Top 10 Leonardo DiCaprio Performances

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It’s kind of amazing that everyone’s favorite heartthrob circa 1997, the guy who gave us Jack Dawson himself, has turned into one of cinema’s most fascinating, exciting, and reliable actors.

While a gold statue has still managed to elude him, Leonardo DiCaprio has a resume many actors would kill for. He’s Scorsese’s new golden boy (The Wolf of Wall Street is coming later this year), and has played key roles in films from directors like Christopher Nolan, James Cameron, Sam Mendes, and Quentin Tarantino.

This weekend, he’s Jay Gatsby—one of American literature’s most unforgettable individuals. We’re still a few days from finding out if his work in Baz Luhrmann’s adaptation of the famous F. Scott Fitzgerald novel is another J. Edgar or worthy of rating up there with DiCaprio’s best work. Until then, I’ll remember only the good times. Presenting the ten best Leonardo DiCaprio performances…

10.) What’s Eating Gilbert Grape

Number ten by default because I haven’t seen the film. It feels a little odd to not even mention DiCaprio’s breakout role and first Oscar nomination on a list of his greatest acting achievements. So it gets this quasi-honorable mention spot. *Moves Gilbert Grape to the top of my Netflix queue*

9.) Gangs of New York

I love this 2002 Martin Scorsese film more than perhaps any human being out there. It’s a masterpiece and one of the director’s five (four? three?) best films. DiCaprio is far from the best thing about it, but there are signs that these two are capable of making beautiful cinematic music together. That alone is reason enough to give it a mention on this list.

8.) Inception

A very complex, layered performance that probably got overshadowed some by superior work the very same year (more on that below). In Christopher Nolan’s mind-bender, DiCaprio plays Dom Cobb, an extraction specialist planning the toughest job in the business. He’s haunted by demons that reveal themselves slowly over the course of the film. DiCaprio really gets every aspect of this complicated man. This is much better work than you’ll get in your average summer blockbuster.

7.) Titanic

Though he’s overshadowed, even these 15 years later, by the hype, the posters, the magazines, and the rest of the nonsense, it’s not half-bad work. Truly. Jack Dawson is simply a wide-eyed optimist thrown into a situation that’s larger than life on one hand, and inches away from the end of his life on the other. James Cameron found the perfect fresh-faced kid to play the character, and in Jack, DiCaprio found the perfect vehicle to become the actor, I’m assuming, he always wanted to be.

6.) The Aviator

This is probably the performance that really shifted DiCaprio’s career into “Phase Two.” By playing an iconic historical figure for an all-time great director, DiCaprio was able to shed his pretty boy image and basically had free reign to choose the roles he wanted for the rest of his life. It helps, of course, that his work in The Aviator is exceptional. Hell, take Cate Blanchett out of the equation, and DiCaprio is the only exceptional thing about The Aviator. Almost single-handedly, he makes that film what it is, and while he still missed out on Oscar glory (Jamie Foxx was not going to be denied in 2005), he was closer here, I’d argue, than he has been before or since.

5.) Catch Me If You Can

DiCaprio had his first experience with Scorsese the same year he had his first (and only) experience with Spielberg. That’s a pretty damn good year. And he does pretty damn good work as con artist extraordinaire Frank Abagnale, Jr.

4.) Revolutionary Road

A Titanic reunion between DiCaprio and Kate Winslet always seemed likely (the two are great friends), but you can’t deny it was a little weird watching the two viciously bicker for two solid hours. It’s made more palatable because Sam Mendes’ domestic drama is exceptionally powerful, and DiCaprio is picture perfect as the frighteningly volcanic Frank, but hell if this isn’t one of the more depressing entries on this list.

3.) Shutter Island

So curiously similar to Inception on a thematic level, Scorsese’s 2010 horror film is twisty and turny like Nolan’s thriller, but it’s much less hopeful. DiCaprio’s performance strikes a similar chord. There’s nothing but tragedy in the character of Teddy Daniels, and we’re left scratching our heads as to what horrifying reality is true. DiCaprio, for his part, sells the whole thing brilliantly.

2.) Django Unchained

It seemed like a great fit on paper—DiCaprio as a Tarantino villain—and the results lived up to expectations. While his wasn’t the best performance in the movie (all I’m saying is Christoph Waltz earned his second Oscar), there’s no denying DiCaprio owned the second half of Django Unchained—popping off in ways the man never has before.

1.) The Departed

There’s been no question in my mind since that fateful October afternoon when I first laid eyes on Martin Scorsese’s Boston-set, cops-and-criminals epic that this was Leonardo DiCaprio’s finest hour as an actor, and nothing has topped it since. Not even his Calvin Candie could touch his Billy Costigan.

Now, there’s strung out and then there’s Billy Costigan. A mole for the cops within the upper echelon of Frank Costello’s criminal organization, this guy is hanging on by the thinnest of threads, and it’s all there on DiCaprio’s face, in his eyes. He holds nothing back. It’s career-defining work and easily the number one reason I look forward to each and every Leonardo DiCaprio performance.

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2 Responses to Top 10 Leonardo DiCaprio Performances

  1. Dan Heaton May 9, 2013 at 4:29 pm

    I did a Top 5 recently on Leo, and we ended up with very similar picks. You’re clearly very wise. My top choice was The Aviator, but The Departed and Django were right up there. I’m also in the camp that prefers his more recent performances rather than Gilbert Grape. The one I still need to see is Revolutionary Road. Nice job!

    Reply
  2. Meghan May 8, 2013 at 9:37 pm

    Really good list 🙂 Besides the performances you mentioned, my list of the best Leonardo DiCaprio performances would have included This Boy’s Life and The Basketball Diaries. You should watch those movies if you haven’t seen them already. I would consider Leonardo DiCaprio’s performance in What’s Eating Gilbert Grape to be his best.

    Reply

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