This is all of Crowley's minor relationships throughout the series.
Romantic relationshipsEditreaper who allies herself with Crowley due to the demise of Death. She assists Crowley by providing him and Dean with a witchcatcher, used to take control of Rowena. They meet face to face onscreen in the season 11 finale, where it is implied that they may have been in a romantic relationship, due to her greeting him in a flirty way and his gaze at her. This earned much confusion and discomfort from everyone else.
If this is the case, then Billie is the third known lover of Crowley and the second angel he has been romantically involved with. Billie's death at Castiel's hands is a bit ironic given that Crowley had been the one to murder Meg, whom Castiel likely had feelings for.
At some point, Crowley became Lilith's second-in-command, and presumably her lover. This led Lilith to hold any and all of the crossroad deals she chose, namely Dean Winchester's.
This led Dean and Sam on a hunt for Lilith, in hopes that they could get her to break off the deal, if not outright kill her. The plan proved unsuccessful, and Dean was ultimately dragged to Hell at the end of season 3.
Crowley likely did not hold much (if any) affection for Lilith, since he accepted the Colt from Bela Talbot and chose not to pass it onto Lilith. He eventually gave the Colt to the Winchesters, and by doing so, he was fighting against The Apocalypse which Lilith had sacrificed her life to start.
|“||If you remember our time in Mesopotamia the way I do, you know I'm a lover, not a fighter.||”|
— Crowley in Goodbye Stranger
They both seek out the Angel Tablet, which has ended up in the possession of Castiel. Ultimately, Crowley is the one who gets his hands on it by literally pulling it out from inside the angel.
They meet again when Crowley attempts to keep Bobby Singer's soul to prevent the Winchesters from completing second trial to lock up Hell. Naomi comes to the Winchesters' aid and allows Bobby's soul to go to Heaven, where it belongs.
Naomi is later killed by Metatron, a fact which Crowley may or may not be aware of.
Their relationship is the second one featured to be between a demon and an angel. The first one is Castiel and Meg, which also ended in the death of the female partner, ironically by Crowley himself.
Gavin was Crowley's son from his time as a human. Gavin was born to an unknown mother, who is never mentioned. Like with Rowena's treatment of Crowley, Crowley treated his son abusively, so badly that he worked Gavin harder than he worked the horses, and wouldn't let him go to school, rendering Gavin illiterate.
Due to a crossroads deal he made, Crowley was eventually dragged off to Hell by hellhounds. Gavin presumably buried his father's body, and began planning for a new life. At some point, Gavin became a captain of a trading ship and left Scotland to sail to America. Unfortunately, his ship went down, killing him and his entire crew.
In Weekend at Bobby's, Bobby and Rufus use a ring retrieved from Gavin's sunken ship to summon his spirit. Out of pure spite for his father, Gavin revealed all he knew about Crowley's former life and revealed to them the location of his human remains. This gave Bobby a bargaining chip for the return of his soul.
In King of the Damned, the demon Abaddon kidnaps Gavin from the year 1723, shortly before he boards his ship. Abaddon attempts to use him and torture him to make Crowley surrender. At first, Crowley is not entirely moved, but does give into her demands. Afterwards, Gavin is livid at his father now being a demon and his previous abuse to him as the latter tries to please Gavin. He grants Gavin the ability to read and even the title "Prince of Hell" which ends up pleasing the latter.
After Abaddon is defeated, Crowley refuses to send him back to his own time, since it would mean his death and teleports him away from the Winchesters. Therefore, he allows his son to start a new life in the 21st century, due to lingering feelings he has from being injected with purified human blood. At this point, Gavin seems to forgive his father, nearly hugging him before they go their separate ways.
|“|| Gavin : So this is goodbye, then? |
Crowley : Yes. Forever. Unless of course I catch you smoking, in which case, I'll smack you stupid.
Gavin : Goodbye, then. And thank you...father.
— Crowley's last words to his son
in King of the Damned
Approximately two years later, Gavin discovers that by arriving in the future, he had caused his beloved fiancé to board his ill-fated ship, which resulted not only in her death, but in her becoming a vengeful spirit. When Gavin decides to go back in time to undo these events, he decides to call Crowley to bid him farewell. Having already refused to allow the Winchesters to go near Gavin, Crowley arrives to stop Gavin from returning to his own time, which will result in his death.
Gavin refuses to obey, firmly stating that he has made up his mind. When Crowley tries to grab a hold of Gavin, Rowena paralyzes him to allow Gavin to go with the Winchesters and complete the spell. Gavin apologizes to Crowley and leaves the area. The loss of his son drives Crowley nearly to tears, showing he had now grown to care for his son. He was left even more distraught when he learns that his mother Rowena helped Gavin as payback for the death of Oskar which Crowley forced her to commit, so he would know the pain of losing one's child.
During Somewhere Between Heaven and Hell, Crowley is shown to still be angry about Gavin's fate as seen in his call with Dean who he yells at for forcing him to send his son away.human. She claimed to have conceived him during a winter solstice orgy, but later confessed to having had him with a rich man who shortly after his birth, abandoned them. Rowena refuses to love Crowley, and was said to have been abusive towards him during his childhood, since she views love as a weakness. She once attempted to sell him for three pigs.
Rowena abandoned Crowley at a work house when trouble with the Grand Coven forced her to flee. They did not meet again for three hundred years. At some point, Rowena discovered her son Fergus' death, and upon reuniting with him, she would continue to refer him to as "Fergus". Crowley himself would utilize magical skills taught to him by Rowena.
In 2015, Rowena is on a hunt for members to add to her very own coven. A skirmish with Raul draws her to Crowley's attention, who promptly sends his demons to capture and torture her. Upon seeing her face, Crowley instantly recognizes her, and refers to her as "mother".
Crowley is momentarily shocked to see her, though he keeps her imprisoned. The realization that her son is a powerful King leads Rowena to manipulate her way into his favor, by convincing him that his demons are disloyal and that only she can be trusted, because she is his mother and that she loves him. Crowley listens to her for a time, due to a sense of obligation.
It isn't until Dean convinces Crowley not to listen to her simply because of their shared blood that Crowley finally decides expels Rowena from his presence.
|“||"Just because someone is blood that doesn't make them family. A wise man once told me, 'Family don't end in blood. But it doesn't start there, either. Family cares about you, not what you can do for them. Family's there through the good, bad, all of it. They got your back, even when it hurts.'" - Dean Winchester.||”|
While they mostly loathe each other, the two are often forced to work together, especially for the Winchesters. When Rowena succeeds in freeing Dean of the Mark of Cain, she turns on the group and casts a spell on Castiel and orders him to kill Crowley. By luck, Crowley escapes his vessel in time. He clearly wants her captured for this as one of his voice mails asks for her whereabouts.
They work together again when the Winchesters require help in contacting Lucifer. Much to Crowley's rage, Rowena is revealed to be working for Lucifer. As Crowley waits for Dean to bring him a witchcatcher so he can force Rowena to do his bidding, they order tea, and answer simultaneously that they want it with "honey and a splash of milk".
Using the witchcatcher, Crowley commands Rowena to send Lucifer back to his Cage, and then to remain by his side in Hell. It is then that Rowena reveals to him why she hates him. Their moment is interrupted by Lucifer himself, who kills Rowena and takes Crowley prisoner.
Weeks later, Rowena reveals herself to Crowley, writing a message that says "BACK FROM THE DEAD FERGUS!". Neither Crowley nor the Winchesters are thrilled to see her alive, with Crowley adding that he does not want her "mucking about" like last time. Mother and son help the Winchesters trap Lucifer in hopes of expelling him, but ultimately fail. The two decide to flee separately, as Sam later remarks "like mother like son".
They reunite when God formulates a plan to use witches, demons and angels to attack the Darkness. Rowena shows mutual fascination in God, much to Crowley's chagrin, who tells God later on that he refuses to call him "dad". Both survive the plan's failure, and regroup and stay together as the second plan which involves using a Soul Bomb goes underway. At the end of Alpha and Omega, the two part ways.
In Season 12, Rowena has chosen to begin a new life, however, Crowley needs the throne of Hell back, but he cannot do so as long as Lucifer is free. He seeks out Rowena to help trap Lucifer back inside his Cage, and uses threats against Rowena's boyfriend Ben to convince her to help. Once the pair confront the archangel, they try to weaken his vessel, though unfortunately, Lucifer proves too powerful for them. Crowley flees the scene, leaving Rowena at the mercy of Lucifer.
Crowley is unsympathetic towards his mother, though knowing her to be the type to sell her services in exchange for survival, he understands how important it is to retrieve Rowena from the archangel. He hunts the pair down with Castiel's help, only to discover Rowena had blasted the archangel to the bottom of the ocean. Fortunately, despite her continued desire to have nothing to do with the, Rowena willingly offers her help in getting rid of Lucifer should her son manage to corner him.
The moment arrives when Lucifer goes after the President. Crowley personally comes to pick Rowena up but finds her having a vicious argument with another man who is her fiancé. Crowley instantly kills him, causing blood to splatter all over Rowena, yet she smiles at him gratefully and considers this act to be the nicest thing he has ever done for her. Crowley is briefly bewildered but returns the smile nonetheless.
Seemingly bonded, Crowley and his mother track down Lucifer to Jefferson Rooney's location and with the help of the Winchesters they manage to expel Lucifer from his latest vessel. However, Crowley disrupts the spell and sends Lucifer back into his old vessel Nick, in order to make a prisoner out of him. Regardless, Rowena banishes Lucifer away and saves the President. After which, Crowley flees the area with his mother.
Unfortunately, mother and son continue to have issues despite somewhat getting on better terms. Rowena still desires vengeance over the death of Oskar, a child she loved more than her own son. When a chance to pay Crowley back for the pain she suffered presents itself, Rowena immediately takes it. She prevents Crowley from stopping his son - and her grandson - Gavin MacLeod from returning to the past, which will result in his death. Crowley is visibly distraught, and Rowena reveals after the fact why she stopped him.
Crowley and Rowena do not interact after this meeting. In a sense, this is Crowley's own fault. He had prevented the spell meant to trap Lucifer in his Cage, hoping instead to keep Lucifer in a makeshift prison so he can use the archangel. The plan eventually backfires with Lucifer's escape. Lucifer targets Rowena and kills her off, much to Crowley's dismay, who had hoped to do the deed instead. Crowley himself is driven to commit suicide in order to lock Lucifer away in an alternate universe.
It is unknown if Crowley really planned to kill her or was masking his pain.
During Various & Sundry Villains, a resurrected Rowena inquired about the whereabouts of her son before she was informed that Crowley was dead. Rowena appeared to be genuinely grieved by his death, stating that Crowley was her only son "and I'd much rather have a living son, even one that hated me than a dead hero!" Rowena is also shocked by Crowley sacrificing himself in the end, since it didn't seem like something he'd do, causing Sam to admit that Crowley had "changed a lot."
Abaddon was a powerful demon who served as a knight that sought to reclaim the throne of Hell from Crowley, whom she deemed was a 'mere salesman'. This attempt was made possible when the Winchesters kidnapped Crowley for their trials, leaving the throne vacant. After learning of Crowley having the throne, Abaddon tries to kill Crowley directly, but he is saved by Sam Winchester who forces Abaddon from her vessel with holy fire. While imprisoned by the Winchesters, Crowley grows disgusted with Abaddon's new policy of calling in soul deals early after learning of them from a Goblet of Blood call with her.
Following Crowley's release in exchange for helping free Sam from possession by Gadreel, Crowley actively fights a war with Abaddon with the intention to kill her and retake the Throne of Hell. To this end, Crowley is even willing to ally with the Winchesters, his mortal enemies in order to win his "campaign".
At the end of Abaddon and Crowley's war, Abaddon kidnaps Crowley's son Gavin MacLeod to force Crowley to aid her in betraying the Winchesters. Though Crowley previously hated his son, his lingering humanity forces him to give in to Abaddon's demands and help her. However, at the end, Crowley betrays Abaddon by warning Dean Winchester of the trap. Immobilized by a devil's trap bullet, Crowley watches as Dean and Abaddon fight it out, ending with Dean killing Abaddon and brutally mutilating her corpse. Following Abaddon's death, Crowley is able to regain control of Hell but is still forced to deal with a few lingering loyalists and the impact of her reign.
|“|| Bobby : Well, then get the hell off my property before I blast you so full of rock salt, you crap margaritas. |
Crowley : That's a mite unfriendly, seeing as I could be getting you Death's location in about the time it'd take you to reload.
— Bobby and Crowley
in The Devil You Know
After siding with the Winchesters and giving them the location of Pestilence, Crowley appears to Bobby and offers him the location of Death in exchange for his soul, as Bobby predicted. Since the world is about to end, Bobby agrees to the deal and kisses Crowley to seal it. The kiss itself was photographed and shown to the Winchesters, much to Bobby's discomfort, with Crowley berating him for using his tongue.
Later on, Crowley reveals that he also restored Bobby's mobility as part of their deal. Somehow, after Bobby is killed by Lucifer and resurrected by Castiel, his soul remains in Crowley's possession, and throughout the first half of season 6, Bobby attempts to get it back.
By contacting the spirit of Crowley's dead son, Bobby was able to find out where Crowley's human bones are buried, and sends Dean and Sam to its location, so he can force Crowley to break the deal, but he insists on keeping his legs. Crowley reluctantly accepted the offer and Bobby regained his soul.
The two do not interact much afterwards, though Bobby actively tries to help the Winchesters stop Crowley from opening Purgatory. Occasionally, Crowley makes flirtatious jokes about Bobby. After Bobby dies and moves on at the end of season 7, Crowley hires the reaper responsible for Bobby's soul, Ajay , to take him to Hell, where Bobby gets tortured but manages to maintain his humanity until he is discovered and rescued by Sam.
Just as the Winchesters attempt to send Bobby's soul to Heaven, Crowley intervenes, intent on making the Winchesters fail in their trials and to keep Bobby close. Naomi comes to the rescue and sends Bobby's soul to Heaven. This is the last time either of them mention or see each other.
As the King of the Crossroads, Crowley had a handful of personal bodyguards and every crossroad demon under his rule. He was respected enough that no crossroad demon was willing to disobey him.
When he became the King of Hell, discontent began to reveal itself with one demon admitting that Crowley was called "Lucky the Leprechaun" behind his back. This may have something to do with the fact that Crowley was the only demon to defy Lucifer during The Apocalypse, making him an enemy of the entire demon race.
Demons still did as they were told, killing and causing havoc at his command, but some went rogue or openly against him. Crowley himself did not seem to care for the demons. He always made sure his subjects were devout followers, but their personal well-beings meant very little to him. Any attempt to cross him would result in either brutal torture or death, or both. Demons who despised him saw him as weak and Winchester-obsessed.
Although unpopular among demons, Crowley did not lose every demon's loyalty until Lucifer made a return. The humiliation he suffered under Lucifer made it virtually impossible to reclaim the throne unless Lucifer was re-imprisoned. Crowley opted to torture Lucifer into submission so Lucifer's strength and title as Creator of the Demon race held no weight. His plan was not easy to accomplish since Lucifer was hard to break.
After Lucifer's breakout, Crowley visited the Winchesters in the hopes of defeating Lucifer for good. He admits though, that he doesn't want to be the King of Hell anymore.
Crowley initially sought out Kevin for his ability to read God's tablets. After Dick Roman was defeated, Crowley kidnapped Kevin, cut his hair, and forced him to translate the demon tablet. Unfortunately for him, Kevin was able to outsmart the demon and run away with the tablet as well as kill two of his demon guards.
While on the run, Kevin successfully reunited with Sam and Dean, but they were soon disrupted by the arrival of Crowley, more demons, and Kevin's possessed girlfriend Channing Ngo. Crowley ordered Kevin to come back to him so his girlfriend would be spared, but Kevin chose to run away with the Winchesters, leading Crowley to order Channing's death.
Kevin, Dean and Sam later dispatched the demons Crowley had sent to guard Linda Tran and her house, so mother and son could be reunited. Due to the demon tablet being stolen from its hiding place, the four go to an auction held by the pagan god Plutus in order to retrieve it. Crowley also went there, and took possession of Linda Tran and stole the tablet after killing Plutus. Dean nearly tried to kill Crowley while possessing Linda, leading Kevin to take his mother and run away from both the Winchesters and Crowley.
Crowley captured Kevin again after his mother accidentally hired a witch working for Crowley. Kevin was brought to a warehouse where all future prophets had been gathered. Crowley killed one of them and cut Kevin's pinky finger to force him to translate the tablet. Kevin revealed information about closing the gates of Hell forever before Castiel and the Winchesters arrived, the former who then broke the tablet in half before Crowley could escape with it.
On the request of the Winchesters, Kevin began translating his half of the tablet and provided the brothers with information on how to close the gates of Hell. This led to the death of Crowley's hellhound and the retrieval of Bobby's soul from Hell. However, stress drove Kevin to develop hallucinations of Crowley. The real Crowley soon found him on Garth's boat, and by claiming he had killed Linda, he drove Kevin over the edge with despair. Crowley then kidnapped him. Kevin was put under an illusion of Garth's boat while two demons posed as Sam and Dean and ordered Kevin to translate Crowley's half of the tablet. Kevin saw through the trick and trapped the fake Winchesters in a Devil's Trap while secretly sending messages to the real Sam and Dean.
Furious, Crowley began strangling Kevin, but was interrupted by the interference of Metatron, who rescued Kevin. With Crowley's half of the tablet, Kevin went to retrieve his own half which he had buried during his paranoia, and he was reunited with Sam and Dean. To complete the third trial, Sam and Dean kidnapped Crowley and attempted to cure him of his demonhood, however, the brothers could not go through with it since Sam would die.
In Season 9, the brothers returned to the Bunker with Crowley in tow, much to Kevin's frustration, but the brothers order him to translate the angel tablet and find a way to reverse Metatron's spell, which had banished all the angels from Heaven. During research, Kevin was taunted by Crowley, and in a fit of rage and vengeance, he beat up the demon. Crowley told Kevin that if he let him out of the dungeon, he'll lead Kevin to his mother, who's still alive, and added that the Winchesters don't really care about him. Kevin ultimately refused.
In need of a way to read Elamite Cuneiform, which was the only language Kevin could translate Metatron's spell into, the brothers decided to use Crowley, though Crowley wanted to contact Abaddon first, using Kevin's blood. The trio agreed and Crowley read the transcript for the spell, only to inform them that Metatron's spell was irreversible. Keeping a syringe of Kevin's blood, Crowley, who had become addicted to human blood thanks to the third trial, injected himself with it.
Not long after, Kevin was killed by the angel Gadreel on Metatron's orders, and the tablets were stolen. Dean was forced to ask for Crowley's help in expelling Gadreel, who was using Sam as a vessel. Crowley was noticeably distressed upon finding out about Kevin's death and seemed rather remorseful, apparently having genuinely cared about Kevin despite their tumultuous relationship.
|“|| Lucifer : My old friend, Crowley. |
Crowley : A mere acolyte, carrying your torch.
Lucifer : You’re too kind...to yourself.
— Lucifer and Crowley in O Brother, Where Art Thou?
Lucifer managed to find out what Crowley had done and sent his demons to kill him. Crowley spent months evading death until he met the Winchesters again and offered them help in finding the four rings of the Horsemen. The success in throwing Lucifer back into the Cage can thus be blamed on Crowley as well.
In Lucifer's absence, Crowley took control over Hell as the new ruler. Aside from Abaddon, this position would remain undisputed for five long years until Sam and Dean requested his help in contacting Lucifer about the Darkness. Crowley joined Sam and Rowena on their journey to Limbo, where they intended to summon the archangel. Lucifer greeted the King of Hell before being directed to speak with Sam.
Crowley had intended for this meeting to run smoothly, but his mother turned out to be working for Lucifer. Crowley firmly told her that he would not let Lucifer escape his prison, and sought out Dean to help him get Lucifer sent back to the Cage. The plan initially appeared to be a success, but shortly after the Winchesters left Hell, Crowley was approached by Lucifer in possession of Castiel's vessel.
The archangel tortured Crowley for weeks, and reclaimed the throne of Hell while Crowley became his slave. All the demons flocked to Lucifer's side, leaving Crowley with no allies. He was forced to lick the floor and live inside a kennel. Simmons helped Crowley escape and followed him to his lockup, so that Lucifer could obtain the Hand of God Crowley had stashed there.
Through his perfecting of the double cross, Crowley was able to fool Lucifer and use the Rod against him. He tried to use its power to kill the archangel, but Simmons shielded him. Defenseless, Crowley made a run for it. An enraged Lucifer sent his demons after him again.
Crowley assisted the Winchesters in luring Lucifer into a trap so they could get Castiel to expel him. Crowley initially wanted to just kill Lucifer with another Hand of God, but agreed to the Winchesters' wish. When the spells failed, Crowley entered Castiel's vessel and tried to communicate with him directly. Unfortunately, Lucifer appeared and began assaulting Crowley, while expressing his rage at being overthrown by a "second rate bean counter".
Lucifer failed to kill Crowley, since Crowley had left Sam and Dean with a message to rescue him, which they managed to do just in time. Before Lucifer could do harm to him outside, Crowley ran away. When Lucifer later failed to return to Hell, Crowley made a move to reclaim it, but the demons no longer wished to have him back. Crowley was left sad over this.
Dean approached him a few weeks later with an offer to have him work with God to defeat the Darkness. Crowley agreed, and met with the team, including Lucifer, at an abandoned warehouse. The two had a brief argument over whose species was more superior.
At the conclusion of the battle, Lucifer was expelled from his vessel, while Crowley remained with the Winchesters. He made a move to reclaim Hell again once the world had been saved, and upon finding out Lucifer was alive, Crowley sought out his mother for help in forcing the archangel back into his Cage.
The first attempt ended in failure, with Lucifer chasing him off and taking Rowena hostage. To combat this, Crowley sought the help of Castiel instead. The two hunted down Lucifer as a team.
Their hunt lead them to discover a plan to murder a group of fans loyal to Lucifer's vessel Vince. With Sam and Dean's help, Crowley and Castiel rushed to intervene but were both beaten to the ground. Lucifer personally beat Crowley with a guitar, calling him a "bad doggie" and ordering him to "sit". Once Lucifer escaped his vessel, Crowley is left badly injured with a severely damaged eye.
After Crowley recovers, he joins Castiel and the Winchesters in freeing the President from possession by Lucifer. Crowley personally retrieves his mother and with her help the team manages to banish Lucifer back to the Cage.
Months later it's revealed that Crowley manipulated Rowena's spell to his own benefit in order to capture Lucifer for himself. To this end, he had his demons locate Lucifer's old vessel and repair and improve it so that it would be a suitable permanent vessel for Lucifer. Crowley also bound Lucifer's vessel in chains, trapping Lucifer inside of it once Rowena cast her spell. Crowley appeared to alternate between keeping Lucifer in a small cage and chaining him to a chair, calling Lucifer "dog" as Lucifer once did to him. As Crowley's prisoner, Lucifer was more amused than threatened and took great glee in taunting Crowley at every opportunity.
An opportunity for Lucifer to escape presents itself when two demons distract Crowley and release Lucifer from his chains. Lucifer immediately kills them and waits for Crowley to return so he can mock and torture Crowley. However, this plan backfires when Crowley reveals that the chains were just an accessory and Lucifer's true prison was the vessel itself, which he could manipulate and break with a snap of his fingers. Lucifer crumbled the floor in agony, as Crowley promised to kill Lucifer's son and make him watch, and even then, Crowley's torture of Lucifer has only just begun.
|“|| Lucifer: (licks the floor)|
Crowley: What are you doing?
— Lucifer "submits" to Crowley
in The British Invasion
In his confidence that the archangel has now been tamed, Crowley reveals his intention to use both Lucifer and Lucifer's son as tools to wipe out his enemies. He tries to goad the unborn baby's location from Lucifer by revealing the baby is with Castiel following Dagon's death. Lucifer says nothing.
Upon his return to the cell, Lucifer has gained the upper hand due to the system giving Crowley control over Lucifer's vessel now working in the opposite direction. As Lucifer gains control over Crowley's vessel, Crowley is visibly terrified and even tries to offer his services, but they both know Lucifer wishes to torture him and Lucifer proceeds to do just that, beating up Crowley before delivering what was intended to be the killing blow. Lucifer reclaims the throne of Hell before leaving the demons to carry away Crowley's "corpse".
Crowley, having survived death through possession of a rat, goes to the Winchesters for help in defeating Lucifer. When Lucifer ends up in the inside of an alternate dimension conjured by his own son, Crowley chooses to sacrifice himself to ensure Lucifer stays trapped forever. This renders the throne of Hell vacant, but also proves how much Crowley is willing to go to defeat Lucifer once and for all.
Crowley had acute knowledge concerning the Princes of Hell and knew where they lived. After he had helped Sam and Dean defeat Lucifer and avert The Apocalypse, he approached Ramiel at his house and introduced himself. He immediately apologized when Ramiel reprimanded him for not knocking before entering.
Crowley offers Ramiel, a known weapon's collector, the Lance of Michael and The Colt, as a coronation presents. Crowley intends to give Ramiel the throne of Hell as well, given that Hell needs a ruler and Ramiel is next in line to the throne. Ramiel is uninterested, and advises Crowley to become King of Hell instead. Crowley is fascinated by the prospect, but Ramiel warns Crowley that from here on, if anyone bothered a Prince of Hell, it would be on Crowley's head.
As per their agreement, Crowley crowned himself the King of Hell and kept Ramiel and his siblings safe and undisturbed. Things changed when, years later, the British Men of Letters learn that a powerful demon has The Colt and send their new recruit, Mary Winchester to retrieve it. Mary goes on to recruit Sam, Dean, Castiel and Wally, without telling them the full details.
The invasion at Ramiel's house prompts Crowley to send two demons to protect Ramiel. The demons successfully kill Wally but are killed in return by Sam and Dean. Mary also manages to steal The Colt. Unfortunately, Ramiel had attacked Castiel using the Lance of Michael, which gradually killed the angel. Crowley chose to help the Winchesters as a result, seeing them as useful, but Ramiel ignored the demon's request and threw him through a barn where the Winchesters were before he continued his fight against the Winchesters.
It was Sam who killed the demon. Crowley then retrieved the Lance and destroyed it, saving Castiel. Crowley was horrified however, when he found out later on that The Colt had been stolen.
Ramiel is so far the only Prince Crowley has interacted with.
Crowley was initially on the side against Raphael during Heaven's civil war, though not actively, by providing Castiel with souls so he could power up and defeat Raphael. Crowley and Castiel aimed to obtain more souls from Purgatory, but when Castiel turned against Crowley, the demon sought out an alliance with the archangel, and offered to help him obtain Purgatory's souls himself.
Their alliance was short-lived however, since Castiel had outsmarted them both by giving them the wrong blood needed to open Purgatory. Crowley fled the scene, just before Castiel killed Raphael.