From a 19-year-old stealing scenes from Johnny Depp to a middle-aged movie star falling off a roof for a laugh, Leonardo DiCaprio has had quite a venerable career. Whether due to cultural impact, box office reach, deft application of the craft, or a combination of these factors, these are 10 of DiCaprio’s most significant film roles of all time. Warning: Spoilers ahead.
1. Arnie Grape in “What’s Eating Gilbert Grape” (1993)
Playing a disabled character comes with a specific set of demands: The performance has to be accurate and honest, with no trace of pandering or exaggeration. DiCaprio clears that bar as Arnie, the mentally ill teenage brother of protagonist Gilbert Grape (Johnny Depp), with a devastating character arc that culminates in Arnie’s discovery of his deceased mother’s body. It’s a tall order for any actor and a staggering one for DiCaprio, who was 19 at the time and notching only his fourth credited film role. For his work here, DiCaprio received his first Oscar nomination, making him one of the youngest-ever nominees in the best supporting actor category.
2. Romeo in “Romeo + Juliet” (1996)
When Baz Luhrmann cast DiCaprio as Romeo in his 1996 modern-dress adaptation, teenage girls in English class rejoiced—and for good reason. DiCaprio plays the star-crossed lover with a boyish charm that makes Shakespeare feel spontaneous and alive. Young actors, take note: You’re never too famous, too in demand, or too cool for the Bard. Eat your proverbial vegetables and brush up on your iambic pentameter.
3. Jack Dawson in “Titanic” (1997)
Another year, another star-crossed lover for ol’ Leo—this time playing third-class passenger Jack Dawson opposite Kate Winslet’s Rose DeWitt Bukater. “Titanic” has become such a cultural touchstone in the nearly 30 years since its release that it’s nearly impossible to watch with fresh eyes, with its most iconic moments long since consumed by parody and memes. But viewed as audiences experienced it in 1997, the film’s success was due in no small part to DiCaprio’s performance. His chemistry with Winslet is undeniable, and it’s that romantic charge that simultaneously offsets the tragedy and makes it sting. Even though (say it with us) there was room for both of them on that door.
4. Frank Abagnale Jr. in “Catch Me If You Can” (2002)
In Steven Spielberg’s “Catch Me If You Can,” DiCaprio plays real-life con man Frank Abagnale Jr., who spent his youth in the 1960s impersonating a pilot, a doctor, and a string of other high-status professionals he had no business pretending to be. The film’s success hinges on the audience rooting for a man it can’t condone—and DiCaprio delivers the charm in spades, playing Abagnale with an assuredness that makes every ruse feel inevitable. While you might not think a Hollywood A-lister has much in common with a career grifter, DiCaprio found a genuine point of connection. “I was playing a great actor,” he told IGN. “I was an actor getting to play a great actor. But his stage was the real world.” Never say never when it comes to relating to your character.
5. Dom Cobb in “Inception” (2010)
Christopher Nolan’s “Inception” is a mind-scrambling film about infiltrating dreams within dreams (within dreams?). But the labyrinthine plot isn’t the only layered item on screen. DiCaprio’s portrayal of the deeply troubled Dom is just as intricate: a hardened man carrying secrets, navigating the most complex of premises without ever losing his emotional center. And if you’re confused about the plot, don’t look to him for clarity. “What happened? I have no idea,” DiCaprio admitted in a podcast interview. “You’re just focused on your character, man.” Lesson learned: Don’t let plot get in the way of a great performance.
6. Jordan Belfort in “The Wolf of Wall Street” (2013)
“The Wolf of Wall Street” made waves on release largely for breaking the record for the most uses of the f-word in a narrative feature film. But audiences who came for the profanity and excess likely left reassured of DiCaprio’s talents. As the morally compromised but undeniably magnetic Jordan Belfort, DiCaprio commands the screen with a frat-boy swagger and a smooth New York accent, making it entirely believable that a man this reckless could talk his way into—and out of—almost anything. Belfort is a scam artist, but DiCaprio understands that you can only get away with that level of bad behavior if you back it up with charisma.
7. Jay Gatsby in “The Great Gatsby” (2013)
Playing a character audiences already know is its own particular challenge, and there are few literary figures more familiar than Jay Gatsby. What makes DiCaprio’s interpretation memorable is the degree to which he makes the role entirely his own, independent of any prior stage or screen adaptation. His Gatsby is suave, effortlessly cool, and quietly intense, the kind of man who can throw lavish parties for a single, impossible reason without ever letting the desperation show. That makes it all the more thrilling—and unsettling—when he finally cracks in his confrontation with Daisy’s husband Tom (Joel Edgerton).
8. Hugh Glass in “The Revenant” (2015)
“The Revenant” was far from the territory that made DiCaprio famous: pretty boys, suit wearers, and suit-wearing pretty boys. Yet that distance from type may be precisely why he shines so brightly in it. DiCaprio is ruggedness incarnate as frontiersman Hugh Glass, delivering a hardened, almost wordless performance that could come only from someone who truly understands what it means to be swallowed by the wild. This was the film that finally earned DiCaprio his Oscar, after more than two decades in the industry and four prior nominations.
9. Rick Dalton in “Once Upon a Time… in Hollywood” (2019)
“Once Upon a Time… in Hollywood” gave audiences a lot: a buddy comedy pairing DiCaprio with Brad Pitt, an alternate-history reckoning with the Manson murders, and a meme for the ages. What makes this performance stand among DiCaprio’s best is the sheer range compressed into a single role. Rick Dalton has all the hallmarks of a classic DiCaprio character—charming, a little rough around the edges, instantly relatable—but he also gets to be the film’s comic relief. His trailer meltdown over forgetting his lines is legitimately, squirmingly funny. And for those not yet convinced of DiCaprio’s comedy chops: he improvised the bulk of it.
10. Bob Ferguson in “One Battle After Another” (2025)
In Paul Thomas Anderson’s “One Battle After Another,” DiCaprio plays Bob Ferguson, a washed-up ex-revolutionary forced out of hiding to protect his daughter. The role is a study in contrasts. On one hand, Bob is a down-on-his-luck dad living on the margins; on the other, he’s an action hero who may or may not be up to the job. In one unexpectedly hilarious scene, he falls off a roof and is immediately tased by the police. DiCaprio may be a 51-year-old Oscar winner, but the gag was entirely his idea. “That was all Leo,” stunt coordinator Brian Machleit told The Film Stage. “He came up with that fall. We had a Plan A, but here comes Plan B. Everything was designed for him to do everything he wanted to do, and he is totally game for doing everything. It astounds me, his level of commitment that he puts into everything.” The takeaway: You’re never too old—or too decorated—to engage in some physical comedy. And if you’ve got a great idea for a scene, don’t be afraid to pitch it to your stunt coordinator.
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