Maybe poorly reviewed, but breakout Leo in my eyes. It's an ultimate coming of age flick that tackles the trouble and struggles of a group of Catholic school kids in New York City.

Watch as Leonardo DiCaprio plays the boy who has everything (basketball future, friends, great life) until his friend dies and he falls into the ever-so-popular heroin trap. Things start going all wrong in his life, and he falls deeper and deeper into a life of addiction.

Sounds like a downer, I know. But thought provoking, I promist.

THE ORIGINAL CATHOLIC BOY STORY! THE BASKETBALL DIARIES STARS LEONARDO DICAPRIO AND MARK WAHLBERG! BASED ON THE LIFE OF POET JIM CARROL AND HIS RIDE THROUGH THE HELL THAT IS DRUG ADDICTION, GROWING UP, AND TRULY LIVING A HARD KNOCK LIFE!

This is one of my favorite Leo movies. He plays a heroine addict who plays basketball with his Catholic school friends. (via amazon.com)