15 Best Leonardo DiCaprio Movies of All Time (2026)

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 the actor 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 strong 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.

Romeo + Juliet was an essential member of the one-two punch of films in 1997 along with Titanic that made DiCaprio a bonafide leading man for years to come. We’ve seen Romeo on stage and screen countless times, but DiCaprio found a way into the classic tragic character that felt as fresh and compelling as director Baz Luhrmann's interpretation of Shakespeare’s masterpiece. 

DiCaprio’s performance in Romeo + Juliet also effectively silenced any naysayers that he was coasting on his pretty face, his facility with Shakespeare’s verse proved that DiCaprio had genuine talent and impressive range as an actor.

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. However, 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.

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 Ruffalo, 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.

This Warner Bros 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.

It might be a stretch to include this film in a list of the best Leonardo DiCaprio movies since his part is relatively small. He's only in it for approx. 23% of the entire runtime. But he delivers one of his most malevolent performance in 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.

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. Read the original Forbes article on Belfort and you'll see the excess in the film was not fiction.

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.

Watching The Revenant is a truly visceral experience. If you know anything about the production, you know it was grueling. 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. We can really feel the effort and intensite from our leading man. 

As we near the top five best Leonardo DiCaprio movies, we see the actor at his most refined; where commercial appeal meets complex, demanding performances, and every movie pushes the actor to new levels of greatness.

DiCaprio gives one of the best performances of his career as American business titan Howard Hughes. 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. And yet, The Aviator is another great DiCaprio/Scorsese collaboration.

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 his second ever Oscar nomination.

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. Remember, our criteria for ranking the best Leonardo DiCaprio movies leans more towards the quality of the film than for his performance alone.

DiCaprio and Scorsese’s latest collaboration only further cemented their versatility on screen. DiCaprio plays the film’s doomed protagonist Ernest with a completely believable and identifiable air of someone in way over his head, a crucial tone to strike given the gravity of the atrocities his character commits throughout the film.

His struggle between his wife and uncle is palpable, making both DiCaprio and the three and a half hour film captivating to watch and an easy pick for a list of the best Leonardo DiCaprio movies.

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 Hanratty is a real person (he’s a composite) because the story is just so dang good.

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.

The Departed has one of the all-time great casts. There’s Nicholson, Damon, Sheen, Wahlberg (who was nominated for Best Supporting Actor), and, of course, DiCaprio. While Damon and Wahlberg, both Boston natives, deliver naturally convincing accents, some of the other actors appear to struggle 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 the actors most iconic works and would be a glaring omission on anyone's list of the best Leonardo DiCaprio movies.