Super-Frenemies: The Best Superhero Allies Turned Enemies

Captain America, Winter SoldierWalt Disney Studios

When you think about it, superheroes can be a pretty fickle bunch. Through several decades of comic books and the dozens of comic book films released over the years, it’s become abundantly clear that there’s no such thing as a binding alliance. Comic book characters switch over the moral dividing line so often that keeping track of it all can be headache-enducing, a fact that one Captain America knows all too well.  In the upcoming sequel, Captain America: The Winter Soldier, Cap sees himself facing off against an old friend, and in his honor, we’ve decided to list our favorite comic book movie frienemies. 

Harry Osborne and Peter Parker (Spider-Man)
High school best buds turned mortal foes, Peter Parker and Harry Osborne are the original frenemies. When Harry discovers that Spider-Man killed his father Norman (the OG Green Goblin), and later finds out that Peter Parker is Spider-Man, the news sets him on a raging path of revenge. Harry picks up the mantle of the Green Goblin and tries to put a stop to the webslinger’s heroics once and for all. 

Loki and Thor (Thor)
Being second sucks, doesn’t it? Brothers Thor and Loki were always thick as thieves, but under the surface, certain injustices began to slowly gnaw away at their friendship. Jealousy over Thor’s birthright plus the discovery of his true frost-giant origins were enough to send the already mischievous Loki into full villain mode. 

Dr. Connors and Peter Parker (The Amazing Spider-Man)
Peter Parker and Dr. Connors had a budding Teacher/protege relationship in The Amazing Spider-Man, but Connors was slowly driven crazy by his limb re-growth serum and becomes the Lizard. When the Lizard decides to turn the whole of New York into gigantic reptilian creatures, Spidey had to take the respected scientist down.

Andrew, Matt, and Steve (Chronicle)
There’s nothing like finding alien superpowers to make a friendship stronger. In Max Landis’ Chronicle, Andrew, Matt and Steve bond after accidentally obtaining powers, but Andrew gets consumed by his new found abilities and his terrible home life. After possibly killing Steve, Andrew goes on a rampage through the streets of Seattle, and it’s up to Matt to stop him before more people get hurt.

Todd and Dave (Kick-Ass 2)
In the sequel to Kick-Ass, the eponymous hero continues to wage his inept war against crime, but when his best friend Todd feels left out of the superheroics, he almost unwittingly becomes a henchmen of Christopher Mintz-Plasse’s The Motherfu****, and inadvertantly get’s Kick-Ass’ father killed. Things between the two are reconciled at the end, but there are some things you probably shouldn’t forgive.

Magneto and Professor X (X-Men: First Class)
Did I say Harry and Peter were the original frenemies? Nope, that honor clearly goes to Magneto and Professor X. While  Erik Lehnsherr and Charles Xavier were originally united in their fight for Mutant rights in the 60’s, Professor X sought more peaceful methods, while Magneto was very much an ends-justifies-the-means type of guy, and the two have been at each others throats ever since.  They still have mutual respect and affection for one another, but it’s buried under years of hate.

Mystique and Professor X (X-Men: First Class)
Wait, hold on. Did I say Magneto and Professor X were the original frienemies? Well, according to X-Men: First Class, the good Professor knew Mystique back when they were both children. The two were basically siblings growing up until Raven started to side with Magneto’s more forceful ideas about Mutant rights.

Harvey Dent and Bruce Wayne (Batman Forever)
Harvey Dent was a by-the-books district attorney that protected Gotham with law and order, while allowing Batman clean up whatever scum slipped out of the court and onto the streets. Their tag-team was broken up when Dent’s face was burned by a disgruntled crime boss in the middle of a court proceeding, and Dent is driven insane by his disfigurement, becoming the villain Two Face.

Sabertooth and Wolverine (X-Men Origins: Wolverine)
Bound by blood and death, Wolverine and Sabertooth were half-brothers that spent the better part of two centuries fighting through American military conflicts across the globe. After being recruited by William Stryker to join a group of mutant military group called Team X and carrying out some wet work on behalf of the government, Logan leaves the team, feeling dismayed by all of the killing, and Sabertooth sees this as the ultimate betrayal.