An actor as polarizing as many of his characters, Leonardo DiCaprio’s name is sure to arouse as many groans as adorations. While many of his performances are rightfully lauded, many others are dismissed as “pretty boy” pandering. Whether or not it’s fair to hold an actor to task for his very first performances is a question that will have to wait for another article, but the fact remains that while DiCaprio has 
delivered performances adored by fans and critics alike, he has yet to receive an Oscar Award for Best Actor.
DiCaprio’s career began in television, but his second film, What’s Eating Gilbert Grape, proved quickly that he was a serious actor with serious capabilities. Within four years, DiCaprio blossomed into a heartthrob and an A-list celebrity with roles in Baz Luhrmann’s Romeo and Juliet, and
James Cameron’s mega block buster, Titanic. In the years between Titanic and his first collaboration with Martin Scorsese, Gangs of New York, Leo began to develop his darker side, taking on roles like Richard in Danny Boyle’s, The Beach, and the titular role in The Man in The Iron Mask. These roles prepared him for some of the highlights of his career, many of which came at the direction of Martin Scorsese.
Leonardo DiCaprio’s career has moved steadily in a direction toward darker and more complex characters well suited for such an intense and classic actor. He is a classic leading man, clean cut with a pretty smile and a steely gaze, and if he keeps delivering performances like The Wolf of Wall Street’s Jordan Belfort, he will continue to be.
The Wolf of Wall Street – 2013
Django Unchained – 2012
J. Edgar Hoover – 2011
Inception – 2010
Shutter Island – 2010
Revolutionary Road – 2008
Body of Lies – 2008
Blood Diamond – 2006
The Departed – 2006
The Aviator – 2004
Catch Me If You Can – 2002
Gangs of New York – 2002
The Beach – 2000
The Man in the Iron Mask – 1998
Titanic – 1997
Romeo + Juliet – 1996
The Basketball Diaries – 1995
What’s Eating Gilbert Grape – 1993