14. The Basketball Diaries, “Jim Carroll” (1995)
It?s both uncomfortable and captivating to watch DiCaprio portray the real-life Carroll’s downward spiral into the world of hard drugs. While the film hasn’t necessarily aged well, DiCaprio is still remembered for the way he handled the chameleon-like Carroll in one of his earliest roles. It wasn’t easy to like or root for Carroll, but DiCaprio made that possible through his performance.
Image Source: IMDb