25. 'The Basketball Diaries' (1995)
Leo went full Brando in this overbaked adaptation of Jim Carroll's memoir about his teenage descent from high school basketball star to broken, homeless drug addict. You have to have some respect for a movie willing to go so over the top, but the scenery-chewing acting, the deliriously overdone montages, the addiction-drama cliches … it's all a bit much. Still, coming on the heels of his Oscar nomination for What's Eating Gilbert Grape?, this performance made it clear that this was a young actor willing to take huge risks.