Leonardo DiCaprio’s Best Roles: When Will He Get That Oscar?


Hollywood A-lister Leonardo DiCaprio has come alone way since he first graced the silver screen opposite fellow Hollywood star Johnny Depp in the 1993 film What’s Eating Gilbert Grape?

Widely recognized as the poster boy for the pretty boys in the Entertainment business, DiCaprio has proven that he is more than just pretty face in a world constantly lauded by criticism. Yet before DiCaprio came to the seen, he like many aspiring child actors underwent the same grueling process of falling in line to audition for a role. Although born in Los Angeles, California, jump starting his acting career was not easy.

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It was his parent’s encouragement despite failed audition that landed him jobs at commercials which became his first stint in the industry. He also had recurring roles in the television series Santa Barbara and Growing Pains during the early 1990’s but it was not until he landed the supporting role of Arnie Grape in the 1993 comedy drama movie What’s Eating Gilbert Grape that he gained caught the attention of movie industry. Since then he had landed several breakthrough roles that gained him public recognition in the movies: The Basketball Diaries ( 1995) and Romeo + Juliet (1996).

But it was not until he landed the leading role of Jack Dawson in the 1997 James Cameron Romance Titanic that catapulted both him and co-star Kate Winslet into superstardom. Since the, he has appeared in several critically acclaimed movies which include: Catch Me If You Can  (2002), Revolutionary Road (2008), Shutter Island (2010), Inception (2010) and The Wolf of Wall Street (2013).

In a decade that spans for more than two decades, DiCaprio’s flourishing career has earned him ten Golden Globe Awards where he won two and five nominations form the Academy Awards. In celebration of his career and brilliance as an actor, here are some of the most memorable roles ever portrayed by the actor throughout the years.

17. Gangs of New York (2002)

Gangs of New York

DiCaprio played the role of the mob leader and protagonist Amsterdam Vallon in this cut-throat movie that chronicled the Irish immigration and the ongoing Civil War. It follows the story of Bill Butcher and his role as both a crime boss and a political kingmaker under the helm of Boss Tweed. The movie culminated in the New York Draft Riots of 1863.

16. The Beach (2000)

The Beach

The actor played the role of a college student in this film adaptation of the novel of the same name. He stars opposite Hollywood greats like Tilda Swinton, Robert Carlyle, and Paterson Joseph.

15. Body of Lies (2008)

Body of Lives

In the movie, DiCaprio played the role of CIA operative turned Station Chief Roger Ferris. Based on the novel of the same name, Body of Lies tells the story of the attempts of both the CIA and the Jordanian Intelligence Unit to catch “al-Saleem,” a jihadist. Frustrated over their target’s elusiveness and the difference in both parties’ approaches, a train develops between a CIA operative, his superior and the head of the Jordanian Intelligence.

14. The Basketball Diaries (1995)

The Basketball Diaries

One of the movies that gained DiCaprio recognition from the industry, The Basketball Diaries chronicles the real life story of Jim Carroll, played by DiCaprio, a promising basketball player who becomes addicted to drugs due to a group of misguided friends.

13. Inception (2010)


The critically acclaimed movie that cemented Hollywood director Christopher Nolan his directorial status, Leonardo plays the role of Dominick “Dom” Cobb, an extractor who performs corporate espionage with the use of experimental military technology in order to infiltrate the subconscious of their target and extract information while experiencing shared dreaming.

12. Romeo + Juliet (1996)

Romeo and Juliet

It is not easy to miss the fact that these modern day Romeo played the role of Romeo Montague in this classic yet modern retelling of William Shakespeare‘s masterpiece Romeo and Juliet.

11. Revolutionary Road (2008)

Leonardo Dicaprio Revolutionary Road

Teaming up again with Titanic co-star Kate Winslet, Revolutionary Road sees DiCaprio as Frank Wheeler who becomes involved with Winslet’s character April Wheeler.

10. Titanic (1997)

Leonardo DiCaprio Titanic

DiCaprio played the other half of the star crossed pair Jack Dawson in James Cameron‘s 1997 epic romance film Titanic. The movie chronicles the eventual sinking of the world’s biggest ship told in the eyes of two star-crossed lovers namely Jack and Rose.

9. The Great Gatsby (2013)

Leonardo DiCaprio the great gatsby

Based on the literary classic written by F. Scott Fitzgerald of the same name, DiCaprio plays the tragic role of the eponymous Jay Gatsby whose life story was a classic tale of a self-made millionaire.

8. Catch Me If You Can (2002)

Leonardo Dicaprio catch me if you can

Based on the true story, the actor played the role of American con artist Frank Abagnale. Abagnale, through a series of frauds, was able to successfully con worth millions of dollars by posing as a Pan American World Airways pilot, a Georgia doctor, and a Louisiana parish prosecutor.

7. Blood Diamond (2006)

Set during the Sierra Leone Civil War from 1996–2001, Blood Diamond refers to the diamonds mined in war zones and sold to finance conflicts. DiCaprio plays the role of Danny Archer who becomes involved int he conflict.

6. Django Unchained (2012)

Leonardo Dicaprio Django Unchained

This 2012 Western film by Quentin Tarantino sees the actor as Monseigneur Calvin J. Candie. The film is set against the backdrop of antebellum era of the Deep South and explores the subject of slavery.

5. What’s Eating Gilbert Grape (1993)

Leonardo Dicaprio what's eating gilbert grape

The Hollywood actor played the role of Arnie Grape the brother of Gilbert Grape played by fellow Hollywood actor Johnny Depp. Based on the novel of the same name, DiCaprio’s performance in the film garnered him an Academy Award Nomination for Best Supporting Actor.

4. The Wolf of Wall Street (2013)

Leonardo Dicaprio the wolf of wall street

Directed by legendary Hollywood director Martin Scorsese, The Wolf of Wall Street tells the events that took place in the life of former Wall Street broker Jordan Belfort.

3. The Aviator (2004)

Leonardo Dicaprio the aviator

This critically acclaimed film saw DiCaprio int he shoes of legendary American business tycoon, aviator, and aerospace engineer and inventor Howard Hughes. The film depicts the life of Hughes both as an aviation pioneer and director of Hell’s Angels.

2. Shutter Island (2010)

Shutter Island leonardo dicaprio

Shutter Island sees DiCaprio as US Marshal Edward “Teddy” Daniels. The movie chronicles the investigation Daniels does in a psychiatric facility on Shutter Island when a notorious criminal escapes within its premises.

1. The Departed (2006)

The departed leonardo dicaprio

This gangster film sees the actor in the shoes of undercover state trooper William “Billy” Costigan who goes undercover to infiltrate the group of Irish mobs led by Francis “Frank” Costello portrayed by Jack Nicholson.

These critically acclaimed roles have proven that this Hollywood actor is not all about having the look but also having the talent to make a name for himself in this cut throat industry.

Watch Leo in talk about his Oscar snub and also a heartwarming speech at the Golden Globes.


 Click on the links below for more celeb stories

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