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13 Hero-To-Villain Transformations That Actually Broke Our Hearts

Updated July 27, 2021 431 votes 70 voters 1.4k views13 items

List RulesVote up the heroes you were devastated to see turn to the dark side.

No one sets out to be the villain of a story. But, sometimes, there are heroes who become villains by the time it is all said and done. And when a hero-to-villain transformation is done well? That can be an immensely powerful thing to watch play out on screen.

This kind of transformation is at the heart of some of the most beloved stories in entertainment history. The GodfatherThe Dark KnightGame of ThronesStar WarsMacbeth. Sometimes, a fall from grace can grab your heartstrings and rip them to shreds. And you just can't look away.

  • The Hero: When it comes to the struggle against the underworld in Gotham City, Batman is short on allies. He's got Alfred. He's got the Bat Family (in the comics, at least). He's got James Gordon. And that's kind of it. So when Harvey Dent arrives on the scene as a genuine colleague in the fight against the scum of Gotham, Batman is happy for the help. And Dent is willing to do whatever it takes to make Gotham a friendlier place to live.

    The Corruption: If you come up against the Joker, you best not miss. Because the Clown Prince of Crime does not play around. Well, he does... but he plays hard and he plays to win. And the Joker's machinations leave Dent with a dead girlfriend and a horrifically disfigured face. Harvey Dent is gone and Two-Face is officially born.

    The Villain: Gotham's "White Knight" is replaced with a broken man who's comfortable leaving everything to chance. If you wrong him? He flips a coin for your life. He's that kind of guy before his inevitable demise. How does he keep that eye without an eyelid from drying out? That's a fantastic question...

    Tragic fall?

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  • Photo: Star Wars: Revenge of the Sith / 20th Century Fox

    The Hero: In The Phantom Menace, the young Anakin Skywalker is heralded as the "one who could bring balance to the Force." Of course, anyone who considered themselves a Star Wars fan (or looked at the theatrical release poster) knew this Padawan had nothing but tragedy in his future. As soon as he left Tattooine, his fate was sealed.

    The Corruption: Darth Sidious is pretty good at what he does. And what does he do? Bring the Sith to power over the entire galaxy by eradicating the Republic and forming the Galactic Empire in its place. He does all of this through duplicitous schemes while pretending to be an honest politician. A major part of his plan ends up being the corruption of Anakin from a noble if headstrong Jedi Knight into Darth Vader. And by the time Revenge of the Sith ends, Anakin is no more.

    The Villain: You know Darth Vader. It's Darth Vader. He stands as one of the most unforgettable villains in the entire history of cinema. He's got the voice of James Earl Jones and an awesomely unique costume. Remember that hallway scene in Rogue One? Of course you do! It's the best part of that whole movie! Vader may end up killing the emperor at the end of Return of the Jedi, but Anakin will always and forever be one of the great film antagonists of all time.

    Tragic fall?

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  • Photo: X-Men: First Class / 20th Century Fox

    The Hero: Can we ever truly describe Erik Lehnsherr as a hero? Perhaps before Sebastian Shaw got his evil hands on the boy when he was in the Auschwitz concentration camp, but we hardly get to see Erik then and he was only a child. The Erik of First Class is definitely best described as an antihero whose violent tendencies are curtailed by his friendship with Charles Xavier. 

    The Corruption: By the end of First Class, Erik has fully embraced the Magneto persona and has begun to form his Brotherhood of Evil Mutants. Would a group who sees themselves as being in the right call themselves "evil"? It's hard to say. But after giving up Xavier's "make peace with humans" form of living, Erik ends up deciding mutants need to be above humanity - not a part of it.

    The Villain: Magneto is the "big bad" of the original X-Men trilogy of films. He has a cartoony plot involving the Statue of Liberty in X-Men. He teams up with the X-Men before (unsurprisingly) turning on them in X2: X-Men United. And he is the major player in the mutant-versus-mutant battle at the end of X-Men: The Last Stand, but the less said about that particular X-Men film, the better.

    Tragic fall?

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  • Photo: The Godfather Part II / Paramount Pictures

    The Hero: Michael Corleone was supposed to be the "good son" - and for a while, he lived up to that title. He wanted nothing to do with the family business. He went away to Dartmouth College to get away from the Mafia lifestyle before enrolling in the military after the strike on Pearl Harbor and becoming a war hero.

    The Corruption: The Godfather trilogy is an epic American tragedy that catalogs Corleone's fall from grace. Through events he largely had nothing to do with (at least until he pops Sollozzo and McCluskey in the diner), he ends up taking the reins of the Corleone crime family - and one of the most iconic film characters in the history of Hollywood is born.

    The Villain: Michael Corleone does a lot of terrible things in the Godfather trilogy. By the end of the final film, he is a tragic figure who clearly isn't happy with the way his life has turned out. The guy punches his wife in the face at one point in The Godfather Part II, for goodness sakes.

    Tragic fall?

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