Leonardo DiCaprio – Ten Best Performances

In honor of Leonardo DiCaprio finally winning Best Actor, here’s a retrospective of some of his best performances. 

10. Titanic (1997) – Jack Dawson

For better or worse, Titanic catapulted DiCaprio from “up and comer” to “Hollywood superstar.”  The film itself has taken its share of criticism over the years, but it remains popular largely due to DiCaprio’s performance.  Jack Dawson isn’t close to the deepest character that DiCaprio would tackle over the years, but his charisma and heroism carry the movie.

9. The Basketball Diaries (1995) – Jim Carroll

After DiCaprio was nominated for an Oscar for What’s Eating Gilbert Grape (1993), The Basketball Diaries was the first time he demonstrated that he could carry a movie in a leading role.  His balance of charisma and personal demons here would serve him well in later roles.

8. Revolutionary Road (2008) – Frank Wheeler

DiCaprio plays of lot of larger than life figures, so Revolutionary Road was something a bit different for him.  Frank Wheeler isn’t a great hero from an interesting time in history.  Instead, he’s the stereotypical 1950’s “man in the grey flannel suit.”  The fact that DiCaprio snagged an Oscar nomination for this role is a testament to his versatility.

7. Inception (2010) – Cobb

Inception is a great film with fine performances.  Even so, DiCaprio gives Cobb a deep sense of pathos and connects with the audience.  This is no easy feat, Inception is a high-concept film and could have easily looked silly if its lead role was in the hands of a lesser actor.

6. The Wolf of Wall Street (2013) – Jordan Belfort

Jordan Belfort is a scumbag, but you wouldn’t necessarily know it by watching DiCaprio’s performance here.  He’s charming and charismatic.  Even as he sinks deeper and deeper into to depravity, violence, and stupidity, we kind of feel bad for the guy.

5. The Revenant (2015) – Hugh Glass

I wrote before that this was DiCaprio’s fifth or sixth best performance, and I’ve settled on number five.  It is certainly his most physically demanding role, but Glass himself is not a particularly deep character.  He deserves an Oscar here for degree of difficulty, but he’s been better when he’s had more to work with character-wise.

4. The Departed (2006) – Billy

The Departed has the strongest cast of the films that DiCaprio has appeared in.  He is excellent here, but his role is really a co-lead with Jack Nicholson and Matt Damon.  It gets moved down a couple of slots because in some ways, it’s easier to be part of an ensemble than to be asked to carry a movie yourself.

3. Gangs of New York (2002) – Amsterdam Vallon

Gangs of New York is one of the best movies of the 2000’s, and DiCaprio’s performance comes across as particularly powerful and authentic.  This is no small feat, since he’s opposite Daniel Day-Lewis here.  If DiCaprio’s performance wasn’t well-balanced against the great Day-Lewis, the film could have come across as far more melodramatic.  Instead we have a powerful glimpse into a dark corner of American history.

2. Blood Diamond (2006) – Danny Archer

I was debating putting this performance as #1, and it certainly has a lot to recommend it for that spot.  DiCaprio’s character arc is long and filled with pitfalls here.  For instance, he comes across as an authentic mercenary at the beginning, but leaves just enough room for a potential redemption.

1. The Aviator (2004) – Howard Hughes

There’s a reason why playing well-known historical figures often wins Best Actor awards.  How do you say something new and interesting about someone the audience feels like they know so much about?  DiCaprio pulls out all the stops here, and delivers a haunting performance as a man with control over everything except his own advancing mental illness.

(c) 2016 D.G. McCabe