The Basketball Diaries (1995)

This is one of the few based-on-a-true-story movies that actually FEELS like it's based on a true story. There's no overdramatization, no cute wrapping up loose ends... just the story of someone whose life falls apart. Even the ending feels completely unforced. Leonardo DiCaprio is particularly impressive in the scene where he begs his mother for money - it is completely unromanticized. It is pathetic and painful to watch. Beautifully, beautifully done. 4 stars.