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5 Memorable Leonardo DiCaprio Performances

the revenant dicaprio

This year, Leonardo DiCaprio is the favorite to win the Academy Award for his performance as Hugh Glass in the brutal and beautiful The Revenant, a survival and vengeance story that takes place in the uncharted American wilderness in the 1800s. DiCaprio has had a very prolific career (The Basketball DiariesTitanic, Gangs of New York, Inception, etc.) and he always gives Oscar worthy performances. With The Revenant, DiCaprio takes it a step further by committing himself fully to the physically demanding role and brutal filming conditions that director Alejandro Iñárritu puts him through.

With all the Oscar buzz surrounding him, we look back at five memorable performances that Leonardo DiCaprio gave throughout his long career.

wolf of wall street dicaprio

Jordan Belfort
The Wolf of Wall Street

While it’s certainly not the best movie he’s been in (or close), Leo’s portrayal of Jordan Belfort in The Wolf of Wall Street is the most bonkers, diverting and intense of his career (notwithstanding The Revenant, which I have yet to see). In Scorsese’s ode to gluttony, Leo’s Belfort is a friggin’ missile entering every scene, destroying everyone in his path not named Matthew McConaughey. Every single one of his speeches are somehow simultaneously ridiculous, stupid and inspiring. And he has a lot of speeches in this too-long movie. But every minute of it is fascinating, with Leo seemingly having fun on screen, which I feel he sometimes has lost sight of since Titanic. The capper is his adventure with quaaludes, which is absolutely an all-timer and what makes Belfort the winner. — Andy

calvin candie

Calvin Candie
Django Unchained

In a sadly neglected (at least by the Academy) performance as the villainous Calvin Candie in Quentin Tarantino’s Django Unchained, DiCaprio is on his A-game, bringing a charming amiability to a frankly despicable human being. Candie is the brutal and sweet-spoken owner of a plantation, the captor of Kerry Washington’s runaway slave Broomhilda, and the target of the film’s two heroes (Jamie Foxx’s eponymous Django and Christoph Waltz’s brilliant Dr. King Schultz in an Oscar-winning turn).

DiCaprio doesn’t much chew the scenery as devour it, allowing him to dive headlong into Tarantino’s speeches and giving them a sickly sheen of geniality. Underneath Candie’s cordial manners and Francophile leanings, he is a coiled snake and when he strikes, his ferocious venom is unmatched; so much so that DiCaprio injured himself on set by accident, kept running the take while incorporating the injury, and ensuring it became part of the final film. That’s commitment, people. His performance here is mesmerising and he makes an okay film infinitely more enjoyable. — Chris

the departed dicaprio

Billy
The Departed

Oh Leo, how I hope this is your year. As a huge fan, I’ve found myself cheering and shortly thereafter crying for Leonardo DiCaprio year after year when he doesn’t win an Oscar. He’s been in so many amazing films in which he’s shown us the limits he can exceed as an actor and yet I still don’t understand why The Academy won’t give him the acknowledgment he deserves. It’s so difficult for me to even try and choose a specific performance of his that I love, but I definitely have to say that “Billy” in The Departed  is one of my ultimate favorites.

I have two words for you: BOSTON ACCENT. This Scorsese crime drama follows Billy Costigan, an undercover cop who is assigned to infiltrate the Irish American mob in effort to take down the big bad boss, Frank Costello (Jack Nicholson). And let me tell you, Leo’s character steals the show even alongside big stars like Martin Sheen, Jack Nicholson, Mark Wahlberg and Matt Damon. DiCaprio’s transformation from a young undercover cop to a distressed mob soul is exceptional. Unfortunately the Academy didn’t agree with me on this one. But here’s to hoping that Leo gets his award for his transformation in The Revenant. If not, I can’t say I won’t love the many more memes that I’m sure will come of it. Cheers Leo, I wish you the best! — Yara

the aviator dicaprio

Howard Hughes
The Aviator

DiCaprio is no stranger to award season. Besides his recent Golden Globes win, he has been nominated for 11 Golden Globes and won three, nominated for six Academy Awards, and won nine Screen Actor Guild Awards. Will this year be the year of Leonardo DiCaprio?

The Revenant has generated award buzz since they began filming and with 12 Oscar nominations for the Alejandro Iñárritu directed movie, DiCaprio is ruling award season. But this is not his only critically acclaimed award season buzzed about film. In 2004, Dicaprio played Howard Hughes in The Aviator which earned 11 Academy Award nominations and grossed $214 million at the box office. DiCaprio played Howard Hughes, an aviation pioneer who made his jump into the film industry producing and directing. He was known for his Hollywood flings with actresses such as Katharine Hepburn, Jean Harlow and Ava Gardner. Hughes was a complex person with mental illness including OCD, anxiety and paranoia. DiCaprio was a joy to watch play such an icon. He really put himself into character and it translated on camera. He was a contender in the 2005 Academy Awards for Best Lead Actor but lost to Jamie Foxx for Ray.Whitney

what's eating gilbert grape dicaprio

Arnie Grape
What’s Eating Gilbert Grape

Leonardo DiCaprio plays the developmentally disabled younger brother of Johnny Depp’s Gilbert in the 1993 family drama What’s Eating Gilbert Grape. DiCaprio, who was only 17 years old when he played this role, absolutely steals the movie as the sweet, adventurous, and vulnerable Arnie Grape; he gives a heartbreaking performance that people still remember after all these years. When you look back at DiCaprio’s career, this is the performance that solidifies DiCaprio as one of the most naturally gifted actors of our generation. It’s also the first time he was recognized by the Academy and given an Oscar nomination in the category of Best Supporting Actor. DiCaprio recently paid homage to What’s Eating Gilbert Grape after winning the Golden Globe, calling it one of the biggest risks of his career — one that definitely paid off.