Make the Case: 5 Essential Leonardo DiCaprio Movies

For an award that no one supposedly cares about, there are an awful lot of people who want to see Leonardo DiCaprio win an Oscar. It’s a shame Peter O’Toole or Richard Burton didn’t have social media to bring attention to their respective positions as two of the biggest “losers” in Oscar history. Both men were nominated several times. Neither man won, although O’Toole eventually got the honorary Oscar that almost no one cares about.

One of the main differences between our perennial Oscar underdog and Burton or O’Toole is that DiCaprio will eventually win an Academy Award.

Is he going to win for The Revenant? He’s certainly the favorite, if only because it really is that hard for people to fathom that DiCaprio hasn’t won shit at the Academy Awards. For my personal money, his performance in The Revenant isn’t the best of the Best Actor lot (god help me, but it’s probably Michael Fassbender for Steve Jobs).

However, the Academy has a long history of giving out Oscars to people for accumulative achievements, even though it’s technically for a specific film. They did it for Martin Scorsese. They did it for Denzel Washington. They even did it for Al Pacino. It is what it is, and it’s one of the many, many silly things about this very silly award that you need to keep in mind. If DiCaprio wins, the award will have a lot to do with the fact that he should have won something twenty-three years ago.

As you’ll glean from this list of 5 essential Leonardo DiCaprio performances, it’s not going to take very long to understand what I’m getting at.

1. What’s Eating Gilbert Grape (1993)

Although not quite DiCaprio’s first movie (that honor belongs to Critters 3), What’s Eating Gilbert Grape is still an amazing display of a young actor’s emerging talents. In the same remarkable year, DiCaprio also appeared in This Boy’s Life, impressing Robert De Niro.

Of those two films, Gilbert Grape is the slightly more impressive of the two. DiCaprio completely avoids playing a developmentally disabled child named Arnie for laughs, or with any noticeable trace of pretense. The character is instantly tragic and wonderful in equal amounts. He is a perfect balance for Johnny Depp’s frustrated, unhappy misfit. A lot of people will tell you that as far as Leonardo DiCaprio and the Oscars go, Leo should have won 20+ years ago. Watch the scene in which Arnie Grape tries to wake up his mom. That opinion is not unfounded.

 

2. Total Eclipse (1995)

The movie isn’t great by a long shot, but Total Eclipse does offer a young DiCaprio elevating a mediocre movie with a nuanced, instantly engaging performance. Once again, this time, through his scenes with the equally-good David Thewlis, DiCaprio proves he can hold up his hand of exceptional on-screen chemistry with just about anyone. His performance as the poet Arthur Rimbaud is remarkably layered for such a young actor. Rimbaud is portrayed here as an over-the-top personality, but DiCaprio does not give an over-the-top performance.

Again, the movie suffers from terrible direction, as well as a script that tries to shed the art house sensibilities that the film simultaneously tries to embrace. But then DiCaprio is so good, you forgive an awful lot. It would be a little while longer, before DiCaprio started hooking up with directors who could make movies that were as good as his performances. Total Eclipse shows him looking to challenge himself as an actor. The amazing thing is that in this film, as well as in others, he succeeds. Even when the film is lacking, he isn’t.

3. The Aviator (2004)

Yes, we skipped Titanic. No, I don’t think it’s essential. However, if it really bothers you, pretend it is #2.5 on this list of top 5 Leonardo DiCaprio movies.

The Aviator was DiCaprio’s second collaboration with Martin Scorsese. Although The Aviator is not the best overall collaboration between Leonardo DiCaprio and Martin Scorsese, you can make a compelling argument that DiCaprio as Howard Hughes is his best work thus far with the legendary filmmaker. Playing someone as contradictory, glamorous, and ultimately as mysterious as Hughes is a task that would crush even the best actors.

Thankfully, The Aviator gives DiCaprio plenty of space to explore Hughes as a public and private figure. He moves seamlessly between the man who could charm just about anyone, and a man who was tormented by emotional instability, enormous doubt, and idiosyncrasies that would eventually consume him. DiCaprio brings all of it to life, from the stunning victories against common sense, Congress, and the many obstacles Hughes bested (many of which he arguably created himself), to his slow-burn-death from insanity. At just twenty-nine years old, he already made greatness look easy.

4. Django Unchained (2012)

Leonardo DiCaprio in Django Unchained is the movie’s secret weapon. It is one of those elements to the film that is absolutely essential to its success. However, of all the great things Django Unchained has going for it, DiCaprio is the one thing that’s the least discussed.

We understand what Django (thanks to Jamie Foxx’s electrifying performance) stands for, or rather, what he stands against. What really drives that understanding home is Leonardo DiCaprio’s performance as the sadistic plantation owner Calvin J. Candie. Although Candie is not the only villain Django and Dr. King Schulz (Christoph Waltz’s most enjoyable performance to date) encounter, certainly not the only slave owner, there is something extraordinarily hideous to DiCaprio’s Candie. For many of the other monsters encountered by Django and Schulz, those are, if nothing else, monsters of economics. They don’t particularly enjoy exploiting humanity, but for them, it’s a great way to make a buck.

DiCaprio provides a frightening contrast to that. There is a perverse, gleeful light in Candie’s eyes, as he watches people he perceives to be lower than him suffer and die. DiCaprio managed to slice open his hand, as he portrayed the kind of bad guy we needed to see Django confront and destroy. That part is really just trivia. It really shouldn’t influence your opinion of his performance. Even so, it’s a clear indicator of just how much intensity DiCaprio brought to Calvin. It’s hard not to be at least a little impressed.

5. The Wolf of Wall Street (2013)

The creative collaboration between DiCaprio and Scorsese seems to get better with each passing film. Neither Scorsese nor DiCaprio try to glamourize the life and crimes of scumbag Jordan Belfort. However, for the movie to be successful, we have to be able to understand how Belfort was so successful at seducing so many people.

DiCaprio’s natural charisma makes that part easy, but pay close attention to some of the more low-key moments of the movie. DiCaprio doesn’t try to give us a sympathetic portrayal, but he does go for something much deeper than some Wall Street Super Villain. Even in the movie’s quiet moments, DiCaprio’s Belfort is restless, perhaps maddeningly so. Combining a massive ego with that kind of restlessness, and it’s easy to see why Belfort makes destroying lives while lining his pockets as easy as breathing.

When Belfort finally realizes that professional success will never make him happy, the desire to live a full-tilt life for the hell of it becomes a spectacular, horrible death spiral. He doesn’t quite make it to death, but by the time DiCaprio gets us to the end of the film, he shows us a Jordan Belfort who may as well be dead. All that accomplishment, and even less to show for it than he had at the beginning.

DiCaprio takes us from a brash, enthusiastic young man to that depleted, hollow, pitiful shell. We buy all of it. We understand at least one of the reasons why people like Belfort get away with their crimes.