Leonardo DiCaprio's 15 Best Roles

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Leonardo DiCaprio's 15 Best Roles

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.

10. Jack Dawson, Titanic
Academy Award Nomination: No
Golden Globe Nomination: Yes
This was the film that launched LeoMania, plastering the actors face over every magazine cover in 1997 and 1998 and earning him his first Golden Globe nomination for lead actor.

9. Fee “The Kid” Herod, The Quick and the Dead
Academy Award Nomination: No
Golden Globe Nomination: No
Before Titanic, DiCaprio played a young gunslinger, delivering a heart-wrenching performance in his final scene. Spoiler alert: Though his character just wants to be loved by his father, his father shoots him, leaving him to worm on the ground, professing over and over that he doesn’t want to die. It was the most believable moment in the 1995 western.

8. Amsterdam Vallon, Gangs of New York
Academy Award Nomination: No
Golden Globe Nomination: No
His first collaboration with Scorsese received a plethora of Academy Award nominations, but his supporting role was overlooked. His transformation to a vengeful, 19th-century gangster was a departure from the safer roles he’d settled into. He proved himself a valuable asset to the high-profile director as they worked together on the next two of DiCaprio films.

7. Danny Archer, Blood Diamond
Academy Award Nomination: Yes
Golden Globe Nomination: Yes
The 2006 historical drama set in 1999 cast DiCaprio as a South African, and despite an unconvincing accent, he earned him his second Academy Award nom for Best Actor. But it wasn’t even his best roll of the year—just another case of critics and award voters preferring period pieces over modern dramas.

6. Dom Cobb, Inception
Academy Award Nomination: No
Golden Globe Nomination: No
In one of the most-mind blowing films in recent memory. Christopher Nolan’s writing and directing was buoyed further by the acting. Cobb’s descent into paranoia and his drive to see his children brings a realness to the dreamlike setting.

5. Howard Hughes, The Aviator
Academy Award Nomination: Yes
Golden Globe Nomination: Yes
Another double nomination for DiCaprio, his 2004 portrayal of the estranged tycoon gave him his only Globe win. Another spiral into insanity, here he is completely transformed. The only reason it isn’t higher on this list is because he didn’t have to carry the film by himself. Scorsese helmed the project and Cate Blanchett helped with an Oscar-winning performance.

4. Arnie Grape, What’s Eating Gilbert Grape
Academy Award Nomination: Yes
Golden Globe Nomination: Yes
A very young DiCaprio was nominated as a supporting actor in 1993 as a mentally challenged teenager in this film starring Johnny Depp. His ability to channel the tics of Arnie expressed in the screenplay is vivid and a New York Times review said he was initially hard to watch and praised the realism of the performance. He earned the Best Supporting Actor Award by the National Board Review.

3. Frank Abagnale Jr., Catch Me If You Can
Academy Award Nomination: No
Golden Globe Nomination: Yes
It’s DiCaprio’s highest rated film on Rotten Tomatoes, and with good reason. It was a box-office hit, playing both on his ability to be a leading heartthrob (it was released in 2000, only three years after Titanic), and to descend his character to unexpected places.

2. Billy Costigan Jr., The Departed
Academy Award Nomination: No
Golden Globe Nomination: No
The fact that the Academy overlooked his role in this film in preference for Blood Diamond in 2006 is perhaps one of the main reasons DiCaprio is Oscar-less. The actor’s ability to transform into something he is the opposite of what he is (a Boston cop/mole) at its highest point here, but the Best Picture had so many positives that he was simply overlooked.

1. Frank Wheeler, Revolutionary Road
Academy Award Nomination: No
Golden Globe Nomination: Yes
DiCaprio’s role as Frank Wheeler might possibly be the most sincere portrayal he’s yet delivered. It went largely unnoticed in a year when Sean Penn and Mickey Rourke turned in two of the best performances in recent memory. The film was extremely character-driven and DiCaprio and Golden Globe winner Kate Winslet turned it an emotional rollercoaster. DiCaprio unceremoniously tapped into the character and stopped acting. He simply was Frank Wheeler.