|“|| Crowley : First impressions can be deceiving, Moose. For instance, I once thought of you as dull and plodding. |
Sam : .....
Crowley : Oh, never mind. Bad analogy.
in Hell's Angel
Sam Winchester and the demon Crowley are never friends, but repeatedly become allies throughout the series. Their first mutual adversary was Lucifer. Due to his previous experience with Ruby, Sam did not trust Crowley at all and tried to kill him many times. He did not develop much trust in Crowley unlike Dean when the Winchesters first met him. Crowley affectionately refers to Sam as "Moose".
Season 5 Edit
Sam and Dean meet Crowley when Becky Rosen reveals to them that the demon has the Colt. The brothers infiltrate his house but find themselves rather welcomed, with Crowley giving them the Colt as well as more ammunition. The brothers then attempt to use the Colt against Lucifer, but when the Colt proves ineffective, they both blame Crowley for providing them with false information.
Crowley approaches them weeks later, having barely survived being hunted down by other demons. Sam makes a move to stab Crowley with the demon-killing knife, but Crowley insists he too didn't know the Colt wouldn't work. He offers them help in locating Pestilence, having somehow found out that they are after the Four Rings worn by the Four Horsemen.
Crowley convinces Dean to leave Sam behind while the two of them hunt down a certain demon, at first claiming it was because he didn't like Sam due to Sam's tendency to constantly try to kill him. It is later revealed that said demon has a history with Sam, and Crowley wanted to avoid the plan being jeopardized.
After they obtain Pestilence's ring, Crowley continues to aid the Winchesters in finding Death. By this point, Sam seems to trust Crowley more, but still remains wary of him.
Season 6 Edit
Sam returns from Lucifer's Cage through unknown means, and instead of going back to Dean, he resumes hunting and also starts working with the Campbells, unaware that by doing so, Sam is also working for Crowley, who is using them to capture monsters and Alphas.
When Bobby needs help getting his soul back from Crowley, Sam and Dean fly to Scotland and dig up Crowley's bones. While Dean is tempted to just kill the demon, Sam stops him, saying that a deal was a deal.
When Sam does find out, Crowley holds Sam's soul, which he claims to be in possession of, as ransom, forcing the Winchesters to continue working for him.
Eventually, Sam works with Dean, Meg and Castiel in an attempt to kill the demon. He and Dean also convince Crowley to return Bobby Singer's soul by locating Crowley's human remains. When the demon proves to have survived an attempt on his life, Sam and Dean begin hunting for him, also to stop him from opening Purgatory.
Season 7 Edit
In season 7, Sam reluctantly allies with Crowley again to fight against the Leviathans, notably when they need his blood for the weapon that can kill Leviathans. Despite this, Sam still doesn't trust Crowley. After Dean kills Dick Roman and disappears with Castiel, Crowley appears and taunts Sam about being "well and truly on your own" and kidnaps Kevin Tran, refusing to tell him where Dean and Castiel are.
Season 8 Edit
Shortly after Dean's return from Purgatory, Sam works with him to try and seal up Hell forever, so they could be rid of the demons, including Crowley. As part of the trials necessary to complete this task, Sam attempts to turn Crowley human in the episode "Sacrifice", even saving him from Abaddon, but stops at the last moment at Dean's insistence.
Season 9 Edit
Sam reluctantly works with Crowley to stop Abaddon. After Dean kills Abaddon, Sam lets Crowley go free but refuses to help him remove a devil's trap bullet, saying that letting him live should be enough for him. He gets angry when Dean works with Crowley to hunt Metatron and sends him away.
Season 10 Edit
Sam yells at Crowley when he finally gets him on the phone and learns that he is sending demons after Dean. Crowley lets Sam track Dean down to force him to get moving and helps Sam capture Dean in order to stop him as Dean as a demon is completely out of control. Sam hands him the First Blade in exchange.
Season 11 Edit
|“|| Crowley : Makes your flesh crawl, doesn’t it Moose? I get it. I’m the King of this place. It’s still not my cup of tea. |
Sam : I don’t know, Crowley. I’d say it suits you. Dark. Empty.
Crowley : Fascinating; the utter contempt, when I’m in the midst of saving the Winchester’s bacon, again.
— Crowley and Sam, in O Brother, Where Art Thou?
Sam experiences mysterious visions which beckon him to seek out Lucifer. After Dean relents, the brothers seek out Crowley and Rowena's help. The plan was initially to wait for Dean to come back after checking out a crime scene, but Sam decides to go ahead without him and travels to Limbo, where the trio meet Lucifer.
Unfortunately, Rowena had been working for Lucifer all along and Sam ends up trapped inside a cage with his former torturer. Crowley thus calls Dean and informs him of Sam's predicament. With Dean's help, Crowley manages to force Rowena to cast a spell to send Lucifer back to the Cage, using a witchcatcher. Once Sam is safe, Crowley orders him and his brother to get out of Hell.
Sam and Crowley do not hear from each other for a couple of weeks. A demon informs Sam that Crowley has become Lucifer's bitch-boy, and Crowley himself, upon escaping Lucifer's clutches, tells the brothers of some of the things Lucifer did to him. Both Sam and Dean express joy at the Crowley's suffering.
With Crowley and Rowena's help, the brothers set up a trap for Lucifer with the intent of expelling him from Castiel. Their combined efforts accomplish nothing, aside from Crowley getting momentarily trapped inside Castiel until Sam expels him using an incantation.
Weeks pass by again before Sam and Crowley see each other again. God reveals himself to the brothers and devises a plan to use angels, witches and demons as part of their attack against Amara. The main members gather at a warehouse, though Sam and Crowley do not converse.
They remain on the same side following the attack's failure. While Crowley and the rest feel hopeless, Sam encourages them to think up another plan, and they end up using a Soul Bomb as their last resort. Dean is selected to carry the bomb to Amara, while Sam and Crowley and the others wait for the results inside an abandoned bar.
When the sun returns to full glow, Sam and Crowley along with everyone else deems the mission complete, and Dean to be dead. The hunter and demon therefore, go their separate ways.
Season 12 Edit
In "American Nightmare", Sam is informed by Dean that Castiel and Crowley are working as a team to try and hunt down Lucifer. In "Rock Never Dies", Sam and Dean go to Los Angeles to help the pair prevent Lucifer from hosting a concert and then killing the fans.
Sam joins Dean in chasing the fans out while Crowley joins Castiel in confronting Lucifer. Together they are successful, and Lucifer departs from his vessel towards a new, more influential vessel. Sam meets up with the team outside, and he and Dean both take notice of the state Crowley is in.
- Mark Sheppard revealed that his favorite insult is "Moose", which is Crowley's nickname for Sam.
- Mark, like the rest of the cast, is a target of Jared Padalecki's pranks. Mark attempted to get back at Jared during the filming of "Hell's Angel", but found he was unsuccessful.
Also Check Out Edit
Dean and Crowley - Crowley's relationship with Dean Winchester.