Since he first emerged as a major heartthrob in the 1990s, Leonardo DiCaprio has consistently been one of the biggest movie stars in the world. Thanks to his collaborations with some of the best directors in the world, and his insistence on choosing only the roles that he cares most about, Leo has established the kind of career that few modern Hollywood stars can match; he’s been in everything from great action movies to outright comedies.
These are the movies that most define Leo’s career and the ones that any new fan of the actor should check out first.
If you like the movies on this list, you should also check out our lists of the best Jonah Hill movies, the best Brad Pitt movies, and the best Bradley Cooper movies.
10. Gangs of New York (2002)
168m
Genre
Drama, History, Crime
Stars
Leonardo DiCaprio, Daniel Day-Lewis, Cameron Diaz
Directed by
Martin Scorsese
It’s not widely regarded as one of Leo’s best movies, but Gangs of New York fires on so many cylinders that it feels almost irresponsible to exclude it. The film is all about the integration of the Irish into New York City in the 1860s, and it follows Leo’s character has he attempts to enact revenge for his father’s death. Thanks to a brilliant performance from Daniel Day-Lewis and vigorous direction from Martin Scorsese, Gangs of New York holds up well, even if it only received mix reviews upon its release.
9. Django Unchained (2012)
165m
Genre
Drama, Western
Stars
Jamie Foxx, Christoph Waltz, Leonardo DiCaprio
Directed by
Quentin Tarantino
Perhaps Leo’s most villainous turn, Django Unchained sees the actor playing Calvin Candy, a slaveowner who is sadistic even by those already low standards. Leo’s role in the film is certainly a supporting part, but Quentin Tarantino managed to unlock something new in the actor, proving that Leo could improvise and deliver the director’s dialogue with the best of them. Calvin Candy gets what’s coming to him by the end of the film, but Leo is never less than captivating during his section of Django’s broader narrative.
8. The Departed (2006)
151m
Genre
Drama, Thriller, Crime
Stars
Jack Nicholson, Leonardo DiCaprio, Matt Damon
Directed by
Martin Scorsese
As a cop from the wrong side of the tracks who has to go undercover inside the mob, Leo’s performance in this movie never got the credit it deserves. That may be because Leo is just one piece in a much broader ensemble in the movie, but none of The Departed‘s emotional throughlines would work without Leo’s steady hand to guide them. Given how big Jack Nicholson decides to go in many of the scenes that the two share, Leo found exactly the right pocket in his portrayal of a wounded cop trying to prove that he isn’t defined by where he came from.
7. Once Upon a Time… in Hollywood (2019)
162m
Genre
Comedy, Drama, Thriller
Stars
Leonardo DiCaprio, Brad Pitt, Margot Robbie
Directed by
Quentin Tarantino
Leo’s second collaboration with Tarantino proved even more fruitful than the first. Here, he plays a former TV star who has seen his career diminished in recent years, but who nevertheless relishes his life in Hollywood and the career he’s had to date. Leo is excellent as an actor struggling with self-loathing and his feelings of insignificance, and he’s matched by an equally great performance from Brad Pitt. The incendiary ending of Once Upon a Time in Hollywood is easy to focus on, but it’s everything that happens before that ending that makes the whole movie feel satisfying.
6. Inception (2010)
148m
Genre
Action, Science Fiction, Adventure
Stars
Leonardo DiCaprio, Joseph Gordon-Levitt, Ken Watanabe
Directed by
Christopher Nolan
The biggest blockbuster Leo has ever made, Inception saw the actor loaning his talents to Christopher Nolan for the only time thus far. The two teamed up for one of Nolan’s most innovative projects, telling the story of a group of dream thieves who have been given the impossible task of implanting an idea into someone’s mind. As the leader of this group of thieves, Leo’s character is forced to deliver a heavy load of exposition, and he carries it off with aplomb. Leo is excellent in Inception, even if it’s the kind of role that was never going to nab him an Oscar.
5. The Wolf of Wall Street (2013)
180m
Genre
Crime, Drama, Comedy
Stars
Leonardo DiCaprio, Jonah Hill, Margot Robbie
Directed by
Martin Scorsese
Perhaps the fiercest performance he’s ever given, Leo’s role in The Wolf of Wall Street probably should have been the one to win him his first Oscar. Telling the true story of Jordan Belfort, a normal stock trader who begins to scam and con his way into a massive fortune, The Wolf of Wall Street is filled with the kind of manic energy that only sustained cocaine use can produce. Crucially, Wolf of Wall Street also serves as a showcase for Leo’s comedic chops, especially in a fairly late sequence in which his character and Jonah Hill’s character do Quaaludes.
4. Romeo + Juliet (1996)
120m
Genre
Drama, Romance
Stars
Leonardo DiCaprio, Claire Danes, Jesse Bradford
Directed by
Baz Luhrmann
Baz Luhrmann is not known for subtle filmmaking, but Romeo and Juliet isn’t exactly a subtle play. This adaptation of Shakespeare’s text keeps the language but updates the setting to Venice Beach in what could roughly be described as the modern day. Leo is at the peak of his heartthrob era here, and the movie itself knows how to take advantage of his beauty. His performance as Romeo is excellent, and it’s matched by cast members who all seem highly committed to playing their parts in this doomed but utterly captivating romance.
3. The Aviator (2004)
170m
Genre
Drama
Stars
Leonardo DiCaprio, Cate Blanchett, Kate Beckinsale
Directed by
Martin Scorsese
Featuring the performance that proved that Leo was much more than just a matinee idol, The Aviator tells the story of Howard Hughes as he rises to prominence and eventually falls apart. Leo’s performance in Scorsese’s epic is riveting, and he’s on camera for almost every frame of the movie’s extended runtime. Although it would be more than a decade before Leo finally took home an Oscar, his performance as the sad, lonely, obsessive Hughes put him in strong contention for what would not be the last time.
2. Catch Me If You Can (2002)
141m
Genre
Drama, Crime
Stars
Leonardo DiCaprio, Tom Hanks, Christopher Walken
Directed by
Steven Spielberg
Leo’s sole collaboration with Spielberg turned out to be one of the best films that either of them would ever make. Leo stars as Frank Abagnale, Jr., a young con man who manages to con and cheat his way across America, charming men and women alike as he does. Leo’s good looks and charm make him a perfect fit for the role. Even though he cheats and lies for a living, the main thing you come to feel for Frank by the end of the movie is pity. He’s a boy who misses his family, and he ran away to hide from the problems he was facing at home.
1. Titanic (1997)
194m
Genre
Drama, Romance
Stars
Leonardo DiCaprio, Kate Winslet, Billy Zane
Directed by
James Cameron
Above all others, Titanic is the Leo movie that will endure. He’s never been more beautiful, and his chemistry with Kate Winslet is still unmatched. In the end, Leo’s Jack is more of a facilitator for Rose’s journey, but that’s part of what makes the performance so endearing. Jack in living life to its fullest, and in showing Rose how to find the kind of life worth living, he has an immeasurable impact on what happens to her. Jack saves her in every way a person could be saved, and Leo’s performance ensures that our love for him, just like our hearts, will go on.
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