10) Harry Osborn
Though the character from the comics isn’t often described as such, Harry Osborn in Sam Raimi’s Spider-Man trilogy is best summed up as an anti-hero. While he begins the series as Peter Parker’s loyal best friend, after he believes Spider-Man killed his father Norman he becomes obsessed with Spidey’s downfall, something that is complicated when he finds out that his enemy and his best friend are one and the same.
In Spider-Man 3, he is given the, let’s say, ambitious story arc of becoming a fully-fledged villain as the New Goblin then becoming good again as he gets amnesia, before going bad again and then good again just in time to fight at Peter’s side and then die at the climax.
He might not have the neatest character trajectory ever, and he isn’t as badass as the other characters on this list, but an anti-hero is surely defined by their murky morals, and there aren’t many comic book movie characters who switch sides as much as James Franco’s Harry Osborn.