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