Every Supernatural Villain That Became An Ally (& How)
Which Supernatural villains eventually became friends, and what triggered their respective redemption arcs? No TV series lasts fifteen seasons without doing a few things right, and across its lengthy run, Supernatural excelled at delivering brotherly tension, horror-tinged folklore, and endearing character chemistry. Supernatural also boasts an embarrassment of riches when it comes to baddies. Whether it be one-off weekly antagonists or long-running supervillains, Sam and Dean Winchester came face to face with everything from Amazonian temptresses to the Devil himself, and encountered pretty much everything in between on the way. Sure, CGI bugs are no fun, and the likes of Asmodeus and the Styne family proved less than memorable, but Supernatural can count far more hits than misses when it comes to Winchester enemies.
The popularity of Supernatural's villains might just explain why so many eventually come good. Throughout the Supernatural story, an old nemesis of the Winchesters will return to lend a hand, perhaps even redeeming themselves in the process. Invariably, new facets of the character's personality come to light, and the reformed souls become recurring figures in future seasons, evolving into fan favorites if they're lucky.
Turning villains who once seemed beyond reproach into antiheroes or protagonists is a delicate business. How the character becomes an ally and their motivations for doing so are both vital in convincing the audience to change their opinion. Here's how each of Supernatural's villains-turned-friends changed their ways, taking into account only those who actively fought for the side of good, rather than remaining morally ambivalent throughout (like Michael or Death), or simply ceasing to be a menace (Heaven's Naomi).
Few Supernatural villains redeem themselves as spectacularly as Fergus MacLeod, otherwise known as Crowley. Beginning as a regular crossroads demon, Crowley uses intelligence and cunning to claim Hell's throne - a position he desperately clings onto thereafter. Debuting in Supernatural season 5, Crowley lacked the typical demonic thirst for violence, and conspired with the Winchesters against Lucifer. Make no mistake though, Mark Sheppard's character was still very much a villain initially, double-crossing Sam and Dean at every opportunity.
Though being injected with human blood marks a vital step on his road, Crowley's journey to redemption is more a gradual evolution than any single act. Over the course of their rivalry, Crowley developed a grudging respect for "Moose & Squirrel," which eventually mutated into genuine fondness. From the Winchesters' point of view, Crowley's self-serving nature meant he only caused trouble with good reason, and this alone made him easier to handle than most sadistic high-ranking demons. Supernatural increasingly gave the Winchesters and Crowley common enemies, from Lucifer and Abaddon to the dastardly Dick Roman. These experiences pushed Crowley closer to the sibling hunters, and his betrayals soon became less frequent. Crowley's redemption was completed upon a season 12 sacrifice designed to imprison Lucifer. With revenge on his mind, the act wasn't entirely selfless, but Crowley saved the Winchesters and the world nonetheless.
Redemption runs in the MacLeod family, apparently, as Crowley's mother also got in on the hero act. When Rowena first appears in Supernatural's tenth season, her primary aim is more power, and she doesn't much care how many people die in the process. At the height of her villainy, Rowena even sides with Lucifer, coming close to releasing the Devil from his cage again. But just as Crowley's roguish wit made him too likable to hate, Rowena's straight-talking charm quickly endeared her to fans. When the character was revived following Lucifer's betrayal, Supernatural's flame-haired witch soon started helping the Winchesters more than hindering them.
Rowena's transformation into a Winchester ally ramps up in Supernatural season 13. Killed by Lucifer (again) and resurrected (also again), Rowena is genuinely affected upon learning of her son's sacrifice - far more than Crowley was when she kicked the bucket. This marks a change in Rowena, who begins assisting the Winchesters more frequently, taking less convincing each time, and growing especially close to Sam. Like Crowley, Rowena's turn is completed with a moment of sacrifice; throwing herself into hell to close a rift opened by God. Also like Crowley, however, the witch's motivations were partly selfish in nature - she became the new Queen of Hell.
Unlike the MacLeods, Lucifer's morality is a back-and-forth affair. For much of Supernatural's first half, the Devil serves as Sam and Dean's overarching enemy, responsible for much of their misery and almost triggering the apocalypse in season 5. Lucifer ends his Supernatural tale as a villain also, stealing his own son's power and only meeting defeat when Dean becomes the vessel of Michael. But between his evil schemes, there's a small window where Lucifer began to genuinely make amends. Supernatural always presented Lucifer as a tragic figure; evil, certainly, but also thoroughly messed up by his father, and this backstory forms the basis for Mark Pellegrino's character to, even so briefly, become an ally.
Lucifer's flirtations with virtue come between Supernatural seasons 11-13, beginning with the emergence of his Auntie Amara. The threat of The Darkness forces Lucifer to bury the hatchet with his dad, and Satan's trademark wickedness is tempered as a result, as he joins the Winchesters in battle. Though he continues to kill, Lucifer's lust for world domination is replaced by paternal instincts when Jack is conceived, and during the Devil's time in Apocalypse World, he not only bonds (a little) with Mary Winchester, but revives Sam too. Unfortunately, there's only so many new tricks this ancient dog can learn, and the lure of Jack's power tempts Lucifer back to old habits.
One of the earliest demons Sam and Dean Winchester encounter, Meg terrorizes the brothers during Supernatural's fledgling years. The devilish diva possesses Sam Winchester and kills using his body, before later targeting Dean's favorite FOW (friend-of-Winchesters), Jo Harvelle. Even after shifting into a second vessel, Meg remains a villain, supporting Lucifer in his season 5 apocalypse campaign. Meg's turn from evil only begins once her interests align with those of the Winchesters, and a common enemy appears in Crowley. Time heals all wounds, and the longer Meg spends around less unscrupulous folk, the less unscrupulous she herself becomes. Developing a sort-of-romance with Castiel pushes Meg further into antihero territory, and that fondness gradually morphs Meg into a FOW herself, demonstrating her loyalty to the brothers by resisting Crowley's torture.
A primordial entity on par with God, The Darkness is easily the most powerful enemy the Winchesters face - before her brother reveals his true intentions, at least. Embittered by an eternity imprisoned and completely devoid of empathy, Amara embarks on a reign of terror that the Winchesters fail to halt. Indeed, rather than defeating The Darkness through force, Amara's apocalypse ambitions are ended when Dean Winchester and God convince her that humanity, and the universe, is worth saving. This alone should've been a hint that Amara was on the road to heroism, and those teases finally paid off in Supernatural's final season.
Where some Supernatural villains come good due to common enemies, and others because of a profound change in their life, Amara just needed some rest and relaxation at some of Earth's finest spa resorts. Finding her zen, Amara starts to doubt her brother's world-ending intentions in Supernatural season 15, and aligns with Dean Winchester, helping the good guys track her brother down. Unfortunately, the word of God proves too mighty to resist, and Chuck convinces his sister to combine their powers ahead of the final battle.
If there's anyone Supernatural fans never expected to find redemption, it's the British Men of Letters' ruthless, arrogant, Mary-Winchester-seducing Arthur Ketch. Despite being in the same line of work, Ketch and the Winchesters don't exactly see eye-to-eye when it comes to hunting. Ketch kills various Winchester allies (including Eileen), is complicit in brainwashing Mary, and even turns his gun on a longtime friend, killing Mick as punishment for empathizing with the Winchesters. When Ketch was finally defeated in Supernatural season 12, few suspected he would one day become an ally to Sam and Dean, but resurfacing in season 13, the former villain claims to regret the pain he made them endure.
Although reluctant at first, the Winchesters are forced to accept Arthur's help after the Brit rescues Gabriel from Asmodeus. An uneasy alliance against Lucifer soon becomes a respectful working relationship, and by the time Supernatural season 15 rolls around, Ketch is a fully-fledged FOW.
As the scribe of God, Metatron didn't originally possess villainous intentions. Only when God's disappearance forced Metatron to exile himself on Earth did the translator develop vengeful designs, manipulating the Winchesters and casting a spell that banished all angels from Heaven. Asserting himself as the new God, Metatron causes endless trouble for the Winchesters in Supernatural season 8, right up until his defeat at the hands of Castiel.
Though Metatron's megalomania is checked, the villain escapes, only to emerge in Supernatural season 11 a markedly different character. Witnessing God's reveal, Metatron requests Chuck reclaim his old position, restore order, and help the people of Earth. The Scribe then returns to the mortal plane and joins Team Winchester in their crusade against The Darkness, ultimately sacrificing himself so the others can escape and earning a well-deserved redemption.
Morally ambiguous to start with, Balthazar begins his Supernatural story with no real intentions beyond having a damn good time on Earth. Problematically, this involves stealing human souls, which the Winchesters take issue with. Though not an out-and-out baddie, Balthazar causes further issues after joining Castiel's army, but when Sam and Dean reveal their angel friend's true plan to open purgatory and absorb the souls within, Balthazar backs out. He sides with the Winchesters, allowing Dean and Bobby to catch up with Castiel, and feels the sharp end of an angel blade for his betrayal.
Debuting in Supernatural season 11, Lady Toni Bevell is another among the British Men of Letters who lacks the usual poise and reserve associated with British nobility. Despite not plumbing the same moral depths of depravity as Arthur Ketch, Lady Bevell tortures Sam, brainwashes Mary, and is involved in her employers' plan to exterminate the U.S. hunters. Bevell's ethical 180 is first teased through her obvious discomfort with the extreme methods Ketch employs but, not for the first time, it's spending time with the Winchesters that truly changes the Lady's mind. Watching the Winchesters fight for each other in a way the British Men of Letters do not inspires Bevell to help Dean rescue his mother from mental imprisonment - an act she pays for dearly.
Misguided and desperately seeking redemption after letting Lucifer deceive him back in the day, Gadreel hides inside Sam Winchester in the wake of Metatron's Fall. Though he claims to want atonement, Gadreel kills Kevin Tran and is deceived by the villainous Metatron, after which he commits even more terrible deeds. Though the light bulb moment is an awfully long time coming, Gadreel finally sees through Metatron's facade, and realizes his own desire for atonement was mere selfishness, inspiring the angel to give his life to free Castiel. As a direct result of Gadreel's Supernatural sacrifice, Metatron's reign is brought to a timely end.