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 was not only one of the highest-grossing movies of all time but is also tied with 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 are 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 diamond 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 the Best Supporting Actor category. It remains one of the earliest signals that Leonardo DiCaprio's filmography would be defined by emotional range and bold choices. 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 exorbitantly violent and one of the best Quentin Tarantino movies.

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.

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

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

More Great Leo DiCaprio Movies

Honorable mentions

While this list focuses on DiCaprio’s most iconic work, his filmography is filled with performances that merit recognition. These additional titles showcase the full range of his talent—physically, emotionally, and thematically—proving just how expansive the DiCaprio filmography truly is.

J. Edgar (2011)

This moody biopic, directed by Clint Eastwood, finds DiCaprio's portrayal of FBI founder J. Edgar Hoover with chilling precision. Though the film divided critics, his physical transformation and complex emotional range stood out.

Revolutionary Road (2008)

Reuniting with Kate Winslet, DiCaprio delivers one of his most emotionally raw and devastating performances. As a man crushed by 1950s suburban expectations, he channels regret, fury, and longing with quiet mastery.

Don’t Look Up (2021)

In this dark satire of media and climate denial, DiCaprio plays Dr. Randall Mindy, a scientist in freefall. It’s a rare comedic turn that lets him explore vulnerability, anxiety, and absurdity, proving that he's still evolving even late in his career.

Romeo + Juliet (1996)

Baz Luhrmann’s hyper-stylized adaptation introduced “Leo mania” to the world. Though unconventional, his turn as the doomed romantic made Shakespeare newly electrifying for a generation.

These films may not have cracked the top 15, but each reveals something essential about DiCaprio’s evolution—from teen heartthrob to one of the most respected actors of his generation. Together, they remind us why this list of the best Leonardo DiCaprio movies barely scratches the surface of his range.

The Leonardo DiCaprio filmography is a study in risk-taking, with roles that consistently challenge audience expectations and industry norms.

As we enter the top five, we see the DiCaprio filmography at its most refined, where commercial appeal meets complex, demanding performances.

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, but he was also subject to constant admiration, and he struggled enormously with OCD. But DiCaprio gives a masterful performance in the leading role, which earned him an Oscar.

I’m sure the role of Rick Dalton in Once Upon a Time in Hollywood (2019) is one that almost any actor would have died 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 an excellent job.

DiCaprio and co-star Brad Pitt’s chemistry makes 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 stockbroker Jordan Belfort, a convicted fraudster who made millions trading penny stocks.

This might be the wildest 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 one of the best thriller movies of all time. 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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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 are so many great films in his expansive Rolodex. In this article, we look at the best films of his career and rank them.

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