Requiem for a Dream (2000)
I don’t think I’ve cried as much during a movie as I did at the end of Requiem for a Dream. And then, the next day, I watched it again. While this might speak to my sickening emotional masochism, if I’m going to watch a film that is going to make me feel sad, I want it to be as compelling and engaging a watch as this, a tour de force in style, dramatics and montage. The climax of this film is one of the greatest montages ever committed to film and also one of the most gut wrenching.