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Leonardo DiCaprio's 15 Best Roles

November 8, 2011  |  9:23am

Leonardo DiCaprio has come a long way since his stint as a teen heartthrob on Growing Pains alongside fellow Tiger Beat love interest Kirk Cameron to starr in the now-second highest grossing film of all time. He’s yet to win an Oscar but that could change with J. Edgar opening this week. Today we look back at his most memorable roles throughout his prolific career.

15. Richard, The Beach
Academy Award Nomination: No
Golden Globe Nomination: No
Though the film was widely panned by critics and fans, DiCaprio stretched himself in an edgier role. At this point in his career, the only award he was considered for was a Razzie.

14. Hank, Marvin’s Room
Academy Award Nomination: No
Golden Globe Nomination: No
Released in 1996 while he was still relatively unknown, Marvin’s Room is often overlooked by DiCaprio fans. His role was limited and overshadowed by an Academy Award nominated performance by Diane Keaton and a Golden Globe nom for Meryl Streep. His portrayal of Hank, a teenager committed to a mental institution for setting fire to his mother’s house, hints at the career to come.

13. Jim Carroll, The Basketball Diaries
Academy Award Nomination: No
Golden Globe Nomination: No
Not all early DiCaprio roles were squeaky clean. As Jim Carroll, a real-life heroin addict, he shows his range in playing an off-kilter character. The film is lackluster, but you can see DiCaprio finding his way around certain characters.

12. Edward “Teddy” Daniels, Shutter Island
Academy Award Nomination: No
Golden Globe Nomination: No
Martin Scorsese cast DiCaprio as a U.S. Marshall in the 1950s. The role allowed the actor to delve into his infinite bag of accents, but didn’t transform his so much as other roles had in the past.

11. Romeo Montague, Romeo + Juliet
Academy Award Nomination: No
Golden Globe Nomination: No
This polarizing take on Shakespeare won him Berlin International Film Festival’s Silver Bear for Best Actor as Romeo and helped him land his role in Titanic. He was able to play off of his pretty-boy persona, but still have another layer hidden, showing his drive to be a down-to-earth drama actor.

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