10 Movies So Sad You Can Only Watch Them Once
9. American History X (1998)
What makes so American History X so powerful is how it takes one man who represents the worst of society and turns him into a redeemed hero who, despite everything, can't escape his past.
The man in question is Derek (Edward Norton), a white supremacist who's jailed for manslaughter and in prison comes to realise his way of life is both ruinous and wrong. Unfortunately, when he gets out, he finds his impressionable brother (Edward Furlong) doesn't see things the same way.
Though it's hard to root for Derek given his crimes, there can be no doubt his journey from neo-Nazi to atoned protagonist hoping to save his brother from his own mistakes is deeply affecting, which is exactly why it hurts so much to see his hard work pay off...and then be cruelly destroyed at the last second.
American History X is a laborious watch, and its final moments in particular will most likely tip you over the edge.