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10 Times Leonardo DiCaprio Deserved an Oscar

Arnie Grape, "What’s Eating Gilbert Grape" (1993)

Even at an early age, DiCaprio showed his promise as an actor. Here, he plays the title character’s developmentally challenged younger brother. However, he does so with refined sense of grace and a sensitivity toward the character’s affliction without trying to oversell it.

(Image via Malik)

Jack Dawson, "Titanic" (1997)

DiCaprio's role in Titanic cemented his place in Hollywood. To this day, you can be certain that Leo routinely gets asked by fans to “draw me like one of your French girls.”

(Image via Titanic)

Frank Abagnale, Jr., "Catch Me If You Can" (2002)

DiCaprio displayed his capabilities as a serious actor in Catch Me if You Can, proving that he could hold his own working with Tom Hanks and Steven Spielberg. This is the movie that showed that he was no longer just a teenage heartthrob; he became a talent to keep an eye on. 

(Image via Catch Me if You Can)

Howard Hughes, "The Aviator" (2004)

Starring in a biopic normally gives you a better chance of grabbing an Oscar. DiCaprio scored the nomination, but he went home empty-handed. Not only was his role in The Aviator one of his most memorable performances, this was also DiCaprio’s credit as executive producer.  

(Image via The Aviator)

William “Billy” Costigan, "The Departed" (2006)

Even in a movie that displays several outstanding performances (The Departed also stars Matt Damon and Mark Wahlberg), DiCaprio carries the bulk of the film. As Billy is torn between his ethical responsibility to uphold the law and his loyalty to the mob he is infiltrating, the audience is able to truly feel the conflict under the surface.  

(Image via The Departed)

Danny Archer, "Blood Diamond" (2006)

Blood Diamond was one of the most intense movies DiCaprio has been in (which is saying a lot). This role gave him a chance to earn his third Academy Award nomination, though he ended up losing to Forest Whitaker. This political war thriller still resonates in the hearts and minds of viewers who saw it nearly a decade ago.

(Image via Blood Diamond)

Frank Wheeler, "Revolutionary Road" (2008)

Kate Winslet and DiCaprio had already demonstrated their chemistry a decade prior (in a little movie called Titanic), so when they teamed up again, people were eager to see what the end result would be. In this dramatic period piece, Leo gives a performance that had everyone in tears when they left the theater.

(Image via c.osmos_j)

Edward “Teddy” Daniels, "Shutter Island" (2010)

Much of this movie’s emotional fortitude rests on Leo’s shoulders, as he is forced to distinguish myth from reality. This psychological thriller follows DiCaprio’s investigation of a mental ward on a remote island, showing us the events through his perspective. Here, he displays some of his best concerned looks.  

(Image via Shutter Island)

Calvin Candie, "Django Unchained" (2012)

Even as a brutal slave owner, DiCaprio's charisma still managed to shine through. The scene where he famously actually cut his hand (IRL) and continued to deliver his lines should be enough to convince even his toughest critics of his dedication and his prowess as an actor.  

(Image via Django Unchained)

Jordan Belfort, "The Wolf of Wall Street" (2013)

This real-life man was larger than life, so of course it took an over-the-top performance to bring his story to the silver screen. Whether he's ingesting his weight in mind-altering substances or delivering motivational speeches, we are with him 100% of the way.

(Image via The Wolf of Wall Street)