Fergus Roderick MacLeod
|Actor|| Mark Sheppard|
Lauren Tom (8.02)
Marco Soriano (9.16)
Kirsten Robek (11.01)
|Dates|| 1661 - c. 1723 (human life)|
???? - 2017 (sacrifices self)
|Occupation|| King of the Crossroads|
King of Hell
Don't worry about -- what, like Lucifer didn't worry? Or Michael? Or Lilith or Alastair or Azazel didn't worry?! Am I the only game piece on the board who doesn't underestimate those denim-wrapped nightmares?!
– Crowley, 6.20 The Man Who Would Be King
Crowley says he was a 17th century Scottish tailor named Fergus MacLeod from Canisbay, Scotland who sold his soul in life for three more inches in length on his penis, to hit "double digits." His mother, Rowena, was a witch and taught him a few things about witchcraft, like how to make and use hex bags. Fergus had a son, Gavin MacLeod, but Crowley indicates that he "...[I] loathe the little bastard." Gavin, who is summoned in ghost form in 6.04 Weekend at Bobby's, reciprocates the feeling, and reveals that he betrayed personal information on Crowley to Bobby Singer. Dialogue suggests that Fergus died 291 years before 9.21 King of the Damned took place, which would put the year of his death at around 1723 and his age at his time of death at around 62, taking into consideration his 1661 birthdate.
Sometime after going to Hell and becoming a crossroads demon, Crowley rose to become the right-hand man of the first demon and then the de facto ruler, Lilith. He says his current meatsuit belonged to a "moderately successful" New York literary agent. Crowley's eyes are revealed to be red like other crossroads demons, and it is also revealed that his "smoke" form is red as well, unlike the traditional black smoke that is characteristic of most demons.
Crowley betrayed much of Hell's hierarchy by providing the Colt to be used by Dean Winchester to attempt to kill Lucifer. He additionally provided the location of Death to Dean, which allowed for the collection of the final key to re-open Lucifer's Cage, which would later allow Lucifer to be re-imprisoned there.
After taking charge of Hell, Crowley transforms it into place where torture is exemplified by endless waiting in line. Despite not being a Lucifer loyalist, he is seen using the Devil's Trident as a sigil, and also is pictured on painting on a wall in the halls of Hell dressed in a uniform with it as an insignia.
It is Crowley who proposes to Castiel the plan to locate Purgatory and share the power of the souls of the monsters there. Through the resurrected Samuel Campbell, he employed hunters, including Sam, to capture monsters that he hopes will lead him to Purgatory.
He was thought killed when Castiel burned what was presumed to be his bones. However, it is later revealed that Crowley faked his death with Castiel's assistance. Castiel eventually reneges on their deal to share to the souls of Purgatory, causing Crowley to ally briefly with Raphael. After Castiel opened Purgatory and absorbed all the souls there, proclaiming himself a god, he allowed Crowley to escape saying he has plans for him.
After the Leviathans escape from within Castiel, Crowley offered an alliance with their leader, Dick Roman. Roman rejected him, and Crowley later allies briefly with the Winchesters against the Leviathans, helping to defeat them.
Crowley later sought the translation of the demon tablet to throw open the Gates of Hell and release all demons upon the world. He is also searching for the angel tablet. In his attempts to translate the tablets, he had previously kidnapped current prophet Kevin Tran. He has also tortured angel Samandriel to learn the names of inactive future potential prophets, who he would also kidnap in a failed attempt to get one to translate the demon tablet for him.
Crowley also reminisced about his experiences in Mesopotamia, when meeting with the angel Naomi, remarking that he hasn't seen her in a "dark age." It is also implied that he had a sexual relationship with her at that time. Although Crowley's mention of Mesopotamia does not fit his timeline, it can be reasonably concluded that during their sexual relationship, Naomi took Crowley back in time to Mesopotamia for a short period of time.
Crowley was captured by the Winchesters as part of a final trial to close the Gates of Hell, and despite this trial not being completed, remained imprisoned in the Bunker for a time with a coup underway for Hell's leadership. As part of a deal with Dean, Crowley helped Sam expel Gadreel by possessing him to communicate with Sam and then was released to start a war against Abaddon.
In his war with Abaddon, Crowley forms an alliance with the Winchesters, more specifically Dean to kill her and regain full control of Hell. To this end, Crowley enlists Dean's help to get the Mark of Cain and the First Blade, the two things that together can kill a Knight of Hell. After Cain gives Dean the Mark, Crowley starts a search for the First Blade, but when it is located, he takes it for himself, not trusting the Winchesters to not use it against him. His reign falling apart around him, Crowley began losing the war to Abaddon who turned even his most loyal demons to her side and bringing his son forward in time to use as leverage against him. Crowley helps lure Sam and Dean into a trap, but double-crosses Abaddon and warns them. With the First Blade and the Mark of Cain, Dean is able to kill Abaddon, effectively restoring rule of Hell to Crowley. Though the Winchesters spare his life, they insist he allow his son to return to his own time to die as he's supposed to, but Crowley refuses and takes him to safety.
After being restored to full rule of Hell, Crowley works with Dean to track Metatron and visits him after his death to aid in his resurrection as a demon. After Dean is cured by Sam, Crowley's existence is complicated when the witch Rowena, Fergus McLeod's mother, resurfaces seeking to reclaim her lost power base.
Rowena reunites with Crowley, and attempts to manipulate him for her own ends. Crowley is aware of Rowena's manipulations but does capture the head of the Grand Coven, Olivette for her. Under torture by Rowena, Olivette reveals the Grand Coven is now much diminished in its power.
Frustrated by Crowley's continued dealings with the Winchester, Rowena attempts to drive a wedge between them. When this fails, she leaves Hell. Sam tracks Rowena down and Sam engages her for her help in decoding the Book of the Damned in the hope it will reveal how to remove the Mark of Cain from Dean. Rowena agrees to help, on the condition that Sam kill Crowley for her. Sam eventually holds her captive so she cannot escape while she decodes the Book of the Damned.'
Crowley makes repeated attempts to win Dean back, and make him give into the Mark of Cain but to no avail.
When they require help in creating the spell to remove the Mark from Dean, Castiel summons Crowley who brings them the ingredients and Oskar. Rowena kills Oskar and casts the spell to remove the Mark, which also releases the Darkness at the same time. Rowena takes the opportunity to escape with the Book of the Damned and the codex, casting the attack dog Spell on Castiel so he will kill Crowley.
Personal life and Powers
Crowley was born Fergus Roderick MacLeod in 1661 Scotland, his mother Rowena carried on an affair with a man above her social class, who soon abandoned her and Crowley once he was born. Rowena was a neglectful mother, preferring to drug the young Fergus with whiskey, rather than sing lullabies, even attempting to trade him for three pigs when he was a child. At some point Rowena is accused of witchcraft and flees Scotland, abandoning Fergus to live in a squalid workhouse. Fergus would grow up to be a "two-bit" tailor who sold his soul for an extra three inches below the waist. He had a son named Gavin MacLeod who, after Crowley died, set sail for America and died in a shipwreck. Gavin and his father have a strong mutual dislike for each other. The dislike is so strong that Gavin - when his spirit is summoned to get information on Crowley - betrays Crowley's burial spot, leaving him vulnerable to being killed by salting and burning his remains.
Crowley was in possession of his remains after returning Bobby Singer's soul until Castiel recovered them, sealing his fate. Crowley is shown to possess a refined skill with telekinesis and is particularly powerful for a demon, though he is discreet about displaying his abilities. He claims to have taken on a "nest" of demons and came out with barely a scratch on him. He was able to cause a man to cough up blood and even caused a girl to explode by snapping his fingers. Crowley is pyrokinetic, often making fire appear and disappear at a thought.
He also controls and owns a hellhound that is notably larger (standing or sitting at about 5 feet tall) and more aggressive than others. He refers to it as "my pup." It appears alongside Crowley in 5.20 The Devil You Know and is used against another hellhound in a dog fight. Sometime after the re-imprisonment of Lucifer and Michael, Crowley uses his hellhound to get Bobby to release him from a devil's trap.
While he occasionally responds to crossroads summonings in person, to be certain of summoning Crowley himself, and not another crossroads demon, a ritual involving a sigil, candles, a bowl of herbs, human blood, and an incantation is required.
He also has some knowledge about the Colt, as he is able to provide more bullets for it, and also about magical coins that he plants on Sam and Dean to track their movements and listen to their conversations. He owns an Apple iPhone and is able to acquire (through his position as King of the Crossroads) Death's scythe, which Death claims he lost. Crowley also possesses an angel blade.
Crowley's powers and abilities likely have substantially increased after assuming control and leadership over Hell's domain due to his access to the power of the souls there. With the capacity of his abilities enhanced, he hexed and jinxed an entire building, preventing all the demons inside from leaving their meatsuits. He can also dispel the fire of holy oil.
It seems that Crowley is more apt to teleportation than his fellow demons, he frequently uses it to cover even small distances such as in 5.21 Two Minutes to Midnight, where he teleports barely 20 feet from a car to a street corner and back. He also uses it to surprise the Winchesters or other supernatural beings.
Crowley's favorite drink is "Craig. Aged 30 years at least. I've been drinking it since grade school." "Craig" refers to the whisky Glencraig. According to Rufus, it's a kind of Scotch currently only made and sold in a tiny area on the north tip of Caithness County. It's peaty and sharp with a long finish of citrus and tobacco notes. Glencraig may have been a more common drink in the 1700's when Crowley was alive.
The first time Crowley's eyes turned red from his real vessel was in 10.22 The Prisoner. The other times his eyes turned red were when he possessed Linda Tran in 8.02 What's Up, Tiger Mommy?, André Develin in 9.16 Blade Runners, and Marnie in 11.01 Out of the Darkness, Into the Fire. His eyes are red with black pupils and red demon smoke pulsing from them.
Becky Rosen speculated that Crowley may have been Lilith's lover, and he has possibly had a past sexual relationship with Naomi. He seals a deal with a male banker with a kiss and teases him about his homophobia. He also seals his deal with Bobby with a kiss, and later shows off a picture of the moment that he took on his iPhone. During his addiction to human blood he has a demon lover called Lola, who betrays him to Abaddon. Crowley appears to enjoy sexual sadism and we see in him relishing the "erotic value"of inflicting pain. .
In order to set Brady up as a traitor with the other demons, Crowley uses the line that he and Brady are "lovers in league against Satan." Which the other demons readily believe. In 6.07 Family Matters, he makes a joke about knowing Samuel, "but not in the biblical sense" and later refers to Cas as the bottom in their relationship. He also often makes sexual remarks to Sam and Dean.
In 11.01 Out of the Darkness, Into the Fire, Crowley engages in an orgy while possessing the woman Marnie. Waiting till after it was done to kill everyone in the house and call his demon minions to pick him up.
Crowley was a Scottish human before he was a demon. The other demons call him Lucky the Leprechaun, a description suited to an Irishman. While he says his current meatsuit belonged to a literary agent from New York, and speaks with an British accent. However, when Crowley gives an impassioned speech after Sam saves him from Abaddon's assault in 8.23 Sacrifice, Crowley's accent slips out of his British accent into an American one. It happened again in 12.12 Stuck in the Middle (With You) when Ramiel told him to take the crown after declining the offer.
Nicknames for Sam
Crowley seems obsessed with Sam's height and has a range of amusing nicknames for him based on this:
- Jolly green
His phone lists Dean's number under "Not Moose"
Crowley is first mentioned by the crossroads demon Sam summons as part of his attempt to force her to break the contract to Dean's deal. The demon explains that her "boss" holds the contract instead of her and that he won't let Dean out of it because he wants Dean's soul to go to Hell. She refuses to give out her boss's name when Sam asks for it. However, given that Crowley was first introduced as the King of the Crossroads and that this boss is referred to as a "he," it is most likely that the demon was talking about Crowley.
Crowley is referenced again when Sam and Dean interrogate a demon for the identity of the demon who holds Dean's contract. The demon doesn't give the information away because he fears retribution from Crowley, instead challenging Sam and Dean to just exorcise him, which they do. Later on, Bela refers to the one she sold the Colt to as a "he" and challenges Dean to find him, saying he might catch up to Crowley "eventually." She reveals to Dean that the demons she was dealing with (i.e. Crowley and Lilith) changed their deal with her after she gave them the Colt, forcing her to kill Sam as well in order to get out of her contract. She fails and is implied to be killed by a hellhound.
Crowley is mentioned for the first time by name when, at the end of the episode, Becky tells Sam that Crowley had been the one whom Bela gave the Colt to, rather than Lilith (as Bela had claimed at the end of 3.15 Time Is on My Side). Becky describes Crowley as Lilith's "right-hand man" and speculates that he might also have been Lilith's lover.
- "So, the Hardy boys finally tracked me down. Took you long enough."
Castiel tracks Crowley to his Enochian sigils protected mansion after witnessing him make a deal with Mr. Pendleton, a 60-year-old businessman seeking a bank bailout. Sam and Dean, with Jo's help, kill Crowley's demon gate guards and break into the building, cutting off the power. They attempt to catch Crowley in a devil's trap, but he locates it, and another pair of guards capture the Winchesters. Crowley produces the Colt and uses it to shoot the guards, much to Sam and Dean's surprise. He then offers them the gun, telling them to use it to kill Lucifer. They are shocked that he would want the Devil dead, and Crowley explains his reasoning:
- Crowley: Lucifer isn't a demon, remember? He's an angel. An angel famous for his hatred of humankind. To him, you're just filthy bags of pus. If that's the way he feels about you, what can he think about us?
- Sam: But he created you.
- Crowley: To him, we're just servants. Cannon fodder. If Lucifer manages to exterminate humankind, we're next. So, help me, huh? Let's all go back to simpler, better times, back to when we could all follow our natures. I'm in sales, dammit! So what do you say if I give you this thing, and you go kill the devil?
Crowley gives them the Colt and Lucifer's location. Sam takes the gun and attempts to kill Crowley with it, but finds that it is out of ammunition. Crowley initially does not react, then comments that they will need additional bullets. He goes to his desk, and Dean speaks up:
- Dean: Oh, uh, excuse me for asking, but aren't you kind of signing your own death warrant? I mean, what happens to you if we go up against the Devil and lose?
- Crowley: Number one, he's going to wipe us all out anyway. Two, after you leave here, I go on an extended vacation to all points nowhere. And three, how about you don't miss, okay! Morons!
Crowley disappears after tossing Dean the ammunition. His fears about Lucifer's opinion of demons are confirmed later when Lucifer sacrifices a group of demons to raise Death and apathetically says to a shocked Sam, "What? They're just demons."
- "Please. I've sold sin to saints for centuries. You think I can't close one little deal?"
Following the Winchesters' failed attempt to assassinate Lucifer with the Colt, Crowley is forced to hide from other demons, who apparently destroy his mansion and eat his tailor. Using a magical coin that was placed in the Impala by his valet, Crowley finds the boys and offers to help them locate Pestilence, one of the Four Horsemen of the Apocalypse. When he first appears, Sam repeatedly tries to kill Crowley with Ruby's knife, accusing him of setting them up for failure in their last encounter. Sam and Dean also blame him for Jo and Ellen's deaths. Crowley counters that he thought the Colt would kill the Devil, and that he is not responsible for anyone that Sam and Dean ask to accompany them.
Eventually, Dean is willing to give Crowley a chance, and together he and Crowley infiltrate Niveus Pharmaceuticals to capture the Horsemens' "handler," a demon called Brady. Crowley uses Dean as bait - without informing him - to lure Brady out into the open, throw a hood over his head, and knock him out with a tire iron. Crowley tries to prevent Dean from returning to Crowley's hideout, where Sam is waiting, but is reluctant to say why. He finally admits that Sam and Brady have "history." They do return to Sam, who is furious - Brady was a friend of his at Stanford and introduced him to Jess. Sam does however acknowledge that they need the information Brady possesses.
Crowley is unable to convince Brady to divulge Pestilence's location, so he attacks a demon "nest" and kills all but one, leaving the remaining demon with a rumor that Brady had abandoned his post to assist Crowley. Faced with eternal torture over this supposed betrayal, Brady agrees to tell them where to find Pestilence. Moments later, a hellhound arrives, having followed a tracker placed on Crowley at the demon's nest. It prepares to attack, but Crowley vanishes, then reappears with his own hellhound, a beast much larger than the other. The hounds fight while Crowley, Brady, and the Winchesters escape in the Impala.
While the Winchesters deal with Brady (Sam kills him out of revenge for Jess), Crowley visits Bobby and suggests a way to locate Death, the last of the Horsemen: exchange his soul for the information. Bobby shoots him twice, but Crowley persists with the bargaining, promising to release Bobby from the deal as soon as Death is located.
- "Stock up on... everything. Cos' in two weeks we'll all be in Zombieland."
After revealing his deal with Bobby to the Winchesters, Crowley explains that he intends to use Bobby's soul as insurance so Sam and Dean won't kill him. He promises to return it after Lucifer is defeated. He later shows them an article in the newspaper that tells of flu vaccinations from Niveus Pharmaceuticals that are about to be distributed nation-wide. Crowley correctly believes they are packed full of the Croatoan virus. Sam, Bobby, and Castiel decide to sabotage the deliveries whilst Dean and Crowley face off against Death. Crowley uses his crossroads connections to obtain Death's scythe and gives it to Dean, believing from hearsay that it may kill Death. He also reveals that as part of Bobby's deal, Crowley has returned his ability to walk, for which Bobby is very grateful. In Chicago, Crowley finds the Horseman sitting alone in a pizzeria and leaves Dean to face him.
- "Paragraph 18 subsection B, which is on your naughty bits: I only have to make 'best efforts' to give you back your soul."
One year ago, following the imprisonment of Lucifer, Bobby summons Crowley, who says that he's "been celebrating" Lucifer's defeat. Bobby offers him a drink, but Crowley declines on the grounds that Bobby does not have his favorite scotch. Bobby then asks Crowley to follow through on the deal they made in 5.20 The Devil You Know, the return of Bobby's soul following the prevention of the Apocalypse. Crowley refuses. Bobby then reveals he has trapped Crowley in a devil's trap made with fluorescent paint, which Crowley couldn't see until Bobby turned off the lights. Crowley demands to be let go but Bobby refuses, so Crowley summons his hellhound with a whistle, and gives Bobby the choice of living out the ten years included in his deal, or "ten years as Alpo." Bobby frees Crowley, and the demon leaves.
The following year, Bobby captures a crossroads demon and holds her captive in his basement. He shows her that he has her bones, the remains of her human body. He demands that she reveal Crowley's real name from the time that he was human. She refuses, telling Bobby that Crowley is now the King of Hell, and that she fears his reprisal. Bobby takes a blowtorch to her bones, causing the demon to burn inside her meatsuit. She reveals that Crowley's real name is Fergus MacLeod, and that the demons call him "Lucky the Leprechaun" behind his back. Bobby soon disposes of her.
While helping Rufus Turner bury the body of an okami in his lot, Bobby tells Rufus about Crowley's real name and his affinity for a specific type of scotch, and that he plans to look for more information in Scotland. Rufus is familiar with the scotch, and what part of Scotland it's from; he tells Bobby he has contacts in Scotland and offers to make some calls.
Later, Rufus reveals that his Scottish contacts found out that Crowley's full name was Fergus Roderick MacLeod, and he was born in Canisbay, Scotland in 1661. He also says Crowley had a son named Gavin MacLeod, who left for America after his parents died. He captained a trading ship that went down in Massachusetts in 1723. The wreck was found thirty years ago, and divers recovered Gavin's signet ring, which is now part of the "Treasures of the Deep" exhibit at the Maritime Museum in Andover, Massachusetts. Rufus speculates that Bobby will use the ring to summon Gavin's ghost and make an exchange with Crowley: Gavin's ghost for Bobby's soul.
Rufus gets the ring but is captured by the authorities. He swallows the ring so that police can't seize it from him as evidence. Sheriff Jody Mills is able to extradite him from Andover, Massachusetts to Sioux Falls, South Dakota for a phony murder charge as a favor to Bobby. When he arrives, Rufus gives Bobby Gavin's ring. Bobby summons Gavin's ghost, who asks him if this is Hell. Bobby says that depends on him.
Bobby summons Crowley, who arrives and discovers he is stuck in a devil's trap, again. Bobby comments that he looks like "hammered crap," and asks him about being "the Big Kahuna" in Hell. Crowley produces a flask and a shot glass, pours himself a drink, and drops two antacid tablets in it. He complains that he thought being in charge would be all "rainbows and two-headed puppies," but instead it's "Hell." He says that he tried to show demons a new, better way, and they did not respond well. He also admits that sometimes he thinks Lucifer's idea of killing "anything with black eyes" was not such a bad plan.
Crowley repeats his refusal to return Bobby's soul. At this point Gavin manifests. Crowley feigns emotion at the sight of him, before revealing to Bobby that he and Gavin hated each other, and that Bobby picked the wrong bargaining chip. He encourages Bobby to go ahead and torture Gavin. Bobby says that Gavin gladly told him everything about his father. In life, Crowley, formerly Fergus MacLeod, was "nothing but a two-bit tailor who sold his soul in exchange for an extra three inches below the belt." Bobby knows where Crowley's bones are located. He hands Crowley a telephone.
Dean is on the other end, and tells the demon that he and Sam are standing over Crowley's bones in Scotland. Crowley nervously tells them the burning bones story is a myth; Bobby responds by relating what happened to the crossroads demon he interrogated and killed in his basement earlier. Bobby makes Crowley an offer: his bones in exchange for Bobby's soul. Dean can be heard flicking his lighter over the telephone. Crowley finally agrees, and the writing on Bobby's arms disappears. Bobby tells him to leave in the part of the deal that returned the use of Bobby's legs. Crowley does so. Bobby releases him from the devil's trap.
Sam: Dean, he's a dick. But a deal's a deal.
Crowley: I don't need you to fight my battles for me, Moose. Get bent.
Crowley picks up the bones and puts them in a large black leather bag. He says "Now if you'll excuse me, I have a little hell to raise," and disappears.
- "Location, location, location. I'm a developer. Purgatory is vast, underutilized, and Hell-adjacent, and I want it."
Dean and Sam track Samuel Campbell to where he is holding the Alpha Vampire. The Alpha tells Dean and Sam that Samuel has been torturing him for information about Purgatory, where creatures like himself go when they die, and hints that Samuel is working for someone else. Dean and Sam are then discovered talking to the Alpha and are held at gunpoint, and, while they argue with Samuel, the Alpha escapes his cage. They resolve to kill it if possible, but it quickly gains the upper hand and is about to turn Sam when demons arrive and take the Alpha Vampire away with them. It is revealed that Crowley is behind Samuel's actions. As the new King of Hell, Crowley had the power to resurrect Samuel and Sam, and he did so because he wanted their help. Since his resurrection, Samuel has been working for Crowley, gathering high-ranking creatures and trying to learn the location of Purgatory because Crowley is interested in "developing" it. Crowley then tells them that if Sam ever wants the return of his soul, he and Dean need to help Samuel continue to capture creatures for him. Currently, they don't see any other option but to help Crowley, but Sam and Dean are determined to get him back eventually.
- "I own your brother, do you understand me?!"
Crowley visits Sam and Dean at a roadside diner and instructs them to capture another Alpha for him, specifically the Alpha Werewolf, whom he believes might be behind several daylight evisceration's mentioned in the local tabloids (though it later turns out to be the work of a skinwalker).
Dean immediately refuses and demands Crowley return Sam's soul, so the demon taps Sam's hand, burning a mark into it to prove to Dean that he is stuck in a hostage situation. He must do everything Crowley tells him to do, or else risk having Sam returned to Lucifer's Cage. Dean reluctantly agrees and Crowley promises to return Sam's soul "with a cherry on top" so long as they bring him another living Alpha before vanishing in his usual manner.
Dean: I've done some shady stuff in my time, but I am not doing this. No.
Crowley: Ten quid says you will. [taps Sam's hand]
Sam: [grabs his hand and grunts in pain]
Crowley: You like pain, Sam? You like hell? (to Dean) You need to stop thinking of this as some kind of deal. This is a hostage situation, you arrogant little thug. I own your brother, do you understand me?
- "I was lucky to get this much of you out. Going back in there for the sloppy bits? No way. I’m good, but those two in there? Forget it."
Crowley, wearing an apron and armed with iridium tools, interrogates the Alpha Shapeshifter for Purgatory's location. The Alpha has taken on his form. It doesn't reveal Purgatory's position, so Crowley threatens the Alpha by telling it that he will personally slaughter its children in front of it if it does not properly cooperate. The Alpha informs Crowley that it will just create more shapeshifters. Crowley ruthlessly retaliates by cutting off the Alpha's head, killing it.
Later on, Sam, Dean, Castiel, and Meg attempt to capture Crowley, but he has been forewarned by Samuel. He has set up a trap wherein Castiel is banished and the boys and Meg are captured. Crowley condemns the Winchesters to death by feeding them to ghouls, but Sam escapes his cell and saves Dean. Together they free Meg.
Crowley, busy interrogating the djinn Brigitta, is lured into a confrontation by the sounding of a fire alarm. He is hit from behind with a wrench by Sam, which forces him to stumble into a devil's trap. Meg then tortures Crowley while the Winchesters demand to know if he really can retrieve Sam's soul. Crowley admits that he cannot, as rescuing Sam's body was a miracle in itself, let alone trying to liberate Lucifer's "only source of amusement." Accepting this claim, Dean gives Meg Ruby's knife and she enters the devil's trap to stab Crowley, but he quickly disarms her and uses the knife to break the trap.
Crowley pins the boys to opposite walls and threatens Meg with the knife, until Castiel suddenly reappears with the demon's bones. Surprised, Crowley doesn't immediately believe they're his bones. Castiel convinces him otherwise, however, and uses this as leverage to find out if Crowley genuinely cannot retrieve Sam's soul. Crowley repeats his earlier assertion that he cannot, prompting Castiel to incinerate his bones. Crowley's spirit and host burn in agony, turning to dust.
- "Really, Cas. This is getting ridiculous. How many times am I gonna have to clean up your messes?"
Eve traps Dean and Sam in a diner and explains that her actions in rising from Purgatory, and mobilizing all the supernatural beings are in reaction to Crowley capturing and torturing "her children." She speculates that Crowley is after the souls from Purgatory as together they would form a powerful weapon. Later, Sam, Dean, Bobby and Castiel go to find the young boy who has been made into a monster. They find both the boys dead and sulfur present, indicating a demon killed them. Castiel leaves, ostensibly to discover if Crowley is still alive. At the diner where Eve died, Crowley is waiting and tells Cas he's "tired of cleaning up his messes."
- "Purgatory, my fine feathered friend. Purgatory. Just think about it. An untapped oil well of every fanged, clawed soul. I mean, what's that over the years? 30 million? 40 million? Just sitting there, plump and rich for the taking."
Through a series of flashbacks from Castiel's POV it is revealed that, following the Apocalypse being averted, Crowley approached Castiel with a proposal that they join forces to locate Purgatory. Castiel is highly reluctant to trust Crowley, but the King of Hell brings the wayward angel around to his way of thinking by revealing his plan to plunder the souls of the 30-40,000,000 monsters trapped in Purgatory, so that they can be used as a means to "go nuclear" against Raphael and his followers. Crowley even offers an advance loan of 50,000 souls from Hell in exchange for half the souls in Purgatory. Castiel, seeing no other way to stop Raphael from rebooting the Apocalypse, agrees to Crowley's proposal and uses the power of the 50,000 souls to deliver his first strike against Raphael and declare civil war in Heaven.
In the present, Crowley examines the body of Eve and demonstrates to Castiel the lingering connections between it and the monsters by jabbing Eve's brain with a silver stake, causing extreme agony for the nearby vampire prisoner. Castiel asks if he has made any progress in locating Purgatory, to which Crowley angrily retorts not as much as if Eve were captured alive; as she was their best hope of finding a doorway to Purgatory. Upon closer examination, Crowley realizes that Castiel has been spending more time with the Winchesters and expresses his displeasure with having to hide from them and pleads with Castiel to let him kill them. Castiel refuses.
After several of his demon monster hunters are wiped out by Castiel to stop the Winchesters from using them as a route to Crowley, the King of Hell sends three of his very best demons to kill Sam, Dean and Bobby but Castiel intervenes and smites them all. He later returns to an infuriated Crowley who reasons "If you're allowed to kill my hunters, why can't I kill yours?!" - to which Castiel forcefully reminds Crowley that if anything happens to the Winchesters the deal is off and he will destroy Crowley for real. He then vanishes, to which a shaken Crowley comments: "This is not how synergy works!"
When Castiel's dealings are revealed, he is captured by Sam, Dean and Bobby in a ring of holy fire and interrogated, forcing him to admit to working with Crowley. He tries to explain to them his reasons for siding with a demon, that Raphael's quest to release Lucifer and Michael would destroy the world and everything in it, but the Winchesters do not feel his actions are justified and that he has learned nothing from their mistakes. Before they can question him further, however, a cloud of demons surrounds the house and at Castiel's insistence they flee. From amongst the demons appears Crowley, who chastises Castiel for his predicament before releasing him and once again trying to convince Castiel to see the error in his compassion towards the boys, but Castiel simply warns Crowley to get out of his face. Crowley obliges, leaving with the remark: "You wanna know the difference between you and me, Cas? I know what I am. What about you?"
- "As long as I have the woman and boy, your fop-coiffed little heroes will be scouring the Earth for them, therefore not you, and not me. Everybody wins."
In an effort to deter the Winchesters from interfering with his plans, Crowley kidnaps Ben and Lisa and calls Dean to offer an ultimatum: their safe return in exchange for his and Sam's cooperation. Dean counters by capturing demons and torturing them for Ben and Lisa's location. Meanwhile, Castiel tries to convince Crowley to let them go, but he refuses to reveal their location. As an insurance policy should Dean find them, Crowley instructs a demon to occupy Lisa to keep Dean from rescuing them. This partially succeeds, as the demon fatally wounds Lisa before being exorcised. Dean rescues her and Ben, the former being healed by a remorseful Castiel, who also later locates and captures a "native of Purgatory" for Crowley.
- "We made a pact. Even I don't break contracts like this."
Crowley and Castiel interrogate Eleanor Visyak and learn the ritual required to open the door to Purgatory. After Crowley has collected the blood required (from a virgin and a Purgatory native), Castiel informs him that the deal has changed - Castiel will not share the souls of Purgatory with him. His options, Castiel says, are "flee or die." Crowley seeks out Raphael and they make a deal, returning to demand the blood from Castiel, who gives it to them and leaves. Together they draw the sigils and, while the moon is eclipsed, Crowley recites the incantation to open the door. He is interrupted by Dean and Bobby, but he disables them while he completes the ritual. However, the door does not open, and Castiel - having switched the blood and given them dog blood - returns, full of the souls he's taken in from Purgatory. Crowley flees. When Raphael asks Castiel why he let the demon escape, Castiel replies that he has plans for him.
- "Fancy a drink before you smite me?"
Castiel finds Crowley living in a trailer in Tennessee, which he enters easily despite it being covered in angel proofing sigils. Crowley assumes Castiel has come to kill him, but Castiel reveals he wants Crowley to return to being King of Hell as he needs Hell as a threat for his enemies. However, from now on Castiel will determine where souls go, and will restrict the number going to Hell. With no other choice on the table, Crowley accepts Castiel's offer. Later, Dean, Sam and Bobby summon Crowley and ask for help in summoning and binding Death. Though initially reluctant to cross Castiel, Crowley later delivers a binding spell to them, with a note attached "Bye forever you fools. Kisses C."
- "You and I control large interests I feel strongly could meld to the benefit of all."
Crowley appears inside Dick Roman's (the leader of the Leviathans) limo and introduces himself as King of Hell. He offers Dick a gift basket of muffins made from "infant uvula" and proposes an alliance between the forces of Hell and the leviathans. But despite having a hand in their release from Purgatory, Crowley is unable to convince Dick that he is anything more than a "bottom-feeding mutation" and needless to say; Crowley fails to sell his idea.
- Crowley: I'll cut to the chase, Mr. Roman.
- Dick Roman: Please. Dick.
- Crowley: Dick. You and I control large interests I feel strongly could meld to the benefit of all.
- Dick Roman: You think?
- Crowley: I know. Straight talk: we should be friends, you and I.
- Dick Roman: Why? Why in the world would we be?
- Crowley: W-Well I brought you here, Dick. I-I found a way to open a door to Purgatory...
- Dick Roman: To steal every last soul, you mean. You and that angel friend of yours. Don't roofee me and call it romance.
- Crowley: I-I think you've got me wrong.
- Dick Roman: Now it's your turn to listen. I'd sooner swim through hot garbage than shake the hand of a bottom-feeding mutation like you. You demons are ugly, lazy, gold-digging whores. You're less than humans and they're not good for much but to dip deep in garlic sauce. I'd never work with you, Crowley. In fact, if I wasn't busy with other things I might actually wipe your kind from the face of the universe. And you deserve it. Are we clear?
- Crowley: Keep the muffins.
Visibly shaken by Dick's rejection, Crowley makes a prompt exit, leaving the muffins behind.
- "I have one rule: make a deal, keep it."
A crossroads demon named Guy starts exploiting a loophole in his deals to collect the clients' souls before their 10 year due date by having another demon called Jackson kill them, as the rules of the contract prohibits Guy from interfering directly. But Jackson sells his partner out to Crowley who arrives just in time to save the wayward demon from being killed by Dean Winchester. However, he berates the demon for cheating on the deals as it threatens their future negotiations; who will deal with a demon if they're worried about a chandelier accidentally falling on them the next day? The demon realizes his mistake but Crowley is unsympathetic and intends to use Guy as an example to the others.
- Crowley: There's a reason we don't call our chips in early; consumer confidence. This isn't Wall Street. This is Hell! We have a little something called integrity. This gets out who'll deal with us? Nobody! Then where are we?!
Crowley negotiates a prisoner exchange of sorts: hand over the demon and every deal he made will be terminated. Dean agrees, and Crowley honors his end by ending the contracts. When asked why they haven't encountered him since 7.01 Meet The New Boss, Crowley reveals that he has ordered the demons to leave the Winchesters alone as they are hunting the Leviathans. Crowley then returns to Hell with the crossroads demon, and presumably makes an example of him.
Dean reminds an attacking demon that Crowley ordered a hands-off policy with regards to the Winchesters, but the demon dismisses this because Sam and Dean haven't stopped the leviathan yet and Crowley will want Emmanuel captured more than he wants Dean kept alive. Dean, however, kills the demon before he can take Emmanuel (actually an amnesiac Castiel) to Crowley. Meg reveals that she still harbors intentions of killing Crowley and that Crowley in turn put a price on her head, causing her to be hunted by other demons. As the rest of her fellow Lucifer loyalists having all been killed or captured by Crowley and she needs allies, she seeks Dean out and gets him to resume their alliance against Crowley. Meg's insinuation that Crowley would seek revenge on Castiel if he learned that Castiel is alive and helpless, implies that Crowley still has a grudge against Castiel for the latter's betrayal. Later on, when Castiel regains his memory, he briefly has a flashback of Crowley from 6.22 The Man Who Knew Too Much.
After Meg is spotted by two of Crowley's men, she persuades them not to take her to Crowley in order to claim the bounty he's set on her because she promises that she has something else that they can give to Crowley that he would care about far more. Misinterpreting her, Rosco states that Crowley won't care if they bring in Sam and Dean, but his interest is peaked when he realizes that Meg is offering to give them a still-living Castiel, indicating that Crowley would indeed value capturing Castiel over capturing Meg. It turns out to be a trick, with Meg killing the other demons before word gets back to Crowley that Castiel is still alive. When she goes back to Sam, Dean, and Castiel, it is revealed that Sam and Dean have been anticipating her turning them over to Crowley's forces, leading her to explain that currently her only goal in life is to kill Crowley. Dean dismisses him as a threat when compared to the Leviathan, but Meg insists that Crowley is "always" the problem, just laying low and manipulating events until the time is right for him to take advantage of the situation.
- "I'm all for chopping Dick, but I can't have you running around with a vial of my blood, now, can I?"
Crowley is summoned by Sam and Dean who clue him in on their plan to take out Dick Roman. Crowley happily offers his blood for the weapon, but only after they've gathered all the other components for fear of his blood falling in the wrong hands. He then vanishes on the promise to return next time they call. Crowley later reappears in Dick Roman's office, having been summoned beneath a devil's trap. Dick greets him jovially, stating that they have much to discuss.
- "You got what you wanted – Dick's dead, saved the world. So I want one little prophet. Sorry, moose. Wish I could help. You certainly got a lot on your plate right now. It looks like you are well and truly... on your own."
Trapped in Leviathan custody, Crowley deduces that Dick has already discovered the Winchesters' plan and captured the prophet; therefore he also knew that the key to killing Dick lies with Crowley's blood. Dick proposes a truce in exchange for Crowley's assistance in duping the Winchesters: he delivers them a vial of blood not his own, and Crowley can have Canada when all is said and done. Knowing he hasn't any other choice, Crowley accepts and starts on the paperwork (which takes all night to finalize). He then answers the Winchesters' summons and is surprised to find Meg and Castiel in their company. Meg tries to flee but Crowley prevents her, promising to take her back to Hell once Dick is dealt with. Crowley also desires revenge against Castiel for his betrayal, but upon discovering the damaged state he's in, Crowley decides to wait until "sparkles" is himself again. He gives the boys his blood, informing them of the offer Dick made; leaving it ambiguous as to whether he should be trusted or not. Crowley then vanishes. He later reappears in SucroCorp following Dean and Castiel's successful slaying of Dick and their subsequent banishment to Purgatory. He explains to a panicking Sam that he has an army of demons mopping up the rest of the Leviathans, two of which have also captured Meg. Sam demands to know where Dean is but Crowley offers no answers, instead leaving him with the knowledge that he is "truly alone" before vanishing along with Kevin Tran as a prize.
- "Hello, boys. Dean. You're looking... well, let's just say Purgatory didn't do you any favors. Where's your angel?"
A year before the events of the episode, Crowley has Kevin Tran spiffed up and then taken to a warehouse where he has somehow gotten his hands on another Word of God tablet. He has Kevin translate it for him and Kevin tells him that it’s all about demons and that there is a way to open all the Devil's Gates in the world and release every demon in existence upon the Earth. Kevin directs Crowley to a Hell Gate in Wisconsin where Crowley goes while Kevin casts a spell to open the gate. Crowley stays in contact with his men through a cell phone while Kevin casts the spell, however, Kevin betrays him and casts a different spell, this one to destroy demons and escapes with the tablet.
Looking for Kevin, Crowley has a demon possess Kevin's girlfriend Channing and she informs him through a goblet of blood that while Kevin hasn't come to see her, the Winchesters had. Apparently by following Sam and Dean, Crowley is able to locate Kevin and after Sam and Dean kill his minions, steps in himself with Channing. Crowley offers Kevin a deal: Channing's life and freedom for Kevin, proving that Channing is still alive by letting her regain control temporarily. Kevin agrees to the deal and goes to get his stuff. When he takes too long, Crowley goes after him, heating up Ruby's knife to stop Dean from using it on him. Crowley and Channing enter the backroom where Kevin drops a bucket of holy water on them, allowing himself and the Winchesters to escape. Watching the three drive away in the Impala, Crowley orders the demon possessing Channing to find a new meatsuit and then, as Kevin watches horrified, dramatically snaps Channing's neck with telekinesis, killing her.
- "I know we're not mates, Kevin, but one word of advice – run. Run far and run fast. 'Cause the Winchesters – well, they have a habit of using people up and watching them die bloody."
After learning that the demon tablet is at an auction run by Plutus, Crowley travels there to bid for it as Plutus has put up protections against any sort of magics or violence. Crowley asks why Sam and Dean are bothering to get the tablet as all they can get from it is information on how to kill a few demons, but they brush him off. After learning that Crowley is the one who kidnapped her son, Linda Tran punches him in the face, amazing him and causing him to warn Sam and Dean not to try anything as further violence could get them kicked out.
During the auction, Crowley sits behind Sam, Dean, Linda Tran and Kevin and taunts Sam and Dean on the failure of their plans. He bids the real Mona Lisa, Alaska and the moon for the tablet, but is rejected and Kevin is added to the sale. Crowley is outbid by Linda who offers up her own soul in exchange for the tablet and her son. Crowley tries to outbid that by offering up a million souls, but Plutus is only interested as she is sacrificing everything she is to win the bid. Crowley offers up his own soul, but Plutus rejects the offer as Crowley has none.
Desperate, Crowley makes a deal with Plutus' assistant Beau: a private island in exchange for Kevin and the tablet. With Beau's help, he possesses Linda and pretends to seal the deal before Sam and Dean realize what is going on. Beau kills Plutus and Crowley uses the stake Beau used to kill Plutus' guard. Crowley gets the tablet, however after Dean retrieves Ruby's knife, he decides to flee without Kevin. Dean chases him while Sam dispatches Beau who tries to keep Kevin to trade for another private island, but Dean catches up with Crowley and tries to kill him even though it will kill Linda Tran also. Crowley manages to throw Dean off of him and abandons Linda as a cloud of red smoke and reenters his usual meatsuit which is in a nearby room. As Sam, Dean and Kevin are distracted with Linda, Crowley reenters the room and retrieves the tablet, having learned of Sam and Dean's plans to permanently close the Gates of Hell from Linda's mind. Before departing, Crowley advises Kevin to flee Sam and Dean, telling him that they will dispose of him once they no longer need him.
- "It's all very West Side Story, but let's be logical. You look like hell, and I should know. You're not up for this."
Desperate to get the Word of God tablet translated, Crowley captures Samandriel and tortures the angel with an angel blade for the names of all the future prophets. After getting them, Crowley has his demons kidnap them and eventually stops torturing Samandriel after learning that the next generation of prophets hasn't been born yet. Crowley tries to get the future prophets to translate the tablet for him, but none of them can and frustrated, he kills one.
After learning the location of Kevin Tran and his mother from Delta Mendota, Crowley arrives and kidnaps Kevin once again, ordering a demon minion to kill Mrs. Tran. Crowley takes Kevin back to his warehouse headquarters and demands Kevin read the tablet or he will kill him and have the next prophet read it for him, proving his point by killing another future prophet. Kevin refuses, but as Crowley wants Kevin to read it for him and not someone else, he tortures Kevin, cutting off his finger to force him to agree.
Crowley has Kevin read the titles of the sections of the tablet to him, which include the sections on how to kill demons and closing the Gates of Hell, interesting Crowley as he realizes that the gates really can be closed. Kevin finds a note from the angel Metatron, writer of the tablet, in which he says he will be taking his leave of God and Heaven after he writes the tablets and leaves them for humanity. It interests Crowley as it reveals that there are more Word of God tablets than just the ones on leviathans and demons.
Before Crowley can learn anymore, Castiel arrives, having come to rescue Kevin with Sam and Dean. Castiel draws his angel blade on Crowley, but Crowley is unconcerned as Castiel is in a clearly weakened state and Crowley doesn't think he is a match for him. Castiel makes his wings appear and reaches out to smite Crowley. Crowley initially believes he's bluffing, but realizing that he's serious, he grabs the tablet and tries to make a run for it. To stop him, Castiel breaks the tablet in half and Crowley only gets away with half of it while Castiel and the Winchesters get the other half.
- "What on earth could you possibly need now, Viggo? I've given you every torture instrument known to man – short of a Neil Diamond album."
Crowley sets Viggo to torture Samandriel for whatever they can get out of him and is annoyed when Viggo summons him until he realizes that Samandriel has gone back to "factory settings" and that Viggo has tapped into his "operating system" with his torture. Crowley continues the torture personally to get what he can out of the angel who speaks in Enochian which Crowley can understand. Crowley gets annoyed with Samandriel's various babbling until he starts talking about an angel tablet which is apparently hardwired into all angels. As Sam and Dean try to break in, Crowley continues the torture as he appears to be getting close to something and is shocked when Samandriel reveals that there is an angel tablet. Crowley flees as Sam and Dean finally break in.
Dean, desperate for a way to kill a hellhound in order to close the Gates of Hell considers summoning a crossroads demon and forcing them to summon a hellhound for him to kill, but Sam is sure that if Crowley gets wind of what they are up to, he will send a hundred instead to kill them.
While investigating a family they believe has made a deal, Sam learns that Crowley himself made the deal with the people, posing as a traveling salesman back when he was just King of the Crossroads. Crowley was summoned by Carl Granville who wanted Alice Cassity to be his wife, but stuck around and made deals with Margot Cassity and Ellie for the family to strike oil and her mother to be cured of Parkinson's disease respectively. However, Dean learns that Crowley failed to mention the fact that in ten years he would be back to collect their souls.
- "What’s that old expression? If you want something done right... blah, blah, blah."
Looking for the angel tablet, Crowley figures out that it was in the hands of Lucifer and that he had it hidden in one of his many crypts. Needing someone who knows their location, he tortures Meg who knows from her time with Azazel. Meg gives him general locations so Crowley has his demons possess people who know things about the various towns and use their knowledge to dig for the crypts.
One of his demons calls him to report his failure to find the crypt and that all of the other demons are dead and Meg is gone. Crowley himself appears while the demon is on the phone with him and angered at the failure, stabs with the demon with an angel blade, killing him and decides to take up the search himself.
After the two demons he sends to attack Sam and Meg at the location of the crypt are killed by them, Crowley appears and tells Sam he's angry that he killed one of his hellhounds. Even though they have demon-proofed the building, Crowley tells them it won't hold him off long and Meg tells Sam to go find Dean and Castiel while she holds him off. Crowley is annoyed that Castiel has been foiling him again and tries to convince Meg to turn on the Winchesters, telling her that they plan to seal all demons in Hell and kill him. However, Meg tells him he sold her on their plan with the fact that they want to kill him and the two fight with their angel blades. Meg proves to be no match for Crowley, but her actions allow Sam, Dean and Castiel time to escape, Castiel with the angel tablet. Meg taunts Crowley over how Castiel apparently has the tablet as Sam and Dean are leaving without him and stabs Crowley through the shoulder with her sword. Barely affected, Crowley removes the sword and stabs Meg with his own sword, killing her.
In the crypt, Crowley meets the angel Naomi who is also looking for the tablet. Crowley indicates a previous sexual relationship between the two and realizes that the tablet is indeed gone and that Castiel has it. Naomi tells him that Castiel is doing exactly what he is meant to do: protect the tablet, apparently even if it means from her too. Crowley starts to offer Naomi a deal and is annoyed when she disappears when he turns away as that is what he usually does.
- "What you people never seem to understand is that you ARE NOTHING! Fleeting blips of light. I. Am. Forever."
After learning from one of his demons that rogue reaper Ajay was seen making a deal with the Winchesters, Crowley approaches him in his cab for answers. After learning that Ajay took Sam to Hell for an unknown reason and that he is due to pick him up in 17 hours, Crowley kills Ajay with an angel blade so he can't get him.
Talking with his assistant, Crowley puts everything together: the killing of his hellhound, the trip into Hell and the fact that Sam and Dean apparently have the good half of the tablet while he has the boring half and realizes that they are trying to close the Gates of Hell and orders his assistant to find Kevin Tran.
When Sam returns from Purgatory with Bobby Singer's soul in his arm, Crowley intercepts it as it rises to Heaven and prevents Sam and Dean from interfering as he starts to take it back to Hell. However, Naomi shows up to stop him. Crowley tries to convince her not to help as he believes the Winchesters will seal Heaven as well, but telling him that she hopes he gets sealed up first, Naomi tries to smite Crowley who flees. Naomi then releases Crowley's hold on Bobby's soul and he rises into Heaven.
Crowley finds Kevin despite his protections and reveals that he tortured Linda Tran for Kevin's location. Linda didn't break, so Crowley killed her and got the location off of her smartphone. Crowley captures Kevin and takes all of his notes on the tablet, fixing the damage so it looks like Kevin simply ran away.
- "I was born to direct."
After capturing Kevin Tran Crowley puts him in a fake Fizzles' Folly set after scrubbing his short-term memory so that he does not remember being abducted. Two demons masquerade as Sam and Dean to keep Kevin working on deciphering Crowley's half of the tablet and to try and get the location of Kevin's half from him, while Crowley observes and offers character notes from a large room with a series of monitors hooked up to hidden cameras observing Kevin.
Crowley then crashes Naomi's interrogation of Castiel and kills an angel using a gun, with bullets that were created by melting down an angel blade, and wounds another. Naomi retreats and Crowley reveals that the wounded angel, Ion, is working for him. He takes Castiel and deduces that the angel tablet is inside Castiel, which he then removes after shooting Castiel in the stomach.
Crowley's plan to break Kevin backfires when Kevin sees through his trick and sends his fake Sam and Dean into a trap. Crowley reveals himself to Kevin and asks how he figured it out, Kevin explains that his fake Sam and Dean were too polite and accommodating, and that Crowley will not be able to break him. Crowley claims that he has already won as he has the angel tablet and has many deals in play that they do not know about. Before he can kill Kevin the angel Metatron appears, in his true form, and throws Crowley into a wall, burning his vessel quite badly, and escapes with Kevin, who also managed to take Crowley's half of the tablet leaving him with only the angel tablet.
- "What's the line? 'Saving people, hunting things. The family business.' Well I think, the people you save, they're how you justify your pathetic little lives. The alcoholism, the collateral damage, the pain you've caused... The one thing that allows you to sleep at night - the one thing is knowing these folks are out there. Still out there. Happy and healthy because of you. You great big bloody heroes. They're your life's work and I am going to rip it apart. Piece by piece. Because I can. Because you can't stop me. Because when they're all gone, what will you have left?"
Attempting to recover the tablet, Crowley uses the Supernatural books to find people that the Winchesters have saved in the past and kill them, reasoning that the Winchesters will be left feeling guilty and grief-stricken about the fact that they have failed the people they saved, their victories in saving lives defining their own existences. These deaths include making Tommy Collins explode and boiling Jenny Klein in her oven. Dean and Sam attempt to save Sarah Blake when Crowley announces his intention to kill her, but his 'murder weapon' is revealed to be a hex bag hidden in Sarah's phone, which causes her to choke to death.
- "Seriously? Me, seriously? We just shared a foxhole, you and I. We beat back the Tet Offensive, outrun the --the Rape of Nanking, together! And still you're gonna do me like this?! Band of Brothers? The Pacific? None of this means anything to you? All those motels, you never once watched HBO, not once? Girls? You're my Marnie, Moose. A-and Hannah -- she just -- she needs to be loved. She deserves it. Don't we all -- you, me -- we deserve to be loved. I deserve to be loved! I just want to be loved."
Sheriff Jody Mills is on a date with a man that she thinks is named Roderick but is actually Crowley. The two get along great and Crowley claims to have lost someone special too, reminding Jody of the deaths of her son and husband and to start crying. Jody goes to the bathroom to calm down, but falls under a spell Crowley casts that causes her to choke on her own blood - there is a hex bag in her handbag. Sam and Dean call Crowley and demand he stop and he offers them a deal, using the little time Jody has left to force the issue. The deal is that they stop the undertaking the trials to close the Gates of Hell and give him the demon tablet, and he will stop killing Jody and everyone else they've ever saved. Dean agrees on the condition they trade the angel tablet for the demon tablet and Crowley agrees if they say "I surrender."
At the ruins of Singer Salvage Yard, Sam shows Crowley the demon tablet to prove he has it while Crowley shows them the angel tablet. Crowley produces a contract many yards long, and Dean insists on reading the fine detail. As he does, he gets close to Crowley and snaps handcuffs etched with binding sigils on him, trapping him. Sam and Dean take Crowley to a small church to undergo the third of the trials - to cure him. They secure Crowley in the middle of a devil's trap.
Castiel arrives, telling Dean he needs his help in undertaking the trials. Dean is reluctant to go, but Sam insists he will be fine. After confessing his sins, Sam starts injecting Crowley with his blood. At one point Crowley bites Sam, and when he leaves to get a bandage, Crowley casts a spell and uses the blood to send a call for help. Abaddon arrives, and throws Sam through a window, but she tells Crowley she is not there to help him, but to take over ruling Hell. Before she can kill the helpless Crowley, Sam douses her meatsuit with holy oil, setting her on fire and she vacates the body and leaves. Crowley, who is obviously regaining his humanity, tries to bond with Sam, tearfully declaring that he deserves to loved. He also asks what he could do to even begin to ask for forgiveness. Sam suggests he could start by going along with the cure and Crowley willingly does.
Dean arrives just as Sam is about to complete the ritual, and begs him to stop warning it will kill him. Sam does and Crowley is left as Dean takes a collapsing Sam outside. As the angels fall to Earth, Crowley, still stuck in the devil's trap, listens confused.
After the angels apparently refuse to answer his prayer to save Sam, Dean decides to turn to Crowley who he has locked in the Impala's trunk. He asks for Crowley to knock once for yes and twice for no and then asks him if he's still alive. At first Crowley does nothing, but eventually answers "yes." However, before Dean can do anymore, an angel shows up and interrupts him and as Ezekiel offers his help afterwards, he no longer needs Crowley's help.
- "Blah blah, boohoo. Done? Good. 'Cause this is what I know. I'm not giving you anything. Why would I? You have no leverage, darlings. You're not gonna close the Gates of Hell, because you didn't, you're not gonna kill me, because you haven't. So what's left?"
Sam and Dean take Crowley to the Bunker and lock him in the dungeon to the panic of Kevin as Crowley had previously tortured him. Sam and Dean question Crowley as to the names of the demons on Earth, pointing out that he had previously been close to being human again, but Crowley is unimpressed with their questions and tells them that they can't torture him more than he already tortures himself all the time. Sam and Dean lock the dungeon and shut the lights to leave Crowley to reflect, which he does, remembering how he nearly became human.
Hearing Kevin in the next room getting a file, Crowley taunts him, causing Kevin to beat him with his fists and a sledgehammer. Crowley claims to Kevin that he never killed his mother and that he will lead Kevin to her if he releases him. Crowley also tells Kevin that the Winchesters will use him and then discard him as there will always be more prophets. While Kevin considers releasing Crowley, he decides not to and leaves him in the dungeon.
When Sam and Dean return to the Bunker, Crowley reveals the names of two demons to them that he claims they would be doing him a favor by killing. Crowley offers them a deal: he has the names they want and they have the ability to help him with the things he wants. If they help him, he'll help them. He also tells them that he told them the names because he got enjoyment out of Kevin's predicament. Dean has Sam check on the names Crowley gave them while he stops Kevin from leaving, telling him that even if Crowley was telling the truth, his mother is dead in all the ways that matters.
- "Wow. If it isn't the Scarecrow and the Tin Man. Your new houseguest, so misunderstood — neither of you saw Wicked?"
Sam gives Crowley a pen and paper for more demon names, but Crowley refuses unless he can stretch his legs. Sam just leaves the paper and pen with Crowley and leaves.
When the Wicked Witch of the West escapes, she finds Crowley and he has her write what she wants on the paper. When she writes "key," Crowley tells her that the Winchesters keep the keys in the kitchen. When Sam and Dean find him, he agrees to tell them what the Witch wanted in exchange for being allowed to stretch his legs. Sam releases him from the collar keeping him in his chair, but he stalls so Dean shoots him. Crowley shows them the paper and tells them what he told the Witch. Sam and Dean then leave him alone.
After the Wicked Witch is killed, Sam secures him to his chair again and puts a pen and paper in front of Crowley again. When Crowley tries to get more out of him, Sam leaves without ever saying a word, leaving the paper for Crowley. Annoyed, Crowley mutters "bollocks."
- "It may look like bean-counting to you, it may lack a certain adolescent flair, but my way... works! You think you can control Hell with chaos alone, without the support of those who are still loyal to me?! Your way will backfire. You. Will. Burn."
Kevin tells Sam there is some smudging on the tablet, as if the scribe does not want anyone to read it. He and Sam cannot translate it. Sam suggests they get Crowley to translate Crowley can read the tablet, but refuses. When Sam tries to reason with him, Crowley crumples the paper up and throws it in Sam’s face. Sam threatens to give Crowley up to Abaddon. Crowley asks for one phone call.
Crowley proves that he can read the translation. Sam decides to let Crowley have one phone call. Kevin says letting the King of Hell and Abbadon communicate with each other is a terrible idea. The phone call involves drawing blood. When Sam starts to do it, Crowley demands Kevin’s blood. He says he has had enough of Sam’s blood, he wants something fresh. After some coaxing, Kevin agrees. He fills a syringe with his blood. With the blood bubbling in a bowl, Crowley contacts Hell. When he says he is their King, he is put on hold.
Crowley reaches Abaddon. Abaddon gleefully tells Crowley that she has doubled his projections by voiding his contracts and bringing more souls to Hell. She insults Crowley and tells him she will soon replace him. Crowley yells that you cannot rule Hell with chaos, and she will burn. “I can’t wait,” she snarls. Crowley passes the bowl back to Sam. Crowley asks for the transcripts, saying that he keeps his promises. Crowley reads the transcripts, and gives them the bad news: the angel spell is irreversible.
When Sam is washing out the bowl of blood, he notices something amiss with the set of syringes. Opening it, he finds one gone. Crowley palmed one of the syringes. Heading to Crowley, he sees Crowley injecting himself with Kevin’s blood and leaning back, sighing with relief.
- "It's a campaign. Hearts and minds, that's what's important. See, the demons have a choice -- take orders from the world's angriest ginger -- and that's saying something -- or join my team, where everyone gets a say, a virgin, and all the entrails they can eat. So, think on this, lads. Spread the word -- vote Crowley."
Dean asks Castiel for help. Castiel reminds Dean of the angel Samandriel and says that the demons were able to dig into his mind, and they might be able to bypass the angel and talk directly to Sam.
Dean tries to bargain for Crowley’s help and offers him a syringe of human blood, believing Crowley to have a craving for it, Crowley refuses and asks for a massage by Kevin, Castiel informs him that Kevin is dead. Crowley then taunts Dean saying that people, who get close to him, get killed. Crowley agrees to help them crack open the angel in return they will allow him a little field trip with the chains still on. Castiel and Dean get in argument about accepting Crowley’s deal, Crowley then suggest to ask for Sam’s opinion, after seeing Dean’s reaction to Sam’s name Crowley then deduces that it’s Sam that is in trouble. Dean then agrees to the deal.
Crowley, Dean and Castiel drive using Castiel’s car to a source of Crowley’s, Cecily, who can track anything. Cecily insists on meeting Crowley alone in a warded room, thus making Castiel unable to listen in. Cecily then updates Crowley on the high points of the months he's missed; she admits Hell is in chaos, and that Abaddon has not yet taken over. She also implies that she is not totally loyal to Crowley but that she is playing both sides. She then locates the Impala for Crowley.
Once Gadreel is captured, Crowley begins to access Gadreel's "programming" and is able to make the angel reveal his identity, but Crowley is still unable to bypass the angel and talk directly to Sam. Dean then asks for Castiel to posses Sam and help him kick Gadreel out. But Castiel can’t possess a vessel without permission. Crowley then offers to do it if they remove the chains and set him free. Dean agrees and releases Crowley from his bindings, allowing him to jump into Sam's body. Once in Sam's mind he convinces him that an angel is possessing his body and he is tucked away in small dark corner of his mind, but then Gadreel finds them and a fight ensues but Sam is strong enough and expels Gadreel from his body. Crowley leaves voluntarily.
As Sam starts to wake up, Abaddon arrives, and Crowley tells them to leave. Dean then says that this don't make them square and if he sees him again he is dead, Abaddon orders the demons with her to kill Crowley, they refuse, and Crowley points out she does not yet rule all the demons. Abaddon wants to fight, but Crowley likens their conflict more to an election - whoever wins over the demons will rule hell
- "You're good. But I'm Crowley."
Searching for the First Blade, the only weapon that can kill Abaddon, Crowley approaches Dean for help, revealing that the only demon who knew about the Blade was captured by John Winchester before Crowley could get to him. Following a clue in John Winchester's Journal, Dean and Crowley travel to John's Lock-Up where they find a file on an old case John worked with a hunter named Tara where he interrogated and exorcised the demon who did mention the Blade. Finding Tara, she recognizes Crowley as a demon and initially refuses to help until she is told about Abaddon. After Tara reveals that the last ingredient of a locator spell for the Blade is the essence of kraken, Crowley takes off to get it. With the spell, Dean and Crowley are able to track the Blade to Missouri. Arriving at the location the spell indicated, Crowley is terrified to find Cain who silences him and keeps him from fleeing. Cain reveals that he created the Knights of Hell and slaughtered them which Crowley knew and didn't tell Dean, but refuses to give them the Blade. Four demons arrive to attack and Crowley kills one with an angel blade while Dean kills the rest. As an army of demons arrive, Cain agrees to help, revealing that Abaddon murdered his wife. He gives Dean the Mark of Cain, the source of the Blade's power and tells them that the Blade itself is in the ocean. Cain teleports Crowley and Dean outside as he takes on the demon army and they flee. Dean realizes that Crowley was actually using him all along, having known the truth about the Blade and Cain the whole time. Crowley confirms it, saying that while Cain wouldn't help him, he knew he'd help Dean. While Dean threatens to kill Crowley once they have dealt with Abaddon, the two are forced to work together for the time being as Crowley is the only one who can find and retrieve the Blade.
- "You don't know what it's like to be human... it's your DNA. My addiction. My cross. My burden!"
Crowley has grown addicted to human blood and relies on a demon named Lola to get it, not knowing that she is betraying his secrets to Abaddon. After discovering her betrayal and killing her, Crowley calls in Sam and Dean who force him to detox from the blood. Crowley reveals that he tracked the Blade down from where it was retrieved from the bottom of the Marianas Trench years earlier and helps Sam and Dean find who it was sold to by possessing the man sent to meet with them briefly. Sam and Dean learn that a man going by Magnus got the Blade and realize he was one of the Men of Letters. Crowley reveals that Magnus was a rogue member who he had been trying to track down but lost track of. Sam and Dean learn that Magnus was once the MoL's spellmaster and manage to convince him to let them into his lair, but Crowley is left behind. After Sam is sent back without Dean when Magnus decides to add Dean to his "collection," Sam and Crowley work together to get inside his lair. Once inside, though he is powerless, Crowley avoids capture and frees Dean, allowing him to kill Magnus with the First Blade. However, knowing Sam and Dean will likely betray and try to kill him, Crowley steals the Blade from them until such time that they track down Abaddon and use it to kill her.
- "Well, I was going to, but then after very little soul-searching, I decided to embrace my addiction. What about you? Takes a junkie to know a junkie. You just want to touch that precious again, don't you?"
After Dean calls him and then hangs up, Crowley tracks him down at a bar and tries to convince him to embrace the Mark of Cain and the killer instinct that comes with it, but Dean refuses. While Crowley is using the bathroom, Dean stops a hunter from going after him and confronts Crowley as he believes Crowley was shooting up again with human blood. Crowley doesn't deny it but believes Dean is hunting Abaddon so badly so that he can touch the First Blade again and get the rush it gives him. Dean denies it, telling him he's focused on killing Abaddon and can't worry about the consequences of using the Blade though Crowley is unconvinced. Crowley agrees to bring Dean the Blade when he finds Abaddon, but meets with the "hunter," Jake, that was supposedly after him. Its revealed that Jake is actually a demon working for Crowley who he used to test Dean to see if Dean would save him. Crowley is pleased, stating that he knew Dean would as they're "besties" and that Dean is "ready."
- "You betrayed me! No one in the history of torture has been tortured with torture like the torture you'll be tortured with!"
Abaddon pulls Crowley's son Gavin MacLeod to the present to use his lingering humanity and affection for his son against him to force him to help her kill the Winchesters. After Abaddon causes Gavin great pain, Crowley agrees and informs Sam and Dean of where to find the First Blade, calling off a hellhound guarding it. He then tells them where to find him and that he has found Abaddon, but tells Dean "Poughkeepsie," the code word Dean taught him that means "drop everything and run" to warn him of the trap. To keep Crowley from interfering, Abaddon shoots him in the shoulder with a bullet engraved with a devil's trap, binding his powers and trapping him, the way the Winchesters and their grandfather initially defeated her. When Dean arrives, Crowley tells him Abaddon is close then warns him with his eyes of an attacking demon. Dean kills the demon and faces off against Abaddon while Crowley watches immobile. As Crowley watches, Dean displays immunity to Abaddon's powers and telekinesis, allowing him to gain the upper hand and kill Abaddon. Afterwards, Crowley uses a knife to dig out the bullet, annoyed that Sam and Dean won't help him. Sam informs him that they are letting him live and he should be happy with that. Crowley is amused to find out that Dean didn't tell Sam he'd warned them it was a trap and is upset that Sam and Dean insist on sending Gavin back to his own time as Crowley doesn't want him to die. Pretending to say goodbye to his son, Crowley teleports him to a park where he tells him of his fate and that he should build a new life in the present
- "Listen to me Dean Winchester, what you're feeling right now is not death, it's life. A new kind of life. Open your eyes Dean, see what I see, feel what I feel. Let's go take a howl at that moon."
Having regained his post as King of Hell, Crowley is summoned by Dean while he is getting a massage. When summoned he informs Dean that the Mark of Cain's side effect is that the more you kill, the better you feel. And the less you kill, the worse you feel. When Dean states that Cain was not affected like this Crowley reminds him that Cain is a demon and that a human body is not strong enough to handle the power of the Mark. Telling Dean, unless he keeps killing, he will die. Crowley helps Dean escape the Bunker, retrieve the First Blade and start hunting down Metatron.
During a brief stop in a restaurant, where Crowley insists Dean order some food so that the waitress will get a bigger tip, he asks Dean if he ever wonders if 'this' is all there is, and whether or not Dean has ever just wished to abandon it all and "go howl at the moon." He also states that he's kicked human blood, and Hell is secure but, complicated. To which Dean tells him that it's him that's complicated, not Hell. Before Dean can ask what they are two of Crowley's demons enter the restaurant and inform him of Metatron's recent actions. Both Dean and Crowley leave, though Crowley asks Dean if he plans to eat his food to which Dean replies that he isn't hungry.
Tracking down a woman that Metatron resurrected both Crowley and Dean find Sam outside her house, who implores Dean to work with him instead of Crowley. Dean agrees and tells Crowley to go, who sarcastically quips that he has been "Winchester'd," telling them he would wish them good luck, if he thought it would actually do anything.
After Dean has died Sam attempts to summon Crowley, little realizing that Crowley is already inside the Bunker and with Dean's corpse. Crowley tells Dean that he has never lied to him, but he did omit certain truths or only half-tell them. He tells Dean's corpse that there is another story about Cain, that one day he realized what the Mark was doing to him and in desperation took his own life... but the Mark would not let him die. He tells Dean that he isn't really dead but is entering a new life, where he will see what Crowley sees and feel what Crowley feels. He tells Dean to open his eyes, which Dean does revealing that he has become a demon.
- "We've howled. We've bayed. We've done extraordinary things to triplets, all of which have been massively entertaining. I will treasure our Flickr albums forever. But now it's time for us to accept what we are and go back to work."
Crowley is with the "new Dean" at a bar called The Black Spur. After Dean has sex with a waitress named Ann Marie, Crowley walks in on the two of them in his bed, and is upset with them for "soiling" his room. Later, Dean and Crowley play foosball with two people at the bar. They lose, and Dean blames Crowley for interrupting him while playing. When Dean almost kills a man that was harassing Ann Marie outside the bar, Crowley is seen watching the whole fight silently. When looking through the phone of an Abaddon loyalist by the name of Neely, Sam discovers a text that had alerted the demon of Dean's presence and whereabouts. When Sam calls the number, Crowley answers, revealing that he has been sending the "Abaddon loyalists" after Dean the whole time. Sam promises Crowley that he will save his brother or die trying. Crowley tells Sam that he is jealous of the fact that Crowley and Dean are best friends now, and that his brother is not just possessed, but has been twisted into a demon by the Mark of Cain. Sam tracks Crowley using the phone number in the text message, which Crowley had anticipated. Back at the Black Spur, Crowley tells Dean about Sam and that they have to leave immediately, but Dean doesn't agree. Crowley urges Dean to be his second-in-command, and tells him that they could rule Hell together and be unstoppable. When Dean still refuses, he tells Dean the truth, admitting that the "Abaddon loyalists" were sent by Crowley. He knew Dean would make quick work of them, and that Dean needed to "feed" the Mark of Cain by fulfilling his new-found lust for killing. Crowley then tells Dean that he must decide if he really wants to rule Hell with him or not.
- "Kids. Am I right? In my day, we respected our elders. Of course, back then, anyone over 30 was ancient. Now 40-year-olds are still living with mommy, lying on OkCupid, and taking pictures of their food."
- "Why can't you people just sit on clouds and play harps like you're supposed to?"
Crowley has gone back to ruling Hell, including sentencing to death those demons that were loyal to Abaddon, as well as any demons that annoy him. When a demon questions Crowley's ability and competence in light of his time with Dean Winchester, protesting Crowley's rule, the demon self-immolates himself in front of Crowley and the other demons with holy oil, shocking the King with the turn of events.
Crowley had been keeping tabs on Castiel, and when he learns of Adina attacking Cas and Hannah, Crowley arrives at the gas station before Adina is about to kill Hannah. He slices Adina's throat and steals her grace before fatally stabbing her. He then gives Cas her grace which allows him to power up again. Crowley tells Cas the reason he helped him was because he wants Cas to help fix the problem that is the demonic Dean Winchester.
- "So you and your half-wit pal threw me into the sex trade? I'm evil, that's just tacky."
Crowley is angered to learn that two of his demon minions -- Gerald and Raul -- went behind his back to create a demonic brothel to increase the number of souls in Hell by having people sell their souls for sex with hookers, as he finds it tacky rather than evil. After learning that Raul was killed, Gerald convinces Crowley to go after the witch that killed Raul.
Later, Gerald reports to Crowley, saying that while their alpha team were killed by the Winchesters, the beta team caught the witch responsible. Crowley enters the room to confront her and is shocked as the witch, Rowena, is his mother.
- "She was a horrible mother. Did I tell you the time that she almost traded me for three pigs, three! I was an attractive child, I could juggle. I was worth five pigs, at least."
Crowley is venting to Gerald about how horrible Rowena was as a mother, when Gerald asks Crowley why he just doesn't kill her, he tells him he has his reasons. Gerald then offers to kill Rowena for Crowley, telling him he would have no problem with it as he killed his own mother over burning him with cigarettes, though Crowley does not give him an answer.
When Crowley finally decides to see Rowena, he berates her for being a horrible mother to him, but Rowena deflects that by saying she was motivating him for bigger things. When he brings up she abandoned him when he was eight, she tells it was because she ran afoul of the locals and had to flee. Rowena tells Crowley she wishes to be a family again, and that he can trust her unlike the demons who will turn on him at the first chance. After their chat, Crowley and Gerald escort Rowena back to the dungeon. It's there that Rowena accuses Gerald of smuggling demons out of Hell, to which Trish confirms. Gerald denies the accusations, and begins to strangle Rowena. When he doesn't listen to Crowley's repeated orders to stop, Crowley stabs Gerald through the neck with an angel blade, killing him. As Crowley leaves the cell, he asks Rowena if she is coming. She smiles and follows him out the door.
- "Mummy. Bored, suicidal, or both?"
- "Don't give a damn about the kid. I'm talking about the risk to us."
Crowley presides over his court, extremely bored and playing games while a Crossroads Demon complains about not getting enough credit. While Crowley initially decides to give him the credit he wants, he instead takes Rowena's suggestion of cutting the demon in two. Afterwards, Rowena approaches him to help her eliminate one of her rivals, Olivette which Crowley ultimately agrees to despite knowing her help before was so she could manipulate him into helping her with Olivette. As they plan their attack on Olivette, Dean calls Crowley and tells him that Cain is killing again and he needs the First Blade to stop him. Crowley refuses at first until Dean tells him Cain wants Crowley dead too. Crowley retrieves the First Blade and goes to meet with the Winchesters and Castiel despite Rowena's objections that the Winchesters are using him and they are not his friends.
At a barn in Ohio, Crowley refuses to turn over the First Blade until they have Cain where they want him. Crowley, Sam and Castiel use Rowena's illusion spell to draw Cain into a devil's trap to weaken him for Dean to fight. Crowley then reluctantly turns over the First Blade to Dean after being promised its return if Dean returns in a sound state of mind. After Dean kills Cain, he hands the First Blade over to Castiel instead of Crowley who is shocked that Dean lied to him. He is even more shocked when Dean reveals that he lied about Cain coming after Crowley and Crowley disappears without a word.
Back at his lair, Crowley finds Rowena preparing to leave and she tells him he is no longer a king but the Winchesters' lap dog and bitch, something that he is left considering.
- "Listen, we’ve been through this. My relationship with the Winchesters is my business. I’ll handle them. I’m not killing them."
As Crowley sits on his throne going over documents, a demon minion approaches him begging Crowley to speak with Rowena regarding her abuse of the court revealing he has grown a second face in the back of his head due to her. Crowley calls Rowena into the throne room, where she vents her frustration regarding the Grand Coven and Crowley's failure to act in her interests and siding with the Winchesters before leaving the throne room.
Sometime later, Crowley once again summons Rowena to the throne room. He goes on to tell Rowena how can sympathize with her plight and reveals to her that he has kidnapped the High Priestess of the Gran Coven, Olivette, for her to extract her revenge on. After Rowena has had her fun, Crowley returns to find that Olivette has been turned into a hamster, commenting it is the type of poetic justice he might have done in her place as well. He quickly realizes that Rowena is looking for something else from him and upon Rowena asking about the Winchesters, Crowley cuts her off and tells her the Winchesters are his buisness to handle and he is not going to kill them.
- "I'm bloody Crowley! I'm the King of Hell. I do what I want, when I want. And I don't take orders from you."
After Rowena begins her plan to kill the Winchesters she manages to track Dean to a bar where he is hustling pool. Rowena uses a Gaelic spell on Dean which is supposed to rip him apart, but to no avail due to the protection of the Mark of Cain. Back in Hell, Rowena cuts and beats herself and tells Crowley that Dean did this to her in hope of Crowley retaliating. To her surprise, Crowley ignores her and tells her she deserved what she got for going up against Dean.
Crowley finds Dean and the two have a drink together. Dean schools Crowley about the meaning of family - its not whether they are a blood relative or not, but how they treat you that matters. Crowley reveals to dean that Rowena knows the Mark of Cain is a curse. Crowley forces Rowena to leave, stating that the only reason she is clinging to him is he is being useful to her. Rowena then packs and leaves her son's lair.
- "Just for once, I wish you trolls would bring me some good news. 'Sire, Missouri has boils.' Something cheerful."
Crowley is in his throne room throwing darts at a minion's chest when two subordinates appear telling him Rowena has disappeared. He picks up an [[angel blade and stabs one of the messengers, and threatens the other one with death unless he returns with news of where his mother has gone. Having gotten no new news about the whereabouts of his mother, Crowley resorts to questioning Olivette, who regales him with tales of how terrible Rowena was. He tells Olivette he wants any dirt that he would be able to hold over Rowena, and learns that she once had a demon lover as well as the name of Oskar. He gives a minion Oskar's name, and tells him to track him down, and that failure to do so will result in horrific torture.
- "You're right I am a monster, and I've done bad, I've done thing you can't even imagine. Horrible, evil, messy things. And I've loved every damn minute. So thank you Sam, for reminding me who I really am."
As Crowley is sitting in a diner, he compliments the waiter on the coffee, saying it's the best he's ever had. As it appears that Crowley is about to make a deal, he gets a call from Dean asking for his help and a text giving him the location to meet. Crowley arrives at the abandoned warehouse, and calls for Dean. A gun fires, and Crowley collapses against a wall, unable to move, holding his hand over where the bullet entered. Sam emerges from the shadows, and tells Crowley he used a recording of Dean to trick, and he plans on killing him. He places a hex bag in Crowley's pocket, much to his confusion, however when Sam tells him, "By the way. She said to tell you, she should have taken the three pigs." He realizes Rowena is behind this, and all of a sudden tenses up in pain, eyes wide. He slides down the wall and falls onto the floor, unable to breathe, coughing blood and demon smoke, while Sam stands over him, unemotional.
Crowley, continuing to puke up demon smoke, laments to Sam that this is what he gets for trying to be better and change Hell. Sam tells him nothing he did matters, calls him a monster, and tells him he is going to watch him die screaming. Crowley continues to cough, and admits to Sam that he is terrible and evil. He then turns his head to look up at Sam, his eyes have turned a dark red, with red smoke emanating from them, and tells him he loved every minute of it. He pulls the bullet out from his wound, and stands up to Sam's shock. He flicks his hand sideways and sends Sam flying across the room, smashing through glass windows into the next room. Crowley walks over to Sam, holding the hex bag which then bursts into flames. Sam sees Ruby’s knife on the ground and tries to reach it, but Crowley sends it flying away with a wave of his hand. Crowley stands over Sam, with his fingers ready to make a snapping motion, which Sam can only watch defenseless. He tells Sam he can kill him easy, but lowers his hand. He tells him the only reason he's alive is because he allows it, and to give a message to his mother, "You tell that ginger whore that I gave her a chance to walk away and she spat in my face. So now, she’ll never see me coming." Before vanishing.
- "The Quince cost me a major IOU with a Palestinian warlock. The gold from the calf -- well, let's just say I'll be hanged under certain sexual-deviancy laws if I ever show my face in Jordan again."
At a crossroads, Castiel summons Crowley, seeking his assistance in removing the Mark of Cain from Dean. When Crowley refuses, Castiel raises his hand and threatens to smite him where he stands, for which Crowley dares him to try and kill him or to do it his way and simply beg him. Castiel acquiesces and gives Crowley a list of the ingredients need for the spell, Crowley agrees and disappears.
At Oskar's diner, he is serving a patron some coffee, as he turns his back to the counter to place the coffee pot back on the burner. There is a loud sound of glass and silverware breaking/falling, causing Oskar to jump and as he turns around he sees Crowley standing in the middle of the diner with all the customers seemingly knocked unconscious. Crowley flicks his hand and Oskar is pushed back and pinned against the serving counter. He takes a seat at the counter and begins telling Oskar a story about a witch who was taken in and cared for by Polish family, and the young child she grew to love. Learning that the young boy was terminally ill, as thanks the witch performs two spells one to heal the boy and another that would give him immortality when he was an adult. Revealing that he knows who he is and his relationship to his mother, Rowena.
Crowley arrives at the abandoned distillery with the first two ingredients in hand, when Rowena asks for the third (something she loves) Crowley snaps his fingers, and Oskar walks into the room. Rowena berates Crowley for bringing her Oskar as a "a cruel, shameful, disgusting low." But Crowley only retorts that, "It's only cruel if you actually go through with it." As Rowena gives Oskar a hug, she looks angrily over her shoulder at Crowley before stabbing Oskar in the neck with a fountain pen and draining his blood into a bowl. With all the ingredients prepared, Rowena preforms the spell, causing a shock wave that knocks her, Crowley and Castiel back. Free from her iron bonds, Rowena freezes Crowley where he stands with a word, and places the attack dog spell on Castiel and sicks him on Crowley. Castiel begins advancing towards Crowley, angel blade in hand raises it to strike Crowley.
- "The Darkness? Please. Myth. It's a bedtime story, something daddy demons threaten toddler demons with to get them to eat their vegetables. Even if it was true, what's the concern? Darkness, King of Hell -- natural allies."
As Castiel advances on Crowley, he raises the angel blade to strike it down on Crowley, but Crowley is able to block the attack. As he begins to tell Castiel how he can't be killed, Castiel knocks him to the ground, and proceeds to stab him in the back. However, Crowley was able to vacate his meatsuit and escape through a drain near his head.
After escaping Castiel and possessing a suburban housewife, Crowley plans on murdering the people in her home so he can call his minions. When he goes inside he is surprised to find the Marnie's husband has granted her wish to be in an orgy with their friends for her birthday. After the orgy, a pair of minions survey the room, which is strewn with dead bodies, once Crowley arrives in the room, a minion gives him a report on his preferred meatsuit being tended to for repossession. Once the body has had Rowena's immobilization spell removed, Crowley reenters it at the abandoned distillery. It's there that the demon minions break the news to him that the Darkness has been released, for which he doesn't believe, as he sees the Darkness is merely a myth. However, his mood changes once a minion mentions that something happened in Lucifer's Cage. Which causes Crowley to take pause, he asks the minion what happened and he tells him all of Hell heard an animalistic scream emanating from the Cage, and assume it is either Michael or Lucifer trying to warn everyone about the Darkness.
- "We have no idea what ancient world shattering evil we're dealing with, but go right ahead and let them know we're coming!"
- "Well...Actually, now I come to think of it, if everyone was dark and damned, wouldn't be much of a challenge. Watching a human reject the light and embrace depravity... Yes, well, that's where the gratification really is. Never gets old. This bemuses you?"
- "Do you know how disturbing it was to realize that I couldn't bring myself to kill you? I've had tons of chances over the years, some you don't even know about, but... Still, I made peace with it. Embraced my softer side, learned to accept that there was just too much going on between you and I -- bromance. But you know what? I think I am gonna kill you today. I feel different somehow, ready. What can I say? Fatherhood changes a man."
- "It was sealed by God himself. Of course I don’t 'have a key.' The mechanism is of divine manufacturer. I believe its secrets, along with the spells for warding Sam were recorded where many such mysteries are found – the Book of the Damned."
- "I mean Lucifer needs the moose. He’s not going to kill him, probably. You versus the Devil... trust me there’s easier ways of committing suicide. We need to focus on Rowena."
- "You're not strong enough. You've had your weapons delivered. You realize they won't be enough. If you thought you could beat Amara, you'd be taking the fight to her, right now."
Crowley was revealed to have been "broken" by Lucifer, stripped of his fine tailored suits and placed in a dog collar as well cargo pants and a Hawaiian shirt. Lucifer treats Crowley like his dog, but is able to sense that Crowley is only playing along, waiting for an opportunity to take back Hell and hasn't actually been broken by him.
- "So this is what it feels like to be God. Not bad. Tingly."
- "First impressions can be deceiving, Moose. For instance, I once thought of you as dull and plodding. Oh, never mind. Bad analogy."
- "We can do this. Lucifer stole the throne, but his authority weakens the longer he’s MIA. The time is ripe for a coup. That’s why I brought you here. Together, we can reclaim the throne. Together, we can make Hell great again. Of course, I’ll need your help recruiting others. When the numbers are in our favor, we’ll strike, and each and every one of you will have earned a place at my side."
- "One little apocalypse and they shut up shop. Quitters. Your round, Moose."
- "Keep telling yourself that, dear. That dust-up with the Darkness must've really taken it out of the old boy. That's why he's jumping from vessel to vessel to vessel. It's why Lucifer's running -- because he's weak."
- "I have a proposal. I mean, why in Hell would you want to rule over a motley, witless crew of demons? God's on sabbatical again. You could reclaim Heaven. Now, that's real estate that's worth ruling. I can handle the branch office."
- "It's not about saving her. Lucifer has made off with a colossally powerful witch who, by the way, is the only person alive who can slam him back in the Cage. He will either kill her, control her, or she will offer her services to the biggest bad in town in order to save her neck, like she always does. Do any of those sound like particularly good outcomes to you?"
- "Hello, boys. Long time. We team up to save the world, and then bupkis. You don't call, you don't write."
- "Can I get you without the flannel? No. Still, I endure."
- "As do I. I was bloody one of them. And Sam and Dean, they're like herpes. Just when you think they're gone, 'Hello' the boys are back leaving a trail of bodies in their wake. So wherever they are, whoever has Sam and Dean. In the immortal words of Lawrence Tureaud, 'I pity the fool.'"
- "I admit they don’t sound like much. But every Armageddon, every bloody, 'this is the end of all things,' a Winchester stopped it. Like it or not, they’re an asset we can’t afford to lose."
- "I know there's an ugly, rancid, spiteful reason why you sent my son, your grandson, to his death. I wanna know what it is."
- "You cross me, I crush you. You hit me, I hit you back twice as hard. You make me your dog, I make you my slave."
- "My loyal...ish subjects, these troubled times, I'm aware there might be some confusion as to where you're supposed to place your loyalty. Even with Lucifer back in the Cage, there are those of you who would try to help him... because he scares you or engorges you. Just the chance that Lucifer could come back, the rumor, would've been enough to keep some of you working against me, undermining me, being a royal pain in my... pert, royal ass. But lo, the beast has been humbled."
- "So to be clear, I accept that you are now in charge. I-I like this new arrangement better. You're more the big picture guy. I'm the day-to-day minutiae guy."
- "Bye, boys."
The character may be a reference to:
- British occultist Aleister Crowley, who during his day was dubbed "the wickedest man in the world" by the press. At one point, Led Zeppelin guitarist Jimmy Page developed an interest in Crowley. Page once owned Boleskine House, Crowley's estate on the shores of Loch Ness. Also, as numerous Black Sabbath and Ozzy Osbourne references have been made throughout the show, Osbourne's song "Mr. Crowley" from the Blizzard of Ozz album may also be of play.
- Anthony Crowley, a character in the book Good Omens by Terry Pratchett & Neil Gaiman, shares of number of similarities. Anthony Crowley is a well-dressed, elegant mid-level demon who manipulates humans to sin using his sophisticated understanding of modern society. However, as the end of the world nears, Crowley's attachment to the human world causes him to rebel against Hell and ally with humans and a rebel angel in an attempt to stop the Apocalypse.
- In an episode of The Twilight Zone titled "Escape Clause", a man named Bedecker, desperately seeking immortality, strikes a deal with a devil named Cadwallader, who resembles Crowley both physically and in his mannerisms and accent.
- Crowley's surprise reappearances in Supernatural in 6.07 Family Matters and 6.19 Mommy Dearest have been carefully guarded secrets, including Mark Sheppard insisting his name was left out of the opening credits of these episodes.
- Mark Sheppard has said that the hellhound is called "Growly" (Source). The name was also mentioned in 10.01 Black when Crowley was talking to Sam on the phone about his new friendship with Dean which he called "The Mis-Adventures of Growley and Squirrel."
- Mark Sheppard said at Salute to Supernatural Dallas 2012 "Is Crowley gay? I don’t think he cares. He just likes making people uncomfortable."
Crowley in Fandom
- @ADevilYouKnow - Crowley RP on Twitter
- @DaringestDevil - Crowley roleplay on twitter
- Community for Crowley fanfiction on LJ
- Casting call for Crowley
- Casting announcement for Crowley by the Chicago Tribune.
- Tweets from Mark Sheppard during filming: here and here.
- 6.04 Weekend at Bobby's
- 9.21 King of the Damned
- 5.21 Two Minutes to Midnight
- 5.09 The Real Ghostbusters
- 8.22 Clip Show
- 5.20 The Devil You Know
- 8.02 What's Up, Tiger Mommy?
- 6.10 Caged Heat
- 6.22 The Man Who Knew Too Much
- 6.20 The Man Who Would Be King
- 8.01 We Need To Talk About Kevin
- 8.17 Goodbye Stranger
- 5.10 Abandon All Hope...
- 9.16 Blade Runners
- 8.10 Torn and Frayed
- 9.06 Heaven Can't Wait