Special Report

Best Movies Starring Leonardo DiCaprio

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With the Academy Awards around the corner, some people may be thinking “…Wait, did any movies even come out last year?” One answer is: certainly not any starring Leonardo DiCaprio. On the bright side, he won’t risk being upstaged by his co-star, as he was at the 2020 Oscars when Brad Pitt snagged the Best Supporting Actor Award for his role in “Once Upon a Time in…Hollywood.” (Leo was nominated in the Best Actor category for the same film, but didn’t win.)

Although he isn’t up for any Oscars this year, Leo has received six Academy Award nominations for acting since 1994. He finally won Best Actor in 2016 for his starring role in “The Revenant” — a role he prepared for by eating raw bison liver and sleeping in an animal carcass. He has also taken home three Best Actor Awards from the Golden Globes, including one for his star turn in “The Wolf of Wall Street,” one of the 50 best movies based on true events.

DiCaprio’s dedication as an actor can’t be denied, and his work with big directors like Christopher Nolan, James Cameron, Quentin Tarantino, and Martin Scorcese has produced some of the best films of the last 30 years. (Leo will work with Scorcese again in the upcoming “Killers of the Flower Moon,” set to shoot this summer.) Here are the 55 best movies ever made.

Using multiple ratings from IMDb and Rotten Tomatoes, 24/7 Tempo has compiled a list of Leonardo DiCaprio’s best movies.

Click here for the best movies starring Leonardo DiCaprio

Courtesy of Twentieth Century Fox

24. The Beach (2000)
> Fellow leads: Daniel York, Patcharawan Patarakijjanon, Virginie Ledoyen
> Director: Danny Boyle
> Domestic box office: $39.78 million

In “The Beach,” DiCaprio portrays Richard, a young American traveler whose discovery of a secret island commune brings about its untimely demise.

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Courtesy of Warner Bros.

23. J. Edgar (2011)
> Fellow leads: Armie Hammer, Naomi Watts, Josh Hamilton
> Director: Clint Eastwood
> Domestic box office: $37.31 million

DiCaprio stars in this biographical drama about J. Edgar Hoover, a former director of the FBI who had secrets of his own.

Courtesy of Metro-Goldwyn-Mayer

22. The Man in the Iron Mask (1998)
> Fellow leads: Jeremy Irons, John Malkovich, Gérard Depardieu
> Director: Randall Wallace
> Domestic box office: $56.97 million

DiCaprio portrays both the spoiled King Louis XIV and his brother Philippe, whom Louis has imprisoned in an iron mask to conceal his identity and to prevent him from taking the throne.

Courtesy of TriStar Pictures

21. The Quick and the Dead (1995)
> Fellow leads: Sharon Stone, Gene Hackman, Russell Crowe
> Director: Sam Raimi
> Domestic box office: $18.55 million

In this western, young DiCaprio plays The Kid, an arrogant gunslinger who seeks the approval of the man he believes to be his father: John Herod, an outlaw and the de facto leader of the town of Redemption.

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Courtesy of Warner Bros.

20. The Great Gatsby (2013)
> Fellow leads: Carey Mulligan, Joel Edgerton, Tobey Maguire
> Director: Baz Luhrmann
> Domestic box office: $144.84 million

DiCaprio portrays Jay Gatsby, a mysterious millionaire and veteran with humble roots and a foolishly undying love that leads to his undoing.

Courtesy of Warner Bros.

19. Body of Lies (2008)
> Fellow leads: Russell Crowe, Mark Strong, Golshifteh Farahani
> Director: Ridley Scott
> Domestic box office: $39.39 million

In this action thriller, DiCaprio plays an insubordinate CIA operative in Jordan who is on a quest to track down a terrorist leader.

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Courtesy of New Line Cinema

18. The Basketball Diaries (1995)
> Fellow leads: Lorraine Bracco, Marilyn Sokol, James Madio
> Director: Scott Kalvert
> Domestic box office: $2.42 million

Based on the memoir of Jim Carroll, “The Basketball Diaries” follows Jim (played by DiCaprio) as a troubled teenage basketball player who develops a heroin addiction and turns to prostitution to make ends meet.

Courtesy of DreamWorks Distribution

17. Revolutionary Road (2008)
> Fellow leads: Kate Winslet, Christopher Fitzgerald, Jonathan Roumie
> Director: Sam Mendes
> Domestic box office: $22.95 million

In this drama set in 1950’s Connecticut, Frank Wheeler (played by DiCaprio) is a restless romantic who hates his job and struggles to find contentment in suburban life.

Courtesy of Miramax

16. Marvin’s Room (1996)
> Fellow leads: Meryl Streep, Diane Keaton, Robert De Niro
> Director: Jerry Zaks
> Domestic box office: $12.80 million

In this story of an estranged family attempting to reunite in the face of medical struggles, DiCaprio plays troubled teen Hank who has just burned down his family’s house.

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Courtesy of Twentieth Century Fox

15. Romeo + Juliet (1996)
> Fellow leads: Claire Danes, John Leguizamo, Harold Perrineau
> Director: Baz Luhrmann
> Domestic box office: $46.34 million

In a reimagining of this Shakespeare classic, DiCaprio plays young Romeo, who falls into forbidden love with a girl from a rival family, amidst deadly street feuds.

Courtesy of Warner Bros.

14. This Boy’s Life (1993)
> Fellow leads: Robert De Niro, Ellen Barkin, Jonah Blechman
> Director: Michael Caton-Jones
> Domestic box office: $4.10 million

In this biographical drama based on a memoir by Tobias Wolff, DiCaprio portrays the teenage Toby growing up with an abusive father figure in Washington state and attempting to escape to the East Coast.

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Courtesy of Paramount Pictures

13. Shutter Island (2010)
> Fellow leads: Emily Mortimer, Mark Ruffalo, Ben Kingsley
> Director: Martin Scorsese
> Domestic box office: $128.01 million

DiCaprio stars in this psychological thriller as U.S. Marshal Teddy Daniels, whose world turns upside down as he investigates the disappearance of a patient at a psychiatric facility.

Courtesy of Miramax

12. Gangs of New York (2002)
> Fellow leads: Cameron Diaz, Daniel Day-Lewis, Jim Broadbent
> Director: Martin Scorsese
> Domestic box office: $77.73 million

In a tale of immigration and tribalism in Civil War-era New York City, DiCaprio plays Amsterdam Vallon, a second-generation Irish-American who seeks vengeance against the gang leader who killed his father.

Courtesy of Sony Pictures Home Entertainment

11. Once Upon a Time… In Hollywood (2019)
> Fellow leads: Brad Pitt, Margot Robbie, Emile Hirsch
> Director: Quentin Tarantino
> Domestic box office: $142.50 million

In this revisionist-history comedy, DiCaprio plays Rick Dalton, a washed-up actor in 1969 Hollywood who, along with his stunt doublle and best friend, ends up intercepting the Manson Family murderers.

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Courtesy of Warner Bros.

10. Blood Diamond (2006)
> Fellow leads: Djimon Hounsou, Jennifer Connelly, Kagiso Kuypers
> Director: Edward Zwick
> Domestic box office: $57.38 million

Attempting a rather difficult accent, DiCaprio plays Rhodesian ex-mercenary Danny Archer, who teams up with an imprisoned fisherman to recover a rare pink diamond during the Sierra Leone civil war.

Courtesy of Paramount Pictures

9. Titanic (1997)
> Fellow leads: Kate Winslet, Billy Zane, Kathy Bates
> Director: James Cameron
> Domestic box office: $659.36 million

In this historic-fiction blockbuster, DiCaprio portrays Jack Dawson, a free-wheeling traveller with a knack for portraiture, who falls in love with an upper class beauty on a doomed ocean liner.

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Courtesy of Miramax

8. The Aviator (2004)
> Fellow leads: Cate Blanchett, Kate Beckinsale, John C. Reilly
> Director: Martin Scorsese
> Domestic box office: $102.61 million

In the Aviator, DiCaprio portrays aviation pioneer Howard Hughes during his rise to fame as a film producer, while detailing his struggles with obsessive-compulsive disorder.

Courtesy of Twentieth Century Fox

7. The Revenant (2015)
> Fellow leads: Tom Hardy, Will Poulter, Domhnall Gleeson
> Director: Alejandro G. Iñárritu
> Domestic box office: $183.64 million

In a role that secured him his first Oscar, DiCaprio portrays a fictionalized version of frontiersman Hugh Glass, who is attacked by a grizzly bear and abandoned by his fellow trappers in the harsh Dakota winter.

Courtesy of Paramount Pictures

6. The Wolf of Wall Street (2013)
> Fellow leads: Jonah Hill, Margot Robbie, Matthew McConaughey
> Director: Martin Scorsese
> Domestic box office: $116.95 million

DiCaprio stars in this biographical drama that chronicles the rise and fall of Jordan Belfort, a scheming stockbroker with a penchant for drugs, prostitutes, and endless profits.

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Courtesy of Paramount Pictures

5. What’s Eating Gilbert Grape (1993)
> Fellow leads: Johnny Depp, Juliette Lewis, Mary Steenburgen
> Director: Lasse Hallström
> Domestic box office: $9.17 million

In a performance that would earn him his first Oscar nomination, DiCaprio portrays Arnie Grape, an autistic teenager growing up in a struggling but tight-knit family in small town Iowa.

Courtesy of The Weinstein Company

4. Django Unchained (2012)
> Fellow leads: Jamie Foxx, Christoph Waltz, Kerry Washington
> Director: Quentin Tarantino
> Domestic box office: $162.81 million

In “Django Unchained,” DiCaprio plays villain Calvin Candie, a ruthless cotton plantation owner whose side business is charging admission to view forced slave fights.

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Courtesy of DreamWorks Distribution

3. Catch Me If You Can (2002)
> Fellow leads: Tom Hanks, Christopher Walken, Martin Sheen
> Director: Steven Spielberg
> Domestic box office: $164.61 million

In this biographical crime comedy, DiCaprio stars as teenager turned con artist Frank Abagnale who makes millions by impersonating an airline pilot, a doctor, and a lawyer.

Courtesy of Warner Bros.

2. Inception (2010)
> Fellow leads: Joseph Gordon-Levitt, Elliot Page, Ken Watanabe
> Director: Christopher Nolan
> Domestic box office: $292.58 million

In this sci-fi action film, DiCaprio plays Dom Cobb, a professional thief who can enter people’s dreams and retrieve information from their subconscious. For a chance to wipe his record clean, Cobb must reverse his craft and plant an idea into a target’s mind.

Courtesy of Warner Bros.

1. The Departed (2006)
> Fellow leads: Matt Damon, Jack Nicholson, Mark Wahlberg
> Director: Martin Scorsese
> Domestic box office: $132.38 million

In this crime drama, DiCaprio plays undercover cop Billy Costigan, who infiltrates a gang in Boston while attempting to keep his identity secret from a mole in the police department.

 

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