Oscar-winning actor Leonardo DiCaprio has made it his business to work with the most acclaimed filmmakers of the modern era. The star, whose first real breakout role came on the ABC sitcom “Growing Pains,” has worked with Martin Scorsese no less than six times with the latest being “Killers of the Flower Moon.”. He’s done double-duty with Quentin Tarantino (with “Django Unchained” and “Once Upon a Time in Hollywood,” the latter of which earned DiCaprio an Oscar nomination), and made blockbuster films with Best Director winners James Cameron, Clint Eastwood, Alejandro Gonzalez Inarritu, and Steven Spielberg, and nominees Ridley Scott and Adam McKay.
Beginning with 1993’s “What’s Eating Gilbert Grape,” for which he received his first Academy Award nomination at age 19, DiCaprio has earned eight total nominations from the Oscars: seven as an actor — including most recently for “Once Upon a Time In Hollywood,” plus his Best Actor win for “The Revenant” — and one as a producer, for Best Picture nominee “The Wolf of Wall Street.” DiCaprio has also won a Screen Actors Guild Award (for “The Revenant”) out of 11 nominations (including the ensemble and solo bids for “OUATIH”).
With McKay’s “Don’t Look Up” for Netflix in 2021, he worked with an all-star cast, which included fellow former Oscar winners like Meryl Streep, Jennifer Lawrence, Cate Blanchett and Mark Rylance.
Tour our photo gallery above of his 18 greatest films, ranked from worst to best. Our list includes the movies mentioned above, plus “Titanic,” “Catch Me if You Can,” “Blood Diamond,” “The Aviator,” “The Departed,” “The Wolf of Wall Street” and more.
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18. MARVIN’S ROOM (1996)
Image Credit: Moviestore/REX/Shutterstock Director: Jerry Zaks. Writer: John Guare, based on the play by Scott McPherson. Starring Meryl Streep, Leonardo DiCaprio, Diane Keaton, Robert DeNiro, Hume Cronyn.
In Jerry Zaks‘ film version of Scott McPherson‘s play (adapted by John Guare), DiCaprio plays Hank, a young man who had been committed to a mental institution after setting fire to the family home. After his grandfather (Hume Cronyn) suffers a debilitating stroke, and responsibility for his care falls upon his mother Lee (Meryl Streep), Hank finds himself being pulled in to share the caretaking duties. As a member of the “Marvin’s Room” ensemble, DiCaprio was nominated for his first Screen Actors Guild Award.
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17. J. EDGAR (2011)
Image Credit: Malpaso/Warner Bros/Kobal/REX/Shutterstock Director: Clint Eastwood. Writer: Dustin Lance Black. Starring Leonardo DiCaprio, Naomi Watts, Armie Hammer, Judi Dench.
Clint Eastwood‘s look at the notorious FBI director starred DiCaprio as J. Edgar Hoover, who turned the bureau into his own personal fiefdom as he used his investigators to dig up dirt on his political enemies while trying to cover up his gay relationship with lawyer Clyde Tolson (Armie Hammer). While the film garnered largely mixed to negative reviews, DiCaprio’s performance was widely hailed. For his performance as Hoover, DiCaprio earned his eighth Golden Globe nomination and his eighth nomination for a Screen Actors Guild Award.
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16. REVOLUTIONARY ROAD (2008)
Image Credit: BBC/Evamere/Neal Street Prods./Kobal/REX/Shutterstock Director: Sam Mendes. Writer: Justin Haythe. Starring Leonardo DiCaprio, Kate Winslet, Michael Shannon, Kathryn Hahn, David Harbour.
DiCaprio reunited with his “Titanic” love interest Kate Winslet in Sam Mendes‘ film set in the late 1940s in which Frank Wheeler (DiCaprio) and his wife April (Winslet) move to the suburbs in hopes of having a better life. April’s goal to become an actress has flopped, and Frank is unfulfilled in his job. Frank is a rare unsympathetic role for DiCaprio, but his faithfulness to the character was impressive enough to earn his seventh Golden Globe nomination.
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15. THE GREAT GATSBY (2013)
Image Credit: Bazmark Films/Warner Bros./Kobal/REX/Shutterstock Director: Baz Luhrmann. Writers: Baz Luhrmann, Craig Pearce. Starring Leonardo DiCaprio. Tobey Maguire, Carey Mulligan, Joel Edgerton, Isla Fisher.
In the fourth film version of the F. Scott Fitzgerald‘s 1925 masterpiece, DiCaprio plays the film’s title character, Jay Gatsby, whose enormous wealth has been gained under somewhat suspicious auspices. Gatsby throws fabulous parties in his Long Island mansion and invites guests he doesn’t know, confiding to new friend Nick Carraway (Tobey Maguire) that he does it only in hopes that one day the one woman he has loved and lost, Daisy Buchanan (Carey Mulligan), will show up. Gatsby is an enigmatic character that really requires a movie star to pull it off, and DiCaprio more than fills the bill.
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14. INCEPTION (2010)
Image Credit: Warner Bros/Kobal/REX/Shutterstock Writer/Director: Christopher Nolan. Starring Leonardo DiCaprio, Ken Watanabe, Marion Cotillard, Joseph Gordon-Levitt, Ellen Page, Tom Hardy, Tom Berenger.
The star of any Christopher Nolan film is, of course, Christopher Nolan, and for an actor such as DiCaprio who specializes in intricate character work, it’s challenging to do that work in a high-concept sci-fi epic. Yet DiCaprio is able to work his magic here as Dom Cobb, a thief who has the ability to steal secrets from his victims by infiltrating their subconscious thoughts, who is offered a chance for redemption by agreeing to try to implant another person’s idea into the mind of a target. It’s not DiCaprio’s deepest performance, but he does manage to keep the character interesting.
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13. BLOOD DIAMOND (2006)
Image Credit: Jaap Buitendijk/Warner Bros./Kobal/REX/Shutterstock Director: Edward Zwick. Writers: Charles Leavitt, Marshall Herskovitz. Starring Leonardo DiCaprio, Jennifer Connelly, Djimon Hounsou, Michael Sheen.
To someone with totally untrained ears, DiCaprio delivers a spot-on South African accent in his role as Danny Archer, a gunrunner jailed for smuggling diamonds and finds himself imprisoned with fisherman Solomon Vandy (Djimon Hounsou), who has discovered a valuable pink diamond. Danny is a real character part for DiCaprio, and for his performance he earned his third Academy Award nomination, his sixth Golden Globe nod and his seventh Screen Actors Guild nomination.
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12. GANGS OF NEW YORK (2002)
Image Credit: Miramax/Dimension Films/REX/Shutterstock Director: Martin Scorsese. Writers: Jay Cocks, Steven Zallian, Kenneth Lonergan. Starring Leonardo DiCaprio, Daniel Day-Lewis, Cameron Diaz, Jim Broadbent.
DiCaprio collaborated with director Martin Scorsese for the first time in this story set in the mid 1800s in a Manhattan slum, which is run by crime lord William “Bill the Butcher” Cutting (Daniel Day-Lewis). As a child, Amsterdam witnessed his father being stabbed to death by Bill, and the boy has kept the knife so that, as an adult (DiCaprio) he can use it on Bill to avenge his father’s murder. This is a big brawny performance from DiCaprio, which will pay off in dividends with further films with Scorsese later in the actor’s career.
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11. THE AVIATOR (2004)
Image Credit: Moviestore/REX/Shutterstock Director: Martin Scorsese. Writer: John Logan. Starring Leonardo DiCaprio, Cate Blanchett, Alan Alda, John C, Reilly, Alan Alda, Kate Beckinsale.
In his second collaboration with director Martin Scorsese, DiCaprio takes on the enormous role of billionaire-turned-madman Howard Hughes. If DiCaprio had chosen to go big-big-BIG! with this character (which given Hughes’ famed eccentricities, he could have easily have done), “The Aviator” could have gone flying off the rails. But DiCaprio approached it as a character actor would, and that’s why it worked. For his performance as Hughes, DiCaprio won his first Golden Globe Award and earned his second Academy Award nomination, as well as his third and fourth Screen Actors Guild nominations.
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10. WHAT’S EATING GILBERT GRAPE (1993)
Image Credit: Paramount/Kobal/REX/Shutterstock Director: Lasse Hallström. Writer: Peter Hedges, based on his novel. Starring Johnny Depp, Juliette Lewis, Leonardo DiCaprio, Mary Steenburgen, Darlene Cates.
At age 19, Di Caprio received his first Academy Award nomination as Arnie Grape, the mentally-challenged younger brother of Gilbert (Johnny Depp), who must serve as caretaker to both Arnie and their obese mother Bonnie (Darlene Cates). This was a daring role to take on for DiCaprio, whose brilliant underplaying said to Hollywood that this is an actor to be reckoned with. For his performance as Arnie, DiCaprio was also nominated for his first Golden Globe Award. Not bad for the little kid from “Growing Pains.”
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9. DON’T LOOK UP (2021)
DiCaprio has long made the subject of climate change his key philanthropic objectives, but he has perhaps his biggest platform yet with Adam McKay’s “Don’t Look Up.” The sharp satire substitutes an approaching comet for the slow collapse of the environment and puts DiCaprio in a position to mix broad comedy with furious outrage. McKay has said DiCaprio is a sneaky hilarious performer and that’s borne out in the film. But his showcase scene — which calls to mind Peter Finch’s legendary “mad-as-hell” speech in “Network” — is anything but funny, and it’s hard to imagine another current star being able to pull it off with such precision.
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8. DJANGO UNCHAINED (2012)
Image Credit: Columbia/The Weinstein Company/Kobal/REX/Shutterstock Writer/Director: Quentin Tarantino. Starring Jamie Foxx, Christoph Waltz, Leonardo DiCaprio, Kerry Washington, Samuel L. Jackson, Walton Goggins.
In a career that includes finely attuned character work, DiCaprio had the chance to let it all hang out in this Quentin Tarantino Western that allowed him to let the famed Tarantino dialogue just ooze out of his mouth. As evil plantation owner Monsieur Calvin J. Candie, DiCaprio just personifies Southern decadence, from his brocade vest to his elaborate cigarette holder and is having a blast playing a villain. For his performance as Calvin, DiCaprio earned his ninth nomination for a Golden Globe Award.
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7. THE DEPARTED (2006)
Image Credit: Snap Stills/REX/Shutterstock Director: Martin Scorsese. Writer: William Monahan. Starring Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Alec Baldwin.
DiCaprio led an all-star cast in Martin Scorsese‘s Oscar-winning Best Picture as Billy Costigan, a Massachusetts cop who is ordered to go undercover to infiltrate the Irish-American mob in South Boston led by gangster Frank Costello (Jack Nicholson). DiCaprio really engages the audience’s sympathy here, and he gets us to worry that, with every encounter with Nicholson, he might just fatally slip up. For his performance as Billy, DiCaprio was nominated for his fifth Golden Globe Award, as well as his fifth and sixth Screen Actors Guild nods.
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6. CATCH ME IF YOU CAN (2002)
Image Credit: Moviestore/REX/Shutterstock Director: Steven Spielberg. Writer: Jeff Nathanson. Starring Leonardo DiCaprio, Tom Hanks, Christopher Walken, Amy Adams.
In this real-life crime film directed by Steven Spielberg, DiCaprio portrays young con-man Frank Abagnale, Jr. who, by the time he turned 19, had swindled his way into millions of dollars. Posing as various people (including a Pan Am airline pilot), Frank Jr. conducted an elaborate check fraud scheme, which came to the attention of FBI agent Carl Hanratty (Tom Hanks). The two pursue each other in a cat-and-mouse game that is just delightful. For his performance as Frank Jr., DiCaprio earned his third nomination for a Golden Globe Award.
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5. KILLERS OF THE FLOWER MOON (2023)
Image Credit: Apple / Paramount Director: Martin Scorsese. Writers: Eric Roth, Martin Scorsese, from the book by David Grann. Starring Leonardo DiCaprio, Robert De Niro, Lily Gladstone, Jesse Plemons.
Ever since Leonardo DiCaprio reached his movie star/heartthrob peak with “Titanic,” the actor boldly began to explore darker, more complex roles that expanded his range as an actor. Yet few of his roles have been as shadowy and twisted as that of Ernest Burkhart, the nephew and dim-witted tool of Robert De Niro’s William King Hale, a ruthless 1920s gangster plotting to pillage the newly-acquired wealth of the Osage nation. What makes DiCaprio’s work here as Ernest so compelling is that he is able to show his dark side in his plot to marry and then kill the wealthy Mollie (Lily Gladstone) but combine it with his seductive charms that are needed to allow his scheme to work. A powerful blend.
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4. TITANIC (1997)
Image Credit: Moviestore/REX/Shutterstock Writer/Director: James Cameron. Starring Leonardo DiCaprio, Kate Winslet, Billy Zane, Kathy Bates, Gloria Stuart, Frances Fisher.
DiCaprio went from respected actor to worldwide movie star in the James Cameron‘s phenomenal hit, the second highest-grossing film of all time. DiCaprio manages the tricky feat of being convincing as Jack Dawson, a penniless stowaway to passing as a first-class passenger complete with formal wear. And his romantic chemistry with Kate Winslet is one for the record books. For his performance as Frank, DiCaprio earned his second nomination for a Golden Globe Award and, as a member of the film’s ensemble, garnered his second nomination for a Screen Actors Guild Award.
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3. ONCE UPON A TIME IN HOLLYWOOD (2019)
Image Credit: Sony Pictures Writer/Director: Quentin Tarantino. Starring Leonardo DiCaprio, Brad Pitt, Margot Robbie, Al Pacino, Emile Hirsch, Kurt Russell, Margaret Qualley.
In what writer/director Quentin Tarantino calls his penultimate film (we’ll see), “Once Upon a Time in Hollywood” stars DiCaprio as actor Rick Dalton, who became famous as the star of the TV Western “Bounty Law.” But it’s now 1969, and Rick, along with his stuntman/double Cliff Booth (Brad Pitt), finds himself at a crossroads — audiences’ tastes have changed, and his kind of roles have dried up. Reduced to villainous guest parts on TV shows, Rick looks for career salvation from his new neighbors — director Roman Polanski and girlfriend Sharon Tate (Margot Robbie). DiCaprio delivers a moving performance as a man who must put on a happy face to the world, all the time knowing that his world may be falling apart.
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2. THE WOLF OF WALL STREET (2013)
Image Credit: Appian Way/Paramount/REX/Shutterstock Director: Martin Scorsese. Writer: Terence Winter. Starring Leonardo DiCaprio, Jonah Hill, Margot Robbie, Matthew McConaughey.
Working once again with Martin Scorsese, DiCaprio won his second Golden Globe Award for his performance as the real-life stockbroker Jordan Belfort, whose underhanded and fraudulent practices made him a small fortune which he spent on a decadent lifestyle of sex and drugs. After a career filled with a number of interior-based performances, it was fun to see DiCaprio let loose on screen. The film also earned DiCaprio’s fourth and fifth Academy Award nominations for Best Actor and producing the Best Picture nominee.
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1. THE REVENANT (2015)
Image Credit: 20th Century Fox/Regency Enterprises/Kobal/REX/Shutterstock Director: Alejandro G. Iñárritu. Writers: Mark L. Smith, Alejandro G. Iñárritu. Starring Leonardo DiCaprio, Tom Hardy, Domhnall Gleeson.
DiCaprio won his first Academy Award, his third Golden Globe Award and his first Screen Actors Guild Award for his performance in Alejandro G. Iñárritu‘s film as Hugh Glass, a frontier guide in 1823, who is left for dead by a group of trappers after he is mauled by a grizzly bear. Miraculously, Hugh survives and swears vengeance on the men who abandoned him. Hugh is an enormously physical role while at the same time giving DiCaprio enough room to offer some powerful character work. A much-deserved win.
