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50. Harry Osborn
Spider-Man movies (2002-2007)

Barely making the cut, spoiled rich kid Harry Osborn hardly poses a threat to Peter Parker in the Spider-Man movies. He blames Spidey for killing his father, Norman, even though Dad was a homicidal maniac. When he discovers Spider-Man is Peter, his best buddy, Harry wavers but still wants to kill him. Eventually he sees the light at the end of Spider-Man 3... just in time to die.