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* ''WesternAnimation/MonstersUniversity'' reveals that Randall and Mike, who are enemies in the [[WesternAnimation/MonstersInc original film]] were roommates in college and were good friends until Mike got kicked out of the scaring program and Randall attached himself to the "cool kids".
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* ''WesternAnimation/MonstersUniversity'' reveals that Randall and Mike, who are enemies in the [[WesternAnimation/MonstersInc [[WesternAnimation/MonstersInc1 original film]] were roommates in college and were good friends until Mike got kicked out of the scaring program and Randall attached himself to the "cool kids".
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* In the old kung-fu western, ''Film/TheFugitive1972'', the hero Liao Fei-Lung and villain Ma Tien-piao were sworn brothers who robs banks together and watches each other's backs. The latter however got greedy with stolen gold and abandons the former to the police in the prologue, leading to the rest of the film. [[spoiler:Which ends with a ShowdownAtHighNoon where they killed each other at the same time]].
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* ''Webcomic/{{Nimona}}'': Lord Blackheart and Sir Goldenloin were once best friends [[spoiler: and later revealed to have been lovers]], until a tournament in which Goldenloin decided to be a sore loser and used a weaponized lance to ''blow Blackheart's arm off.'' With his career as a knight ruined, Blackheart's only remaining role was to be the scapegoat for the Institution: committing crimes, gaining a villainous reputation, and serving as an enemy for the Institution to defeat. Goldenloin himself acts like this never happened, having a FriendlyEnemies relationship with Blackheart and claiming that the event was an accident whenever it's brought up. [[spoiler: He eventually admits that the whole thing was set up by the Director, that the only reason he lost was because the new lance threw off his aim, and he doesn't even remember pulling the trigger afterwards.]]
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* ''Webcomic/TheLastDimension'': Alex is strongly implied to have once been Phillip's best friend, up until Phillip made the mistake of revealing his true form to him. Alex claims that Phillip "tricked him into thinking he was normal." Alex currently bullies Phillip quite a bit, but Phillip is still somehow more comfortable with him than most people and even a bit snarky. Beyond that, Alex hasn't told anyone what Phil's true form looks like, implying he still somewhat cares for him.
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* In the web novel ''Literature/{{Worm}}'', Taylor and Emma's childhood friendship ended after Emma ends up being attacked and, seeking to change her world views, cuts ties with Taylor and starts bullying her.
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* In the web novel ''Literature/{{Worm}}'', Taylor and Emma's childhood friendship ended after Emma [[spoiler: ends up being attacked and, seeking to change her world views, become "strong,"]] cuts ties with Taylor and starts bullying her.
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* In ''Webcomic/ElGoonishShive'', Elliot used to be friends with [[TheBully Tony]] back in the 3rd grade. It's implied that their friendship ended in bad terms after Tony [[http://egscomics.com/comic/2013-11-29 gay-bashed]] someone.
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* In ''Webcomic/ElGoonishShive'', Elliot used to be friends with [[TheBully Tony]] back in the 3rd grade. It's It was implied that their friendship ended in bad terms after Tony [[http://egscomics.com/comic/2013-11-29 gay-bashed]] someone. Since then, however, it's been revealed that Tony initially started bullying kids because they kept accusing him and Elliot of being gay, and then eventually started bullying more people, including Tedd.
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* Played straight in the ''Literature/AstralDawn'' series. Caspian Knoll and Ciaran Devlyn were once the best of friends in another life. After their deaths, Caspian went on to be reborn in other lives while Devlyn went straight to Hell. That put a pretty big gap between the fellows who would eventually become deeply at odds over the fate of Celestial City.
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* Played straight in the ''Literature/AstralDawn'' series. ''Literature/AstralDawn'': Caspian Knoll and Ciaran Devlyn were once the best of friends in another life. After their deaths, Caspian went on to be reborn in other lives while Devlyn went straight to Hell. That put a pretty big gap between the fellows who would eventually become deeply at odds over the fate of Celestial City.
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* ''Literature/TheCalfOfTheNovemberCloud'': Konyek and his first cousin Parmet used to be like brothers, often playing in each other's hutch. However, Parmet started resenting and hating Konyek, because he had realized that he was their grandfather's favorite. Konyek had noticed Parmet had changed, becoming colder and more prideful, but he didn't imagine that his cousin hated him enough to want him dead.
-->''Sometimes Konyek would meet his cousin Parmet herding the cattle. Formerly they had gone out together, and been glad of one another's company, for they were like brothers. They lived in the same manyatta, and the mother of one was a mother to the other, so that every child had many mothers and fathers, and many grandparents also. But lately, Parmet had changed. He had grown loud and boastful, and he avoided Konyek's eye because he was jealous of him. He saw that Konyek was the favourite of their grandfather Ol-Poruo, who was famous throughout the land for his wisdom and for his bravery. He saw, too, that the girls favoured Konyek with their glances, and the boys listened to his words. But Parmet was stronger and older, and he competed with his cousin by a show of words, and a display of strength, so that sometimes the others were afraid of him.''
-->''Sometimes Konyek would meet his cousin Parmet herding the cattle. Formerly they had gone out together, and been glad of one another's company, for they were like brothers. They lived in the same manyatta, and the mother of one was a mother to the other, so that every child had many mothers and fathers, and many grandparents also. But lately, Parmet had changed. He had grown loud and boastful, and he avoided Konyek's eye because he was jealous of him. He saw that Konyek was the favourite of their grandfather Ol-Poruo, who was famous throughout the land for his wisdom and for his bravery. He saw, too, that the girls favoured Konyek with their glances, and the boys listened to his words. But Parmet was stronger and older, and he competed with his cousin by a show of words, and a display of strength, so that sometimes the others were afraid of him.''
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* ''Literature/TheWolfDenTrilogy'': Amara and [[spoiler: Victoria]] were once very close. They protected each other as brothel slaves, Amara risked losing her patron's support to free her friend, and after all that... said friend [[spoiler: told Felix, Amara's greatest enemy, about her secret affair with her patron's slave.]]
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* ''Literature/TheWolfDenTrilogy'': Amara and [[spoiler: Victoria]] were once very close. They protected each other as brothel slaves, [[spoiler: Victoria]] saved Amara's life, Amara risked losing her patron's support newfound wealth to free her friend, friend from slavery, and after all that... said friend [[spoiler: told Felix, Amara's greatest enemy, enemy and Victoria's love interest, about her secret Amara's illicit affair with her patron's slave.]]]] The two never reconcile, even after a three-year time skip.
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* ''Literature/TheWolfDenTrilogy'': Amara and [[spoiler: Victoria]] were once very close. They protected each other as brothel slaves, Amara risked losing her patron's support to free her friend, and after all that... said friend [[spoiler: told Felix, Amara's greatest enemy, about her secret affair with her patron's slave.]]
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* ''Webcomic/{{Unsounded}}'': Bastion and Prakhuta became friends together while trapped under Delicieu's abuse, and after [[spoiler: killing Delicieu]] they worked together in their freedom. Unbeknownst to Bastion his old friend has turned even more cruel and murderous than their old master and he has a significant crises of faith when he realizes Prakhuta does not even see himself as the same being anymore, and plans to kill an untold number of victims even if pits him against Bastion.
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* In the ''Literature/BoneChillers'' story, "Scare Bear", protagonist Timmy's bully is Ross, his ex-friend who stopped hanging out with him since joining some "cool kids" in sixth grade. While Ross never really plays rough with Timmy, he does deliberately tries making life difficult for Timmy by hooking up with the girl Timmy has a crush on and leading other kids in laughing at Timmy for messing up in gym class.
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* ''Series/TheBeautyQueenOfJerusalem'': Lovers, even. Ephraim and Victoria were lovers and even engaged at one point, but [[spoiler:he cheats on her, her son finds Ephraim's gun and hurts himself, and Ephraim plants a bomb that kills her daughter]].
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The previous image was much better than the previous one.
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Cool Loser cleanup, has been renamed to Unconvincingly Unpopular Character and is a YMMV audience reaction.
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* Dori Hillestad Butler's ''The Truth About Truman School'' combines this trope with FormerFriendOfAlphaBitch. [[CoolLoser Cool Losers]] Zebby and Amr begin an anonymous online newspaper about their school to which anyone may contribute, and someone calling himself "milkandhoney" begins using the site to bully Lilly, a popular classmate, including spreading a rumor that she is a lesbian. Lilly goes from popular girl to outcast literally overnight, with her former friends, AlphaBitch Hayley and her BetaBitch posse, initiating much of the torment. The twist is that Lilly, once an awkward fat girl, was also once close friends with Zebby and Amr but cut them off after she lost weight and was accepted into the popular clique, and thus has reason to suspect Zebby and Amr of being "milkandhoney." [[spoiler:They aren't; the culprit turns out to be another outcast named Trevor, to whom Lilly once made a cruel comment about his dead mother.]]
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* Dori Hillestad Butler's ''The Truth About Truman School'' combines this trope with FormerFriendOfAlphaBitch. [[CoolLoser Cool Losers]] Zebby and Amr begin an anonymous online newspaper about their school to which anyone may contribute, and someone calling himself "milkandhoney" begins using the site to bully Lilly, a popular classmate, including spreading a rumor that she is a lesbian. Lilly goes from popular girl to outcast literally overnight, with her former friends, AlphaBitch Hayley and her BetaBitch posse, initiating much of the torment. The twist is that Lilly, once an awkward fat girl, was also once close friends with Zebby and Amr but cut them off after she lost weight and was accepted into the popular clique, and thus has reason to suspect Zebby and Amr of being "milkandhoney." [[spoiler:They aren't; the culprit turns out to be another outcast named Trevor, to whom Lilly once made a cruel comment about his dead mother.]]
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* ''Series/LizzieMcGuire'': [[CoolLoser Lizzie]] and [[AlphaBitch Kate Sanders]], until [[SheIsAllGrownUp Kate's figure filled out]] and she became a popular cheerleader. [[spoiler:They seemed to settle their differences permanently in TheMovie.]]
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* ''Series/LizzieMcGuire'': [[CoolLoser Lizzie]] Lizzie and [[AlphaBitch Kate Sanders]], until [[SheIsAllGrownUp Kate's figure filled out]] and she became a popular cheerleader. [[spoiler:They seemed to settle their differences permanently in TheMovie.]]
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* Betty Wynne-Davies and Elizabeth Arnett in the ''Literature/ChaletSchool'' series. While they start off as partners in crime at St Scholastika's, Elizabeth begins to break away from Betty in ''The Chalet School Goes to It'', partly because of her admiration for Miss Linton - which Betty mocks her over - and partly because she is growing up and becoming more mature. Betty doesn't take it very well and [[SlowlySlippingIntoEvil gets worse and worse until she is eventually expelled for treason.]]
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* Betty Wynne-Davies and Elizabeth Arnett in the ''Literature/ChaletSchool'' series. While they start off as partners in crime at St Scholastika's, Elizabeth begins to break away from Betty in ''The Chalet School Goes to It'', partly because of her admiration for Miss Linton - which Linton--which Betty mocks her over - and over--and partly because she is growing up and becoming more mature. Betty doesn't take it very well and [[SlowlySlippingIntoEvil gets worse and worse until she is eventually expelled for treason.]]
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* ''Literature/TheDresdenFiles'': As a result of Harry suspicious actions of the past few years and refusal to trust him, Ramirez has had enough of Harry putting his secrecy above their friendship. It comes to a head at the end of Literature/BattleGround2020 with Ramirez fed up with being lied to or rebuff when he just trying to help and he ends their friendship for seems like for good.
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* ''Literature/TheDresdenFiles'': As a result of Harry Harry's suspicious actions of the past few years and refusal to trust him, Ramirez has had enough of Harry putting his secrecy above their friendship. It comes to a head at the end of Literature/BattleGround2020 with Ramirez fed up with being lied to or rebuff rebuffed when he just trying to help help, and he ends their friendship for seems like friendship, it seems, for good.
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** It's also revealed in ''Deathly Hallows'' that Dumbledore was "friends" with [[spoiler:Grindelwald]] for a while while they were teenagers. It ended not too shortly thereafter when his sister died in a chaotic [[MeleeATrois three way fight]] between the two of them and his brother.
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** It's also revealed in ''Deathly Hallows'' that Dumbledore was "friends" with [[spoiler:Grindelwald]] for a while while they were teenagers. It ended not too shortly long thereafter when his sister died in a chaotic [[MeleeATrois three way three-way fight]] between the two of them and his brother.
