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"He was their friend, and he betrayed them. He was their friend!"
—Harry Potter, Harry Potter and the Prisoner of Azkaban
So you have your Eccentric Mentor and with his backing you're facing off against the nefarious machinations of the local Evil Sorcerer, when suddenly you learn a shocking truth — in their youth, rather than being bitter enemies, these guys were best friends!
This trope occurs whenever a good aligned character (sometimes The Hero, but more commonly The Obi-Wan, the Eccentric Mentor, the Supporting Leader, or the Big Good) is revealed to have had a history as friend, ally, mentor, or even student with a major villain (commonly the Big Bad, but sometimes The Dragon or another high-ranking Evil Minion). Usually the friendship fell through simply because the future villain went power mad and the other character didn't want any more to do with it, but more complex and unusual variations exist. Sometimes it will be known all along, but sometimes it will be the subject of a dramatic reveal that can lead The Hero and the audience to reevaluate what they know about both characters.
As the top of the page indicates, tends to happen a disproportionate amount of the time with the resident Wise Old Wizard and the Evil Sorcerer. Compare and contrast Big Bad Friend, where the revelation occurs during the story and the "Bad" character was evil all along (or at least had been for a while) and would rather remain friends despite this. Usually, either the evil character will be a Fallen Hero or the good one will be The Atoner (or both, if both started out more morally grey). The evil character will most likely be an Evil Counterpart and/or Shadow Archetype for the good one, and may also be their Arch Enemy. If traces of the past friendship still exist, they might be Friendly Enemies or even have Foe Yay. Compare and contrast Rival Turned Evil, for where the friendship broke up over personal rivalry before one of the characters turned evil (though certain examples will overlap, not all will). A less extreme version of the falling-out is We Used to Be Friends.
Note that this is about friends who turned evil in the Backstory and are either introduced or established in their first appearance as villains. If the friend turns evil over the course of the work, see Face Heel Turn.
Anime & Manga
- In Naruto, Jiraiya, Tsunade and Orochimaru were once on the same squad. Jiraiya was Orochimaru's closest friend, before Orochimaru abandoned the Leaf Village. Jiraiya chased him down and tried to talk him out of it, but Orochimaru laughed in his face.
- Kazuma of the 12 Guardian Ninjas filler arc was one to Asuma, as they served together in the Guardian Ninjas until Kazuma betrayed the group with five of his comrades to make the daimyo the only "king" of the Land of Fire.
- Sasuke has become this to Naruto and Sakura, betraying them and the Leaf village to further his own vengeance-oriented goals.
- Soul Eater's Shinigami and Asura or Shinigami and Eibon
- Yuka Sugimoto is this to Youko Nakajima in The Twelve Kingdoms, sort of. She gets better once defeated, tho.
- In different degrees, also Youko and Yuka's boyfriend Asano. He is closer to Youko than Yuka is, having known the future Queen of Kei from childhood.
- Enchu was formerly close friends with Muhyo and Yoichi, but turned to evil after his mother died and Muhyo became an executor instead of him, and serves as the main antagonist for much of the story.
- Toguro toward Genkai in Yu Yu Hakusho.
- Regius for Zest in Magical Girl Lyrical Nanoha StrikerS. The two used to be friends while serving together in the bureau, and wanted to ensure that the Bureau's ground forces were able to deal with criminals and other threats. Over time, Regius lost sight of his ideals as he fell under the sway of the High Council, and eventually Zest and nearly all his team were killed on a raid on a Combat Cyborg facility. Zest, after being cloned, sought out Regius for answers on why he changed, but Due killed Regius before he could give any.
- In Fushigi Yugi, Miaka and Yui are both best friends until the two are pitted against each other. The odd thing about this particular example is that Yui is deceived into thinking Miaka is the one who turned against her, and that she, not Yui, is the one who is turning evil.
- In Suite Pretty Cure, Siren and Hummy used to be the best of friends until Hummy took Siren's title as singer of the annual "Melody of Happiness", causing the latter to defect to the villains' side. They almost made up early in the series before Mephisto forcefully won Siren's loyalty back. However, they do get a proper reconcilliation about nine episodes later, leading to Siren joining the team as Cure Beat.
- Who else but Guts and Griffith of Berserk? The two men had a bond bordering on brotherhood (or if you're that way inclined, more than that), only for Griffith to turn his back on him and everyone else he led during the events of the Eclipse, which would destroy this bond forever and leave Guts with an undying hatred for Griffith.
- Professor X and Magneto in most versions of the X-Men.
- Superman and Lex Luthor, in some versions.
- Harvey Dent is shown as a close friend of both Batman and Commissioner Gordon before turning into Two-Face, particularly in The Long Halloween.
- On Tatooine, Luke Skywalker only had two friends who shared his desire to go offworld, and both, being older than him, joined the Imperial military before A New Hope. Biggs Darklighter became a pilot, defected to the Rebellion, and died at Yavin. Luke's other friend, Janek "Tank" Sunber, was shown in the comics; he washed out of pilot training and became an infantry officer. Of course, he came into conflict with Luke.
- In the New 52, Nightwing's newest foe Saiko is former friend and fellow former member of Haly's circus Raymond. Raymond was taken by the Court of Owls and put through Training From Hell to become a Talon, only to be washed out and left for dead with his eyes pecked out by birds. Saiko hates Dick Grayson because the Court only took Raymond because they couldn't get Dick, their original candidate, after Bruce Wayne adopted him in the wake of the Flying Graysons' deaths.
- Darth Vader and Obi-Wan from Star Wars are a double-hitter, as Vader (as Anakin Skywalker) was both Obi-Wan's student and his closest friend.
- Count Dooku was also once a respected Jedi Master who got on well with his former teacher Yoda and peer Mace Windu. In this case the revelation, especially to the characters, was the fact that he'd turned evil rather than that he had been someone's friend.
- Toy Story 3 Inverts this: Chuckles the Clown was friends with Lotso, who is the Big Bad. Witnessing Lotso become a monster resulted in him becoming bitter and cynical.
- Alec Trevelyan to James Bond himself in Goldeneye.
- It's a plot-point in Unbreakable, and the last spoken lines in the film are the evil former friend specifically talking about it as a trope in fiction.
- Popular folklore has Billy the Kid and Pat Garret as an example of this, although their friendship was never actually documented.
- Several times in Harry Potter — Albus Dumbledore and Gellert Grindelwald were best friends (and a bit more, at least on Albus's end). Later on, Tom Riddle, the future Lord Voldemort, was Dumbledore's student, and at least one of the Sorting Hat's songs implies that Godric Gryffindor and Salazar Slytherin were once good friends as well.
- Subverted with Sirius Black, who looks like the evil part of this in comparison to Harry's dad, but is revealed to have been framed. Played straight with Peter Pettigrew, another former friend who was guilty and did the framing.
- As well as Lily Evans and Severus Snape, until the latter's Heel Face Turn.
- Gandalf and Saruman from The Lord of the Rings have elements of this, though their relationship doesn't shatter until early in the present storyline (though the books at least show that it had been fraying for a while before that because of Saruman's jealousy).
- They had never been exactly good buddies; according to the Appendix Saruman had been jealous of Gandalf almost as soon as they stepped off the ship in the Gray Havens, but they had had mutual respect and a common purpose.
- Akhlaur and King Zalathorm from Counselors and Kings were once best friends, until Akhlaur proved that With Great Power Comes Great Insanity.
- Warbreaker has Vasher and Denth as an interesting variation because the friendship ended violently over something Vasher, the good guy of the two did. They were originally part of the same group of famous magic-users, and Vasher killed Denth's sister, another member, fearing that her knowledge of how to create Artifacts of Doom would spread. Denth went on a Roaring Rampage of Revenge to avenge her, gradually descending into evil in the process.
- In the Death Gate Cycle, Samah and Zifnab were at least cordial colleagues and possibly friends, at least until Samah went all Knight Templar and Zifnab dedicated himself to opposing him.
- Though calling them "friends" would be a stretch (he was never a particularly nice guy), Zedar from The Belgariad was once a Disciple of Aldur along with the Eccentric Mentor Belgarath, and the two worked closely together and respected each other. Then Torak Mind Raped Zedar into becoming The Dragon, and it went rapidly downhill from there.
- From the Saga of Darren Shan Darren's former best friend, Steve.
- From The Elenium, comparatively rare example of the main hero having a prominent villain as one of these- Martel and Sparhawk were good friends who went through Magic Knight training together, until Martel got caught practicing Black Magic and was expelled from the order. Though now enemies, they're still very polite to each other and respect each other's abilities, and conduct their final duel in a most gentlemanly manner.
- Alan Garner's The Weirdstone of Brisingamen ends with a fight between Cadellin and Grimnir, the evil wizard. When Cadellin kills Grimnir, he reveals that they were once friends and brothers.
- In Memoirs of a Geisha, Sayuri and Pumpkin, who started out as friends, but once Mother adopted Sayuri instead of Pumpkin and she became a more popular geisha than Pumpkin, they became rivals (at least in Pumpkin's mind).
- In Percy Jackson and The Olympians, Luke to the main cast, especially Annabeth and Thalia, until Death Equals Redemption.
- The Doctor and the Master, from Doctor Who. They're still sort of Friendly Enemies, but when they were schoolkids together, they weren't enemies at all, and the Doctor has some serious angst about this.
- Burn Notice has Michael Westen's former partner-in-spying Larry Sizemore, who becomes a Psycho for Hire after he faked his death in Serbia. He shows up in Miami running a sort of freelance assassination business; he shows up in a few episodes, during which he forces Michael into Enemy Mine situations.
- Giles and Ethan from Buffy the Vampire Slayer
Ethan: Oh, so cross Ripper. We used to be friends. When did all that fall apart?
Mythology & Religion
- In Norse Mythology, Odin and Loki were once sworn brothers.
- Many tellings of the Satan story will have pre-Fall Lucifer as God's favorite angel. In some, he was Archangel Micheal's closest friend.
- Delia Ketchum used to date Giovanni in the Pokémon Live musical.
- Wicked has an interesting take on this (and this is true for the novel as well): although neither Elphaba nor Glinda is truly a villain in the novel at hand, its entire premise is that it functions as backstory to the original The Wizard of Oz. If one were to take Wicked as behind-the-scenes canon for Wizard, Elphaba's and Glinda's relationship — as friends in the former and on opposite sides of the conflict in the latter — would certainly qualify.
- Athos and Nergal from Fire Emblem.
- Dr. Light and Dr. Wily had this relationship in Mega Man.
- Revan and Malak in Knights of the Old Republic. Inverted in that it's common knowledge that they used to be friends; the twist is that Revan is still alive and back with the Jedi.
- The lead signature characters of City of Heroes and City of Villains, Statesman and Lord Recluse, respectively, were best friends before Recluse joined Arachnos.
- In one story in the Whateley Universe, Phase muses on how a lot of the time, villains started off as the hero's best friend, and wonders if one day he'll end up enemies with his friends Mal and Jadis, who are the children of supervillains (Mal wants to be a villain and Jadis hasn't said whether she wants to be a hero or not, though the answer is probably yes).
- Fire Lord Sozin, the guy who started the War and the tradition of Fire Lords being Evil Overlords, was once best friends with Avatar Roku on Avatar: The Last Airbender, though in a variation both characters are long dead by the time the viewer learns the details of their history.
- Vlad Masters from Danny Phantom was Danny's parents' best friend in college, until a botched experiment dreamed up by Danny's dad Jack disfigured him (and gave him superpowers, but he didn't find that out until later). Vlad is now dedicated towards three goals- killing Jack, convincing Maddie (Danny's mom) to fall in love with him, and making Danny his apprentice. Ironically, Jack is the only one completely oblivious to all this. Until it was literally spelt out for him in the Grand Finale.
- Plankton to Mr. Krabs in SpongeBob SquarePants.
- The Batman gives us Ethan Bennett, both a high-school friend of Bruce Wayne's and one of the only cops willing to give Batman a chance. Naturally, he's accidentally turned into Clayface into the Season 1 finale. He eventually becomes a good guy again after spending a while in the Heel Face Revolving Door.
- The Shredder had this relationship with the Ninja Tribunal in the second Teenage Mutant Ninja Turtles series.
- In Batman: The Animated Series, Harvey Dent starts off as a close friend of Bruce Wayne before he becomes Two-Face.
- Terry McGinnis also received this treatment when his old friend fell back into crime and became Big Time in Batman Beyond.
- In the original cartoon, Starscream used to be Skyfire's best friend before the war.
- Wheeljack in Transformers Armada was friends with Hot Shot before Hot Shot betrays him... or so Wheeljack thinks. Hot Shot tried to go back and save him, but was barred by his superior officer who believed that no one could have survived the fire.
- Transformers Prime heavily leans into this aspect of Optimus Prime and Megatron's relationship. Millions of years ago, Optimus was swayed by Megatron's rhetoric and arranged for them to speak to the High Council. After Megatron gave a rather entitled speech, Optimus argued his understanding of Megatron's cause so well, the Council agreed and named Optimus the next Prime. Megatron saw this as a betrayal, and started the civil war, anyway. Nice Job Breaking It, Hero, indeed. Prime was not the first piece of media to put forth this idea about the two but it catapulted the concept so powerfully into the collective consciousness of the fanbase that it's now a staple of the franchise.
- Cy-Kill used to be Leader-1's closest comrade in Challenge of the Go Bots. He defected out of jealousy over Leader-1's successes.
- Bionicle Lhikan and Nidhiki use to be close friends as Toa, but Nidhiki betrayed his fellow Toa to the Dark Hunters. When his plan failed, Nidhiki was transformed into an inscetoid monster.
- Once, Emperor Zarkon was the Black Paladin in Voltron: Legendary Defender. After living by the Quintessence field poisoned Zarkon's mind, he waged a war against his fellow Paladins, eventually executing them.