The Long Journey from Teen Beat Coverboy to ManiacalSlave Owner: A Look Back At Leo’s Most Bad-Ass Characters

The best thing about Leonardo DiCaprio is his list of ex-girlfriends. The second best thing about Leo is his acting resume. And even though he has yet to win an Oscar, he happens to be one of the most versatile actors of our generation, transforming from a teen heartthrob into a man capable of infiltrating people's dreams. Did the top stop spinning? Is he still dreaming? What is real anymore?! BWAAAAAAHHHMMM!

Anyways, with his newest role as a racist plantation owner in Quentin Tarantino's western saga Django Unchained now in the books, we decided to take a look back at some of DiCaprio's toughest characters.

Here is a look at the most bad-ass roles of Leonardo DiCaprio's career: