25. Harvey Milk In Milk (2008)
Assassinated By: Dan White
Cause of Death: Multiple gunshots, including one to the back of the head
As openly gay politician and activist Harvey Milk, Sean Penn gives one of his best performances, going against his surly public persona to play an outright jolly and optimistic man. Throughout Gus Van Sant's powerful biopic, Penn is never less than likeable, earning every bit of good will that the real-life Milk certainly did in his time.
Which is what makes his preordained assassination in the movie all the more emotionally potent. His killer is Dan White (Josh Brolin), a tormented politician who feels betrayed by Milk after one of his proposed bills gets declined. Having lost his job, White takes his rage out on Milk by first shooting him in the hand, then the chest, and then executing him via a gunshot to the back of the head.
Just before the final shot, Milk catches one last glimpse of his life's cause. In Penn's control, you get the feeling that, even as he's being executed, Milk still didn't hate White. The same can't be said for the movie's viewers.