that time, he was "cut, carved, and torn" until there was nothing left of him, only to be made whole again just so the demons could start over. Dean reveals that at the end of every day the demon Alastair would offer to take him "off the rack" if Dean would put souls on and torture them. Dean resisted for thirty years (three months), but eventually gave in and spent ten years torturing people in Hell to escape being tortured himself. In Family Remains, Dean confesses to Sam that he enjoyed torturing souls, as he finally had the chance to dish out the same pain that he'd endured for the past thirty years.
- "It was four months up here, but down there ... I don't know. Time's different. It was more like forty years. [..] They sliced and carved and tore at me in ways that you ... Until there was nothing left. And suddenly ... I would be whole again. Like magic. Just so they could start all over. And Alasdair ... at the end of every day ... every one ... he would come over and make him an offer. To take me off the rack ...if I put souls on ... If I started the torturing. And every day, I told him to stick it where the sun shines. For thirty years, I told him. But then I couldn't do it anymore, Sammy. I couldn't. And I got off the rack, god help me I got right off it, and I started ripping them apart. I lost count of how many souls. The-the things I did to them ...[...] How I feel ... this ... inside me. I wish I couldn't feel anything, Sammy. I wish I couldn't feel a damn thing."
- —Dean on his experience in Hell[src]
In Death Takes a Holiday, Dean meets up again with the reaper, Tessa, who wakens his memories of their previous encounter with a kiss; Dean confesses that there has been a "hole" in him since that time and realizes that it is related to her. Soon after, Tessa is taken by Alastair in his quest to break another of the 66 seals; breaking the current seal involves killing reapers. The boys ask their psychic friend Pamela Barnes to help them astral project so that they may find the kidnapped reapers. Once they have, they are captured, but Sam is able to break them out and Tessa is able to continue reaping souls. However, before Dean is able to return to his body, Alastair corners him only to be captured by the angels; Castiel then appears and informs Dean that they have won this seal. As Dean awakes in his body, Pamela is dying from the injuries she obtained during a fight with a demon, while the boys were "out." Dean and Sam sit beside her as she dies, but Pamela secretly whispers to Sam she "sensed" his powers and his intentions are far from pure.
Since he was Alastair's "student" in Hell, Dean is pressed into service by Castiel and Uriel, who need him to torture Alastair for information on who is killing angels in On the Head of a Pin. Dean refuses at first, not wanting to stir his old self who tortured in Hell, but eventually agrees. Dean brutally tortures him and even seems to enjoy it, but is distracted when Alastair succeeds in getting Alastair to reveal that Dean himself was the first seal to break by virtue of giving in and torturing souls in Hell. ("The first seal shall be broken when a righteous man sheds blood in Hell. As he breaks, so shall it break.") It was also revealed John was originally meant to break it, but even after a hundred years of torture, he still didn't break. As a result, Dean is plagued with further guilt and self-loathing as well as the realization he still couldn't live up to his father.
Alasdair manages to free himself, the Devil's Trap set up by Castiel having been eroded by a leaking pipe. Alastair nearly kills Dean and then comes close to sending Castiel back to Heaven when Sam, having grown stronger in his demonic abilities, arrives and uses his powers to torture Alastair in to revealing he does not know who is killing the angels; Sam kills Alastair shortly thereafter. Later, as Dean recovers in the hospital, Castiel informs him about Uriel's betrayal; Uriel had been killing angels who did not join his cause to free Lucifer from Hell. Castiel also confirms Alastair's claim that Dean was the first seal, but adds that because of this, Dean is the only man capable of averting the Apocalypse. However, Dean does not believe he is able to do it and tells Castiel to find someone else as tears run down his face.
Castiel: "It's not blame that falls on you, Dean. It's fate. The righteous man who started it is the only one who can finish it. You have to stop it. [...] I know our fate rests with you."
Dean: "Well, then you guys are screwed. I can't do it, Cas. It's too big. Alasdair was right. I'm not all here. I'm not-I'm not strong enough. Well, I guess I'm not the man either of our dads wanted me to be. Find someone else. It's not me.
– Dean rejecting carrying the fate of the world, On The Head Of A Pin
In It's a Terrible Life, in an effort to put Dean back on the "right path," Zachariah, Castiel's superior, re-writes Dean and Sam's memories to remove their knowledge of supernatural creatures, making them believe they are average people working regular jobs, and drops them in a haunted building. Ironically, Dean, unlike Sam, is the one who most rebels against life hunting monsters, but eventually realizes he wasn't meant for his normal job. After the brothers proceed to defeat the ghost behind the hauntings, Zachariah (who posed as Dean's boss) restores Dean's memories to show him that hunting is in his blood. This only renews Dean's resolve.
In the episode The Monster at the End of This Book, Dean and Sam discover their lives were turned into a book series called "Supernatural by a prophet named Chuck Shurley and that he had a vision of Lilith coming to town and about to sleep with Sam. While Sam wants to use it as a plan to kill Lilith, Dean refuses and knows they're not ready to kill her. Dean admits he doesn't trust Sam, that he knows he how he killed Alastair, but not how and is afraid he'll turn evil. He enlists Castiel and uses Chuck as bait near Lilith, since any threat against him summons a archangel. Lilith flees. Sam tells Dean the vision was Lilith making a deal with him--the deal they both die and she doesn't break any more seals (it's written she doesn't survive the apocalypse)--but he refused it on the grounds of not trusting her. Dean doubts his sincerity, knowing demons rarely break contracts, and fears Sam might now value revenge more than self-sacrifice.
In The Rapture, Castiel contacts Dean in his dreams to warn him about something, but is expelled from his vessel Jimmy Novak and sent back to Heaven for his near-rebellion. Dean witnesses Sam drink the blood of a demon in the midst of battle and then promptly exorcise a demon possessing Amelia Novak, discovering the source of his power. Meanwhile, Castiel, now restored in his true vessel, dismisses his warning to Dean and that his allegiance lies only with Heaven. Later in the Impala, Sam receives a request to go to Bobby's house. Once there, they trick Sam and lock him in Bobby's panic room to detox him from the demon blood.
While Sam is going through painful withdrawal symptoms from the demon blood, Dean asks Castiel for help. He takes an oath to serve God and the angels if it would mean that Sam wouldn't have to kill Lilith. Sam escapes the panic room after Castiel releases him, and Dean tracks him down to a hotel, despite Sam's efforts to shake him. They argue over whether or not Ruby is corrupting Sam, if Dean is supposed to stop the Apocalypse, and if Sam is turning into a monster. The argument leads to a fight that Sam wins. On the floor and in pain, Dean calls to Sam, "If you walk out that door, don't you ever come back" -- the same ultimatum John gave Sam when he left for college years before -- after which Sam leaves the room.
- "She's poison, Sam! Look what she did to you. I mean, she up and vanishes weeks at a time, leaving you cracking for another hit. [...] That is French for manipulating your ass ten ways from Sunday! [...] You don't know what you're doing, Sam. [...] Because it's not something you're doing, it's what you are! It means ... it means you're a monster."
- —Dean'a anguish at Sam's choices[src]
Dean swears his alliance to serve Christ and is then held captive by Zachariah. Dean realizes the angels never wanted to stop the Apocalypse and that they want to free Lucifer to destroy him. Dean does have a "destiny", but only to stop Lucifer. A "paradise" will exist once Lucifer is destroyed, but at the cost of thousands of lives. Sam as well "plays a part". Dean horrified at their lack of concern for the lives of innocent people and is desperate to get free. Castiel, after much resisting, admits Lilith is the final seal and rebels to give Dean a chance to escape. Dean goes after Sam, but arrives too late. Ruby, who had been manipulating Sam all along for this moment, is killed by Dean. Sam, ashamed and broken beyond description, apologizes. The season ends with Sam and Dean watching as Lucifer rises and the Apocalypse begins.
- "Destiny? Don't give me that destiny crap. It's all a bunch of lies, you poor, stupid, son of a bitch! It's just a way for your bosses to keep me and keep you in line. You know what's real? People. Families. That's real. And you're gonna watch them all burn? [...] You can take your peace and shove it up your lily-white ass. 'Cause I'll take the pain and the guilt. I'll even take Sam as is. It's a lot better than being some Stepford bitch in paradise!"
- —Dean to Castiel[src]
Dean: "It's my job. Somebody has to save people's asses', yours included. [...] I mean, it's a damn biblical Apocalypse, and if I don't stop it and save everyone, then no one will and we all die."
Dr.Carthwright: "That's horrible. [...] I mean, apocalypse or no apocalypse, monsters or no monsters ... that's a crushing weight to have on your shoulders. To feel like six billion lives depend on you ... god. How do you get up in the morning?"
Dean: " ... That's a good question."
– Dean's burden, Sam, Interrupted
The fifth season picks up right where season 4 ends when the portal to Hell opens. As Lucifer escapes, the brothers are teleported into an airplane by an unknown force (later revealed to be God). Bobby gets possessed by a demon and instead of killing Dean he kills the demon inside himself, using Ruby's knife, in turn paralyzing himself from the waist down. Dean is told by Zachariah that he is the "Sword of Michael", which means the Archangel Michael will use his body as a vessel to lead the forces of heaven, but Dean must consent to this. Dean refuses and Castiel saves him when Zachariah tries to force Dean to agree by harming him and Sam. Castiel brands them with an Enochian Sigil, hiding them from all demons and angels, Lucifer included. Dean's relationship with Sam is severely damaged by Sam starting to Apocalypse and eventually he admits to him he doesn't think he can trust him the way he did ever again.
Dean and Sam fight the Horseman War in a town where the people think that their neighbors are demons. In this town are Ellen, Jo, and Rufus all trying to hunt the demons, who turn out to be normal people War has altered to make look like demons. Once the brothers cut the ring finger off of war, sending the town back to normal, Dean worries that Sam cannot control his urge to drink demon blood. The brothers then agree to go their separate ways because Sam is a liability with his demon blood lust. Later, Castiel finds Dean and they capture the Archangel Raphael to ask the location of God. Dean also grows closer to Castiel, admitting he had more fun with him in 24 hours than he had with Sam in years.
In The End, Dean is transported five years in the future by Zachariah to the year 2014. He meets his future self, a hardened and cynical leader leading a ragtag group of Croatoan Virus survivors in a post-apocalyptic world. Present Dean realizes Sam said "yes" to Lucifer and that Future Dean's biggest regret was never agreeing to Michael to stop all this from happening. Dean is shocked at his future self's ruthless, both in torture and willingness to sacrifice his friends to defeat the devil, but Future Dean recklessly goes ahead with his plan to use The Colt on Lucifer, only to die at his hands. Lucifer tells present Dean nothing will change this outcome before he is brought back to present. Despite Zachariah and Future Dean's protests, Dean still refuses to become Michael's vessel. Nonetheless shaken by his grim future, Dean calls Sam and decides they should stay together to "keep each other human".
In the episode Changing Channels, the brothers are thrown in an alternate universe where they're in TV shows and have to "play their roles". It's revealed this had been another "lesson" to "accept" their roles as Michael and Lucifer and that the Trickster they know had actually been the archangel Gabriel all along. Dean and Sam learn that their relationship (Dean, the older brother loyal to an absent father, and Sam the younger brother, rebellious to the father's plan) mirrored the relationship between Lucifer and Michael and that was only further proof their was no stopping their "destiny". Sam and Dean still refuse, though began to doubt how they'll be able to stop the "inevitable".
- "No, we’re not. ‘Cause we don’t screw with people the way you do. And for the record, this isn’t about some prized fight between your brothers or some destiny that can’t be stopped. This is about you being too afraid to stand up to your family! Don’t say I never did anything for you."
- —Dean to Gabriel[src]
Sam and Dean learn from the Becky the Colt is in possession of a demon named Crowley, who gives the Winchesters the gun to kill Lucifer and end the Apocalypse. Sam and Dean spent their "last night on Earth" with Jo, Ellen, Castiel and Bobby before setting out to find and kill Lucifer the next day. While looking for Lucifer in Carthage, Missouri, Castiel sees reapers all over the town and is later captured by Lucifer while investigating. The hunters run into Meg, who sicks a pack of hellhounds on the group. Jo is severely injured by one of the hellhounds during their escape while saving Dean.
The group finds shelter in a hardware store where they make bombs out of rock salt and iron nails to kill the hellhounds. Jo plans on setting off the bomb since she is going to die anyways, but Ellen insists on staying with Jo and both die in the blast. Sam and Dean find Lucifer performing his ritual. Dean manages to shoot Lucifer point-blank with the Colt, only to find it has no affect. The Winchesters find out Lucifer is one of the five things in the world the Colt cannot kill. The brothers return home and both grieve with Bobby for Ellen and Jo. Having failed to kill Lucifer and lost two allies and friends, Dean becomes more disillusioned and hopeless.
Sam and Dean check themselves in a mental institution to hunt a monster for their old friend Martin. Dean admits he feels personally responsible for the lives of everyone, not just a few. It's indicted in the hallucinations the wraith conjures for him that this mostly driven out of his own self-loathing enhanced by Jo and Ellen's death along with his failure to kill Lucifer, believing that he can never save anyone and always fails. The brother manage to kill the wraith and break out of the institution.
When Anna travels back in the year 1978 to kill John and Mary, resolving to prevent the Winchesters' birth to stop the Apocalypse and Lucifer, Sam and Dean follow her with help from Castiel. The brothers work with their younger parents, but Anna enlists the help of a past Uriel and soon catches up with them. Ultimately, Anna succeeds in landing a fatal blow on Sam, but Michael at last appears (in John's body) and smites her while restoring Sam and sending him back to his own time. Dean learns his whole bloodline are possible vessels dating back to Cain and Abel (their ancestors), but he is Michael's true vessel. Michael appeals to Dean that he can relate to him for his love to his little brother, but he still has to kill Lucifer for his father. Dean still defies Michael and the archangel sends him back to his own time, but not before telling him free will is a "illusion" and he will say yes. 
Under pressure of his "destiny" combined with his responsibility for the Apocalypse and repeated losses, Dean is gradually driven into depression. After the Horseman Famine plagues a town and affects everyone with insatiable hunger (money, sex, food, etc.), Dean is the only one unaffected. It's indicated by Famine that Dean is so broken and defeated, he's too "dead inside" to want anything. Sam manages to kill Famine with his psychic powers after feeding on demons due to his effect, but is quickly locked away by Dean and Castiel in Bobby's panic room again. This triggers Dean to break down and pray to God for help.
- "That is one deep, dark nothing you got there, Dean. Can't fill it, can't you? Not with food or drink. Not even with sex. [...] I can see inside you, Dean. I can see how broken you are, how defeated. You can't win, and you know it. But you just keep fighting. Keep ... going through the motions. You're not hungry, Dean. Because inside ... you're already dead."
- —Famine to Dean[src]
In Dark Side of the Moon, Dean and Sam are shot by hunters and sent to Heaven. They discover Heaven is just a collection of the person's best memories and that they've both been there before (the angels removed their memories). Dean is upset by Sam's "heaven" being memories away from their family while Dean's is the exact opposite. Sam and Dean meet Joshua---a angel that 'talks' to God--- who tells them God's message is to stop looking for him. He could do something to stop the apocalypse, but he won't. Dean is deeply upset, as God had been his last hope.
Sam and Dean return to Earth in their bodies, this time with memories of their experience in Heaven. Dean, losing faith knowing God doesn't see the battle with Lucifer to be 'his' problem, throws out the amulet Sam gave him and starts to see no way out of his destiny as Michael's vessel.
During Point of No Return, Dean prepares for his possession by Michael before he's found by Sam and Castiel who return him to Bobby's house. Dean justifies he can't bear the guilt of the whole world burning if he didn't agree and later admits to Sam he doesn't trust him enough to say no to Lucifer forever. If anyone will stop him, it would have to be him. They convince Dean to allow them some more time in order to research another method of stopping Lucifer; however, the resurrection of their brother Adam Milligan (who agreed to be Michael's vessel) forces Sam, Bobby and Castiel to keep both Adam and Dean from Zachariah. When Dean escapes and tries to lure the angels, both Castiel and Sam leave to find him, allowing Adam to be removed by angels.
Despite Bobby and Castiel's insistence on keeping Dean from Zachariah, Sam allows him to try to rescue Adam. Castiel dispatches the angelic guards and the brothers attempt to rescue Adam, but Sam's ambush on Zachariah fails and Zachariah causes internal damage to both Adam and Sam to coerce Dean to consent to Michael. Ultimately, he relents, but after Zachariah summons Michael, Dean taunts him into sacrificing himself in order to allow Michael in. Zachariah angrily refuses, and Dean stabs him and ushers his brothers out of the room. Unfortunately Adam does not escape in time and is locked in the room with the approaching Michael. As they leave, Dean admits that he would have accepted Michael, but because of Sam's faith he decides that he will "take the fight to them".
- "I don’t know if it’s being a big brother or what, but to me, you’ve always been this snot-nosed kid that I’ve had to keep on the straight and narrow. I think we both know that’s not you anymore. I mean, hell, if you’re grown up enough to find faith in me, the least I can do is return the favor. So screw destiny right in the face. I say we take the fight to them and do it our way."
- —Dean changing his mind about being Michael's vessel[src]
In Hammer of the Gods, when Dean and Sam are forced to help several other gods against Lucifer, they team up with Gabriel, who finally decided to support their side. They manage to lure Lucifer to their location, but Gabriel is the one that faces him and ultimately dies in the process. Despite, Gabriel gives them the first real key to defeating Lucifer: find the four "keys" to Lucifer's Cage before luring him there and sealing him back in his cage. The four "keys" are revealed as the four rings of the Horsemen. The brothers already have two from War and Famine so set up to find the last two.
Dean and Sam, with help of the Crowley and a now human Castiel, face off against the Horsemen Pestilence and manage to get his ring. However, trouble brews in Chicago from an epidemic of the Croatoan Virus. Dean locates the last Horsemen, Death, who gives his ring to Dean in hopes of locking Lucifer back in his cage. He's "chained" to Lucifer and wants to be free of him. Sam proposes he say yes, somehow takes control of Lucifer, and throw himself in the cage---sacrificing himself to stop the Apocalypse. Dean opposes it, finding it risky and unwilling to sacrifice his brother, but Sam still believes his choice is right. Bobby talks to Dean, telling him to have faith in his brother whatever happens.
- "I'm not gonna lie to you though. It goes against every fiber I got. I mean, truth is ...You know, watching out for you ... it's been kinda my job, you know? But more than that ... it's kinda who I am. You're not a kid anymore, Sam, and I can't keep treating you like one. Maybe I gotta grow up a little too. I don't know if we got a snowball's chance. But ... but I do know, that if anybody can do it .. it's you."
- —Dean agreeing with Sam's plan for Lucifer[src]
It is reluctantly decided that the plan to throw Lucifer back in the cage requires Sam to become Lucifer's vessel. Dean knows he will lose his brother, but tries have faith in him and respects his choice. Once Sam says "yes" to Lucifer, the archangel takes Sam over and closes the portal with ease. He leaves Dean alive as he leaves to go fight his older brother, Michael, who is now in Adam's body.
Just as Lucifer and Michael are about to begin, Dean shows up in the Impala to witness the fight as if to try and stop the inevitable one last time. Having had enough of Dean's attempts to save Sam, Lucifer goes on a rampage and begins to beat Dean to a bloody pulp. Lucifer kills Castiel and Bobby as he continues to beat Dean until Sam is able to regain control long enough to open the portal to Lucifer's cage. Sam grabs hold of Michael and falls into the cage. The portal is then sealed, leaving nothing behind but the key. Castiel, now a seraph returns from the dead, having been resurrected by God, heals Dean and resurrects Bobby. Dean is heartbroken at having lost Sam and resentful towards God for letting all of this happen. Since Michael is no longer in Heaven, Castiel disappears to restore order.
Dean: "He brought you back. But what about Sam? What about me, huh? Where's my grand prize? All I got is my brother in a hole!"
Castiel: "You got what you asked for, Dean. No paradise. No hell. Just more of the same. I mean it, Dean. What would you rather have? Peace? Or freedom?
– Dean and Castiel's goodbye, Swan Song
Dean gives a goodbye to Castiel and Bobby, but cuts contact off them for a very long time. In the end, Dean keeps the promise Sam wanted for him: to not resurrect him, quit hunting, and go to live with Lisa and Ben. Unknown to him, Sam watches outside in the last scene, having been released from the cage.
- "Dean didn't want Cas to save him. Every part of him, every fiber he's got wants to die or find a way to bring Sam back. But he's not gonna do either. Because he made a promise."
- —Chuck over Dean[src]
- "Do you have any idea what walking away meant for me? [...] I showed up at their doorstep half out of my head with grief. God know why they even let me in. I drank too much. I had nightmares. I looked everywhere. I collected hundreds of books, trying to find anything to bust you out. [...] A damn year?! You couldn't put me out of my misery?!"
One year later, Dean is living a normal life with Lisa and Ben, having a normal job and having the Impala covered up with his weapons locked away in the garage. He seems somewhat happy, though still struggles with his grief over losing Sam. Despite retiring, he retains his old hunting habits such as keeping guns handy, hiding a Devil's Trap under Lisa's rug, and sleeping with salt and holy water under his bed. Dean's "apple pie" life is halted when he notices supernatural occurrences around his neighborhood. As he prepares to fight, he has an impossible encounter with Azazel, but it turns out to be a hallucination created by Djinns and he is snapped out of it by none other than his brother, Sam. Dean is happy to see Sam alive but is soon enraged when he learns that Sam has been out of Lucifer's cage and back on earth for over a year and didn't tell him. Dean's "normal life" was far from happy, ranging from having frequent nightmares to excessively drinking. It's revealed he tried finding ways for Sam to get out his Cage despite Sam telling him not to. Soon, he is reunited with his resurrected grandfather Samuel Campbell and other members of the Campbell Family. Dean is distrustful of Sam and Samuel both being brought back and by extension greatly distrusts the Campbells.Dean takes Lisa and Ben to Bobby's for safety, and discovers that Bobby knew Sam was back as well and didn't tell him. Dean and Sam use themselves as bait to lure the djinns in but Dean becomes affected again with hallucinations of Azazel killing Lisa and feeding Ben demon blood. Sam is able to snap Dean out of it as the Djinn are captured. Sam leaves after Dean decides to stay with Lisa and Ben.
Dean relocates Lisa and Ben to a different home and starts acting like his father, getting on edge and limiting their movements to 'protect them'. He is called back to hunting when Sam finds an abandoned baby from a crime scene, and needs help taking care of it. They take the baby to Samuel, where Dean is distrustful of the Campbells. Samuel wants to raise the baby as a hunter which infuriates Dean, but before they can discuss it any further, the Alpha Shifter arrives and kills one of the cousins, also taking down the rest of the Campbells. Then the Alpha defeats Sam and Dean and takes the baby. Dean returns to Lisa and Ben but is conflicted with staying or hunting with Sam. Despite the previous pressure of his hunting life, Dean is still too much of a hunter at his core and can't so easily mesh into a "normal life". Lisa forces him to accept this and suggests a compromise: he can go hunting and come back whenever he can. He agrees and gets the Impala out of the garage.
Lisa: "Maybe we're safer with you here, maybe gone. I don't know. The one thing I do know is you're not a construction worker. You're a hunter. And now you know your brother's out here, things are different. You don't want to be here, Dean."
Dean: "Yes, I do."
Lisa: "Okay, but you also want to be there. I get it. You're white-knuckling, living like this. Like what you are is some bad, awful thing. But you're not. But I'm not going to have this discussion every time you leave. And this is just going to keep happening so I need you to go. [...] Me and Ben will be here and you come when you can. Just come in one piece, okay?"
– Dean becoming a hunter again, Two And A Half Men
They find the child responsible for the deaths and discover that he sold his soul to an angel for the staff. Castiel soul probes the child against Dean's wishes but with Sam's consent. The angel Balthazar is responsible for the transaction and Castiel tracks him down, with Dean and Sam staying behind and fighting Raphael's angel henchmen who have been hunting Cas. They help Castiel trap Balthazar after Raphael is defeated and force him to relinquish the child's soul. Afterwards, Sam joins Dean in the Impala again as his own car was destroyed, and Dean questions Sam's strange behavior and his time in hell, but Sam doesn't want to talk about it at all.
Dean is called to a case by Sam to investigate the mysterious deaths of several cops. Dean suggests they call Castiel, but Sam doesn't believe he'll come. To his surprise, Castiel responds to Dean's call and tells them that the staff of Moses is responsible for the deaths. He also informs them that heaven is embroiled in a civil war as Raphael is trying to take over and resume the Apocalypse that Sam and Dean prevented.
In Weekend At Bobby's, Dean calls Bobby for help with a Lamia. Dean continues to grow more unsettled over Sam's strange behavior and calls Bobby to talk to him about it. Bobby yells at Dean for being selfish and oblivious to Bobby's own problems. Abashed, Dean flies to Scotland with Sam in an effort to help get Bobby's soul back from Crowley. Crowley is forced to give him back his soul and the brothers fly back to America.
Sam and Dean investigate what appears to be a vampire attack, and Dean becomes entangled with the vampire Boris. Sam walks by as Boris attacks Dean, but merely watches as Boris turns Dean into a vampire. Dean notices Sam isn't freaked out about his vampirism, as he can hear Sam's steady heartbeat. Sam tries to reason with Dean, assuring him that Samuel will know what to do. Dean then decides to sneak out to visit Lisa in order to say one last goodbye. While visiting, Dean struggles with his bloodlust for Lisa. He comes close to biting her, but retreats into the hallway. As he is leaving Ben approaches Dean despite Dean's warnings, and Dean shoves Ben into the wall in an effort to put some distance between them. He then leaves and returns to the motel.
Upon Samuel's arrival, Dean demands that he kill him, but Samuel refuses and informs him that there is a cure for vampirism. As long as Dean hasn't fed, then the cure can turn him back. The cure requires blood from the vampire who turned you, so Dean infiltrates the nest, and encounters Boris, who explains to him the vampires' aim. When Boris smells the dead man's blood drop from Dean's syringe, he attacks. Before the vampire can make his move, all the vampires in the nest collapse, including Dean. He has a vision of the Alpha Vampire.
When he awakens, Boris is rallying the coven of the vampire to attack Dean. Dean, however, has the upper hand and takes out the entire nest single-handedly, including Boris. Back at the motel, Dean drinks the cure, and goes through a painful process of turning back. His short time as a vampire flashes before him, highlighting Sam's hesitation to save him from Boris. Dean now has lost trust in his brother completely.
Dean becomes so uncomfortable around Sam, beginning making excuses to stay away from him. He informs Bobby of the situation, and digs up information on whatever could possibly be Sam's diagnosis. He then asks aloud for the truth, and is infected with a truth curse from the goddess Veritas where people tell truths to him against their will. Sam, however, proves to be immune to this, as the curse doesn't affect him and lies to him. Dean believes Sam and feels guilty for suspecting his brother. During this time, Dean's relationship with Lisa ends permanently, as she is unable to deal with his issues stemming from his hunting life and his co-dependence on Sam. In a confrontation with Veritas, Dean admits to her truth spell he did want a family, but now sees himself self-deprecatingly as only being good at hunting and could never be normal. During this, Dean also learns Sam is immune to her truth affect and calls him not human. He loses complete trust in him and puts a knife on his brother. This time, Sam comes clean, fessing up to allowing him to become a vampire to get closer to the alpha and his chilling inability to feel anything ever since he got out of the cage, including the safety of his brother. Dean, emotional, processes the truth about Sam, and responds with beating Sam unconscious.
- "It's the gig. You're covered in blood until you're covered in your own blood. Half the time, you're about to die. Like right now. I told myself I wanted out ... that I wanted a family. [...] But what I'm good at ... is slicing throats. I ain't a father. I'm a killer. And there's no changing that. I know that now."
- —Dean's self-deprecation[src]
Dean takes matters into his own hands, and calls Castiel for assistance with diagnosing Sam. Castiel confirms that Sam has no soul, and that it is still in the cage with Michael and Lucifer. Dean intends on holding Sam in the motel room, but when Sam unties the bonds he's in and refuses, Dean states he'll be watching every move he makes, which Sam agrees to. The two brothers then chase the only lead they have towards Sam's soullessness: Samuel. Samuel has a lead on the Alpha vampire, and Dean volunteers himself and Sam to join the hunt. Samuel reluctantly lets Dean join the hunt.Dean is left with Gwen to stand guard while Sam joins the other Campbells on the hunt. Dean sneaks away and catches Sam helping Samuel and a few other Campbells loading the Alpha vampire into the van. He later confronts Sam about it, and Sam admits that keeping this from Dean was his own idea because they needed to interrogate creatures, and apparently Dean 'messes it up'. Dean is furious about Sam's lack of instinct, and gives him two options: to work with him, or to go off with Samuel and see how that goes. Dean is shocked when Sam comes back, admitting he gave it a 60/40 prediction of whether his brother would come back.
Sam and Dean follow Samuel via his cell phone's GPS to a warehouse where they are holding the Alpha vampire. When Samuel leaves the room, the brothers take the opportunity to question the creature themselves. The Alpha remembers Dean even by name, referring to him as 'his child for a time'. When the brothers ask the Alpha what Samuel wants from him, the vampire reveals that it is Purgatory Samuel is looking for and that Samuel is merely working for someone else. Dean confronts Samuel about it, but is interrupted by the escape of the Alpha. Christian, revealed as a demon, and a few other demons recapture the Alpha and take it away.
Crowley appears on the scene, and reveals that he's Samuel's boss, and is the one who's looking for Purgatory. He is also responsible from raising both Samuel and Sam, and is in possession of Sam's soul. If they cooperate, Sam gets his soul back. If they don't, Crowley shoves Sam back in Lucifer's cage.
Dean is reluctant to work for Crowley, but Sam convinces him it's the only way they'll find a way to get his soul back. Dean is still not convinced that Sam is his brother, and later admits that he doesn't know what he is. When Sam states that he thinks it might be best to go back to being the old Sam, Dean accepts his offer, and says it's 'time to get his brother back.'
Dean and Sam are more on the same page now, but Dean still seems to struggle with Sam's behavior and then starts to act as his 'Jiminy Cricket' to Sam's 'Pinocchio'. They investigate a case of crop circle abductions, leading people to believe it is a UFO sighting. Dean decides to check out the crop circles for himself, but gets abducted.
He returns a while later, and walks in on Sam having sex with a hippie chick. Dean expresses irritation at this, and states that he 'had a close encounter, and won it'. However, it's proven that he didn't exactly 'win' anything, as he starts seeing things that no one else can see. There's one moment when Dean's alone, and the door to the motel bursts open and a "little, glowing, hot, naked lady" flies in and starts hitting him. He traps her in the microwave and cooks her, but when he tries to show Sam her remains, Sam can't see them. Sam then draws the conclusion that the UFO encounters are because of Fairies.
Dean and Sam go to visit Marion, a woman they interviewed earlier who had said that fairies were behind the disappearances. She tells them all about fairies, including that they like cream and that they must count every grain of salt or sugar that is spilled in front of them. After they leave, they see Mr. Brennan loading boxes of cream into his car. Dean breaks into his shop and sees elves working on watches for him. Afterwards, Dean is being stalked by a fairy, a Red Cap in particular, and he mistakenly tackles a midget and is arrested for a hate crime. While in jail, Dean was being beaten by the Red Cap in his jail cell, but is saved by Sam in time and is released from jail the next morning. The midget, who was also the district attorney for Tipton county, dropped the charges against him. Dean learns that the leprechaun struck terms of making a deal with Sam, to lift his soul from the cage (and make him a 'real boy'). He questions Sam's way of thinking, and wonders if Sam is having second thoughts.
Dean quickly becomes tired of working for Crowley, as he sees that it's not getting them anywhere. He tries to reason with Sam that Crowley may not keep his end, but Sam has left the room. When Dean slowly walks the motel room looking for Sam, he gets knocked out by demons, led by none other than Meg. Dean responds emotionally, saying he's been dying to see her again to get back at her for being responsible of Ellen and Jo's deaths. Meg seemingly approves of this, but not before demanding where their "boss" is. While neither of the brothers answer, she puts a knife to Dean's neck, getting impatient. Sam, however, merely laughs at her, and reassures Dean that she can't kill them because she needs them to get her to Crowley so she could kill him. Dean says he hopes they both lose. Sam suggests that she works with them and makes a deal with her, which Dean is not in favor of.
When the demons leave, he confronts Sam about it. He is unsure whether working with a demon again will go anywhere good, and their tendencies to double-cross work against them. Sam assures Dean that they will get the jump on the demons first because he'll be bringing Castiel along for the ride. Dean expresses surprise when Sam actually succeeds in calling the angel.
When Castiel performs a ritual to find Crowley's location and can't find him, Dean suggests they search Samuel's office for a map or any hint on Crowley's base. They are interrupted by Samuel. Dean first suggests that Samuel tells them where Crowley is, which he refuses to do. When all his attempts to obtain the information lead to nothing, Dean consents to ask Samuel what Crowley is holding over him. Samuel takes a picture out of his desk drawer, and hands it to Dean: it's a picture of their mother, Mary. Dean expresses a somber opposition towards working with Crowley to bring Mary back, and tries to convince Samuel to learn from the brothers' mistakes. When Samuel's had enough of his protests, he asks them to leave. Samuel later knocks on their door to give them the location, despite his wishing for them not to go there.
Before they leave for the prison, Castiel talks to Dean about how he doesn't think retrieving Sam's soul is wise. He believes that Sam will be broken beyond repair if they force his "mutilated" soul back in. Dean doesn't want to believe this, and reassures Castiel that they'll deal with whatever complications come up.
Upon arriving and infiltrating the prison, Dean expresses apprehension on how easy it was getting in, which then comes to fruition when the guards are let out and come after the group. When Meg decides to stay behind to hold off the hounds, Dean, Sam, and Castiel head further in the prison in search for Crowley. Castiel is banished by Samuel, much to Dean's surprise, and the brothers are locked in separate cells by demons. When Samuel later tries to make Dean understand, the two express different ways of seeing the betrayal: Samuel saw it as Dean choosing Sam over Mary, while Dean saw it as Samuel choosing Crowley over his own grandsons. He also challenges Samuel that he's going to escape from the prison and the next time he meets Samuel, he'll kill him. Demons then let him out his cell to be taken to a bigger cell to be eaten alive by Ghouls. Dean fights back, but to no avail. Sam later busts in and kills the ghouls.
Dean then finds where Christian has Meg, kills Christian, and then sets off the fire alarm to get Crowley's attention. When the King of Hell enters the room, the brothers confront him and demand he return Sam's soul. Crowley says he can't, and that he was lucky enough to get his body out of the cage. Crowley breaks from the devil's trap, and flings Sam and Dean pinned to the wall. Castiel soon arrives on the scene and rescues them.
Later, outside the prison, Dean thanks Castiel for his help. Castiel tells Dean about the civil war in Heaven, and Dean is genuinely concerned, and asks if there's anything they can do to help. When the angel says there's nothing they can do and apologizes, Dean reassures him that there's no need to apologize, that they understand and are his friends. Dean tries to reason with Sam, who now has second thoughts on all this trouble for his soul, saying that he doesn't know how wrong, how messed up he is without a soul. Sam disagrees and walks away without a word.
Dean, now more desperate than ever for Sam's soul, seeks out Death to ask for his help. Dean requests not only for Sam's soul, but for their half-brother Adam as well (Death however forces Dean to pick one, in which he chooses Sam). Death hints he has the power to jailbreak Lucifer's cage, and makes a wager with Dean: he will restore Sam's soul if Dean agrees to be Death for a day. He also says he will be able to put a mental wall inside Sam's mind to hold back the memories of the cage, as he also confirms that the results of those memories (or of the wall collapsing) would be fatal. Before the horseman can explain why he wants this from Dean, he is resurrected by Dr. Robert.
Dean informs Sam and Bobby on his deal with Death. Sam is very adamant about keeping his soul out of his body, but later backs down and gives Dean false hope not to mess up. Dean, still very suspicious of his soulless brother, tells Bobby to watch him while he's gone.
Dean slips on Death's ring, giving him some of Death's powers and effectively taking his place for 24 hours. The reaper Tessa is assigned to keep an eye on Dean to make sure he has the "minimum screw-up", despite her dislike for Dean's habits of throwing a wrench in everything. Dean does a fair job and kills a few people with a simple touch, following Tessa's list of people, but becomes hesitant when he is supposed to kill a 12 year-old girl. He refuses to kill her, but this sets up a chain of events. The girl survives, but innocent people die in her place as she is disrupting the natural order being alive. Dean tries to save one of these innocent people, going as far as taking off Death's ring. Realizing the mistake he's made, he reluctantly accepts defeat, and finally decides to kill the girl.
Meanwhile, Sam has tied Bobby up and intends to kill him. Dean manages to arrive in time and knocks Sam out and chains him to the cot in the panic room. Dean expresses deep sadness at how he's failed to fulfill his life-long promise of saving his brother: this replicant of Sam could not stay alive; he's dangerous, he's cold, and he's capable of anything.
Dean leaves the basement to let his defeat sink in, and finds Death eating. Dean gives back the horseman's ring, and claims his loss of their wager. Dean then informs him that his wager was rigged right from the start, as he thinks Death would've known he wouldn't last a day. Death denies this, and declares their business is finished, but he offers a bonus: he will still go to Hell to raise Sam's soul. He then encourages Dean to keep digging in what he's learning regarding the souls.
Dean quickly heads to the panic room, as they witness Sam struggling to stay away from Death, who has returned with Sam's soul. Despite Sam's protests, Death restores Sam's soul to his body, with a conflicted Dean watching as his brother screams in pain. A week passes and Sam has still not woken up. During this time, Dean calls Castiel to check on Sam and asks if Cas thinks Sam will ever wake up. Castiel tells Dean that he doesn't think so, leaving Dean alone. Dean heads up stairs and Bobby offers him a drink and a case. Then, to Dean's joy, Sam wakes up and gives Dean a hug, as well as Bobby. Sam later reveals to Dean that he doesn't remember anything other than jumping into the cage. Dean is surprised but relieved to hear this, despite Bobby's suspicion. Dean and Sam go to work on a case involving dragons, during which Dean is overjoyed to have his brother back.
When Bobby finds a sword that could kill the dragons, he sends Dean goes to visit Dr. Visyak. When Dean tries to pull the sword from the stone he only falls off, and has to resort to blowing up the stone instead. He returns to Sam and the two go after the dragons. They fight off the dragons and save the girls they had held captive. Later on as Dean is happily going through the pile of gold they found at the dragon lair, Sam confronts him about being soulless and apologizes to Dean. Dean is shocked that Sam knows and asks who told Sam (who then answers that it was Castiel). Dean tells Sam about the wall inside his head, and that what Sam became wasn't really him.
Then Sam gets a mysterious text message about a case, which gets Dean worried. As they investigate, Dean finds out that Sam has been in this town before, and wants to leave. Sam doesn't want to, which makes Dean angry and he begins to quote John's rules. But they stick around, and Sam begins remembering what happened, much to Dean's displeasure. They do figure out its an Arachne with a grudge against Sam, and defeat it. Afterwards, Sam and Dean have a talk about what happened and Dean tries to make Sam feel better. Then Sam collapses, and Dean rushes to Sam calling his name.
Minutes pass by as a worried Dean tries to wake Sam up. Sam does wake up and Dean helps him up. Dean and Sam talk about what just happened and Dean tells Sam not to scratch the wall again. With that they head out on a case with a mannequin killing people, but Dean gets called away by an "emergency" call from Ben. When Dean arrives, he finds Lisa going out on a date. He and Lisa have a talk, which later results in him leaving permanently. When he comes back, he helps Sam finish the case.
Then things take a turn for the weird when Balthazar shows up with someone on his tail. He gives Dean a "key" and sends the two into the world of "Jared" and "Jensen", where their lives are a television show. After a great deal of effort and in end derailing the entire TV show by "quitting" and telling off Bob Singer, they manage to get back to their own world. Castiel informs them he has Balthazar's weapons now.
- "You heard my brother. That's right, I said "brother". 'Cause you know what, Bob? We're not actors. We're hunters. We're the Winchesters. Always have been and always will be. And where we're from, people don't know who we are. But you know what? We mattered in that world. In fact, we even saved the son of bitch once or twice. And yeah, okay, here maybe there's some---some fans that give a crap about this nonsense. But Bob Singer - if that even is your name - tell me this. What does it all mean?"
- —Dean telling off Robert Singer in an alternate universe[src]
Later on, Dean runs into Samuel again, and it takes Sam and Bobby to hold him back from fulfilling his promise of killing Samuel. In the hall, Gwen goes out to talk to him, and Dean shoots her. It turns out, Dean was possessed by Eve's latest invention. Unsure who its possessing, the group rid themselves of their weapons. In a turn of events, its Bobby who is possessed by the Khan worm, and Dean questions and kills it. Bobby does survive.
Things again become strange when Balthazar alters history and saves the Titanic. With history changed, Dean finally wins rock, paper, sissors when trying to see whos going to cheer Bobby up and now drives a mustang. He and Sam investigate a string of strange murders, and make the connect to the Titanic. They summon Balthazar who tells them why he did and leaves. When almost killed by Fate, Castiel saves them. He tells them, its Fate, and she trying to kill them. The only way to survive is to kill her. So Dean and Sam draw out Fate, and Castiel rights the past. Only Sam and Dean remember the past.
Dean, Sam and Bobby research how to kill the mother of all, and they find that the ashes of the phoenix can kill her. Dean finds the diary of Samuel Colt, which en-tales how he killed on. So they enlist the help of Castiel to send them back that time to find the ashes. Dean is beside himself with excitement to go back to the wild west. So they head back, and find out the Phoenix is killing people. So Dean tries to set up posse, but it backfires and he ends up as sheriff. So Dean and Finch end up having a showdown, and Dean wins. As Dean rushes for the ashes, Castiel transports them back. Lucky for them, Samuel Colt got the ashes and mailed it to them.
So Sam, Dean, Castiel and Bobby, begin to hunt for Eve. Thanks to Lenore's information, they find out that Eve is in Organ Pass, and they head there. There, they discover Eve's experiments, and Dean even names one of her experiments when Bobby gives him naming rights. So Dean names a cross-breed between a wrath and vampire, Jefferson Starship. Then the police show up (Dean hides), but they too are Jefferson Starships. They eventually find Eve in a diner working as a waitress, and she tries to makes a deal with them. She even turns into Mary Winchester to get them to work with her, but Dean refuses nether less, and tells her to bite him. Which she does, only to find out that Dean had swallowed some phoenix ashes earlier. The bite could've possibly turned Dean into a Jefferson Starship, but Castiel cured the infection before it could spread.
After their encounter with Eve, everyone begins to question Castiel. Everyone but Dean who still believes in Castiel. When Castiel comes to save them, he accidentally gives himself away, and Dean catches this. helps them trap Castiel, and questions him. Dean is the most hurt and furious by Castiel's actions but nonetheless still wants him to stop before Castiel goes to far. Castiel still disagrees. When demons come, Dean and the others are forced to flee. Castiel is now free, and later visits Dean to explain himself. Dean does not approve of his actions and chastises him harshly, but admits that Castiel is like a brother to him and that's why he's asking him to stop or else he'll have to "do what he has to." Castiel doesn't budge and disappears, breaking their friendship.
Castiel: "I did it to protect you. I did it to protect all of you! [...] Raphael will kill us all. He'll turn the world into a graveyard. I had no choice."
Dean: "No, you had a choice. You just made the wrong one."
Castiel: "You don't understand. It's complicated."
Dean: "No, actually it's not and you know that. Why else would you keep this whole thing a secret, huh? Unless you knew it was wrong. When crap like this comes around, we deal with it! Like we always have. What we don't do is we don't go out and make another deal with the Devil!
Castiel: "It sounds so simple when you say it like that. Where were you when I needed to here it?"
Dean: "I was there. Where were you?"
– Dean confronting Castiel's actions, The Man Who Would Be King
After Castiel's visit, Bobby reveals that Castiel also stole a diary from Bobby's house. As they read Bobby's photocopies, Dean gets a call from Ben. Ben tells Dean that men are in the house and killed Lisa's boyfriend. Dean tries to help from the phone, but Ben too is captured. Crowley, now on the other line, tells Dean to back off or he will kill Lisa and Ben. Dean refuses to back down, and begins to hunt down Lisa and Ben. He even begins to torture demons for their location. Sam tries to help him, but Dean tells Sam to back off. Then Dean accidentally breaks the Devil's Trap, and the demon attack. Castiel comes in and saves Dean. Dean doesn't want anything to do with Castiel though. Later, its Balthazar who gives Dean Lisa and Ben's location.
So Balthazar transports them there, and they storm the building. Dean finds Ben and Lisa after taking out some of Crowley's goons. He unties them, only to find out that Lisa is possessed by a demon, and she hold Ben hostage. Dean manages to free Ben by splashing holy water at "Lisa". Then he manages to free the knife from "Lisa's" hand and begins to exorcise her. He continues to exorcise her after the demon stabbed Lisa's body. Once the demon is out, Dean moves quickly to save Lisa's life, and carries her out to the car, and rushes her to the hospital. Dean stays by Lisa's bedside, and then Castiel arrives and heals her. Dean asks Castiel for favor to erase Lisa and Ben's memory of him. Dean approaches them after this and apologizes to them. In the car, Sam tries to help Dean, but Dean tells Sam not to mention Lisa or Ben to him ever again, or he will break Sam's nose.A week later, Bobby, Dean and Sam go looking for Dr. Visyak, and they find her in an alley. She is bleeding and tells them how to open the door to Purgatory. Then Castiel appears, and Dean tells Castiel to leave. Castiel tells him he is done playing nice, and promises to put Sam back. This confuses Dean, until Castiel touches Sam, and breaks down the wall inside his head, sending Sam into a comatose state. Dean stays by Sam's bedside, while Sam is comatose. After Balthazar giving them Castiel's location, Bobby manages to convince Dean to go with him after Castiel. Before Dean leaves, he leaves Sam their location. So Dean and Bobby head out. When they arrive they scope out the place, which is full of angels. Then a demon cloud comes, and Dean and Bobby run back to the Impala. The demon smash into the impala, flipping it over.
When Dean wakes up, he checks on Bobby, who is okay. So the two sneak into the place, and walk in as Crowley, and Raphael are doing the ritual. Dean throws Angelic Blade at Raphael, who catches it and flings Dean and Bobby. Then Castiel shows up, and shows his new power. With this he kills Raphael, and Crowley runs away. Dean tries to talk Castiel to powering down without making Cas angry, and even reminds Castiel that he used to be family. But Castiel doesn't want to power down and after Sam stabbing him, proves he is no longer an angel. Dean is very shocked to hearing Castiel proclaiming himself to be god.
Dean: "Listen. I know there's a lot of bad water under the bridge, but we were family once. I'd have died for you. Almost did a few times. So if that means anything to you ... please. I've lost Lisa. I've lost Ben. And now I've lost Sam. Don't make me lose you too. You don't need this juice anymore, Cas! Get rid of it before it kills us all!"
Castiel: "You're just saying that because I won. Because you're afraid. You're not my family, Dean. I have no family."
– Dean's final plea to Castiel, The Man Who Knew Too Much
- "This is stupid. Our quality of life is crap. We got Purgatory's least wanted everywhere, and we're on our third 'The World's Screwed' issue in what, three years? We've steered the bus away from the cliff twice already. [...] I think if we didn't take it's belt and all it's pens away each year, that the whole enchilada would've offed itself already!"
- —Dean losing faith in saving people[src]
When Castiel leaves, Dean and the others head back to Bobby's, and Dean begins to fix the Impala, since there is nothing else he can do. Dean is concerned for Sam's mental health since the wall is gone. Dean admits to Bobby that he can't take anymore hits, and will believe that Sam is "fine". Then they manage to summon and bind Death.
Dean tries to appease Death, and then Castiel shows up and Dean orders Death to kill him. Castiel frees Death and leaves. Death tells Dean the only way to stop Castiel is for Castiel to let the souls back into Purgatory. Dean doesn't think Castiel will do this, until Castiel comes asking for help. In turn, Dean helps Castiel and the souls are released back into Purgatory, but the Leviathans remain. Dean watches them destroy Castiel and spread throughout the water, leaving only his trench-coat behind.
He also deals with Sam seeing Lucifer while looking into a Leviathan killing. When he returns, he finds Sam gone. Dean eventually finds Sam and convinces him that his reality is real. He and Sam return to Bobby's, but find it burned down. Dean calls Bobby, but gets Bobby's voice mail, and finally tells Bobby how he is really doing. He and Sam are soon attacked by Edgar, and Dean's leg gets broken. On the way to the hospital, Dean begs them not to take them to Sioux Falls General, but is ignored.
He wakes up with his leg in a cast, and Bobby comes in and saves Dean from the hospital. Dean spends 3 weeks in a cast until Sam takes off, and Dean saws the cast off. Dean soon catches up with Sam, and punches Sam for taking the Impala. Sam explains the situation to Dean about the kitsune Amy and her decision to stop killing with her son no longer sick, but Dean sees her as only a monster that will kill again. Dean seem to eventually agree with Sam, but actually goes behind Sam's back and kills her. Dean finds Jacob, Amy's son, but spares him even against the kid's threats and tells him to "look him up in a few years".
- "I know, I know. But people ... they are who they are. No matter how hard you try, you are what you are. You will kill again. [...] Maybe in a year, maybe ten. But eventually the other shoe will drop. It always does. I'm sorry."
- —Dean as he kills Amy[src]
Dean feels guilty about the incident with Amy, plus feeling guilty lying to Sam about it and begins drinking more than normal. This guilt is what Osiris hones onto and puts Dean on trial. On trial he encounters Jo's spirit as a witness and so is Sam. It's revealed by Osiris Dean feels Jo died because of him since he let her do her first official hunt with them and blames himself for everything Sam went through since he left Stanford. Before Osiris can call the third witness, Amy, Dean accepts the charges. Jo's spirit is controlled by Osiris to kill him, though Dean apologizes for dragging her and Sam into hunting, admitting he just didn't want to be alone. Dean is saved when Sam stabs Osiris and Jo flickers out.
Dean: "You were a kid. You and Sam. I just - you know, hunters are never kids. I never was. I didn't even stop to think about it. [...] But I didn't want to do it alone. Who does? No, the right thing would've been to send your ass back home to your mom."
Jo: "Like to have seen you try. He was right about one thing. [...] You carry all kinds of crap you don't have to, Dean. Kind of gets clearer when you're dead."
Dean: "Well, in that case you should be able to see I'm 90% ... crap. Take away that, and what's left?"
– Dean to Jo's spirit, Defending Your Life
Dean still has nightmares about Castiel dying and killing Amy along with Sam's mental instability, leading to drink more heavily. Nonetheless, Dean continues working. He and Sam find a case where witches are wreaking havoc in Prosperity, Indiana. When they fail to stop the witches, Sam and Dean manage to get Maggie and Don to calm down. Sam approaches Dean about what's bothering him, but Dean brushes him off.
When Dean is cloned by a Leviathan, Dean is forced to lock the Impala up and it not too happy about it. Although, before he can cut the off his clone, the clone tells Sam that Dean killed Amy. This causes Sam to leave Dean. A week later Dean runs into Sam in Lily Dale. Sam is still angry with Dean, but the two do a case together involving ghosts and psychics. After finishing the case and given some advice from the other side, Dean apologizes to Sam, but says he doesn't feel bad for what he did to Amy and believes all his drinking to be because he didn't like lying to him. Sam and him reconcile.
- "I went with my gut. And that felt right. I didn't trust her, Sam. Of course, ever since Cas, I'm having a hard time trusting anybody. And as far as I've been acting ... I don't know. Maybe it's cause I don't like lying to you. You know, it doesn't feel right. You got me there. I been climbing the walls."
- —Dean explaining his behavior[src]
Dean and Sam are forced to lay low, still having to hide from cops and the Leviathans tracking them who they still don't know how to kill. In combined factors of losing Castiel, Sam's broken wall, and their failure to keep Leviathans out (causing yet another apocalypse), Dean's cynicism and frustration skyrockets. In How To Win Friends And Influence Monsters, even goes as far to say the world seems to want to end and he feels like nothing they do seems good enough. Bobby, however, chastises Dean and tells him to find a motivation to keep doing his job, whatever it is, or he'll wind up dead. Sam, Dean, and Bobby get in a confrontation with the leader of the Leviathans---Dick Roman, who secured himself as powerful businessman for further reach. They narrowly escape, though Bobby is fatally shot in the head as they make their escape.
Bobby: "'The world's a suicide case, we save it, it just steals more pills? [...] I've seen a lot of hunters live and die. You're starting to talk like one of the dead ones, Dean."
Dean: "No, I'm talking the way a person talks when they had it. When they can't figure out why they used to think all this mattered."
Bobby: "You're not a person. [...] You tried to hang it up and be a person with Lisa and Ben. And now here you are with a mean old coot and a van full of guns. That ain't person behavior, son. You're a hunter, meaning you're whatever the job you're doing today. Now, you get a case of the Anne Sextons, something's gonna come up behind you and rip your fool head off. Now you find your reasons to get back in the game. I don't care if it's love or spite or a ten-dollar bet. I've been to enough funerals. I mean it. You die before me, and I'll kill you."
– Bobby's lecture to Dean, How To Win Friends And Influence Monsters
In Death's Door, Sam and Dean rush Bobby to the ER where he falls into a coma. Both brothers are stressed over Bobby's critical condition. Sam brings up the possibility that Bobby might not make it, but Dean refuses to consider it. Ultimately Bobby dies, but manages to wake up a moment to write down coordinates he discovered during their last encounter with Dick Roman.
Weeks pass after Bobby's death. Sam and Dean are devastated, though Dean takes his loss the worst. He becomes obsessed with vengeance against Dick Roman and pays Frank Devereaux to help him track the meaning of the numbers Bobby left them with no luck. Eventually, with help from Frank in Adventures in Babysitting, Dean tracks down a new subsidiary of Dick's and manages to tap into it's surveillance. Dean's apathy towards hunting heightens considerably after yet another loss, but wants revenge on Dick and couldn't bear to leave Sam hunting alone. After advice from Frank, Dean tries to cover up his private misery and continues doing jobs.
In The Slice Girls, it's revealed Dean keeps Bobby's old flask as a memento and frequently uses it. Sam grows frustrated with Dean's drinking and lack of interest in cases that don't revolve around Dick Roman. During this time, Dean unknowingly sleeps with and has a daughter, named Emma, with an Amazon. The Amazons age and grow in a very short period of time until they reach adulthood, and so the baby is birthed in mere hours, and reaches adolescence in a few days. Amazon teens must go through a rite of passage in which they must kill their fathers - the event that Dean and Sam were investigating in the first place. Meanwhile, a clue is given to them by a strange "breeze" in the room. Dean believes it may be Bobby's spirit, but Sam doesn't think so and gets mad at him for the suggestion.
When Dean's daughter comes to Dean, she lies and tells him she needs his help to escape the other Amazons. A wary Dean eventually sees through her scheme and they end up drawing their weapons and stand ready to face one another. Sam, recently enlightened to his brother's situation, upon entering the room decides that Dean cannot bring himself to kill his own daughter, and so, after a short confrontation, he kills her. Sam then reminds Dean that he had to do it, just like Dean "had" to kill Amy.
When Sam's hallucinations eventually worsen and he suffers a complete psychotic break he's admitted to a psychiatric ward in The Born-Again Identity, Dean is determined to find a healer for his brother's mind. He stumbles upon a "faith healer" named Emmanuel, but is revealed to actually be an amnesiac Castiel. Dean is shocked to see him alive and is stricken with mixed feelings, still blaming Castiel for his mistakes to Sam's mind and the world.
- "I just know that ... this whole thing couldn't be messier. You know, I used to be able to shake this stuff off, whatever it was. It might take some time, but ... I always could. What Cas did ... I just can't. I don't know why."
- —Dean to amnesiac Castiel[src]
Him and Meg take Emmanuel to Sam where Castiel slowly regains his memories. Castiel is almost too ashamed to help Sam, but Dean nonetheless convinces him he still can fix it. Thanks to Dean, Castiel shifts Sam's hallucinations to his own mind and saves his brother, though at the cost of Castiel's own sanity. In the aftermath, Dean made an agreement with Meg to keep an eye on Castiel - who was now insane in psychiatric ward - but hadn't completely forgiven him.
Dean continues to work cases with Sam and tries to stop Leviathans, but the strange activity around them continues. Eventually, the brothers discover in Of Grave Importance, Bobby is a ghost and is tied to his old flask that Dean carries around. He had been helping them in small ways with their hunting for a while. Dean is particularly unsettled, glad to be around Bobby but upset that he chose to stay to help them when he could've found peace. Bobby, however, justified his choice. Unsure what to do next with the situation, the brothers at the moment let it rest.
Soon after, in The Girl With The Dungeons and Dragons Tattoo, Sam and Dean receive an automatic email from Frank, who had been recently killed by Leviathans. The message informs them a hacker of Dick's at Roman Enterprises is hacking into Frank's information about them. The hacker turned out to be Charlie Bradbury, who discovered the truth about Dick Roman and Leviathans after hacking it. It's discovered that the Leviathan's ultimate plan is to turn people into "perfect cattle" for their meals. Sam and Dean rush to location by GPS tracker on Frank's hard drive, managing to get a reluctant Charlie to sneak in Dick Roman's office and get his private information. Bobby, however, set on vengeance follows them despite Sam and Dean's warnings.
Charlie manages to get Dick Roman's information and give the brothers a chance to steal a private package being transported to Dick, but is injured accidentally by Bobby who lost control seeing Dick. Sam and Dean narrowly escape, discovering the package to be an tablet. Charlie survives with a broken arm and departs, leaving the brothers with an unknown tablet and concerns of Bobby turning into a vengeful spirit.
Sam and Dean crack open the tablet in Reading Is Fundamental, unknowingly calling forth Kevin Tran as the next prophet. Simultaneously Castiel awakens in the mental ward. The brothers rush over to him, who manages to decipher it a angel tablet called the Word of God. Dean tries to seek answers from Castiel and is still angry over his actions, but Castiel is clearly insane and has given up fighting even to help them. Meanwhile, Kevin tries to steal the tablet and they discover he's a prophet.
After Kevin is stabilized, he fully deciphers the tablet before leaving and they figure out how to kill Leviathans: "a bone of a righteous mortal dipped three bloods of the fallen". Sam and Dean have the first type of blood---Castiel's, a fallen angel---and set out for the other two.
Dick Roman's power grows. Dean and Sam are resorted to eating organic food on a daily basis as all other foods are infected by Leviathans, something Dean is not happy about. The brothers discover the other blood types are from an alpha and Crowley. Crowley refuses to give his blood right away so Sam and Dean go after the Alpha Vampire. After discovering the Leviathans plan to exterminate not just humans but monsters, the alpha grudgingly gives them his blood. Sam and Dean's plan is successful until they go to the motel to find Bobby gone and the place ransacked. Dean is upset at Bobby's violent and reckless impatience to get Dick, unwilling to admit he was close to being a vengeful spirit.
In Survival of the Fittest, Sam and Dean get a bone of nun and try to summon Crowley but he doesn't show. This makes the brothers doubt his word, though sure enough Crowley appears later with a vial of his blood. He explains the deal Dick tried to make with him to bring them another demon's blood, but this was the real deal. Neither Dean or Sam trust them, but know they don't have another option. Meanwhile, Castiel and Meg rally with them. Crowley indicates Castiel can help against the Leviathans, but he still refuses to actively involve himself in the matter. Dean grows frustrated with this.
- "We can't leave it. You let these friggin' things in. So you don't get to make a sandwich. You don't get a damned cat. Nobody cares that you're broken, Cas! Clean up your mess!"
- —Dean to Castiel[src]
Afterwards, Bobby reappears after nearly killing a maid and Sam in his obsession with vengeance against Dick. Bobby realizes he's dangerous and wants his flask burned before he loses himself entirely as a vengeful spirit. Both Sam and Dean are sad at losing their surrogate father yet again, but do the right thing and burn it, putting him to res. The day before they infiltrate Dick's base of operations, Castiel transports Dean to his Impala which had been on lockdown all year since Slash Fiction. Castiel shares his reluctance to fight because he fears he's only bad luck. Dean disregards this and tells him he's the only one left who can help. Dean finally forgives Castiel for his actions and motivates him to fight. Slowly more like his old self and as the only one who could identify the real Dick Roman among to copiers at the base of operations, Castiel agrees.
Castiel: "I'm not good luck, Dean."
Dean: "Yeah, but you know what? Bottom of the ninth and you're the only one left on the bench. Sorry, but I'd rather have you. And anyway, nut up, alright? We're all cursed. Do I seem like good luck to you?"
– Dean motivates Castiel to fight, Survival of the Fittest
The next day, Dean, Sam and Castiel infiltrate SucroCorp. Meg stays out in the open to distract the Leviathans, Sam goes to get Kevin, and Dean and Castiel go after Dick. Castiel is able to locate him and they confront the leader. Dean stabs Dick with the bone, but it has no affect. Castiel holds him place from behind while Dean pulls out the real bone, tricking him into lowering his guard. Dean kills Dick by stabbing him through the neck, causing him to convulse and pulse strangely. Sam appears and watches as Dick suddenly explodes in black goo, Dean and Castiel disappearing with him.
Dean wakes up in shadowed plane with Castiel, now trapped in Purgatory as a side-effect of the weapon. Dean wants to get out, but Castiel grimly tells they're more likely to get ripped to shreds than escape. Castiel suddenly disappears, leaving Dean alone as monsters come up to attack.
- "It was bloody. Messy. Thirty-one flavors of bottom-dwelling nasties. Hell, most days felt like 360-degree combat. But there was something about being there. It felt pure."
- —Dean describing his experience in Purgatory[src]
Following Castiel's mysterious disappearance, Dean survives his brush with Gorilla-Wolves after arriving and sets out to find his friend. Some time passes and already Dean is changed by paranoia and survival instinct. He was constantly targeted by monsters, never had sleep, and was completely on his own. At some point early on, Dean forged a personal weapon from the environment in Purgatory and used it on nearly every monster he came across. It's a implied a part of Dean even enjoyed Purgatory for it's simplicity and the "pureness" of relying on his darker, survival instincts.
Dean finds a lone vampire and interrogates him on information for Castiel's whereabouts, but gets nothing out of him. He kills the vampire with ruthless primal ease, only to be attacked by another. A vampire named Benny saves him. Dean is hostile, but Benny approaches him with the possibility of escape. There was a spell out of Purgatory only a human could do, but he would only give him the details if he gets him out of it too. Dean naturally distrusts him, but agrees to work with Benny if he helps him find Castiel. 
Eventually, after interrogating more monsters, Dean and Benny locate Castiel on the far side of Purgatory. Dean is happy to see Castiel alive until Benny reminds him of the angel's sudden disappearance. Dean believes he was just attacked, but Castiel admits he ran away. He explains he left because the Leviathans in Purgatory want him destroyed more than anyone so he wanted them after him to protect Dean. Castiel requests to stay and Benny admits he doesn't know if the spell works on angels, but Dean refuses to leave without him. 
- "We'll figure it out, Cas. Buddy, I need you. [...] And if the Leviathans want to take a shot at us, let 'em. We ganked those bitches once before. We can do it again. [...] I'm not leaving here without you."
- —Dean to Castiel[src]
Dean, Castiel, and Benny trek throughout Purgatory. Dean still shows distrust towards Benny for being a vampire despite working with him. He also clashes with him over Castiel, who was attracting more monsters coming with them. Castiel agrees that he's only cause trouble going with them, not knowing if he can even make it through the portal, but Dean doesn't care. Eventually, Castiel attracts Leviathans. As they're fighting, Castiel is about to be killed. Dean looks in in horror, but Benny saves the angel. This made Dean begin to trust Benny.
Eventually, Dean, Castiel, and Benny make it towards the portal Dean can activate. Using a spell, Dean successfully transports Benny's soul in his arm and is ready to leave with Castiel. As they make their escape, Dean and Castiel are attacked by Leviathans. Going through them, the portal opens for Dean. Castiel lets go of Dean just as they're about to make it. Dean is sucked up by the portal and returned to Earth. 
- "I can't believe what I'm hearing. Sam, we have an opportunity to wipe the slate clean. We take Kevin to the tablet, he tells us the spell, we send every demon back to hell - forever. Every single bastard that destroyed our lives, killed our mother, killed Jess, and you're not sure?"
- —Dean's determination to close the gates[src]
After spending a year in Purgatory (it is unknown how time differs in Purgatory, so it's possible Dean was there for a significantly longer period of time), Dean uses a spell to return to Earth with help of Benny. Dean carries Benny's soul out of Purgatory and resurrects him on Earth. Dean bids goodbye to Benny and they go their separate ways. Dean travels to the safehouse in Whitefish, Montana and reunites with Sam.
Sam and Dean catch up, though Dean refuses to disclose the fate of Castiel. Dean is disapproving that Sam retired from hunting and even more upset Sam made no attempt to look for him. He checks Sam's old mobiles (which he had ditched) where he played voicemails of Kevin over the course of months that had escaped Crowley and was in hiding. Dean is angry Sam left Kevin alone. It becomes clear Dean's perspective on hunting changed significantly since Purgatory and he now holds tighter responsibility on saving lives than ever. Sam and Dean find him and discover Crowley wanted him to read another Word of God which detailed different ways to defeat demons, including a spell to shut the gates of Hell. Dean is motivated to close the gates of Hell forever through Kevin's help, though Sam is less sure and needs to be convinced. Crowley appears for Kevin, but they escape.
After escaping, Dean gets a call from Benny. Dean tells his friend not to call him for a while, hiding their friendship from Sam. Despite being out of Purgatory, Dean is still continually on edge and seems more guarded than he ever has been before. 
In What's Up, Tiger Mommy?, Sam and Dean go to Kevin's mother's house under Kevin's request to see if she was safe. After rescuing Ms. Tran from demons, she decides to go with the group to help protect her son. When they discover the tablet was stolen from the place Kevin was hiding it, they track it down ultimately to an auction house. The group ends up in a bidding war when Crowley shows up, and Kevin ends up being auctioned off along with the tablet. Ms. Tran offers up her own soul in order to save her son. When that offer is accepted Crowley possesses Ms. Tran's body to steal the tablet. Dean fights against Crowley and nearly killed him despite being inside Ms. Tran's body, highlighting Dean's more ruthless nature since Purgatory. Crowley, however exits out of her body just in time and manages to escape with the tablet. After asking for a moment alone with his mother, Sam and Dean find Kevin and his mother gone and note from Kevin saying he didn't want to end up killed being useless to them like Crowley warned.
Dean continues to hop on every hunting case he can find with remarkable enthusiasm. Sam tags along reluctantly, missing his year of normal and only interested in finding Kevin. This creates strain between the brothers. Eventually Dean's suddenly intense sense of purpose alienates Sam so much he admits after closing the gates of Hell, he wants to quit and live normally. Dean doesn't believe he means it, but Sam insists.
- "All right, man. Look, I get it. You took a year off to do yoga and play the lute. Whatever. But I'm back. Okay, we're back, which means that we walk and kill monsters at the same time. We'll find Kevin. But in the meantime, do we ignore stuff like this? Or are innocent people supposed to die so that you can shop for produce?"
- —Dean's newfound purpose[src]
After another failed attempt to locate Kevin in Blood Brother, Dean receives a call from Benny who needs help taking down the vampires that turned him. Dean leaves without telling Sam about where he's going and finds the vampires' nest. Eventually, Dean gives into Sam's calling and tells him he's with his friend and needs help taking down the nest. Sam shows up after they take down the nest and officially meets Benny, but quickly realizes he's a vampire.
Sam is angry with Dean trusting a vampire in Southern Comfort, but Dean insists he's good. Sam still doesn't trust it. While doing a case with Garth, Dean gets possessed by a specter that forces you to kill the people you have a grudge against. Dean goes after Sam, revealing he still holds resentment for Sam not trying to find him in Purgatory and all his other past mistakes. Dean also highlights his disappointment in both Sam and Castiel, who he feels both betrayed him so trusts Benny because he's the only that hasn't.
- "Mistakes? Well, let's go through some of Sammy's greatest hits. Drinking demon blood? Check. Being in cahoots with Ruby. Not telling me that you lost your soul. Or how about running around with Samuel for a whole year, letting me think that you were dead while you were doing all kinds of crazy. Those aren't mistakes, Sam. Those are choices! [...] Yeah, I might've lied, but I never once betrayed you. I never once left you to die. And for what a girl? You left me to die for a girl?!"
- —Dean's hidden resentment towards Sam[src]
When specter is defeated, Dean tries to brush off what happened between him and Sam. Sam, however, knows he had meant everything he said. Sam stands up to him and tells him he needs to get over it before he drives him away.
In A Little Slice of Kevin, Castiel mysteriously returns to Earth with no memory how while Sam and Dean are examining a case of strange kidnappings. Dean is shocked to see Castiel back, but is wary of his sudden return. They discover Crowley is kidnapping future prophets after losing Kevin in hopes they can analyze the tablet. Soon Crowley kidnaps Kevin and the brothers get a call from Mrs. Tran asking for help. Castiel, Sam, and Dean inflitate Crowley's hideout. With Castiel's help, they manage to secure Kevin tough the tablet breaks in half and half is missing. It's revealed Dean blames himself for not bringing back Castiel, but Castiel tells him he always planned to be trapped in Purgatory for punishment and chose to stay. Dean didn't fail.
- "You can't save everyone, my friend ... though you try."
- —Castiel to Dean[src]
In Citizen Fang, Sam confronts Dean on a trail of a bodies leading towards Benny in Louisiana that Martin Creaser tracked. Dean doesn't believe Benny did it, but is willing to do what he has to only if Sam and Martin give him time to get Benny's side. Benny explains he didn't do it, but another vampire from his past did and he's trying to clean up his mess. Dean trusts Benny and tries to convince Sam and Martin of the same. Martin knocks him out and they go after Benny themselves. Desperate, Dean uses the fake number of Amelia's he swapped on Sam's phone with one of his phones and sends a fake S.O.S protect Benny. Dean tries to help Benny escape, but ultimately Benny is forced to kill Martin in self-defense. Sam, who had left the scene and rush to the rescue as Dean guessed, figures out it the truth later. Sam is angry with his brother, but Dean believes he did the right thing.
In Torn and Frayed, Sam and Dean argue about Benny and the fake text on Amelia. The brothers take a break, but are brought back together to help Castiel rescue the angel Samandriel who was kidnapped by Crowley. Dean and Sam are suspicious over Castiel's strange behavior after seeing Samandriel suddenly dead beside him. They also sort out their issues. Dean admits he could never separate himself from hunting for normal the way Sam could and, tired of arguing with him, gives him his blessing to be with Amelia if it makes him happy.
- "I'm just tired of all the fighting. [...] And y'know, maybe I'm a little bit jealous. I could never separate myself from the job the way you could. Hell, maybe it's time for at least one of us to be happy."
- —Dean gives Sam his blessing to be with Amelia[src]
Ultimately, Sam realizes there are too many important things he has to take care of and choses to stay with Dean. Dean, out of loyalty to Sam, is forced to end direct contact with Benny.
In As Time Goes By, Dean and Sam meet their grandfather, Henry Winchester, who travelled in time on the run from the Knight of Hell Abbadon protecting a vital key. The brothers also discover the Winchester bloodline were composed of the Men of Letters---chroniclers with vast knowledge of the unexplained and supernatural which they passed on to hunters that they deemed worthy. Dean at first resents Henry for leaving John to grow up alone, as he had disappeared doing Men Of Letters duties, but ultimately comes to respect him. They help Henry capture Abbadon and manage to protect the key, but at the cost of Henry's life. Henry dies in 2013 and the brothers bury him with his fallen Men of Letters comrades.
The key left behind by Henry leads Sam and Dean to the Men of Letters headquarters in Everybody Hates Hitler, which is remarkably well-preserved despite being abandoned. After doing a case about the Judah Initiative, Sam and Dean adopt the place as their home and base of operations, becoming official Men of Letters.
In Trial and Error, Dean receives a call from Kevin who deciphered part of the tablet that would close the Gates of Hell forever: three trials completed by somewhere worthy and the first was killing a hellhound. Dean is enthusiastic about this and automatically elects himself to do it. Sam and Dean track down ten-year contracts to find a hellhound and are lead to a farm where Crowley made multiple deals. Dean recklessly sets out to kill the hellhound. Dean expresses his jaded picture of his future and knows these trials will have a fatal consequence, but wants Sam safe and to have a family. Dean is determined to do the trials because he feels he has nothing left to lose.
- "I'm a grunt, Sam. You're not. [...] And you told me yourself you see a way out. You see a light at the end of this ugly-ass tunnel. I don't. But I'll tell you what I do know. It's that I'm gonna die with a gun in my hand. 'Cause that's what I have waiting for me. That's all I have waiting for me. I want you to get out. I want you to have a life- become a Man of Letters, whatever. You with a wife and kids and grandkids, livin' 'til you're fat and bald and chugging Viagra. That is my perfect ending and that's the only one I'm gonna get. So I'm gonna do these trials. I'm gonna do them alone. End of story."
- —Dean' s resolve to do the trials[src]
Dean finds the hellhound and is nearly killed until Sam comes to his rescue, killing it and becoming the person for the trial. Dean refuses to let Sam do this, but Sam expresses his faith in both of them. Dean reluctantly lets Sam carry out the rest of the trials.
In Man's Best Friend With Benefits, Dean is still concerned over the trials and continues to try to convince Sam he can do them instead. Sam, frustrated, admits he believes Dean can't trust anyone but himself. Dean and Sam are infected fight a witch named Spencer Wallis who infected them with some of their worst memories. Dean is affected by remembering everything they went through and decides to stand by Sam's choices to do the trials.
In Goodbye Stranger, Dean spots a bloody tissue of Sam's and realizes he's been hiding the toll the trials have on his health. Castiel returns, telling them Crowley has been searching for Lucifer's crypts. He lies and says he's looking for parchment to decipher the tablet, but Sam and Dean later find out he's searching for an angel tablet. The brother's distrust over Castiel heightens, but they nonetheless work with him and find Meg who knows about the location of the crypts.
When finding the tablet, Dean wants to give it to Kevin, but Castiel wants to take it to Heaven. Dean refuses. Castiel, under control of Naomi, proceeds to beat him brutally. Dean knows Castiel isn't himself and desperately tries to snap him out of it. Just as Castiel is about to kill him, Castiel stops and heals Dean. Castiel apologizes, but leaves with the tablet to protect it from Naomi - and them. Outside, Crowley is there for the tablet. He kills Meg, but the brothers escape. Soon after, Dean confronts Sam about lying and that he's there for him. Dean, still shaken about Castiel, doesn't want to be lied to anymore.
In Taxi Driver, Kevin translates the second trial which is to "rescue a soul from Hell." The brothers contact a rogue reaper and find out Bobby's soul is in Hell. Dean wants to help him save Bobby, but Sam tells him it's his trial and convinces Dean to stay. As Sam rescues Bobby, Dean visits Kevin, who hears Crowley in his thoughts and is convinced he knows where he is. In a panic, Kevin hides the tablet and Dean is visited by Naomi who tries to convince him she's trustworthy.
Kevin: "Just tell me when this all ends 'cause that's the only thing I want to hear."
Dean: "No. Like I told you before, this isn't going to end. Look, man. Other guys, they got it easy, y'know? It's all backyard barbeques ... and bowling teams, but you and me? We got to carry a little extra weight."
Kevin: "I can't take it."
Dean: "Yes, you can. Hey, look at me. Now, this whole thing sucks. I know. But you suck it up and push through because that's what we do. And when you get on board with that, the ride is a lot smoother."
– Dean motivates Kevin, Taxi Driver
When finding out Sam is in Purgatory, Dean contacts Benny and asks him if he can help get him out to get them both out. Dean is guilty, but has to save his brother. Benny agrees, admitting he didn't like being on Earth and Dean reluctantly kills him. Benny rescues Sam and Bobby's soul is sent to Heaven, completing the second trial. Dean is upset Benny didn't come with even though according Sam he chose to stay and decides not to burn his bones, in hopes that one day he'll be able to bring him back. The brothers visit Kevin, only to find him missing.
In The Great Escapist, Dean continues to take care of Sam who's health is rapidly declining from the trials. The brothers receive a automatic message from Kevin, who assumes he's dead and sends them notes from his deciphering of the tablet. This leads Sam and Dean to meet Metatron, the scribe of God. With come convincing needed, he saves Kevin from Crowley. Kevin has the other half of the tablet and has figured out the third trial: to cure a demon.
In Clip Show, Sam and Dean watch a serious of old exorcism videos on the Men of Letters files, proving a curing a demon is possible. The brothers dig up Abaddon's body and intend to cure her, but are distracted when Crowley calls detailing his plans to kill everyone they ever saved if they didn't surrender the tablet. Abbadon escapes and with no demon to cure, Sam and Dean go after Crowley. Crowley massacre is lead to Sarah Blake Sam's old fling. Sam and Dean do everything in their power to save her, but are too late. Sam considers surrendering, but Dean is determined and convinces him to push on.
In Sacrifice, Dean and Sam seem to give in to Crowley's demands after nearly killing Jody Mills. However, when the deal is made, Dean handcuffs Crowley which has a devil's trap on it, steals the angel's tablet, and traps him to use for him to the third trial. Dean is called away by Castiel and gives Kevin the tablet to translate as Sam cures Crowley. Ultimately, it's revealed Castiel's deal with Metatron was trick and Sam will die if he completes the trials. Dean rushes to the scene just as Sam is about to completely cure Crowley. Sam wants to carry out the trials even if he dies, admitting he feels like all does is let Dean down and it hurts him to watch his brother to trust Castiel or Benny more than him. Dean tells him none of that is true and there's no one else in the world he cares about more than Sam. Dean convinces Sam to stop and they agree to save people their own way.
However, Sam is still affected by trials and falls to the ground in pain. Dean calls out for Castiel, but he's nowhere. The brothers watch as angels fall from the sky, Metatron's plan to self-destruct Heaven completed.
- "Listen, man. I know we've had our disagreements, okay? Hell, I know I've said some junk that sets you back on your heels. But Sammy ... come on. I killed Benny to save you. I'm willing to let this bastard and all those sons of bitches that killed Mom walk because of you. Don't you there think that there is anything past or present that I would ever put in front of you! It has never been like that! Ever! I need you to see that. I'm begging you."
- —Dean's final appeal to Sam[src]
When Sam falls into a coma in I Think I'm Gonna Like It Here, he takes him to a local hospital and finds out that Sam is going to die. Dean then goes to a church and prays to all the angels for help. As a consequence, Dean is attacked by several angels looking for Castiel and is forced to banish them all save for one named "Ezekiel". Ezekiel tells him Sam's condition is too severe to be healed and he must possess him to heal both Sam and himself fully. Dean at first refuses, knowing Sam would never agree, but desperate to save his brother, gives in. Ezekiel casts an image of Dean in Sam's head to get him to say yes and it works. Dean guiltily keeps his possession by Ezekiel a secret from his brother.
In Devil May Care, Dean and Sam work together to use Crowley for information to kill all the demons loose on Earth. Meanwhile, they discover Abaddon is still alive and kidnapping hunters for them to give up Crowley. The brothers team up with Irv and Tracy Bell where Dean gets in a violent confrontation one-on-one with Abaddon. She flees from Ezekiel, who took control of Sam to save them from demons. Dean is uncomfortable with the situation and admits he also feels guilty about not closing the gates of Hell after seeing the damage the demons are causing, but Ezekiel reassures him. He is still skeptical about the angel's motives, who only asks him to trust him. Dean also stops Kevin from leaving them, and calls him family.
Dean: "This is on me. I was the one that talked Sam out of boarding up Hell. Okay? So every demon deal, every kill that they make ... well, you're looking at the person that let it happen."
Zeke: "You were protecting your brother. I am in Sam's head. Everything he knows, I know. And I know what you did, you did out of love."
– Dean and "Zeke", Devil May Care
In I'm No Angel, Dean is alerted by Ezekiel the faction that is after Castiel and fears for his safety. He makes an excuse to Sam about his knowledge and together they search for their friend, leading them to a rogue reaper. She kills Castiel, but Ezekiel takes over Sam and brings him back to life. Sam questions again Dean's knowledge about angels and Castiel on how he survived, but he lies to both of them. They take Castiel back to their bunker, only for Ezekiel to possess Sam and warn that Castiel can't be here without drawing attention to himself. Dean initially refuses, but when Ezekiel warns he'll be forced to leave Sam's body if he stays, he reconsiders. Dean reluctantly forces Castiel to leave without explanation.
In Slumber Party, Sam and Dean fight to stop The Wicked Witch from entering Oz. They meet up again with Charlie. After she gets killed by the Witch, Dean begs "Ezekiel" to save her, which he reluctantly does. Later, Dean and Sam get possessed from the Witch and are turned into minions of hers. They then hunt down Charlie and Dorothy to try and kill them. They aren't turned back until Charlies saves them by killing the Witch.
In Dog Dean Afternoon, Sam and Dean solve two bizarre cases in which a dog is the sole witness. Dean uses a spell that gives him the ability to talk to animals. He gets along quite well with their witness The Colonel, despite the fact that he doesn't really like dogs.
In Heaven Can't Wait, Dean works with Sam and Kevin to research ways to undo Metratron's spell on the angels and return them to Heaven. Dean is called away by Castiel for a case where he greets his friend working a mediocre job at a place called Gas-n-Sip. Dean at first believes it's beneath him and encourages him to get back on track, but after facing off against a dangerous angel type Zit Rein, he encourages Castiel to live normal. Dean finds out by Sam through Crowley's there's no reversal for the angels who got expelled for Heaven, but doesn't tell Castiel this and tells him to just leave it to them.
In Rock and a Hard Place, he and Sam catch up again with Sheriff Mills. Dean and Sam also renews their virginity and join a chastity group to get closer to the source of mysterious kidnappings. Dean has sex with an ex-porn star chastity counselor after the meeting. This causes them to get abducted by Vesta, a goddess after virgins that broke their vows. Sam and Jody arrive as Dean tries to free himself and the other victims. Jody kills Vesta and they say their goodbyes. Dean feels increasingly guilty after Sam admits he thinks there's something wrong with him---that he'll never be normal---and is close to telling him about Ezekiel, but the angel stops him and warns the consequences if Sam ejects him. Dean lies to his brother yet again.
In Holy Terror, Dean is still unsure of the idea to not tell Sam about "Ezekiel", but is convinced by the angel to still use the trials as an excuse. Sam and Dean work a case with Castiel, where it becomes apparent Dean didn't tell Sam why Castiel left. Dean finds out from Castiel--now an angel again by stealing another one's grace---that "Ezekiel" died during the fall and the one possessing Sam isn't him. Determined to expel the unknown angel, Dean works with Kevin to perform a ritual weakening the angel for Sam to expel him. Dean performs the ritual and explains to Sam quickly, including his motivations for lying and that he was trying to save him. Sam, actually still possessed and nearly acting, punches Dean and kills Kevin under request of Metatron.
Dean wakes just in time to see Kevin die. It's revealed the ritual had been altered by the angel, making it useless. Dean tries to attack "Ezekiel", but the angel overpowers him and leaves with full possession over Sam. Dean is left alone, having lose both Kevin and Sam.
In Road Trip, Dean is devastated by grief and guilt. He gives Kevin a hunter's funeral and is determined to kill the angel possessing Sam in revenge. Castiel appears and they reluctantly work with Crowley for him to help them expel the angel from Sam. They discover the angel is Gadreel, the angel that first let Lucifer out of his cage and into the "garden". After torturing Gadreel to bring out Sam doesn't work, Crowley temporarily possesses Sam to connect to his mind and expel the angel in exchange for his freedom. Sam expels the angel and Castiel heals the rest of his damage from the trials.
Sam is furious with Dean for tricking him by letting Gadreel possess him, but Dean stands by his reason to save him. Dean brokenly leaves to hunt Gadreel on his own, convincing himself all he does is hurt the people around him. Sam doesn't try to stop him.
- "Kevin's blood is on my hands, and that ain't ever getting clean. I'll burn for that. I will. But I'll find Gadreel and I'll end that son of a bitch. But I'll do it alone. [...] I'm poison, Sam. People get close to me, they get killed. Or worse. You know, I tell myself I-I help more people than I hurt, and I tell myself I'm doing it for the right reasons, and I-I believe that. But I can't. I won't ... drag anyone through the muck with me. Not anymore."
- —Dean's decision[src]
In First Born, alone in a bar, Dean is approached by Crowley for help with finding the First Blade, the only weapon that can kill Abaddon. Dean reluctantly allies himself with the demon and begins the search by looking for information on a hunt his father did where he captured, interrogated and exorcised a demon who claimed to know about the Blade. The information they find leads them to a hunter named Tara and eventually to the biblical Cain who is now a very powerful demon. Dean asks for Cain's help in locating the Blade, telling him they need to kill a Knight of Hell. Dean is pissed at Crowley when Cain reveals that he created the Knights which Crowley knew, but is surprised to learn that Cain was the one that killed them all. When Cain refuses to help, Dean sneaks back with Crowley to search for the Blade only to be caught by Cain. When four demons show up, Dean is left to fight three of them single-handedly. He wins and Cain tells him how he slaughtered the Knights after they kidnapped his wife who was killed by Abaddon. Cain still refuses to help and is unimpressed by Dean's threats. Cain leaves as a demon army arrives, but returns willing to help and explains that the Blade is useless without the Mark of Cain which he can transfer to someone worthy, such as another killer. He'd let Dean fight alone to see if he was worthy and offers him the Mark, trying to warn him that it comes with a terrible price. Dean takes the Mark anyway without learning what the price is and after telling them that the Blade is at the bottom of the ocean, Cain teleports Dean and Crowley to safety while he takes on the demon army, asking for Dean to return after he kills Abaddon to kill him too. Dean is pissed at Crowley as he realizes Crowley used him to get access to the Blade. Crowley confirms this, but while Dean threatens to kill him when everything is over, he recognizes he still needs Crowley and sends him after the Blade.
Sam and Dean run into each other in Sharp Teeth after working on the same case involving Garth (now a werewolf) and a werewolf cult. They work together reluctantly, Sam still furious and Dean still guilty. After the case, Dean again apologizes to Sam and tries to suggest they work together again in hopes they can patch it up. Sam agrees to work with him, but insists to keep it professional because he doesn't think he can't trust Dean. Dean resignedly agrees to his terms.
In The Purge, after another tense case, Dean finally erupts and insists he did the "right thing" saving him. Sam disagrees and believes Dean simply didn't want to let him go if it meant he was alone. Dean challenges Sam that he would've done the same thing if the roles had been reversed. Sam says he wouldn't, shocking Dean.
Dean: "You know, Sam. I saved your hide back there. And I saved your hide at that church ... and the hospital. I may not always think things all the way through, okay? But what I do, I do because it's the right thing. I'd do it again."
Sam "And that is the problem. You think you're my savior. My brother, the hero. You swoop in, and even when you mess up, you think what you're doing is worth it 'cause you're convinced you're doing more good than bad ... but you're not.[...] Please tell me, what is the upside of me being alive?"
Dean: "Are you kidding me? You and me. Fighting the good fight together."
Sam: "Just once, be honest with me. You didn't save me for me. You did it for you. [...] I was ready to die. I should've died, but you ... you didn't want to be alone. And that's what this all boils down to. You can't stand the thought of being alone. [...] I'll give you this much. You are certainly willing to do the sacrificing. As long as you're not the one getting hurt."
– Sam's outlook on Dean, The Purge
In Captives, it's revealed Kevin's spirit is haunting the bunker due to an after-affect of Metatron's spell. Dean is still stricken with guilt over his death and apologizes to him, though Kevin doesn't blame him. By Kevin's last request, Sam and Dean search for Kevin's mother and find her still kidnapped by Crowley. The boys rescue her and Linda reunites tearfully with her son, deciding to take him with her until Kevin can move on. The brothers make peace with him and vow to find a way to send Kevin to Heaven.
In Blade Runners, Sam and Dean work with Crowley to track down the First Blade. Their search leads them to a rogue member of the Man of Letters named Cuthbert Sinclair a.k.a. "Magnus" who tries to keep Dean as a "collectible" upon discovering he has the Mark of Cain. Dean uses the First Blade to kill Magnus, uncharacteristically beheading him as he's pulled by the dark power of the Blade. Sam snaps Dean out of his aggression. The brothers decide to kill Crowley now they have the blade, but Crowley steals it and will only give it back when it's time to kill Abbadon.
In Mother's Little Helper, Dean grapples with the after-effects of holding the First Blade. He struggles between wanting it's power or just using it to kill Abaddon. Dean becomes uneasy over taking up the First Blade again even it means killing Abaddon, afraid of what it'll turn him into. Crowley pushes Dean to accept his role and eventually he reluctantly decides he'll have to do what he'll have to.
- "I want to kill Abaddon. That's what I want. So whatever happens with the Blade, I can't worry about that. [...] What I want, what I fear, none of that means squat. Because this is the one chance we have to kill Abaddon. So I'm all in, no matter what the consequences."
- —Dean taking on the burden of The Blade[src]
In King of the Damned, in the presence of the First Blade, the Mark grants Dean immunity to Abaddon's powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abaddon off her feet effortlessly. However, the Mark and Blade's effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her. Sam confronts Dean about this and Dean explains he knew from the start he had to kill Abaddon alone and whatever else he had to kill it with. Worried about what it's doing to him, Sam tries to tell Dean to stash the Blade away, but Dean refuses.
In Stairway to Heaven, the brothers investigate a case of angels blowing themselves up along with innocent people supposedly in the name of Castiel. Under influence of the mark, Dean is quick to blame Castiel for the crimes and is shown aggressive in his dealings with the angels and Tessa. Despite telling Sam he hadn't, Dean brings the First Blade with him and accidentally kills Tessa, wanting to be free of hearing the lost souls. Castiel is forced to give up his army after refusing to kill Dean under their orders. It's revealed the martyring angels were Metatron's double-agents and used for this very reason. Dean slips in deeper control of the mark and tries to kill Gadreel who arrives to join their side, having to be held back by Sam and Castiel.
- "The Blade's the only thing that can kill Metatron, and I am the only one who can use it. So from here on out, I'm calling the shots. [...] Until I jam that blade through that douchebag's heart, we are not a team. This is a dictatorship. Now you don't have to like it, but that's how it's gonna be."
- —Dean to Sam[src]
In Do You Believe In Miracles?, Dean is shown to be over-aggressive and has no control over his desire to kill Metatron. His need for the First Blade is also very detrimental to his health. He even works with Crowley to hunt down Metatron. When he does find Metatron, he tries to kill him but fails. Metatron then stabs Dean in the heart, killing him. Crowley approaches Dean and tells him that Dean is a lot like Cain who also died because he wasn't willing to kill innocents but Cain's very sacrifice is what made him become a demon. Crowley then tells Dean to open his eyes. Dean does so, but returns as a demon (more specifically a knight of hell).
- "It's better this way. The Mark. It's turning me into something I don't wanna be. [...] I'm proud of us."
- —Dean's last words to Sam as he dies[src]
Crowley: "What are you doing?"
Dean: "Oh, whatever I want."
Crowley: "Really? Because I think you don't know what you want. Tell me, Dean. What are you? A demon? If so, why isn't Lester's wife dead? Did you feel sorry for her? So maybe you're human. Except you have those pretty black peepers and you're working alongside me. Why don't you do us all a great big favor and PICK A BLOODY SIDE?!"
Dean: "Or what? Make a move. See how that ends. I ain't your friggin' bestie and I ain't taking orders from you. When I need to kill, I'll call. Until then, stay out of my way."
– Dean and Crowley, Reichenbach
In Black, six weeks have passed since Dean became a demon. He left Sam a note telling him not to look for him and formed somewhat of a partnership with Crowley. Dean lives in excess---drinking, doing drunk karaoke, sex, and brawl fights---and resists Crowley attempts monitor him. Dean receives a call from Cole Trenton, a man who devoted his entire life to revenge on Dean for killing a father during a hunt two years before the pilot. Cole has Sam tied up and threatens to kill him if he doesn't come. Dean callously tells him Sam isn't his responsibility anymore, but nonetheless promises to kill Cole next time he sees him.
In Reichenbach, Dean continues his carefree and aggressive activities. Crowley grows concerned the mark on Dean will act up if he doesn't kill soon and gives Dean a job to kill a woman her husband sold his soul to be killed for. Dean reluctantly goes to her house, but after seeing Lester outside to "watch the hit" Dean instead kills him. Crowley is appalled Dean ruined his deal (he could no longer get the soul now that Lester was killed without his wife dead) and challenges Dean for not knowing whether he's good or bad. Dean humiliates Crowley and ends their partnership.
Shortly after, Crowley betrays Dean by telling Sam where he is. Dean rejects Sam's attempts to bring him back to cure him and is finally found by Cole, who followed Sam. Dean shows no apparent remorse for Cole's dead father and mercilessly beats him. Sam traps Dean with Devil Trap handcuffs while Crowley takes the First Blade and hides it far away. Sam questions Dean's decision not to kill Cole and believes he showed mercy. Dean replies letting him live with the knowledge he could never get his revenge was the worst thing he could've done to him.
In Soul Survivor, Dean is tied inside a Devil's Trap as Sam starts the curing ritual. Dean expresses his condescension towards hunting monsters ("the natural order") and is completely jaded over any point it ever had. He also calls out Sam for being responsible for Lester's deal and believes him to be just as bad as himself if not worse. As the ritual continues, Dean starts to be in pain, causing Sam to fear if it was killing him. As a demon Dean shows true resentment towards Sam and their family, telling Sam he was the reason their mother died and their father wasted their entire lives hunting for nothing.
- "You notice I try to get as far away from you as possible? Away from your whining, your complaining. I chose the King of Hell over you! Maybe I was just ... tired of babysitting you. Or always having to yank your lame ass out of the fire since ... forever. Or maybe ... maybe it was the fact that my mother would still be alive if it wasn't for you. That your very existence sucked the life out of my life! [...] You never had a brother! Just an excuse for not manning up. But guess what. I quit."
- —Demon Dean taunting Sam[src]
Eventually, Dean is less demon enough to escape the Devils' Trap and tries to kill Sam with a hammer, still not wanting to be human again. Castiel saves Sam and restrains Dean, letting them continue the rest of the ritual. When Sam is upset that a barely demon Dean still didn't want to be human, Castiel comments it was because it was easier for Dean to stay that way in favor of feeling human pain. The ritual is a success and Dean is human again, but with a heavy conscience over everything he did as a demon.
In Paper Moon, Sam and Dean are taking a break from hunting. They relax by a lake, but Dean is quickly motivated by a case. Sam is concerned it's too soon for Dean to get back to work, but Dean insists. The attacks turn out to be werewolf and they run into Kate whose now werewolf sister Tasha is killing off people. Meanwhile, Dean tries to get Sam to open up about killing Lester while Sam tries to get him to open up about his actions as demon, but neither succeed. After Tasha is dead, Dean admits to Sam he's not alright and it's too soon for him to hunt, but he has to because he wants to do the right thing.
In Girls, Girls, Girls, Sam and Dean run into a dangerous witch named Rowena who is trying to train other girls to be to be witches. Dean corners her, but is trapped by Cole, allowing her to escape. Cole quickly realizes he's no longer a demon. Dean tries to apologize for their last meeting and explain he's no longer the same, but Cole attacks. Dean wins the fight, telling Cole his father had been a monster and he had killed him working a case. Dean gives Cole the choice whether to shoot him or spare him, describing himself already as a "lost cause". Cole hesitates, but believes Dean and lets him live.
- "I get it. That was your story. Look, man, I've got one of those too. But those stories we tell to keep us going? Sometimes they blind us. They take us to dark places. The kind of place where I'd beat the crap out of a good man just for the fun of it. [...] Cole, once you touch that darkness ... it never goes away. Now, the truth is ... I'm past saving. I know how my story's gonna end. It's the edge of a blade or the barrel of a gun. So the question is, is that gonna be today? That gonna be that gun?"
- —Dean's speech to Cole[src]
In The Things We Left Behind, Dean is having nightmares of killing people from the mark. He and Sam help Castiel connect with Jimmy's long-lost daughter Claire who's been taken in by a man named Randy to makes her steal to help him pay off his debts. In a conversation with Castiel, Dean makes him promise to kill him if the mark gains too much control, not wanting to be what he was before. Randy betrays Claire after being found out by thugs and they come to her rescue. Castiel and Sam take Claire to safety, but the mark on Dean acts up. Dean's nightmares becomes reality when he mercilessly slaughters all the thugs, causing all three to realize things have finally gotten worse.
In The Hunter Games, Dean is now desperate to have the mark removed. Castiel takes Metatron briefly out of prison to be used for information, only getting that they need the First Blade. Dean is reluctant to take back the Blade, but goes along with it as long as the Blade is kept directly away from him. They enlist Crowley, who takes the Blade out of hiding but refuses to give it back until needed. Dean goes to Metatron for information, but is provoked and nearly kills him. Sam and Castiel stop Dean while Metratron is returned to prison. Dean is upset at how easily he lost control and only has one hint from Metatron ("the river ends at the source"). Sam encourages Dean to fight the mark harder.
In There's No Place Like Home, Dean is trying a series of methods to keep the mark under control. Sam and Dean discover Charlie returned from Oz and was split between her good and bad selves. Dark Charlie gets revenge on the man that killed her parents and tries to stop Good Charlie from conjoining them again. Dean loses control while fighting Dark Charlie, seriously wounding her and causing harm to Good Charlie in the process. Charlie becomes herself again and forgives Dean, but Dean doesn't forgive himself.
In Halt & Catch Fire, Sam and Dean find a case revolving around college students getting killed by a vengeful spirit through the internet. The brothers save the last of the four students and get rid of the ghost. While Sam is still hopeful for getting rid of the Mark of Cain, Dean gives up on the search and decides that he'll just keep fighting the mark until he can't anymore. Sam protests, but Dean can't invest in anymore "false hope".
- "My peace is helping people. Working cases. That's all I want to do. [...] I'm done looking for a cure, Sammy. [...] I appreciate the effort, okay? I do. But the answer is not out there. It's with me. I need to be the one calling the shots here, okay? I can't keep waking up every morning with false hope. [...] So I'm gonna fight it until I can't fight it anymore. And when all is said and done ... I'm gonna go down swinging."
- —Dean giving up on removing the mark[src]
When Cain starts killing off his descendents to "purify" the world of a bloodline made mostly of killers in The Executioner's Song, Dean takes responsibility for this and reluctantly decides he needs to kill Cain with the First Blade. Dean tricks Crowley into giving him the Blade and with Sam and Castiel, follows Cain's trail to a 12-year old boy who they manage to save. Dean is scared of fighting Cain, fearing losing control again, but is adamant on going alone. Dean stands off against Cain while Sam, Crowley, and Castiel wait. Cain declares Dean is living his story in reverse and that eventually he'll kill Crowley, Castiel, and Sam himself before becoming a complete monster.
Cain nearly kills Dean, but Dean manages to immobilizes him. He pleads if there was any chance Cain could stop killing, wanting hope for himself, but Cain knows he won't stop. Dean kills Cain and gives the Blade to Castiel to hide, but is devastated by the bleak future that awaits him.
Dean's fear of becoming a demon and killing again steadily heightens. He's having terrible nightmares in the middle of the night, but tries unsuccessfully to hide this from Sam. After Sam goes out on his own in Inside Man, unbeknownst to Dean to try to find out a way to remove his mark. Dean gets in a confrontation with Rowena. She uses the Attack Dog Spell on college students. Dean stops himself from killing them just in time for Rowena to try to kill him in a flash of light, but it doesn't work. It's revealed bearing the Mark of Cain gives Dean limited immunity to certain types of attacks. Dean wants to kill Rowena, but choses not to she can end her spell on the rabid college students.
In Book of the Damned, Charlie comes to the brothers on the run from the Styne family. She stole the Book of the Damned from them, a powerful dark magic book that might be able to remove the mark from him. Dean starts to think there's hope for him, but when in the contact with the book he senses it's darkness and the mark reacts to it. Sam and Charlie try to translate it, but Dean decides he doesn't want to use it because of the consequences it might have. Sam protests, but Dean is firm and demands he burn it. They're attacked by the Stynes, but make it out. Dean thinks Sam burned the book, but Sam actually burned another and is working with Rowena to translate it.
In The Werther Project, Dean takes down a nest of six vampires by himself. When Sam goes alone to a address, Dean follows him. Sam explains the backstory of the Werther Box and the Men of Letters without giving away why he came there (working with Rowena). Sam opens the box, which drives the people around them to suicide. Dean imagines himself in Purgatory with Benny who tries to get him to die and come here so he wouldn't kill anymore. It's also revealed Dean knows neither Sam or Castiel will do what they have to when he gets out of control. Dean refuses to kill himself because of the mark, but admits he would if he really had to. He breaks out to save Sam, who's trying to shut down the Werther Box with his blood. Dean shuts down the box with some of his own and destroys it, but still doesn't know Sam is lying to him.
- "I gotta tell ya, every women in this place - they want to eat you up."
- —Hooker to Dean Winchester[src]
Dean has green eyes, light freckles on his face and short-cropped Ivy-league hair that is dark blonde. He is 6'1"--ironically making him shorter than his younger brother Sam--and muscular. Dean is noted to be "handsome" or even "pretty" by other characters constantly.
He usually wears a plaid shirt over a T-shirt, jeans, and boots, unless he has to wear a disguise in order to impersonate someone. Until Season 6, Dean often wore his father's leather jacket. He also used to wear a watch and a silver ring. As of Season 4, Dean has a hand-shaped burn scar on his left shoulder from where Castiel pulled him out of Hell. This mark has since disappeared from his body.
For the first four seasons, Dean also wore an amulet around his neck that resembled the head of a bull made of brass, attached to a black cord. This amulet was given to him by Sam as a Christmas gift when they were children. Throughout the first half of Season 5, Castiel attempts to use this amulet to find God, as its claimed power is to burn hot in God's presence. When Castiel is unsuccessful, he declares the amulet "useless," and Dean throws it away.
Dean mentions to Haley Collins in Season 1 that he doesn't wear shorts.
Dean has recently received the Mark of Cain, manifesting just below his elbow. Since separating from Sam his appearance has become more scruffy and unshaven. His hair had also grown out a bit.
Dean briefly possessed a pair of black eyes while he was a demon but they are gone now that he's human again.
Dean is shown to be by turns understanding, funny, mischievous, and, in contrast to his younger brother, a little immature. Dean's shown countless times to be good with kids and the ladies. At an early age, Dean was trained by his father, John Winchester, to hunt and kill creatures of the supernatural. However, unlike his brother Sam, he did not resent his father for having him "raised like a warrior". He seemed to prefer hunting the supernatural over any normal "apple pie" life, though it was revealed that when he was Sixteen, he did in fact desire (or at least hope for) a normal life: He just couldn't leave Sam. This however did not last long, as later on while still Sixteen, following a Werewolf hunt he realized just how unique his life was. However, by Season 7, following all that he has seen and done, Dean admits to Eliot Ness that he no longer wants to be a hunter and would give it up if he could.
Dean is an avid fan of classic rock music. Many of his aliases have included the names of famous rock musicians. He is known to use crude humor, use pop culture references, make sexual innuendos, and indulge in pornography (especially for Busty Asian Beauties). He has even stated once that he does enjoy anime and Japanese animated porn (Hentai).
Dean typically avoids emotional intimacy, preferring to engage with women only as sexual partners. However, he has had a few long term relationships over the years, with Cassie Robinson, pre-series, and Lisa Braeden, in Season 6. After the tragic events that led Dean to ask Castiel to make it as if Lisa and her son Ben had never met him, Dean seemed to give up on ever having a family other than his brother. After his break up with Lisa, Dean was reluctant to get back into his old routine of "New Town, New Girl". However, the one time he was shown to indulge in a one night stand in The Slice Girls he ended up fathering an Amazon that tried to kill him. He was reluctant to defend himself against his Amazonian daughter and Sam ended up making the kill. After these events he became even more reluctant to get in a physical relationship let alone an emotional one.
Dean values his family's safety over anything else, even going so far as to kill a demon and its human host in order to save Sam's life, as well as sacrificing his very soul and suffering in hell to resuscitate his brother.
Even though Dean keeps himself in excellent physical shape, he is known to have very bad eating habits. He is often shown enjoying greasy, fattening or otherwise unhealthy food, especially cheeseburgers and pie, and dismisses salads as "rabbit food".
Dean is terrified of flying and claims that is the reason why he drives everywhere.
Despite his working knowledge of the supernatural, Dean is skeptical with regard to the "good aspects of religion." However, he becomes somewhat more open-minded after meeting the angel Castiel.
Dean has also shown on several occasions that he is a great fan of movies, particularly westerns, and was thrilled to be given a chance to go to the old west. He was also overjoyed when he met and was able to work with Eliot Ness, frequently referencing The Untouchables during the episode.
Dean is typically ruthless and aggressive when he is hunting, a task which he approaches enthusiastically, making him the more merciless of the Winchester siblings. But in spite of that, he is capable of acknowledging whenever he's going too far, as seen with his interaction with Lenore and Gordon (Bloodlust). Whereas Sam is at least willing to sympathize with what they hunt, provided that their motives can be counted as morally gray, Dean mostly sees the world as black and white. He passionately despises what he hunts, especially demons, and is prepared to kill without question more often than not, unlike his brother. This has caused him to develop a bigotry against most supernatural creatures and beings.
He dislikes showing his emotions to monsters, and when facing beings like Abaddon or Azazel he acts threatening and determined. When facing the angels, even knowing what they could do to him, Dean is sarcastic, rude, and insulting. The only being he is openly afraid of is Death; on the rare occasions that they meet, Dean is nervous and cautious, and when Dean is angry or frustrated enough to talk back, he becomes visibly scared and backs off the moment Death appears annoyed.
Despite these traits, Dean is very laid-back and well-disposed when not on the hunt, and he values the safety of his family and innocent civilians above all else, even his own life. Though on occasion he can be somewhat impulsive as well as arrogant, Dean is both extremely intelligent and competent. He is more likely to exhibit irrational behavior when his family is threatened.
Underneath his seeming arrogance and self-righteousness, Dean shows many signs of self-loathing and insecurity. He always blames himself when things go seriously wrong, regardless of whether he's to blame or not. He constantly downplays himself and his achievements. He puts up with abuse from others, simply because he believes he deserves it. Despite being the better hunter, Dean admits he doesn't see himself as anything other than a "grunt". Likewise he constantly is willing to throw his life away, at least in part because he doesn't value it as worth much. He is constantly called out for feeling this way by Bobby and Sam. But regardless his feelings always return. These feelings can be traced back to his relationship with his father John, who at times treated him as a tool rather than as a son and who held him to unrealistic or unfair standards.
Dean enjoys the uncomplicated things in life, such as good food and television. He almost constantly displays some level of humorous behavior, and frequently makes light of tense situations. He sometimes appears foolish due to this habit, but this seems to be merely his means of dealing with the stress of hunting.
Dean shows on multiple occasions a soft spot for children. He is very good with them, able to talk to them with ease, and he is always very sympathetic; this most likely stems from the fact he practically raised Sam when he was a child. Dean's affection extends to nearly all children, particularly young ones, although he also cares about teenagers. Dean is more willing to put his life in danger for children than he is for nearly any others. Dean's affection even extends to monster children, and despite his ruthless approach to hunting he's usually unwilling to kill monster children unless he has a crucial need.
After his extraction from Hell by Castiel, Dean begins to exhibit noticeable anxiety and experience chronic, abominable nightmares of his experience there. He also seems to have some form of flashback after seeing a collection of masks in the episode It's the Great Pumpkin, Sam Winchester, when blood is seen around eyes, such as Alistair's first appearance, when a statue's eyes bled. Initially, Dean denies remembering anything of his time in Hell, but eventually confesses to Sam that he remembers every detail. He rejects any discussion about it, either not wishing to burden his brother with his pain or not wanting to relive the details of the "indescribable things" he saw. He later reveals that he not only saw terrible things, but (in Hell time) was in Hell for around forty years. He confesses that he lasted thirty years without torturing other souls so as to escape the torment himself, but that he finally broke down and tortured for the last ten years. Dean's experience in Hell left a profound mark on him. He exhibits extreme grief and guilt, both for his own torment and for the fact that he eventually gave in and tormented others. Due to this, he believes he was unworthy of rescue. He has also explained to his brother that he wishes he couldn't feel anything, as the sorrow he feels is so overwhelming. He has become obsessed with saving people, often going without sleep in order to save as many as he can. In the episode Family Remains, however, Dean states it is not just the fact he tortured souls, but the fact he enjoyed it which causes his guilt and shame. Taking up the instruments of torture himself gave him the opportunity to put his pain on other unfortunate souls. It was this act, of a righteous man turning on others, that broke the first seal.
Another side of Dean shown recently is his utter disgust at Sam for many of his dangerous or foolish actions, such as drinking demon blood, and having a sexual relationship with a demon, possibly because he is scared of Sam becoming a demon like the ones he saw in Hell. While he remains angry at Sam, he vows to save his brother and still loves him. Dean also realizes family isn't perfect and there will always be times when they hurt him. In the final episode of season 4 after the argument with Bobby when he was in the "safe house", he forgave his brother during the final few moments when Lucifer was rising.
As of Season 5 Dean does not trust Sam, and feels as if he is holding himself back and putting the world in jeopardy just to keep Sam safe. He tells Sam that Lucifer will use the fact that they are family and have love for each other against them until he was sent to the future by Zachariah. Once there, he realized that he and Sam kept each other grounded, and when he got back, he immediately called his brother. They were a team again, even though it was difficult for Dean to trust his brother again, as Sam continued to lie to him.
After his time in Hell, Dean slowly started to use alcohol as a crutch. He cut back on his drinking while he was living with the Braedons between Seasons 5 and 6 but after being kicked out of the Braedon Household after the events of Live Free or Twihard and You Can't Handle the Truth his long term depression worsened and he dove back into the bottle. In Season 7 both Bobby and Sam stated that his drinking was becoming a problem that could potentially cost him his life during a hunt.
Following Bobby's death at the hands of Dick Roman, Dean developed a very strong, obsessive revenge streak in him and spent the entirety of Season 7 hunting Dick down to kill him. As part of Bobby's last wishes he tried to let go of his anger and vengeance, and while in the end he succeeded in killing Dick, it was as part of the job and not for vengeance. However, this caused to him be sent to Purgatory in the process, where he resided for a year (possibly much longer, as time moves differently between dimensions).
The constant life-or-death situations Dean was forced into in Purgatory created an extreme change in him. While he was stuck there, he became emotionless and paranoid of the fear of getting attacked. He killed monsters of Purgatory with ease and was always fighting for his survival. When returned back to Earth, his new outlook on life was clear. He became hardened, emotionless, and at times ruthless; his humor and puns were nonexistent when hunting unlike in Season 7. That has changed with Castiel's return from Purgatory after which he started to show his lighthearted side again.
Having a now haunted sense of self created in him during that year, he became firmer in his belief of hunting. He had personally seen all the monsters they hunted in Purgatory and in doing so, developed a strong sense of responsibility to the people they saved. Dean now believes that it is their duty to save people and quitting out of the hunting business is permanently out of the question. Despite becoming more ruthless, Dean has developed more faith in monsters managing to recover their humanity, as shown with him willing to let Kate go, presumably developed from his time with Benny. However following Castiel's return, Dean began to slowly return back to his previous more laid back personality.
Following Kevin's death, and Gadreel taking complete control of Sam, Dean became desperate to save him. When Sam was freed, Dean's self loathing seems to have reached a new height: He claims he's poison, and that anyone near him dies.
Since acquiring the Mark of Cain, Dean's personality began to alter, turning darker. He has since shown extreme levels of aggression and wrath, an example of this is when he fully attacked a good angel and putting an Angel Blade to her throat in Stairway To Heaven. As well as being openly more hostile, even towards his friends and brother. He's also got more distrusting and suspicious, and more hate-filled toward the supernatural.
From what has been seen so far, Dean's transformation into a demon has darkened his personality. As his soul is twisted, he no longer empathizes for others, and only cares for his own needs and wants. He is so far from his former self, that at one point, he stalked Sam through the bunker and attempted to kill him with a hammer, missing only by inches. He also seems to like taking his time with his tasks. While stalking Sam, he talked in a taunting manner, as though he was enjoying himself. This is furthered by the fact that instead of an axe, he decides to use a hammer to break through a door and kill Sam, despite both tasks requiring much more force with a hammer than with an axe. Dean as a demon apparently cares about the natural order, something old Dean despised. He even considered himself, as a demon, a part of the natural order, and that it was all set up in this certain way.
Sure enough, the transformation has turned Dean more selfish and arrogant, acting like a hedonist and only caring about himself, completely in opposition to his former personality. He has kept some familiar traits, such as a love of drinking, roadhouses and games such as pool, darts and foosball. Dean is now noticeably more brutal, happily beating people and demons beyond a reasonable point, with limited provocation. He is also colder, and while initially coming across down-to-earth and charismatic, he quickly turned cold and ruthless when others proved to be uncooperative, as shown by him outright shaming and humiliating Ann Marie for sleeping with him the moment she rejected his advances, not caring that he had left her near tears.
Dean's transformation has also caused him to no longer care for Sam, shown by how he told Cole that he didn't care what he did to Sam, and even threatening Sam himself. He has also shown to no longer care about innocent people, willing to kill a cheating housewife just to sate the Mark's need for a kill and instead killing her husband, as well as calling his beloved Impala 'Just a car' and not bothering to tend to it's condition. However, after Sam successfully cured Dean with the Demon Curing Ritual he seemed to gain back his normal personality traits. Later in season 10 when Sam and Dean come upon a book filled with black magic that could most likely cure Dean, he declines, saying that the price for this kind of black magic always comes with a price, and insists that Sam stops his investigating.
Dean has been seen using a variety of weapons over the course of the series, and is very inventive while improvising weapons from his surroundings, but there are some particular armaments he seems to prefer. Dean tends to use a brushed stainless steel Colt 1911 with pearl grips, which John is seen using in a flashback, and also uses a Baikal sawed-off double barrel shotgun when he needs extra firepower. However lately he has used a lever action Winchester 1887 shotgun (given to him by Jo before she died) on a more regular basis than his usual shotgun.
He has also been seen with an G3 SG1 marksman rifle in "Simon Said" and "All Dogs Go To Heaven" and was proficient enough with the weapon to act as a sniper and kill several skinwalkers. Dean is shown to possess a large machete in "Dead Man's Blood", and among other regular hunting items. Also, both Dean and Sam have acquired angelic blades which Dean has successfully used. Dean uses one to kill Zachariah, becoming the first known non-angel to kill an angel in the series. After emerging from Purgatory, Dean started using a large, machete-like blade from the monster realm. The blade is crude in design, featuring a large bone hilt and a stone-like blade. The blade is powerful as Dean used it to behead a Leviathan and later a group of vampires.
The trunk of the Chevy Impala contains numerous weapons which are implied as having been needed in the past, notable examples sheath knives and an DefTech 37mm grenade launcher.
Since moving in to the Men of Letters Bunker, Dean has kept many of his weapons hanging up on his wall.
The First Blade is another one of Dean's weapons that can kill any demon no matter their age or power. Because it draws its power from the mark, which has the power of The Darkness, it can kill any supernatural being. The First Blade can only be used if the user has the Mark of Cain which means only Dean could use it and make it powerful to kill anyone. The Mark of Cain gives him incredible strength, telekinesis (only in the presence of the blade) and immunity to all demonic powers, as seen in "King of the Damned".
Dean has also wielded a few supernatural weapons such as the Colt, the Bone of Righteous Mortal Washed in the Three Bloods of Fallen and Death's Scythe successfully, killing powerful enemies with them.
Powers and abilitiesEdit
- Possession - Dean was resurrected as a demon in his own body, but it is likely that he has the ability to leave his own body, and possess the bodies of others, and take control of them.
- Immunity - Dean, as a Knight of Hell and the bearer of the Mark of Cain is much more resilient than most demons. While vulnerable to holy water, he was shown to recover quickly from it. He also retains his demon mannerisms for a longer period of time while being cured than other demons. He also became immune to a Devil's Trap briefly due to his humanity being restored.
- Super strength - As a Knight of Hell, Dean is significantly stronger than common demons: he was able to easily shove Crowley, the King of Hell, to the ground and toy with before quickly overpowering Cole during their fight. He was also easily able to overpower lower demons. However, Castiel was able to restrain him, albeit while Dean was being cured and was in the process of having his humanity restored.
- Regeneration - After being reborn, Dean's wounds, including the stab wound from an angel blade, were completely healed. Dean also healed near-instantly from a knife cut to the face, and a cut from the First Blade that he made in his hand healed within seconds.
- Invulnerability - Knights of Hell are little affected by damage dealt to their hosts, even injuries as severe as being stabbed, gunshot wounds, decapitation, and dismemberment.
- Immortality - Unless he transfers the mark to someone else, and is killed by The First Blade, Dean will never die. It is highly implied that he cannot kill himself with the blade, as it had no effect on him when he slit open his hand.
- Super stamina - Demons do not require food, water, or sleep to maintain themselves. Dean, as a demon, can consume vast amounts of alcohol without dying and very little effect. He was also unaffected by tear gas.
Abilities with the title of DeathEdit
- Super strength - While wearing Death's ring, his strength was increased to that of the level of Death. He was able to knockout soulless Sam with one punch.
- Intangibility - While wearing Death's ring, Dean could phase and walk through physical barriers.
- Invisibility - While wearing Death's ring, Dean could turn himself invisible.
- Teleportation - While wearing Death's ring, Dean could teleport from once place to another in the blink of an eye. He teleported from the street the man crashed his car to Bobby's bunker.
- Killing touch - While wearing Death's ring, Dean could kill anything he touched.
Dean, trained by his father from early childhood as a hunter of the supernatural, possesses excellent combat and hunting abilities; he is established throughout the series as an extremely dangerous individual, and he is more than capable of taking a stand against even the most formidable of opponents, such as demons and vampires. Dean is adept with martial arts and knife fighting as well; he has subdued several human assailants with ease in multiple episodes and bested physically more powerful creatures, often unarmed or equipped with only a blade. Dean has also beaten his younger brother Sam in a fight a few times. Due to his year-long stay in Purgatory and the realm's animal-like survival of the fittest environment, Dean greatly honed his hunting skills and instincts. This is shown on a few occasions such when Dean managed to get the jump on a Leviathan and behead him before the latter could even react and effortlessly killed five vampires single-handedly when helping Benny track down and kill the nest he lived in. When confronted with three demons, despite a hard fight and all three being more powerful than him, Dean was able to take them down single-handedly using only his hand-to-hand experience and the demon killing knife, something which impressed the powerful demon, and his ancestor, Cain greatly.
Dean is well-versed with multiple types of firearms and is an expert marksman, he seldom misses his intended target and can efficiently put down anything vulnerable to bullets. During an old-fashioned duel with Elias Finch, Dean won, killing Finch without being harmed in the process despite Finch getting a shot off. The same also happened in an impromptu duel with werewolf Joy. Dean is also a proficient tracker and possesses prudent tactical skills. Highly resourceful, he frequently utilizes improvised weapons and explosive devices; in Croatoan, he demonstrated in constructing Molotov cocktails and improvised explosive devices.
Dean also possesses extensive knowledge of supernatural mythology. He is well-versed in how police, fire departments and various government agencies (FBI, CDC) typically operate and conduct investigations. He also knows how to both impersonate and evade them effectively. Dean is a virtuoso of escape, evasion, silent movement, and when the situation requires, subtlety and stealth. Lastly, he is also alarmingly skillful in many areas frowned upon by the law: lock picking, breaking into security systems (not so much computers, which often falls on Sam), car jacking and gaining an 'advantageous purchase' comes naturally to him.
Dean has shown on several occasions to be a natural leader, when operating in groups, he commonly takes command, unless the group includes someone who he himself sees as a leader, such as his father or Bobby. Between him and Sam (and Castiel), he nearly always calls the shots, and acts as de facto leader. Dean also has a skill for motivation, and is a capable orator, being able to motivate others to remain strong and carry on, even in darkest moments, with mere words. This skill also allows him to inspire trust in others, something which comes in handy, when he has to explain the existence of the supernatural to non-believers.
An accomplished mechanic, he maintains his Impala in tip-top condition (and once rebuilt the vehicle entirely from being severely disfigured) and has maintained an intimate knowledge of automobiles and engines since childhood. He is also very talented at making electronic devices, most notably his EMF meter which he made using an old Walkman and an electromagnet powerful to wipe out an entire room full of computers in "Ghostfacers".
Due to his time spent in Hell as Alistair's "student", Dean has an in-depth knowledge of torture, able to inflict the maximum amount of pain and agony on a victim while keeping them alive as long as possible. In the season 5 premiere, Dean revealed he had learned the banishing spell from Castiel that sends angels back to heaven.
As shown in the Season 8 episode, Trial and Error, Dean is an adept cook. He makes burgers and they are apparently (according to Sam) delicious.
Dean is also shown to be quite a capable strategist, able to come up with many quite clever, and unorthodox methods of defeating his more powerful opponents, for example he defeated the mother of all, by swallowing Phoenix Ashes (her only weakness) and tricking her in to biting him, causing her to swallow the ashes. He also devised a way to trick Dick Roman so he, Sam and Castiel could not only sneak in, but so that he could catch Dick off-guard and kill him. This was quite a feat as Dick was a master strategist capable of developing very complex and long-term plans. Another show of his strategic abilities is when he manages to capture Crowley by luring him in with a deal and then slapping handcuffs on him when he least expects it painted with a Devil's Trap. Crowley, who is shown to be a cunning strategist himself, is caught completely off-guard by this and doesn't even realize what Dean has fully done until he tells him. However he will also rush into situations, particularly if he doesn't believe there's time to stop and plan. Dean is also a capable survivalist, as he was able to survive a year in Purgatory with limited resources.
In "First Born," Dean bested many demons at once in hand-to-hand combat and won. In "The Things They Carried," Dean was able to squash a Khan Worm twice. In "Inside Man," Dean was able to take on three guys under the Attack Dog spell all at once with relative ease. In "The Werther Project," Dean was able to take on six vampires and win.
Despite all of this, he believes himself to be only a "grunt," but according to Sam, Dean is actually the best at lore (Sam refers to him as a "genius") and is a better hunter than anyone Sam has ever encountered including Sam himself and John Winchester.
Various Supernatural AbilitiesEdit
In "Dream A Little Dream Of Me," Dean temporarily gained the ability of Dream Walking through African Dream Root. This allowed him to enter Bobby Singer's nightmare and help wake him up. He later used this ability in conjunction with dream root again in "Pac-Man Fever" to enter Charlie Bradbury's djinn-induced nightmare and wake her up.
In "Death Takes A Holiday," Dean temporarily becomes a ghost through astral projection and displays all the normal ghostly powers such as intangibility, invisibility and telekinesis, though it took the help of the ghost of Cole Griffith for him to master it and a lot of concentration compared to more experienced ghosts like Cole who could easily do it. However, combined with Sam, he had enough strength to drop a chandelier on a wooden floor from the ceiling with telekinesis.
In "Live Free or Twihard", Dean was turned into a vampire and possessed all their basic abilities, notably enhanced hearing, sensitivity to light, and increased strength, as well as the ability to smell vampires from miles away. He also displayed the ability to jump from a balcony to a lower floor and land on his feet. Using his abilities, Dean was able to take out an entire nest of vampires, including his boss, Boris who was stronger than an ordinary vampire due to his 600 years of age. However, when Dean took the cure that reversed the transformation, his enhanced abilities and vulnerabilities were lost and back to normal human status.
In "Appointment In Samarra", Dean became Death for a day, however it was a bet made by Death in order to bring Sam's soul back from Lucifer's Cage. Dean was required to put on Death's ring and do his work for 24 hours without taking it off, Dean became invisible had the ability to teleport anywhere and kill with a simple touch. He was also likely intangible as he had to take off the ring to interact with the physical world. However Dean lost the bet but Death still retrieved Sam's soul. Dean lost all the abilities after taking off the ring which is now back in Death's possession.
In "Dog Dean Afternoon," as the result of a spell, Dean takes on the personality traits of a dog and the ability to communicate with all animals telepathically. Among the traits he takes on is an ability to sense when people are sick such as with cancer. These abilities disappeared when the spell wore off.
In "First Born," Dean received the Mark of Cain, something that will allow him to wield the First Blade once it is found and kill the Knight of Hell, Abaddon. Any further abilities that come with it are so far unknown. There is also some sort of terrible price, but Dean didn't care and took the Mark without learning what it is. Later, when he used the First Blade for the first time, the murderous rage that he felt did not dissipate after killing. He also displayed a greater strength in "Alex Annie Alexis Ann", able to overpower a vampire who had super strength with ease.
In "King of the Damned," in the presence of the First Blade, the Mark grants Dean immunity to Abaddon's powers at first with great concentration and then no effort. He also displays telekinesis and strength great enough to lift Abadddon off her feet effortlessly. However, the Mark and Blade's effects cause him to go overboard and repeatedly stab the dead Abaddon after he kills her.
During "The Prisoner", Dean displayed enough strength to beat Castiel, a Seraphim effortlessly, nearly killing him when before, when Castiel was just a regular angel, his punches had no affect but to hurt Dean himself.
In "Brother's Keeper", Death informs Dean that the Mark makes him virtually immortal. Even Death himself cannot permanently kill Dean because of the Mark's power and Death is stated to be able to kill God Himself. He also states that by possessing the Mark, Dean's been allowing it to hold back the Darkness. At the end of the episode, the Mark is removed by Rowena and Dean loses all the powers it has granted him.
After becoming a Knight of Hell, Dean possessed these weaknesses.
- Devil's Trap - Just like any other demon, Dean can be imprisoned in a Devil's trap or Devil's trap handcuffs. As he became more human while being cured, he became less susceptible and eventually could walk right out even though he still retained demon mannerisms and desires.
- Holy Water - Dean finds contact with holy water painful and it can be used to stun him. However he still takes it better than a regular demon, recovering from its effects quicker.
- Purified Blood - Dean is affected by purified blood like any demon but as a Knight, he apparently retains his demon mannerisms much longer than other demons. The blood apparently causes him a great deal more pain than it does for other demons, possibly due to the Mark of Cain.
- Demon Curing Ritual - Sam was able to cure him with the ritual.
- Angels - A newly empowered Castiel was able to overpower and restrain Dean from behind. However, at this point he had been subjected to the demon curing ritual so it's possible his physical strength had lessened significantly.
- Death - Death said that while he could not kill Dean while he bore the Mark of Cain, he could remove the mark, and then kill him.
- The First Blade - The First Blade is the only thing able to kill somebody with the Mark of Cain.
Throughout the course of the series, Dean has died many times.
- In In My Time Of Dying Dean came close to death and almost went with the reaper Tessa when in a coma from the car accident, only saved because Azazel resurrected him as part of his deal with John.
- In the episode, "Mystery Spot", Dean dies in a multitude of different ways. They are:
- Shot at the Mystery Spot
- Run over by a car
- Crushed by a falling piano or desk (object disputed)
- Chokes on a sausage
- Slips in the shower
- Poisoned by a taco
- Electrocuted by his razor
- Accidentally killed with an axe by Sam
- Mauled by a golden retriever
- Hit by an arrow (suggested by Sam insulting Doris's archery skills)
- Shot by a robber
- Almost 100 other unknown ways.
- In Season 1 episode 14 "Nightmare" Dean died in Sam's vision by Max Miller
- In the Season 3 finale "No Rest for the Wicked", Dean is viciously mauled by Lilith's hellhounds and dragged down to Hell due to a deal with a crossroads demon to resurrect Sam.
- In Season 5 episode 4, "The End", Dean died in an alternate timeline, in the year 2014, when Lucifer snapped Future-Dean's neck.
- In the Season 5 episode "Dark Side of the Moon" Sam and Dean are once again killed, ambushed by two hunters who blame them for the Apocalypse. Its revealed that this is not the first time they've died as it's mentioned that they've gone to Heaven before but never remembered it.
- In Season 6 episode "Appointment In Samarra" Dean died briefly to contact Death in order to get Sam's soul back.
- In Season 7 episode 12 "Time After Time After Time" Dean died in an alternate timeline. He was strangled to death by Chronos, but Sam and Jody Mills save him using a spell.
- In the Season 9 finale "Do You Believe in Miracles?" Dean is killed by Metatron, but is brought back by the First Blade as a demon (Knight of Hell).
- Dean and Sam - Dean and Sam are brothers.
- Dean and Castiel - Dean and Castiel are best friends, Dean said that Castiel was the closest thing he had to a brother, besides Sam.
- Dean and Crowley - Dean and Crowley were somewhat friends (At the beginning of Season 10, Crowley claimed they were best friends, but it seemed Dean didn't feel the same).
- Dean and Bobby - Bobby was like a second father to the boys.
- Dean and Benny - During his time in Purgatory Dean came to trust and respect Benny, despite the fact that Benny was a vampire. Dean still considers Benny to be his blood brother who always had his back.
- Dean and Bela - Dean and Bela were enemies/allies, but more often enemies.
- Dean and John - Dean worshiped his father, but later admitted during that confrontation with Demon!Dean in "Dream A Little Dream of Me" that John was "an obsessed bastard who couldn't protect his family." Despite that, Dean still loves his Dad very much.
- Dean and Charlie - Dean and Charlie are good friends, Charlie being the closest Dean has had to a sister.
- Dean and Lisa - Possibly Dean's longest term romantic relationship - they lived together for at least one year.
- Minor relationships - People Dean has become acquainted with over the years.
- Dean is a masculine name of English origin. The meaning of the name is "leader" or "valley". Which is quite fitting, as he normally leads the events of the hunt.
- "In The Beginning" reveals that Dean was named after his maternal grandmother, Deanna Campbell.
- Dean: "Why do I have to call him? I mean the guy's busy, it's not like he lives in my ass."
Castiel: *appears behind Dean*
Dean: "Cas, get out of my ass!"
Castiel: "I was never in your...?"
- "You hold him down while we knife him, and then we'll all go out for icecream and strippers."
- (pulls down pants & raises arms) "PUDDINNGGG!....... crazy works."
- "Well that's great, because without your power, you're basically just a baby in a trench coat."
- "Life as an angel condom. That´s real fun."
- "Seriously. Why? Why would anybody want to watch our lives?"
- "What kind of douchebag names a character after himself?"
- Victor: "I-I I shot the sheriff!"
Dean: "But you didn't shoot the deputy!"
- "You married fake Ruby?"
- "Look at these male model sons of bitches. Nice 'Blue Steel', Sam."
- "Misha? Jensen? What's up with the names around here?"
- "I'm not wearing any makeup. Oh crap. I'm a painted whore."
- "So, what? We've got a bunch of killer dolls? Like Chucky?"
- "My Spidey senses are tingling."
- "I'm going to go hit the poop deck."
- "What was I suppose to do? Let T-1000 walk around and hope that he doesn't open fire?"
- Sam: "What kind of thing likes virgins and gold?"
Dean: "P. Diddy?"
- "Shawshank's a great flick, but let's skip the shower scene."
- "Karma's a bitch, bitch."
- Christian: "Who you calling?"
Dean: "Your wife. Let her know I'm not gonna make it over tonight."
- "Let me get dressed, Robo-Cop."
- [to Samuel] "So what's so important that you're the King of Hell's cabana boy? What did he offer you: girls, money, hair?"
- "Gramps threw a barbeque and left us off the e-vite list?"
- "You go with Efron. I've got Bieber."
- Dean: "Are you wearing glitter?"
Kid: "I only do it to get laid, man."
Dean: "...Does it work?"
- "Now I lay me down to sleep, I pray to Castiel to get his feathery ass down here."
- "What, did you loose the ability to send a text message?"
- "We can either take on the Devil together, or you lame-ass bitches can eat me. Literally."
- "What are you, the Hamburglar?"
- "Why does Heaven care if Harry meets Sally?"
- "Team Free Will. One ex-blood junkie, one dropout with six bucks to his name, and Mr. Comatose over there. It's awesome."
- "A bloody, violent monster... and you wanna be Facebook friends with him? Nice, Sammy."
- "Calm down? I am wearing sunglasses at night. You know who does that? No-talent douchebags. I hate this game. I hate that we're in a procedural cop show. And you want to know why. Because I hate procedural cop shows. There's like 300 of them on television, they're all the freakin' same."
- Castiel: "Archangel. The one who killed me."
Dean: "Excuse me?"
Castiel: "His name is Raphael."
Dean: "You were wasted by Teenage Mutant Ninjangel?"
- "Eat it, Twilight!"
- "Well, how bout this, the suite life of Zach and Cas?"
- "I'm sitting in a laundry-mat, reading about myself... sitting in a laundry-mat reading about myself. My head hurts."
- "Go have your Robin Williams 'Oh Captain! my Captain!' moment."
- Tessa: "You don't remember me?"
Dean: "Honestly, if I had a nickel for every time I heard a girl say that..."
- "Boy, three bedrooms, two baths, and one homicide. This place is going to sell like hotcakes."
- "I have been Re-Hymenated."
- "Dude, on my car, he showed up naked, covered in bees."
- "Come on, Sammy. Let's have a beer, talk about it. I'm tired of playing."
- "So tell me which one of us is really the monster."
- "Do it. It's all you."
References Dean Makes to Popular CultureEdit
- Unsolved Mysteries - "Okay, thank you Unsolved Mysteries." / 1x01 - Pilot
- Deliverance - "We talkin', like, misdemeanor kind of trouble, or uh, "squeal like a pig" trouble?" / 1x01 - Pilot
- The X Files - "Agent Mulder. Agent Scully." / 1x01 - Pilot
- Bambi & Yogi Bear - "Tell me, uh, Bambi or Yogi ever hunt you back?" / 1x02 - Wendigo
- The Blues Brothers - "Man, I look like one of the Blues Brothers." / 1x04 - Phantom Traveller
- Star Trek - "You mean, like the Vulcan Mind Meld" / 1x06 - Skin
- Ghostbusters - "Nice job, Dr. Venkman" / 1x07 - Hookman
- National Lampoon's Animal House - "Think we'll see a naked pillow fight?" / 1x07 - Hookman
- Matlock - "Saved your ass! Talked the sheriff down to a fine. Dude, I am Matlock" / 1x07 - Hookman
- The Munsters - "You were kind of like the blonde chick in The Munsters." / 1x08 - Bugs
- The Shining - "First you tell me that you've got the Shining, and then you tell me that I've gotta go back home?" / 1x09 - Home
- Poltergeist - "Missouri did her whole Zelda Rubenstein thing." / 1x09 - Home
- Star Wars - "I love the guy, but I swear he writes like friggin' Yoda" / 1x10 - Asylum
- The Sixth Sense - "Let me know if you see any dead people, Haley Joel." / 1x10 - Asylum
- Medium & Ghost Whisperer - "Hey, Sam, who do you think is a hotter psychic: Patricia Arquette, Jennifer Love Hewitt, or you?" / 1x10 - Asylum
- One Flew Over the Cuckoo's Nest - "Man, electroshock, lobotomies, they did some twisted stuff to these people. Kind of like my man Jack in Cuckoo's Nest." / 1x10 - Asylum
- The Shining - "Spirits driving them insane. Kind of like my man Jack in The Shining." / 1x10 - Asylum
- The Shining - "All work and no play makes Doctor Ellicot a very dull boy." / 1x10 - Asylum
- The Texas Chainsaw Massacre - "Let’s just shag ass before Leatherface catches up." / 1x11 - Scarecrow
- Godzilla - [referring to Godzilla Vs Mothra] "That’s my favorite Godzilla movie! It’s so much better than the original, huh?" / 1x15 - The Benders
- Mommy Dearest - "Daddy dearest isn't here." / 1x19 - Provenance
- That’s Incredible & Twilight Zone - "Sounds more like That's Incredible than Twilight Zone." / 1x20 - Dead Man's Blood
- Ghost - "Dude, I full on Swayze'd that mother." / 2x01 - In My Time of Dying
- Ronald McDonald - "You still bust out crying whenever you see Ronald McDonald on the television." / 2x02 - Everybody Loves a Clown
- Silence of the Lambs - "Put the lotion in the basket." / 2x03 - Bloodlust
- Pretty in Pink - "There's more in here where that came from, it's got unrequited Duckie love written all over it." / 2x04 - Children Shouldn't Play with Dead Things
- Pet Semetary - "I mean come on, haven't you seen Pet Sematary?" / 2x04 - Children Shouldn't Play with Dead Things
- Beaches - "Nah, I think she went out to rent Beaches." / 2x04 - Children Shouldn't Play with Dead Things
- Star Wars - "He full-on Obi-Waned me!" / 2x05 - Simon Said
- Ghostbusters - "That's ectoplasm. Well, Sam, I think I know what we're dealing with here. It's the Stay Puft Marshmallow Man." / 2x06 - No Exit
- The X Files - "What do you think, Scully? You wanna check it out?" / 2x07 - The Usual Suspects
- The X Files - "No, I'm Mulder. You're a red-headed woman. " / 2x07 - The Usual Suspects
- Matlock - "Hey, thanks for the law review, Matlock." / 2x07 - The Usual Suspects
- Let's Make A Deal - "Great. So we've gotta clean up these people's mess for 'em? I mean, they're not exactly squeaky clean. Nobody put a gun to their head and forced 'em to play Let's Make A Deal." / 2x08 - Crossroad Blues
- MTV Cribs - "Though this house probably ain't up next on MTV Cribs, is it?" / 2x08 - Crossroad Blues
- Star Wars - "Wasn't for cash. Oh, who knows. Maybe this place is full of babes in Princess Leia bikinis." / 2x08 - Crossroad Blues
- MySpace - "Yeah, MySpace, what the hell is that?" / 2x08 - Crossroad Blues
- Omega Man - "I feel like Chuck Heston in the Omega Man." / 2x09 - Croatoan
- Night of the Living Dead - "Night of the Living Dead didn't exactly end pretty." / 2x09 - Croatoan
- The Stepford Wives - "That was kind of creepy, right? A little too Stepford?" / 2x09 - Croatoan
- The Shining - "It's about forty miles down to Sidewinder." / 2x09 - Croatoan
- The Incredible Hulk - "For what? For him to Hulk out and infect somebody else?" / 2x09 - Croatoan
- Scooby-Doo - "Old school haunted houses, you know? Fog and secret passageways, sissy British accents. Might even run into Fred and Daphne while we're inside. Mmm. Daphne. Love her." / 2x11 - Playthings
- Weird Science - "You know there's a really good hangover remedy, it's a greasy pork sandwich served up in a dirty ashtray." / 2x11 - Playthings
- Die Hard - "Just let me do the talking. I don't think he likes you very much, Agent Johnson." / 2x12 - Nightshifter
- Touched by an Angel - "But she seriously believes that she was...touched by an angel?" / 2x13 - Houses of the Holy
- Touched by an Angel - "Roma Downey made him do it." / 2x13 - Houses of the Holy
- Batman - "You just got to wait for some divine bat signal. Is that it?" / 2x13 - Houses of the Holy
- Justin Timberlake - "Hi, um, so sorry to bother you, but uh, my son snuck out of the house last night and, uh, went to a Justin Timberlake concert." / 2x14 - Born Under a Bad Sign
- E.T. - "What? You mean between the angry spirit and uh... the sexed up ET?" / 2x15 - Tall Tales
- The Wizard of Oz - "Follow the creepy brick road." / 2x16 - Roadkill
- The Ghost Whisperer - "Sammy's always getting a little J. Love Hewitt when it comes to this." / 2x16 - Roadkill
- The Sixth Sense - "Well, all right, Haley Joel." / 2x16 - Roadkill
- The Incredible Hulk - "Like a really hot Incredible Hulk?" / 2x17 - Heart
- Cujo - "I'd say Kurt's looking more and more like our Cujo." / 2x17 - Heart
- The Beverly Hillbillies - "Yeah, for a vacation. I mean swimming pools and movie stars, not to work." / 2x18 - Hollywood Babylon
- Die Hard - "Come out to the coast, we'll get together, have a few laughs..." / 2x18 - Hollywood Babylon
- Zoolander - "I call this one my Blue Steel…Who looks better – me or Nick Nolte?" / 2x19 - Folsom Prison Blues
- Taxi Driver - "Okay another guy who’s seen Taxi Driver one too many times." / 2x19 - Folsom Prison Blues
- The Great Escape - "I wish I had a baseball. You know, like Steve McQueen." / 2x19 - Folsom Prison Blues
- Escape from Alcatraz - "That’s the Sammy I know. You’re like Clint Eastwood from Escape from Alcatraz." / 2x19 - Folsom Prison Blues
- The Great Escape - "It’s a good thing I’m like James Garner from The Great Escape." / 2x19 - Folsom Prison Blues
- The Wizard of Oz - "Well, we're not in Kansas anymore." / 2x20 - What Is and What Should Never Be
- The Wizard of Oz - "Aunty Em? There's no place like home." / 2x20 - What Is and What Should Never Be
- Apocalypse Now - "Seventeen. You’d think it’d be Apocalypse Now. It’s been five days and bupkis." / 3x01 - The Magnificent Seven
- Se7en - "What’s in the box?" (pause) "Brad Pitt? Se7en? No?" / 3x01 - The Magnificent Seven
- The Lone Ranger - "I'll say it again. Who was that masked chick?" / 3x01 - The Magnificent Seven
- Gumby - "Gumby girl... Does that make me Pokey?" / 3x02 - The Kids Are Alright
- Rain Man - "Don’t worry, Bobby will find a way to break it. Until then I say we hit Vegas. Pull a little Rain Man. You can be Rain Man." / 3x03 - Bad Day at Black Rock
- Batman - "I'm Batman!" / 3x03 - Bad Day at Black Rock
- Looney Tunes - "Say goodbye, wascawy wabbit." / 3x03 - Bad Day at Black Rock
- The Sixth Sense & The O.C. - "Could like Mischa Barton. The Sixth Sense, not The O.C." / 3x05 - Bedtime Stories
- Happy Days - "Well, you say it like that – I guess you guys are the Cunninghams." / 3x08 - A Very Supernatural Christmas
- The Blair Witch Project - "So are we looking for some craggy old Blair bitch in the woods?" / 3x09 - Malleus Maleficarum
- Fatal Attraction - "It’s like Fatal Attraction all over again." / 3x09 - Malleus Maleficarum
- Hellraiser - "I saw Hellraiser, I get the gist." / 3x09 - Malleus Maleficarum
- Pink Floyd ~ Dark Side of the Moon & The Wizard of Oz - "Well, shall we dim the lights and sync up Wizard of Oz and Dark Side of the Moon?" / 3x10 - Dream a Little Dream of Me
- The X Files - "Sounds pretty X-Files to me." / 3x11 - Mystery Spot
- Groundhog Day - "Like Groundhog Day?" / 3x11 - Mystery Spot
- Kojak - "Okay Kojak, let’s get you outside." / 3x11 - Mystery Spot
- Bob Marley ~ I Shot The Sheriff - "But you didn't shoot the deputy." / 3x12 - Jus in Bello
- CSI:Miami - "Okay, great. My man Dave Caruso will be stoked to hear it." / 3x15 - Time Is on My Side
- Dr. Quinn, Medicine Woman - "Zombie with skills. Dr. Quinn, Medicine Zombie." / 3x15 - Time Is on My Side
- Antiques Roadshow - "A little Antiques Roadshow surgery, some organ theft." / 3x15 - Time Is on My Side
- Jesus Christ Superstar - "Hell, she probably wants you to become her little Antichrist Superstar." / 3x16 - No Rest for the Wicked
- Carrie - "What, are you gonna give her the Carrie-stare and Lilith goes poof?" / 3x16 - No Rest for the Wicked
- Ghostbusters - "This is a terrific plan. I'm excited to be a part of it." / 3x16 - No Rest for the Wicked
- Star Wars - "The name’s Antilles, Wedge." / 4x01 - Lazarus Rising
- Touched by an Angel - "Look, all I know is that I was not... groped by an angel." / 4x02 - Are You There God? It's Me, Dean Winchester
- Highway to Heaven - "You know, Michael Landon. Not dicks." / 4x02 - Are You There God? It's Me, Dean Winchester
- Back to the Future - "What, did angels invest in Deloreans?" / 4x03 - In The Beginning
- Chatty Cathy - "Well, you're a regular Chatty Cathy." / 4x03 - In The Beginning
- Hungry Hungry Hippos - "And your appetite's reaching, you know, "Hungry Hungry Hippo" levels." / 4x04 - Metamorphosis
- The Big Lebowski - "Brother, I have been rehymenated. And the Dude does not abide." / 4x05 - Monster Movie
- The X Files - "No, "The X-Files" is a TV show. This is real." / 4x05 - Monster Movie
- The Kids In The Hall - "He's a girl-drink drunk." / 4x08 - Wishful Thinking
- Harry and the Hendersons - "What's this, like a Harry and the Hendersons deal?" / 4x08 - Wishful Thinking
- Forrest Gump - "Run, Forrest, run!" / 4x08 - Wishful Thinking
- Spiderman - "You see, with great power comes great responsi..." / 4x08 - Wishful Thinking
- Girl, Interrupted - "So I'm Girl, Interrupted, and I know the score with the apocalypse. Just busted out of the nutbox. Possibly using super powers by the way. Where do I go?" / 4x09 - I Know What You Did Last Summer
- Angels in the Outfield - "Anna may have sent the angels to the outfield, but sooner or later, they're gonna be back." / 4x10 - Heaven and Hell
- Power Rangers - "So, you just forgot that you were God's little Power Ranger? " / 4x10 - Heaven and Hell
- Touched by an Angel - "So what, you're just gonna take some divine bong hit, and shazam, you're Roma Downey?" / 4x10 - Heaven and Hell
- Dogma - "What would you care? You're junkless down there right? Like a Ken doll." / 4x10 - Heaven and Hell
- Juno - "Geez, rent Juno, get over it." / 4x11 - Family Remains
- Nell - "That's psycho Nell!" / 4x11 - Family Remains
- Cocoon - "I ain't Steve Guttenberg and this ain't Cocoon." / 4x12 - Criss Angel Is a Douchebag
- Dead Poets Society - "Go have your Robin Williams "Oh Captain! my Captain!" moment." / 4x13 - After School Special
- Heathers, Revenge of the Nerds & Hello Kitty - "Look, Martha Dumptruck, Revenge of the Nerds, and Hello Kitty..." / 4x13 - After School Special
- 21 Jump Street - "Not really. I'm like 21 Jump Street. The bus driver sells pot. Yeah. " / 4x13 - After School Special
- The Adventures of Ozzie and Harriet - "Sounds like Ozzie and Harriet." / 4x14 - Sex and Violence
- Basic Instinct - "Holy crap, you did. Middle of Basic Instinct and you bang Sharon Stone?" / 4x14 - Sex and Violence
- Starsky and Hutch - "Well, last we checked, Huggy Bear ain't available." / 4x15 - Death Takes a Holiday
- House - "No, thanks House." / 4x15 - Death Takes a Holiday
- Ghost - "Oh I am so feeling up Demi Moore." / 4x15 - Death Takes a Holiday
- The Karate Kid - "By tonight? Yeah sure, I'll meet you back at Mr. Miyagi's." / 4x15 - Death Takes a Holiday
- The Amityville Horror - "Dude! You are so Amityville!" / 4x15 - Death Takes a Holiday
- Star Trek - "They come on like shady politicians from Planet Vulcan." / 4x21 - When the Levee Breaks
- The Suite Life of Zack and Cody - "What's this supposed to be, the suite life of Zach and Cas?" / 4x22 - Lucifer Rising
- Star Trek - "No, no. Let's... bail on the holodeck, okay?" / 4x22 - Lucifer Rising
- The X Files - "This isn't "X-Files," pal." / 5x02 - Good God, Y'All
- Lord of the Rings - "So, pit stop on Mount Doom?" / 5x02 - Good God, Y'All
- Twilight - "Eat it, Twilight!" / 5x03 - Free to Be You and Me
- Teenage Mutant Ninja Turtles - "You were wasted by a teenage mutant ninja angel?" / 5x03 - Free to Be You and Me
- Thelma and Louise - "So, what -- I'm Thelma and you're Louise, and we're just gonna hold hands and sail off this cliff together?" / 5x03 - Free to Be You and Me
- Spiderman Comics - "Just stick to the basics, OK? Do not order anything off the menu. Go get her, tiger." / 5x03 - Free to Be You and Me
- The Parent Trap - "The last thing they need to see is a version of "The Parent Trap."" / 5x04 - The End
- Back to the Future - "I thought I smelled your stink on this "Back to the Future" crap." / 5x04 - The End
- A Christmas Carol - "Oh well, if it isn't the Ghost of Christmas' "Screw You.""/ 5x04 - The End
- The Love Guru - "And the orgies and the love guru crap?""/ 5x04 - The End
- East of Eden - "I'll go grab East of Eden's keychain." / 5x05 - Fallen Idols
- Paris Hilton's My New BFF - "Hate to break it to you, lady, but I'm no Paris Hilton BFF." / 5x05 - Fallen Idols
- House of Wax - "I've never even seen House of Wax." / 5x05 - Fallen Idols
- Dynasty - "I had some pretty bad babysitters. Like Ms. Chancy. She only cared about two things: Dynasty, and bedtime. " / 5x06 - I Believe the Children Are Our Future
- Babe - "That'll do, pig." / 5x06 - I Believe the Children Are Our Future
- Charlie & the Chocolate Factory - "Now I know who's turning this town into Willy Wonka's worst nightmare." / 5x06 - I Believe the Children Are Our Future
- Facebook - "A bloody violent monster and you want to be Facebook friends with him?" / 5x08 - Changing Channels
- The Incredible Hulk - "Bana or Norton?" / 5x08 - Changing Channels
- The Incredible Hulk - "Lou Ferrigno." / 5x08 - Changing Channels
- The Incredible Hulk - "Spiky-hair Lou Ferrigno." / 5x08 - Changing Channels
- The Incredible Hulk - "No. Uh, no, it's just...is there, uh, would there be any reason that Lou Ferrigno, the Incredible Hulk, would have a grudge against your husband?" / 5x08 - Changing Channels
- The Incredible Hulk - "A Hulk-sized hole." / 5x08 - Changing Channels
- Starksy and Hutch - "Okay, Huggy Bear, just don't lose them." / 5x10 Abandon All Hope
- One Flew Over the Cuckoo’s Nest - "Look here Nurse Ratched, I’ve seen "Cuckoo’s Nest", so don’t try any of that soul destroying authoritarian crap on me." / 5x11 - Sam, Interrupted
- Silkwood - "How was your “Silkwood” shower?" / 5x11 - Sam, Interrupted
- Silence of the Lambs - "Well then, quid pro quo Clarice." / 5x11 - Sam, Interrupted
- Welcome Back, Kotter - "Welcome back, Kotter." / 5x12 - Swap Meat
- Fatal Attraction - "So she’s gone all Glenn Close?" / 5x13 - The Song Remains the Same
- Fatal Attraction - "No-one... just this psycho bitch who likes to boil rabbits." / 5x13 - The Song Remains the Same
- Back to the Future - "So you’re like a DeLorean without enough plutonium?" / 5x13 - The Song Remains the Same
- Dr. Quinn, Medicine Woman - "What do I look like? Dr. Angel, Medicine Woman?" / 5x13 - The Song Remains the Same
- Terminator - "What? That their sons are back from the future to save them from an angel that’s gone terminator? Come on, those movies haven’t even been made yet." / 5x13 - The Song Remains the Same
- Star Trek - "—we beam her right off the starship." / 5x13 - The Song Remains the Same
- When Harry Met Sally - "Why do angels care when Harry met Sally?" / 5x14 - My Bloody Valentine
- Full Metal Jacket - "So he goes "full metal jacket" on us?" / 5x15 - Dead Men Don't Wear Plaid
- Poltergeist - "Okay, thanks Carol-Anne." / 5x16 - Dark Side of the Moon
- Psycho - "And you keep an eye on Norman Bates here." / 5x19 - Hammer of the Gods
- Babar - "Like full-on Babar." / 5x19 - Hammer of the Gods
- Motel Hell - "Motel Hell." / 5x19 - Hammer of the Gods
- The Legion Of Doom - "Or we tell the Legion of Doom about your secret identity." / 5x19 - Hammer of the Gods
- Army of Darkness - "All right, you primitive screwheads, listen up." / 5x19 - Hammer of the Gods
- Austin Powers - "So this is Dr. Evil's lair, huh?" / 5x21 - Two Minutes to Midnight
- Kojak - "Whoa, looking sharp, Kojak." / 6x03 - The Third Man
- The Ten Commandments - "What is Chuck Heston's disco stick doing down here anyways?" / 6x03 - The Third Man
- James Bond - "I was expecting more Dr. No, less Liberace." / 6x03 - The Third Man
- Punk'd - "Hey, any time we get to "Punk" Crowley works for us." / 6x04 - Weekend at Bobby's
- Zac Efron & Justin Bieber - "Alright, you go with Efron. I got Bieber." / 6x05 - Live Free or Twihard
- Twilight - "Hey, try Lautner." / 6x05 - Live Free or Twihard
- Watch Mr. Wizard - "Newsflash, Mr. Wizard: vampires pee!" / 6x05 - Live Free or Twihard
- Twilight - "Oh, God, I'm Pattinson." / 6x05 - Live Free or Twihard
- Taxicab Confessions - "Right, and then big sis' "Taxicab Confession" sends her over the edge." / 6x06 - You Can't Handle the Truth
- God is my co-pilot - "What, Satan is my co-pilot?" / 6x06 - You Can't Handle the Truth
- Marathon Man - "Anything from Marathon Man?" / 6x06 - You Can't Handle the Truth
- Terminator - "You froze? You have been Terminator since you got back." / 6x06 - You Can't Handle the Truth
- Soylent Green - "So all that tribute vanishing from the morgue - what do you think, a Soylent Green situation?" / 6x06 - You Can't Handle the Truth
- Seinfeld - "Hello, Newman." / 6x07 - Family Matters
- Robocop - "And if you weren't RoboSam, you'd feel it, too." / 6x07 - Family Matters
- Batman - "With all that dead blood firing through your veins, I'm not sure you've got enough juice to fire up that psychic Bat-Signal of yours, do you?" / 6x07 - Family Matters
- Fright Night - "I'm asking the questions here, Fright Night." / 6x07 - Family Matters
- Legoland - "Legoland?" / 6x07 - Family Matters
- The Muppet Show - "Well, if the old man's Kermit, who's hand's up his ass?" / 6x07 - Family Matters
- Jaws - "Putting Jaws in a fish bowl?" / 6x07 - Family Matters
- Robocop - "Let me get dressed, Robocop." / 6x08 - All Dogs Go to Heaven
- Scooby-Doo - "Where is this little "Scooby Gang" of yours?" / 6x08 - All Dogs Go to Heaven
- Gigantor - "I mean, it's your gigantor body and and maybe your brain, but it's not you." / 6x08 - All Dogs Go to Heaven
- Dexter - "Thanks, Dexter. That's reassuring." / 6x08 - All Dogs Go to Heaven
- Woodstock - "It's not her fault she took the brown acid." / 6x09 - Clap Your Hands If You Believe...
- Pinocchio - "You want to be a real boy, Pinocchio, you got to act the part.... Until we get you back on the soul train, I'll be your conscience." / 6x09 - Clap Your Hands If You Believe...
- Soul Train - "Until we get you back on the soul train, I'll be your conscience." / 6x09 - Clap Your Hands If You Believe...
- Close Encounters of the Third Kind - "Close encounter! Close encounter!" / 6x09 - Clap Your Hands If You Believe...
- The Elves and the Shoemaker - "It's like the story with the shoe guy and all the elves." / 6x09 - Clap Your Hands If You Believe...
- The Shawshank Redemption - "Shawshank's a great flick, but let's skip the shower scene." / 6x10 - Caged Heat
- The Never-Ending Story - "Dad never wrote anything about dragons. I promise. I'd remember if I read the Never-Ending Story in there." / 6x12 - Like a Virgin
- Lord of the Rings - "Which says what, that they live in Middle Earth?" / 6x12 - Like a Virgin
- Memento - "Let's Memento this thing, shall we?" / 6x13 - Unforgiven
- Monty Python and the Holy Grail - "And none of this "it's just a flesh wound" crap." / 6x14 - Mannequin 3: The Reckoning
- Jersey Shore - "Paterson, New Jersey. Hey, maybe we'll have a Snooki sighting." / 6x14 - Mannequin 3: The Reckoning
- Girls Gone Wild - "Oh - ghost gone wild." / 6x14 - Mannequin 3: The Reckoning
- Nineteen Eighty-Four - "Sam, good news: Big Brother's watching." / 6x14 - Mannequin 3: The Reckoning
- The Muppet Show & Ipad - "They don't even dissect anything good in there. I mean, bigger than Kermit, they use an iPad." / 6x14 - Mannequin 3: The Reckoning
- Child's Play - "Okay, so what we've got a bunch of killer dolls, like Chucky? I mean, come on, that's just freaking creepy." / 6x14 - Mannequin 3: The Reckoning
- Batman - "Riddle me this bat boy: ghosts aren't exactly known for hopping county lines, right?" / 6x14 - Mannequin 3: The Reckoning
- Mannequin - "I don't like the way Kim Catrall's looking at me." / 6x14 - Mannequin 3: The Reckoning
- The Parent Trap - "We've been Parent Trapped." / 6x14 - Mannequin 3: The Reckoning
- Plants vs Zombies - "Well, that's ridiculous. Plants could never kill a zombie." / 6x14 - Mannequin 3: The Reckoning
- Star Trek - "It's like a Khan worm on steroids." / 6x16 - And Then There Were None
- The Waltons - "If these people are the Waltons, then why the hell are they dying?" / 6x17 - My Heart Will Go On
- Batman - "Well riddle me this..." / 6x17 - My Heart Will Go On
- Titanic - "Besides, Titanic didn't suck that bad. Winslet's rack?" / 6x17 - My Heart Will Go On
- Star Trek - "I know where we can find one. March 5th 1861. Sunrise Wyoming. We’ll Star Trek IV this bitch." / 6x18 - Frontierland
- Star Trek - "It’s like I don’t even know you guys anymore. Star Trek IV. Save the whales." / 6x18 - Frontierland
- I Dream Of Jeannie - "C’mon Cas, I Dream of Jeannie your ass down here pronto" / 6x18 - Frontierland
- James Bond - "So we get stuck with Miss Monneypenny" / 6x18 - Frontierland
- Every Which Way but Loose/Any Which Way You Can - "His name is Clyde." / 6x18 - Frontierland
- Walker, Texas Ranger - "This here is Walker. He's a Texas Ranger." / 6x18 - Frontierland
- Blazing Saddles - "Candygram for Mongo!" / 6x18 - Frontierland
- Die Hard - "Yippie Ki Yay, motherf..." / 6x18 - Frontierland
- The Hangover - "Missed you at the posse this morning. I was a one-man wolfpack." / 6x18 - Frontierland
- Zombieland & Pleasantville - "I was expecting more Zombieland, less Pleasantvill" / 6x19 - Mommy Dearest
- Outbreak - "What the hell's going on here? Does every monster in this town have the motaba virus?" / 6x19 - Mommy Dearest
- Perfect Strangers - "He's the Balki Bartokomus of Heaven - he can make a mistake." / 6x20 - The Man Who Would Be King
- Kojak - "Yeah, you think, Kojak?" / 6x20 - The Man Who Would Be King / 6x22 - The Man Who Knew Too Much
- Dreamscape - "We can't just sit here Bobby, I've got to help him... Dreamscape his noggin, something!"/ 6x22 - The Man Who Knew Too Much
- Wayne's World - "Excuse me, you got any Grey Poupon?" / 7x01 - Meet the New Boss
- Star Trek - "Why would the devil holodeck you a whole new life, when he could just kick your ass all over the cage?" / 7x02 - Hello, Cruel World
- One Flew Over the Cuckoo's Nest - "Turning on his GPS in case he tries to fly the Cuckoo's Nest" / 7x02 - Hello, Cruel World
- Beautiful Mind - You cannot be in that crater back there. I can't… If you're gone, I swear I am gonna strap my Beautiful Mind brother into the car and I'm gonna drive us off the pier. / 7x02 - Hello, Cruel World
- Girl, Interrupted - "Before you bail again - Girl, Interrupted over there - any thoughts?" / 7x03 - The Girl Next Door
- James Bond - "With a license? A license to kill!" / 7x04 - Defending Your Life
- Ally McBeal - "Enough Ally McBeal." / 7x04 - Defending Your Life
- That 70's Show - "Don Stark. Why do I know that name?" / 7x05 - Shut Up, Dr. Phil
- Bewitched - "It’s kind of like Bewitched. Don’s Darrin, doesn’t even know it, lots of laughs until you cheat on your wife" / 7x05 - Shut Up, Dr. Phil
- Bewitched - "Hey, Nicole Kidman was in the remake. Redhead, hello!" / 7x05 - Shut Up, Dr. Phil
- Bewitched - "It’s like when they switched Darrins." / 7x05 - Shut Up, Dr. Phil
- Dirty Dancing - "Nobody puts baby in a corner!" / 7x06 - Slash Fiction
- Dirty Dancing - "Swayze movie! Swayze always gets a pass!" / 7x06 - Slash Fiction
- Watch Mr. Wizard - "Okay, let me get Mr. Wizard on speed-dial." / 7x06 - Slash Fiction
- Desperate Housewives - "You want me to Desperate Housewife these mothers?" / 7x06 - Slash Fiction
- Dead Poets Society - "Okay, "Dead Poets Society", fine." / 7x08 - Season 7, Time for a Wedding!
- Star Wars - "Of course, the sketch looks more like a Chewbacca head." / 7x09 - How to Win Friends and Influence Monsters
- Star Wars - "Relax, it's a field not the Death Star. Dick's at a TED conference, it's all over the Huffington Post." / 7x11 - Adventures in Babysitting
- Tales from the Crypt - "Nothing that turns a dude into a Cryptkeeper." / 7x12 - Time After Time
- 12 Monkeys - "Alright, well I am twelve monkeyed no matter what I say so here goes." / 7x12 - Time After Time
- The Untouchables - "I gotta tell you Untouchables is like one of my favorite movies ever. I must've seen it like 50 times." / 7x12 - Time After Time
- Back to the Future II - "He's using the Biff strategy...Chronos is betting on races he already knows the outcome of." / 7x12 - Time After Time
- Back to the Future III - "Back to the Future 3! I'm going to need some paper." / 7x12 - Time After Time
- Wonder Woman - "Like Wonder Woman?" / 7x13 - The Slice Girls
- Hannah Montana - "This morning, Emma was a baby. By sunset, she's Hannah Montana. Early years." / 7x13 - The Slice Girls
- The Beatles - "I am the Eggman." / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Wonder Woman - "You got anything on Wonder Woman?" / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Shark Week - "Shark week man. How do you not watch that? Whole week of sharks!" / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Breaking Bad - "We don't care if you broke bad or whatever." / 7x14 - Plucky Pennywhistle's Magical Menagerie
- Saturday Night Live - "Seriously - Dractopus, Seabiscuit the Impaler, Landshark...what's next?." / 7x14 - Plucky Pennywhistle's Magical Menagerie
- The House of God - "Yeah, your, uh, scooping days are over, Gomer." / 7x15 - Repo Man
- Psycho - "It's not like the guy's freaking Norman Bates." / 7x17 - The Born-Again Identity
- Star Wars - "Quit being Dalai-friggin-Yoda about this. Get pissed!" / 7x17 - The Born-Again Identity
- Ghost - "I mean, who knows more about being a ghost than Bobby? Instant Swayze, right?" / 7x18 - Party On, Garth
- Star Wars - "Perfect, it's in the middle of the Death Star." / 7x20 - The Girl with the Dungeons and Dragons Tattoo
- Veronica Mars - "Doesn't mean I got to be happy about sending in Veronica Mars." / 7x20 - The Girl with the Dungeons and Dragons Tattoo
- Transformers - "The Transformer, it's Megatron." / 7x21 - Reading Is Fundamental
- Pac-Man & True Blood - "I think anyway you slice it we've got Pac Man and True Blood in the same room." / 7x22 - There Will Be Blood
- Family Guy - "Shut up, Meg!" / 7x23 - Survival of the Fittest
- Rain Man - "He's like a crappy little credit-card-counting criminal prodigy Rain Man." / 8x05 - Blood Brother
- Casper The Friendly Ghost - "Yeah, but not before Casper had a chance to make a run for it." / 8x06 - Southern Comfort
- Robot Chicken - "I don't know what we're hunting. Maybe it's a tulpa, maybe it some guy who watched too much Robot Chicken." / 8x08 - Hunteri Heroici
- Sherlock Holmes - "Strike one, Sherlock." / 8x08 - Hunteri Heroici
- Fifty Shades of Grey - "You saw the chainmail. This could be "Fifty Shades of Greyfox" for all we know." / 8x11 - LARP and the Real Girl
- Star Wars - "Your Worshipfulness" / 8x11 - LARP and the Real Girl
- Braveheart - "And dying in your beds many years from now, would you be willing to trade all the days, from this day to that, for one chance – Just one chance to come back here and tell our enemies that they may take our lives, but they will never take...our freedom!" / 8x11 - LARP and the Real Girl
- Star Wars - "So you're like Yodas to our Jedis." / 8x12 - As Time Goes By
- Saturday Night Live - "You mean, how do we "Oh No!" Mr. Bill over there?" / 8x13 - Everybody Hates Hitler
- DC Comics - "I didn't see any letters on Clayface." / 8x13 - Everybody Hates Hitler
- The Three Stooges - "Curly was a freaking genius!" / 8x15 - Man's Best Friend with Benefits
- The Three Stooges - "It's supposed to be obvious, man. Three stooges!" / 8x15 - Man's Best Friend with Benefits
- Dawn of the Dead - "Yeah, and if things go all "Dawn of the Dead" on us, you'll be our first call." / 8x16 - Remember the Titans
- South Park - "What are you, like a real life Kenny?" / 8x16 - Remember the Titans
- Xena: Warrior Princess - "Did you figure out who Xena-wannabe was?" 8x16 - Remember the Titans
- National Lampoon's Vacation - "Yeah, well, you promised, okay? You promised to live a long, Clark Griswold life full of prostate exams and colonoscopies, all right?" / 8x16 - Remember the Titans
- Maximum Overdrive - "Wait, are we talking a Maximum Overdrive situation here?" / 8x17 - Goodbye Stranger
- Zero Dark Thirty - "I saw you Zero Dark Thirty that demon." / 8x17 - Goodbye Stranger
- Indiana Jones - "Cas and I will go in and get our Indiana Jones on." / 8x17 - Goodbye Stranger
- Family Guy - "Shut Up Meg" / 8x17 - Goodbye Stranger
- Bill Nye The Science Guy - "Okay, bottom-line it for me, Bill Nye." / 8x17 - Goodbye Stranger
- Lord of the Rings - "Listen, I may not be able to carry the burden that comes with these trials, but I can carry you." / 8x17 - Goodbye Stranger
- Lord of the Rings - "C'mon man, it's the Rudy-hobbit. Rudy hobbit always gets a pass!" / 8x17 - Goodbye Stranger
- The Apple Dumpling Gang - What, sneaking out in the middle of the night to go hunt monsters with the Apple Dumpling gang? / 8x18 - Freaks and Geeks
- To Kill a Mocking Bird - "Want to tell me what happened back in there Boo Radley?" / 8x19 - Pac-Man Fever
- Wargames - "Okay, Wargames." / 8x19 - Pac-Man Fever
- The Bourne Identity - "Who is she, Jason Bourne?" / 8x19 - Pac-Man Fever
- Tron - "Thanks for stopping by Charlie, I always wanted to get Tron-ed." / 8x19 - Pac-Man Fever
- E.T. - "So this is it? E.T. goes home." / 8x22 - Sacrifice
- The Hunger Games - “You're a crappy shot, Katniss,” / 9x02 - Devil May Care
- Breaking Bad - "Cas is a big boy, if things go Breaking Bad, he's got our number." / 9x02 - Devil May Care
- Zero Dark Thirty - "Well, I figured the King of Hell might know a few things, so why not Zero Dark Thirty his ass?" / 9x02 - Devil May Care
- Marvel characters Iron Man (Tony Stark) and The Incredible Hulk (Bruce Banner) - "Agents Stark and Banner, FBI." / 9x02 - Devil May Care
- G.I. Joe - "And why's she playing G.I. Joe?" / 9x02 - Devil May Care
- United States Navy SEALs - "We gotta flank SEAL team douche in there" / 9x02 - Devil May Care
- Game of Thrones - "You know, after everything that happened, I figured we could use a little break ourselves, so I picked you up Season One of Game of Thrones." / 9x04 - Slumber Party
- Game of Thrones - "Wow. That Joffrey's a dick." / 9x04 - Slumber Party
- The Wizard of Oz - "Okay, pace yourself, Toto" / 9x04 - Slumber Party
- Scooby Doo - "Ruh-roh!" / 9x05 - Dog Dean Afternoon
- The Excorcist - "Your head spins around like The Exorcist." / 9x05 - Dog Dean Afternoon
- Breaking Bad - "What happened? Draw the short straw, decide to break bad?" / 9x05 - Dog Dean Afternoon
- Silence of the Lambs - "Just be careful, don't fall for any of his "quid pro quo" crap." / 9x06 - Heaven Can't Wait
- Saturday Night Fever - "Undo your buttons... That's far enough Tony Manero." / 9x06 - Heaven Can't Wait
- 1966 Batman TV Show - "I gave him the number to the Bat Phone" / 9x07 - Bad Boys
- Casper the Friendly Ghost - "All right, Casper... Where're you at?" / 9x07 - Bad Boys
- G.I. Joe action figures - "So give me your best Kung Fu grip." / 9x07 - Bad Boys
- Gunsmoke - "Let's barbecue old MacDonald here, get the hell out of Dodge." / 9x07 - Bad Boys
- The Omen - "We got ourselves a Damien on our hands?" / 9x07 - Bad Boys
- "Total hail Mary." / 9x07 - Bad Boys
- "Total hail Mary" refers to a Hail Mary pass which is a very long forward pass in American football. Hail Mary passes are commonly made in desperation when a teams chances of winning the game are small. The term became widespread after a December 28, 1975 NFL playoff game between the Dallas Cowboys and the Minnesota Vikings, when Cowboys quarterback Roger Staubach (a Roman Catholic) said about his game-winning touchdown pass to wide receiver Drew Pearson, "I closed my eyes and said a Hail Mary."[source]
- Dr. Seuss' How the Grinch Stole Christmas - "Yeah, like your heart grew three sizes." / 9x11 First Born
- Teen Mom - "I'm gone for two weeks, and you're like an episode of "Teen Mom."" / 9x12 - Sharp Teeth
- "Somebody changed the playbook, man, you know?" / 9x12 - Sharp Teeth
- a playbook is used by american football players to remember the plays for a game
- The Andy Griffith Show - "Oh, what? Sheriff Andy Taylor here wasn’t good enough for you?" / 9x12 - Sharp Teeth
- refers to the character Andy Taylor who watches over the town of Mayberry.
- Marvel character Wolverine - "No, you just go all Wolverine on cattle." / 9x12 - Sharp Teeth
- "No, Rudy was on and then Unforgiven." / 9x13 - The Purge
- refers to the sports movie Rudy
- also refers to the Western film Unforgiven
- Thinner - "A Thinner sitch here?" / 9x13 - The Purge
- a novel by Stephen King
- Saturday Night Live - "Kind of like Hans and Franz, uh, but less German." / - 9x13 The Purge
- Scooby-Doo - "You two clowns are gonna get inside that mystery machine outside and you're gonna leave town or I'm gonna put holes in your knees." / - 9x15 #Thinman
- Bad News Bears - "And what about the rest of the Bad News Bears, huh?" / - 9x15 #Thinman
- Scream - "So there was no teleporting, just a couple of douchebags doing a "Scream" thing." / 9x15 - #Thinman
- Nightmare on Elm Street - "We're working on it, okay? And from what you told us, this thing sounds new ... or Freddy Kreuger." / 9x20 - Bloodlines
- The Godfather - "What is this, Godfather with fangs?" / 9x20 - Bloodlines
- Fiddler on the Roof - "Only if it's Fiddler." / 9x22 - Stairway to Heaven
- Full Metal Jacket - "Oh, so you're a full-metal douche again." / 9x23 - Do You Believe in Miracles?
- Game of Thrones - "Game of Thrones is complicated. Shower sex, that's complicated. Hell ain't complicated."
- The Princess Bride - "What did you think was gonna happen? You just stroll up here and say "my name is Inigo Montoya, you killed my father, prepare to die" and I'd just roll over?" / 10x02 - Reichenbach
- Sons of Anarchy- "This fleabag looks like she ain't done chowing down on Sons of Anarchy just yet." / 10x04 - Paper Moon
- Marvel Comics - "Guy at the bar saw you before you went all Wolverine on his buddy." / 10x04 - Paper Moon
- Grimms' Fairy Tales - "If she's not icing people, why play the Big Bad wolf?" / 10x04 - Paper Moon
- The Brady Bunch Show - "Yeah, you're a regular psycho Brady Bunch." / 10x04 - Paper Moon
- Our Town & Oklahoma! - "You did Our Town, which was cool. But then, you did that crappy musical." / 10x05 - Fan Fiction
- Marvel Comics - "You ran tech, Wolverine." / 10x05 - Fan Fiction
- Rent - "There is no other road. No other way. No day but today." / 10x05 - Fan Fiction
- Mr. Belvedere - "I got news for you, Mr. Belvedere. The jacket's canvas." / 10x06 - Ask Jeeves
- Clue - "Keep an eye on Mrs. Peacock and Colonel Mustard." / 10x06 - Ask Jeeves
- Bram Stoker's Dracula - "Now I don't know why, but he's covering for them. He's acting like their Renfield." / 10x06 - Ask Jeeves
- Clue - "Cut the crap, Wadsworth." / 10x06 - Ask Jeeves
- The Lion King - "Okay, Mufasa. Enough with the Circle of Life crap." / 10x08 - Hibbing 911
- The Girl with the Dragon Tattoo - "Alright. Skip ahead, Dragon tattoo." / 10x11 There's No Place Like Home
- Scarface - "Some scarface-looking dude." / 10x12 About a Boy
- Christine - "Okay, so Trini and everything else in this truck went all "Christine". / - 10x13 Halt & Catch Fire
- Shocker - "This might be a 'Shocker' situation." / 10x13 Halt & Catch Fire
- Lawnmower Man - "So how the hell are we gonna deal with Lawnmower Man?" / 10x13 Halt & Catch Fire
- G.I. Joe - "Hey, Kung-Fu grip, you coming?" / 10x15 The Things They Carried
- Operation - "No, we're done playing 'Operation'." / 10x15 The Things They Carried
- Dr. Seuss's How the Grinch Stole Christmas - "Well, y'know. Scissors to the gut really bring out the Grinch in me." - 10x16 Paint It Black
- The Rocky & Bullwinkle Show - "Boris. Where's Natasha?" - 10x17 Inside Man
- Dr. Phil - "Here I am playing Dr. Phil to the King of Hell. Never saw that one coming." - 10x17 Inside Man
- Speed 2: Cruise Control - "I'd like to get back to the bunker, get my buzz on, and you know, pass out watching Speed 2: Cruise Control." - 10x19 The Werther Project
- Caddyshack - "It's in the hole! It's in the hole!" - 10x20 Angel Heart
- Happy Gilmore - "Happy Gilmore. Well-played." - 10x20 Angel Heart
- Magic Mike - "Is this like a Magic Mike moment?"/ 11x01 Out of the Darkness, Into the Fire
- Dean has killed the most main antagonists in the series, with four. He killed Azazel, Eve, Dick Roman and Abaddon. He's also killed secondary antagonists, Ruby and Zachariah.
- Dean is the first human to kill an angel on the series.
- Dean's leather jacket, that he inherited from John, is nearly identical to the one worn by the title character of the movie Taffin (Played by Pierce Brosnan).
- Dean has time traveled more than any other character. Going back in time 4 times (To the 1800s, the 1940s and the 1970s twice) and going forward once (to an Alternate 2014). If one counts return trips, Dean has time traveled ten times.
- Dean has been aged both forward into an old man and aged back into a teenager on different occassions.
- Dean seems to be rather clueless about Pop culture, evidenced by him not knowing what an Xbox is, and Believing MySpace to be a porn site. However, he seems to have gotten better over time as he now has a phone with apps, something that shocked Sam.
- Dean is a big movie buff. Sam stated that Dean knows all of Clint Eastwoods movies line for line, especially the "the monkey movies." He is also a huge fan of Chuck Norris. He also claims "Untouchables" is one of his favorite movies.
- Dean suffers from Pteromerhanophobia (fear of flying).
- Dean is very good at flirting, proved in notable episodes also he was very impressive in The Girl with the Dungeons and the Dragon Tattoo where he coached a lesbian, i.e., Charlie Bradbury into flirting with a male security guard.
- Dean has been to the most number of different realms, Heaven, Hell, Avalon, and Purgatory.
- Dean is descended from one of the biblical brothers Cain or Abel, the latter who is the first murder victim who died at the hand of his brother.
- During his time in Purgatory, Dean seems to have adopted a new, slightly unstable personality. He’s ruthless, volatile at times, and seems to have developed a underlying blood-lust that bubbles to the surface occasionally. Not unlike his time in hell, he immersed himself the darker aspects of his being in Purgatory. Whereas in hell, Dean gave into his darker thoughts and enjoyed torturing, in Purgatory, he appears to have given into his darker instincts and embraced the warrior lifestyle that he’d basically been raised for his entire life.
- When playing Rock, Paper, Scissors, Dean always loses. The only way he could win is in an alternate universe.
- Dean's Impala was a gift from John, which is why he's so protective of it.
- He is allergic to cats as evidenced in the episode Man's Best Friend With Benefits. He also strongly dislikes dogs for some unknown reason though he develops a bond with the Colonel due to the human/animal mind meld he underwent to talk to him. He also briefly had some dog-like mannerisms as a result of the ritual for about a day.
- He is into hentai (anime porn).
- A running gag on the show is that Dean never gets his pie. Although he seems to have gotten some in "Hammer of the Gods" and "Dead Men Don't Wear Plaid." However, in Hammer it came from a group of pagan gods and in Dead Men it came from a zombie.
- Dean unknowingly admits to watching Oprah, something that surprised Sam.
- Dean was named after his grandmother, Deanna.
- Dean's favorite food (with the exception of pie) is a bacon cheeseburger which, in his heart, believes to be as good as sex.
- Dean is allergic to cats
- One of his favorite weapons seems to be a two shot sawed-off shotgun.
- Dean, unlike Sam, Bobby, and John, has never been possessed by a demon or angel. However, he became close to transforming into a demon while in Hell, and later became one due to the mark of Cain.
- Dean has also shown he is quite good at cooking as seen in Trial And Error. In Brother's Keeper, his food is shown to be so good that even Death enjoyed it.
- In Changing Channels, Dean reveals that he hates procedural cop shows because say how they are all the same. He also thinks that only "no talent douchebags" wear sunglasses at night. He later tells Sam that he thinks that only blind people and douchebags wear sunglasses inside.
- Of all the supernatural beings and creatures that he has met and hunted, Death is the only being that Dean is afraid of.
- Dean is considered an "honorary dog" by at least the Colonel. As a result the Colonel tried to tell him what a dog's true role is as its not man's best friend. The spell he was using wore off before Dean could find out however.
- So far, Dean, along with Cain and Lilith, are the one three known characters to become a demon without going through hundreds of years of torture in Hell.
- Dean's favorite song is a tie between Led Zeppelin's "Ramble On" and "Traveling Riverside Blues."
- Dean is one of only two people known to be cured of being a demon.
- Through his behavior in the early episodes of Season 10, it is evident that Dean considers himself to be superior to Crowley, who is the King of Hell, and may thus have been the strongest demon.
- Even though he has a stronger connection with angels throughout the series he's the Winchester to eventually becomes a demon, specifically a Knight of Hell.
- Dean has proven to be a skilled vampire hunter whenever the Winchesters encounter the species, once killing five vampires single-handedly out of a nest of ten, three of the others having been killed before the hunt during Blood Brother. While briefly a vampire himself, Dean single-handedly slaughtered a massive nest, including a powerful vampire who had easily overpowered him only minutes before. When he was trying to "take the edge off" of the Mark of Cain, Dean single-handedly killed six vampires before Sam even arrived, something he regarded as a new personal best. While Sam has killed a number of vampires himself, he doesn't seem to be as skilled at it as Dean.
- After being turned into a teenager, Dean gained an appreciation for Taylor Swift despite it being far from his usual taste in music. To Sam's surprise, this like of Taylor Swift seems to have stayed with him even after the spell was reversed.
- Dean has been transformed into the most supernatural creatures on the show: a vampire, Death, a dog and a Knight of Hell.
- Dean has killed four angels on the series: the Seraphim Zachariah, the Rogue Angel who was a regular angel and two Reapers, Maurice and April Kelly. In contrast, Sam has killed none.
- Dean has killed some of the strongest creatures of their species. So far, he has killed Azazel, Eve, Cain, and Dick Roman. He has also just recently killed one of the most most powerful beings in existence, Death.
- Before Dean killed Death, while he helped Sam defeat War, he never actually stopped a Horseman on his own unlike Sam and Castiel who stopped Famine and Pestilence respectively.
- As Dean was born in 1979, he is physically 36 years old, but since time is different in Hell than it is on Earth, he is spiritually 76 years old.
- Dean, and Sam, are the only characters to appear in every single episode of Supernatural, since the Pilot.