The Superstar — 15 Top Leonardo DiCaprio Movies

The Basketball Diaries is maybe the least enjoyable movie I’ve ever seen. That’s not a bad thing though. Sometimes films have to challenge the audience into seeing tragedy.

And, oh boy, The Basketball Diaries is a tragedy.

DiCaprio portrays author and musician Jim Carroll during a troublesome period early in his life. Carroll is a promising young basketball star who likes to engage in petty crimes with his friends. But then, he becomes addicted to drugs and everything changes.

The descent that Carroll goes through in the film is heart-wrenching. At times, I had to look away; to shield my eyes from the horrors of this reality. But now I understand that’s exactly the impact the film aimed to provide. The Basketball Diaries is a movie I’ll never forget.

Okay, I’ll bite. I don’t love James Cameron’s movies. And I don’t care much for Titanic. But for the sake of the enormous impact the film has had on cinema and DiCaprio’s career, it’s worth including here. 

Titanic not only was the most financially successful movie of all time for years to come, it also tied the record for most Oscar Nominations and most Oscar Wins.

Martin Scorsese is strangely off his game directing Gangs of New York. But ‘off his game’ for Scorsese is very much ‘on his game’ for almost any other Director. Gangs of New York isn’t the best movie; the opening scene is actually very poor.

But as the story moves on and DiCaprio and Daniel Day-Lewis share more and more scenes, the movie really picks up. By the end, Gangs of New York proves worthwhile, and is hard not to recommend for fans of DiCaprio, Day-Lewis, or Scorsese.

Marvin’s Room features some terrific actors working at the top of their game. Meryl Streep, Diane Keaton and Leonardo DiCaprio all give excellent performances.

DiCaprio in particular does a great job as troubled youth Hank. It was a good role for the actor too. There’s plenty of complexities to Hank’s character and DiCaprio really digs in while exploring them.

Blood Diamond is a big-budget Hollywood rendition of the illicit African jewel business. DiCaprio plays the role of a Rhodesian gun-runner who’s lost everything to the violence of the continent. So he plans to do whatever it takes to get out.

Blood Diamond is a mostly by-the-books action adventure film that comes very close to being something great. Still, it’s a very good movie and offers one of DiCaprio’s best performances.

What’s Eating Gilbert Grape? is the movie that put Leonardo DiCaprio on the map. At the time of shooting, he was just 19 years old! Before this film, DiCaprio had worked on commercials and other small projects so he had considerable experience as a young actor though.

Gilbert Grape also nabbed DiCaprio his first Oscar nomination for his performance in a supporting role. The film is far from perfect, but it’s a good story and a clear “jumping off point” for stars Johnny Depp and Leonardo DiCaprio.

Leonardo DiCaprio gives his most malevolent performance of his career as slave-master Calvin J. Candie in Django Unchained. Usually DiCaprio plays the protagonist of a picture, which makes his villainous Candie that much more disruptive. Django is an exorbitantly violent movie and one of Tarantino’s most well-regarded.

The Departed has one of the all time great casts. There’s Jack Nicholson, Matt Damon, Martin Sheen, Mark Wahlberg (who was nominated for Best Supporting Actor), and of course Leonardo DiCaprio. While Damon and Wahlberg are from Boston and already have convincing accents, some of the other actors struggled to nail the dialect.

DiCaprio’s role is kind of unique within the film as he plays a guy pretending to be another guy. So it’s hard to knock DiCaprio because of the layers of the character he plays. Ultimately, The Departed is one of DiCaprio’s most iconic works and one of the best movies of his career.

This team-up between Christopher Nolan and Leonardo DiCaprio is one of the most mind-bending movies ever made. Inception is a good example of two extraordinary talents working at the top of their craft.

And if DiCaprio’s performance isn’t enough, how about adding the always excellent Tom Hardy and Ellen Page to the cast. Inception is a movie that will forever be associated with its final scene, leaving viewers questioning the reality around them.

Watching The Revenant is a truly visceral experience. It’s incredible just how beautiful cinematographer Emmanuel Lubezki make grotesque images look. Barren landscapes are transformed with intricate details.

Close-ups are so well formatted that it really heightens our view of the actors performances. Perhaps that’s one reason why Leonardo DiCaprio won his first Oscar for his performance as Hugh Glass.

Leonardo DiCaprio gives one of the best performances of his career as American business titan Howard Hughes. The Aviator is yet another great collaboration between DiCaprio and Scorsese. The role of Howard Hughes was no easy task to pull off. There are few real-world people who had as complex a life as Hughes.

Not only was he a pioneer of film and aviation, he was subject to constant admiration, and he struggled enormously with OCD. But DiCaprio gives a masterful performance in the leading role which nominated him for an Oscar.

I’m sure the role of Rick Dalton in Once Upon a Time In Hollywood (2019) is one that almost any actor was dying to play. Fortunately for DiCaprio, he’s the guy Writer/Director Quentin Tarantino chose for the role. And it’s a good thing he did because he did a really excellent job.

DiCaprio and co-star Brad Pitt’s chemistry really make the audience root for these characters. The film is certainly not what I was expecting, but for many, myself included, it was a very pleasant surprise.

Martin Scorsese swapped out the mob scene for the boiler room in The Wolf of Wall Street. But if you expected any less corruption or crime, then you’d be dead wrong. DiCaprio portrays stock-brocker Jordan Belfort, a convicted fraudster who made millions trading penny-stocks.

This might be the most wild movie of DiCaprio’s career, one that’s great fun to watch until you remember that it’s mostly real.

I love Shutter Island. There, I said it. This movie is so wonderfully nuanced and layered. It’s really a perfect mystery-thriller movie. The acting is phenomenal from DiCaprio, to Rufallo, to Sir Ben Kingsley and every other actor from start to finish.

The script from Laeta Kalogridis and Author Dennis Lehane is tight and focused. And of course the Direction from Martin Scorsese is excellent. There are only a very few mystery movies as enjoyable as Shutter Island, while still offering worthwhile commentary.

Catch Me If You Can makes me ponder this question: what’s Cinema supposed to do? To me, Cinema is supposed to expose something about the world we live in. And in the process make us laugh, cry, cheer, and learn something new.

If there’s a prototype for these criteria, Catch Me If You Can is it. Steven Spielberg plays the role of maestro in telling the story of con-man Frank Abagnale. Sure, Abagnale defrauded the American people by bouncing fake checks across the world, but Spielberg makes us care deeply about him. We follow his escape from a troubled home in New York, to Central France, and all the odd places in between.

The main reason why Abagnale is so easy to root for is because of DiCaprio’s wonderful portrayal. In the scene above, all Abagnale wants is to have his family back, but now it’s all a distant memory. I’ll forgive the film for saying Tom Hanks character Carl Handratty is a real person (he’s a composite) because the story is just so dang good.

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15 Best Brad Pitt Movies

DiCaprio’s co-star from Once Upon A Time in Hollywood Brad Pitt is one of the most well-known actors in the world. Pitt is famous for roles in blockbuster hits like Mr. and Mrs. Smith and Troy, but there’s so many great films in his expansive rolodex. In this article, we look at the best 15 films of his career and rank them.

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