|“|| Dean : Tara listen, my, uh, associate -- |
Crowley : Friends -- besties, actually.
Dean : Not helping.
— Dean and Crowley
in in First Born
Dean Winchester and Crowley are occasional allies whenever there is a greater foe to deal with. They first formed a small alliance in the battle against Lucifer, which has since developed into a constant on-and-off thing, during which they are sometimes enemies and sometimes allies. Unlike Sam, Dean was more trusting of Crowley when they first met. Crowley also considers Dean a "bestie". While more than willing to try to kill him when necessary, he is not above showing a surprising amount of trust for Crowley. Crowley's heroic death apparently rids him of any resentment he had of the former King of Hell and he has shown genuine sadness by his death and even goes as far as to say Crowley is one of the things he and Sam had lost and even beg God to bring him, alongside the others he mentioned, albeit in vain.
As seen in Abandon All Hope..., the Winchesters track him through Castiel. After invading the mansion, Crowley is not too surprised to meet them, as he was fully aware they'd come for him. Much to the Winchesters' surprise, Crowley kills two of his lackeys and offers the gun to them without a fight. Dean questioned Crowley on his motives, as he explained that he has seen the bigger picture, after destroying humans, Lucifer will exterminate demons and for that he needs the Archangel dead. Dean and Sam then use the Colt against Lucifer, but the weapon doesn't work, leading them to believe that Crowley had tricked them.
Crowley returns to them some time later and Dean is angry to see him after the deaths of Ellen and Jo but Crowley insists he did not know the colt wouldn't work either. He explains that he found them through a tracking device he implanted on their vehicle and overheard their plan to seal Lucifer away again. Dean stops Sam from killing Crowley after he offers them the location of Pestilence, which can be found by hunting down Pestilence's assistant. However, Crowley takes Dean alone with him, and uses trickery to get Dean to "play his part" and lure the demon into a trap. Dean is annoyed when Crowley seemingly fled after a Hellhound attacks but surprised he returns with his own to kill the other one. Crowley told Dean that he was invested in dethroning their common enemy. At the end, Dean lets Crowley go before trapping Brady with Sam in a salt line.
In Two Minutes to Midnight, Dean becomes annoyed when he discovers Crowley had taken Bobby's soul, but Crowley refuses to give it back until The Apocalypse is over. However, Dean is pleased to see he has granted Bobby back his mobility. Later, Dean and Crowley head to Chicago where Death is, and Crowley lets Dean alone go inside a pizzeria to obtain the final ring.
Their alliance breaks about a year after The Apocalypse. Dean and Sam are recruited by Bobby to help get his soul back, and the brothers fly to Scotland and dig up Crowley's human bones. Dean personally calls Crowley during Crowley and Bobby's conversation, and threatens to torch his bones within three seconds. After Crowley returns Bobby's soul, Dean still wishes to just kill Crowley, but Sam stops him, since a deal was a deal.
Dean is further angered when, in order to keep Dean off his trail, Crowley has Ben Braeden kidnapped and Lisa Braeden possessed. Dean rescues them both and takes them to the hospital. Dean resumes hunting for Crowley to prevent him from opening the doorway to Purgatory.
In Season Seven, Time for a Wedding! Crowley appeared before to the Winchesters. Dean was shocked to see him, as he questions Crowley on why he's present. Crowley states he came to apprehend Guy. He also reveals he ordered his demons not to interfere with the Winchesters as they fight against the Leviathans. Dean was surprised by his support in their endeavors.
When Dean and Sam discover that Crowley's blood is one of the three ingredients needed to make a weapon to defeat the Leviathans, they summon Crowley to tell him what they need. Crowley agrees to help on the grounds that they get the other two ingredients first, in case his blood is used against him. Crowley offers them the location of the Alpha Vampire, whose blood is another ingredient, before leaving.
|“||Crowley. Poncey guy, about yea big, mountain of dicks.||”|
— Dean in Trial and Error
When Dean discovers a spell that will lock up Hell forever, he and Sam set out to complete the three necessary trials. Crowley tries to stop them from achieving this goal, and grows noticeably angry when they kill his hellhound. As the third trial requires a demon to be turned into a human, Dean assists in capturing Crowley.
After keeping Crowley captive in the bunker for some time, Dean turns to him for help in freeing Sam from Gadreel's control in Road Trip. Dean reluctantly agrees to give Crowley his freedom in exchange and lets him possess Sam to communicate with him. Crowley's efforts allow Sam to expel Gadreel, but while Dean is grateful and allows Crowley to go free, he starts to warn him but Crowley states he knows Dean that will try to kill him the next time they meet. The demon mockingly states he loves Dean too and watches him leave
Despite this threat, Dean reluctantly allies himself with Crowley again to take down Abaddon by locating the First Blade. Dean and Crowley hunt the blade together, finally locating a hunter named Tara who provides them with a location. She also warned Dean his father wouldn't have been pleased he was working a demon, to which he agreed. Dean and Crowley later find Cain, who is the creator of the blade. Crowley warned Dean of Cain and attempted to get him to flee but Cain cut off their path. The King of Hell told Dean of Cain's reputation and how he is prevented from retreating. Eventually, Cain gives Dean the Mark of Cain so he can wield the Blade and helps him and Crowley escape after telling him where to look: the bottom of the ocean. However, while Dean got what he needed, he is furious with Crowley as he realized Crowley used him after seeing him let Dean fight off three demons alone when he could've helped. Crowley confirms this, saying he needed Dean's help to locate Cain and to get him to help as Cain would've never helped Crowley. Disgusted with what Crowley has done, especially as it resulted in the death of hunter Tara, Dean promises to kill him once they've dealt with Abaddon, but sends him after the Blade first as for the time being, he and Crowley still need each other.
During Crowley's search, Dean repeatedly calls him for updates and when they find the First Blade, Crowley releases him from where Cuthbert Sinclair has him bound, allowing him to save Sam. Dean is annoyed when Crowley takes the blade out of mistrust, but protects him from a "hunter," not knowing it's really a demon testing him for Crowley. Eventually, Crowley helps Abaddon lure Dean into a trap to save his son, but he secretly warns Dean of the fact, using a code-word Dean had taught him. During the final confrontation with Abaddon, Crowley warns Dean of an attacking demon and seems slightly shocked by Dean's savagery in attacking Abaddon's dead body. Afterwards, as Crowley warned him, Dean lets him go rather than kill him while he's helpless but is angered when Crowley helps his son escape rather than return to his own time.
In the season 9 finale, Dean and Crowley get really close with Dean realizing his powers regarding the First Blade. Crowley also shows compassion and pity for Dean after the latter's death but gives back his blade, bringing Dean back as a demon.
|“|| 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? Hmm? Go ahead. Make a move. See how it 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.
— Crowley and Demon Dean
After Dean is brought back to life as a demon, Crowley takes him in and the two spend a noticeable amount of time together, with Crowley actively trying to become Dean's friend. Unfortunately, even as a demon, Dean disregards Crowley and chooses to do what he wants, acting disobediently.
Realizing that Dean as a demon is more trouble than he can handle, Crowley rescues Castiel from an attack by Adina and uses her grace to power Castiel up. Doing so allows Castiel to possess enough strength to confront Dean, who is in the process of trying to murder Sam. Together, Sam and Castiel cure Dean of his demonhood.
Despite their rocky times, Dean and Crowley remain on talking terms and Dean offers Crowley advice on dealing with his demanding mother. Dean helps Crowley realize the true meaning of family and if Rowena is being cruel, Crowley is not obliged to be nice to her simply because they are family. Crowley uses this advice to banish his mother from his palace.
During The Executioner's Song, Dean fights with Cain, the latter brought how Dean might kill his loved ones when he submits to the mark. He states that he knows Crowley's death by his own hand would likely bring up mix feelings in Dean but he can get the job done.
Sometime later, Crowley assists the brothers in gathering the necessary ingredients to remove the Mark of Cain, the very thing that turned Dean into a demon. Crowley's help enables the spell to be completed, and Dean is finally free of the curse. Meanwhile, Crowley suffers an attack and near-life-threatening assault from a deranged Castiel, who was cursed by Rowena.
Crowley and Dean become enemies once again when Crowley decides to take the newly-released and young Amara under his wing. Dean and Sam infiltrate his palace, in an attempt to kill her. When Crowley discovers Dean inside Amara's room, he decides to kill Dean to finally rid himself of the hunter. However, Amara retaliates and attacks Crowley, and orders him to free Dean.
Crowley briefly develops a dislike in Dean over Amara's favoritism in him.
Dean seeks Crowley out again when he finally agrees to help Sam contact Lucifer. They acquire Rowena and the Book of the Damned and make a plan to go the Hell. Crowley later tells Dean that Sam went to Hell without Dean and is now stuck with Lucifer. Dean and Crowley then help each other bind Rowena since she had been working with Lucifer all along, and force her to send Lucifer back to the Cage.
The plan is unsuccessful, and Crowley is dethroned while Dean is left convinced that everything is alright for a couple of weeks. Dean does not see Crowley again until Crowley manages to escape the archangel's clutches, and calls Dean to meet him at a hidden location.
Crowley reveals that he possesses the Horn of Joshua and intends to use its power to defeat both Amara and Lucifer. When Sam and Dean decline to follow through unless they get Castiel back, who is currently acting as Lucifer's vessel, Crowley mentions the numerous bad things Lucifer did to him, but Dean and Sam simply find them amusing.
When Rowena shows up and reveals herself to be "back from the dead", the four of them work together to trap Lucifer and get Castiel to expel him. When initial attempts fail, Crowley enters Castiel's vessel to speak with him directly. Dean and Sam wait outside, insisting the demon hurries up. They soon discover burnt on the forehead of Crowley's vessel a plea for help.
Dean and Sam work together to expel Crowley from Castiel, who admits that he too failed to retrieve the angel. When Lucifer regains consciousness, Crowley decides to bail on the Winchesters for his own safety.
Dean and Crowley do not meet again until weeks later, when God devises a plan to use demons, angels and witches in an attack against Amara. Dean personally goes to meet with Crowley and get him to join the team. When this plan also fails, Crowley remarks that it was a "dog's breakfast".
The two, as well as the rest of the team, return to the Bunker where they drink off as they await the end of the world. At Sam's insistence, the team figure out another way to combat the Darkness, using a Soul Bomb. Crowley remains at the Bunker while Dean and Sam hunt down ghosts to use as the Soul Bomb's fuel.
After Dean sets out on his mission to destroy Amara using himself as the bomb, Crowley and the rest wait at an empty bar. When they notice the sun's light restored to full glow, Crowley is left to believe, along with everyone else, that Dean is dead.
Crowley is aware that God isn't dead, and has simply left the Earth along with his sister. As a result, Crowley is also aware that Dean is alive, though it is never stated how.
Dean is informed by Castiel through phone calls that he and Crowley are working together in hunting down Lucifer, a fact which baffles Dean. In "Rock Never Dies", Dean and Sam join Castiel and Crowley in foiling Lucifer's plan to host a concert under the guise of Vince Vincente, a famous rock star. Crowley complains about the lack of communication between him and the Winchesters, though Dean brushes him off.
The team decides to split up in dealing with Lucifer, with Crowley joining Castiel in attacking Lucifer while Dean and Sam try to chase the fans out of the bar. Their combined effort forces Lucifer to escape his rotting vessel and his plan is ultimately foiled, though Crowley and Castiel are both left visibly injured, with Dean taking notice of Crowley's black eye.
In "LOTUS", Dean and Crowley work together again to finally reimprison Lucifer in his Cage. Dean is annoyed to see Crowley and Castiel posing as FBI agents again and forcibly removes Crowley's badge, but has no other issues with working with Crowley once more. Dean is also amused by Crowley's comment about his palace. Dean shows some trust in Crowley when he lowers the wards on the Men of Letters bunker to allow Crowley free entry to help them.
In "Stuck in the Middle (With You)", Dean and Sam infiltrate the house of Ramiel, a Prince of Hell on the request of their mother Mary. Since Crowley had promised to protect Ramiel, Crowley sends two demons after the Winchesters. Sam and Dean manage to kill the demons but Ramiel himself proves to be a challenge. Not eager to lose the Winchesters due to their usefulness, Crowley tries to get Ramiel off their tail, but fails. He does however, rescue Castiel from fatal wounds he sustained from Ramiel, a fact Dean witnesses.
Later on, Crowley expresses discomfort when he realizes The Colt was stolen from Ramiel's house. Crowley is, as of yet, unaware that by saving the Winchesters, he had helped Mary steal The Colt as per her orders given by the British Men of Letters. Crowley is also revealed to have messed up Rowena's spell, causing Lucifer to enter a prison-like vessel. This is a secret he is keeping from Dean and Sam.
In "Family Feud", Crowley learns that Dean wishes to speak with Gavin and receives a call asking for him. Having just learned from Lucifer that Dean and Sam did not get rid of Lucifer's unborn child, Crowley not only calls them both "morons" but denies them access to Gavin. Dean resorts to using Rowena's help instead, and the brothers soon come to the conclusion that Gavin needs to go back to his own timeline and accept his fate, for his arrival in the future has caused his fiancé to go on a murder spree.
Gavin calls Crowley to bid him farewell, and Crowley is furious by their decision. Sam, Dean and Rowena intervene and do not let Crowley stop Gavin from returning to his death.
In "Somewhere Between Heaven and Hell", Dean calls in Crowley to help with a hellhound attack. Although bitter about what they convinced his son to do, Crowley nevertheless arrives at Dean's location and reveals to him that the hellhound in question is Ramsey. He goes on to explain the history of hellhounds before helping Dean hunt Ramsey down. During their search, Dean thanks Crowley for saving Castiel, much to Crowley's delight.
Crowley and Dean do not speak to each other for a while. In There's Something About Mary, Dean accuses Crowley of letting another hellhound loose when his and Sam's friend, Eileen Leahy, gets killed by one. Sam talks to Crowley on the phone, but Crowley denies the accusation.
In All Along the Watchtower, Dean learns from Sam - who learned from Doctor Hess - that Lucifer is free upon the Earth again, because of Crowley. When Crowley shows up at the bunker intent on gaining their help to trap Lucifer once more, Dean attacks him. Dean is furious to learn of Crowley's actions, and Crowley fully admits to having kept Lucifer in his palace and not in the Cage, out of greed.
Crowley offers to lock the gates of Hell if they agree to work with him, knowing it will seal Lucifer away forever. Possibly moved by Crowley's admission, and knowing they have no better option, Dean works with Crowley and Sam in locking Lucifer up, but this time they decide to use a portal into an alternate dimension, created by Lucifer's son Jack. Once all four are inside, Dean acts as a distraction while Crowley and Sam prepare the spell. During this time, Dean admits that he believes in Crowley "sometimes."
The final ingredient of the spell is a life so Crowley bids the brothers a final farewell and stabs himself with an angel blade right before Lucifer's eyes. Although the portal doesn't close immediately, Crowley's sacrifice does succeed in locking Lucifer away, but Crowley ends up as one of three loses Dean suffers during the mission, with Castiel's death second and Mary's imprisonment as third. As one of Crowley's last acts, he saved Dean from Lucifer by telekinetically flinging the Fallen archangel away from Dean as Lucifer was about to harm him.
In Lost & Found, Dean lists Crowley as one of the people they have lost to Sam. When Dean prays to God to make things right, he goes so far as to list Crowley as one of the people he wants brought back but Chuck doesn't answer. When saying his goodbyes at Kelly and Castiel's hunter's funeral, Dean says goodbye to Crowley as well as Castiel, Kelly and Mary Winchester and appears upset by his death.
In The Scorpion and The Frog, Dean comments that after Crowley died, he swore that he would never work with a demon again when the Winchesters make a deal with Crowley's former subordinate, Barthamus.
In Various & Sundry Villains, after Rowena inquires about her son, Dean pauses for a moment. When Sam tells Rowena about Crowley's death, Dean can be seen sad as Sam tells her she would have been proud as he sealed Lucifer away.
- According to Jared, the actors who portray Crowley and Dean (Mark Sheppard and Jensen Ackles, respectively) got along with each other from the moment they met.
- Jensen Ackles' daughter J.J. coincidentally shares her birthday with Mark Sheppard.
- Mark Sheppard describes himself as a Dean-girl.
Also Check Out
Sam and Crowley - Crowley's relationship with Sam Winchester.