Entertainment

All 29 Leonardo DiCaprio Movies, Ranked

the best leonardo dicaprio movies
Warner Bros. Pictures

Leonardo DiCaprio took home his first little gold statue for his performance in The Revenant at the 2016 Oscars, a happening that validated his long quest for acting immortality. Now, with his self-deprecating turn in Once Upon a Time in Hollywood, he's back on the awards campaign trail again, hoping to pick up a nomination for his work as cowboy TV actor Rick Dalton. Whether or not that particular role is more worthy of Best Actor glory than others he's taken on over the years is certainly up for debate, but there's no denying this: the dude can act.

Ranking DiCaprio's movies by how Oscar-worthy he is in them was no easy task; his performances were intense even back when he was a sweet-faced child actor. But in service to DiCaprio's commitment to taking emotional risks, working with incredible directors, and growing disparate types of facial hair, we scratched and clawed our way to a definitive list of his best performances. Now, like Leo, we're ready for a beach vacation.

Leonardo DiCaprio in Critters 3
New Line Cinema

29. Critters 3 (1991)

Like Jennifer Aniston (Leprechaun) and Matthew McConaughey (Texas Chainsaw Massacre: The Next Generation), Leonardo DiCaprio's filmography kicks off with a turn in a campy horror movie that likely haunts the award-winning actor to this day. But Critters 3 put him in a role that he'd become accustomed to: a kid surviving a broken home (complete with abusive stepfather). This would be his last encounter with fanged, furry monsters ever again, unless you count Jonah Hill in The Wolf of Wall Street. -- Matt Patches

28. Poison Ivy (1992)

A 17-year-old Leonardo DiCaprio appears in this titillating teenage Drew Barrymore thriller for all of five seconds. It's the most enjoyable five seconds of the movie. Yes, better than Critters 3! -- Anna Silman

Leonardo DiCaprio in The Man in the Iron Mask
United Artists

27. The Man in the Iron Mask (1998)

There's nothing Leo loves more than challenges, so it's unsurprising that he'd follow up his big role in Titanic with this stuffy, melodramatic period drama in which he plays twins. He's great as bratty King Louis XIV, suggesting DiCaprio would've made a great Joffrey Baratheon. But as noble hero Philippe he's a snooze, and the movie itself is too self-serious to work as camp. The only really notable part of the whole thing is you get to see DiCaprio punch himself in the face. -- Dan Jackson

Leonardo DiCaprio in Basketball Diaries
New Line Cinema

26. The Basketball Diaries (1995)

It speaks to DiCaprio's ambitions as a performer that he tackled drug addiction so early in his career, playing a young heroin user in this stark, unremarkable adaptation of Jim Carroll's memoir. DiCaprio didn't have the chops to elevate the material, though it's far from an embarrassing performance. His heartbreaking scenes with Lorraine Bracco (who plays his mother in the movie) have a raw power to them and show that great things were just around the corner. -- DJ

Leonardo DiCaprio in Total Eclipse
Fine Line Features

25. Total Eclipse (1995)

River Phoenix was originally slated to star in this romantic period drama, about the tryst between 19th-century poet Paul Verlaine and Arthur Rimbaud, his libertine contemporary. But when the My Own Private Idaho actor tragically died, DiCaprio took over and it didn't go so well. If Jack from Titanic was even more idealistic, fiery, and poetic, he'd sound like DiCaprio's Rimbaud, and neither scantily clad sex scenes nor Leo's seeming Gollum impression can save this maudlin misfire. -- MP

Leonardo DiCaprio in J. Edgar
Warner Bros. Pictures

24. J. Edgar (2011)

J. Edgar is a weird film destined to cause your less-tapped-in friends to say, "Wait, what the hell was that?!?" when the Leo-as-Hoover part of the clip reel arrives during the presentation for his inevitable lifetime achievement award. But the Oscar-snubbed drama is worth seeking out for DiCaprio's doomed romance with Armie Hammer and all the curious tension that exists on screen between Dustin Lance Black's sly, subversive script and Clint Eastwood's straight-forward, sepia-toned direction. Plus, you get to see DiCaprio emote beneath piles of wet pancake old-age makeup that might fall off his face at any moment. Acting! -- DJ

Leonardo DiCaprio in The Beach
20th Century Fox

23. The Beach (2000)

A movie about beautiful people on a beautiful island making beautiful love on beautiful drugs and the not-so-beautiful real world that poisons the well. DiCaprio dials up the frenetic in this bro-tastic version of Eat, Pray, Love, and a scene in which his protagonist, Richard, trips hard enough to become the character in a Mario-like video game is the closest we have to Strutting Leo: The Movie. But the New Age mumbo-jumbo dialogue can't transcend the privileged core of this Danny Boyle-directed adventure. -- MP

Leonardo DiCaprio in Don's Plum
Polo Pictures Entertainment

22. Don's Plum (2001)

Although it has never been released theatrically in the United States and is primarily known now as "the movie Leonardo DiCaprio and his crony Tobey Maguire don't want you to see!" Don's Plum features a scene-stealing performance by Leo as a heckling, diner-going bad boy. It's an interesting '90s timepiece that fans of Leo, Maguire, Kevin Connolly, Jenny Lewis, and many other co-stars of note would love to see legally. But, thanks to the recently renewed injunction, they'll have to keep waiting to see R.D. Robb's talky indie, which was filmed prior to DiCaprio's star-making roles in Romeo + Juliet and Titanic. -- John Sellers

Leonardo DiCaprio in Body of Lies
Warner Bros. Pictures

21. Body of Lies (2008)

This spy thriller has a lot of things going for it: direction from the reliably efficient Ridley Scott, a smart script from Oscar-winner William Monahan, and performances from peak chinstrap beard DiCaprio and peak cranky Russell Crowe. Then why is this movie so forgettable? For one thing, Crowe spends a good portion of the film in his bathrobe, yelling in DiCaprio's spy character's earpiece, so the two don't even get that many scenes together. DiCaprio is aggressively competent, making all the right concerned faces as ethically compromised CIA field agent Roger Ferris, but he never rises above the tangled web of modern espionage cliches the movie is intent on spinning. -- DJ

Leonardo DiCaprio in Celebrity
Sweetland Films

20. Celebrity (1998)

Adding heartthrob power to Woody Allen's rumination of Hollywood, Celebrity would be DiCaprio's Entourage if it weren't for the neurotic Kenneth Branagh performance at its center. Probably a good thing. DiCaprio slips comfortably -- too comfortably, perhaps -- into the world of Brandon Darrow, a bad-boy actor who chugs Champagne, gambles away stacks of cash, and trashes hotel rooms, all while dolling out script notes to his creative partners. His years in "the pussy posse" served him well. -- MP

Leonardo DiCaprio in This Boy's Life
Warner Bros. Pictures

19. This Boy's Life (1993)

Even at a young age, DiCaprio wasn't afraid of sharing the screen with intimidating co-stars. In this fairly rote adaptation of Tobias Wolff's acclaimed memoir, the bright spots come from watching DiCaprio square off against fellow Scorsese muse Robert De Niro, who alternates from cruel to pathetic as the young actor's stepdad. In the many intense confrontations between the two, it's easy to imagine DiCaprio taking notes on De Niro's fearless, genuinely unlikable performance. It's the type of gutsy, empathetic villain role DiCaprio would later excel at. For now, he's still in apprentice mode. -- DJ

Leonardo DiCaprio in Gangs of New York
Miramax Films

18. Gangs of New York (2002)

In his first collaboration with Martin Scorsese, DiCaprio shakes off his heartthrob Titanic reputation by getting down and dirty as goatee-sporting tough guy Amsterdam Vallon. But Leo has an iceberg-sized problem: Daniel Day-Lewis. As the violent, ill-tempered Bill the Butcher, the method actor extraordinaire is a terror in a top hat, stealing the whole movie with his wild-eyed magnetism. He slices, he dices, and he chops up DiCaprio to little hunk-ish bits. Poor Leo -- he didn't stand a chance. -- DJ

Leonardo DiCaprio in The Quick and the Dead
TriStar Pictures

17. The Quick and the Dead (1995)

There's a bit of crazed debonair Bruce Campbell in Leonardo DiCaprio. He can be kooky. He can be cool. He can be terrified. And he can play it all at once. Evil Dead director Sam Raimi wrings every Campbellian ounce out of him in this canted Western. DiCaprio's "Kid" is a sharp-tongued whippersnapper who oozes confidence. He's also broken, wanting nothing more than impressing his estranged father (Gene Hackman). The Quick and the Dead is DiCaprio unfurled, treating goofy cowboy costumes and Western slang like Pulitzer Prize-winning material. -- MP

Leonardo DiCaprio in Blood Diamond
Warner Bros. Pictures

16. Blood Diamond (2006)

Again, DiCaprio sets up a test for himself: can he do a South African accent? While the jury is still out on the accent's verisimilitude, there's no denying that he fully commits to Rhodesian smuggler Danny Archer, bringing a dose of roguish Bogart-lite swagger to this white-savior narrative. He dodges bullets, wears cool sunglasses, and romances Jennifer Connelly with his trademark combination of charm and intensity. It's just a shame the surrounding movie is so leaden; it's a well-meaning, 143-minute after-school special masquerading as a hard-hitting expose. -- DJ

Leonardo DiCaprio in The Revenant
20th Century Fox

15. The Revenant (2015)

DiCaprio is a physical actor, but not a "tough guy." The difference is the beating, bloody horse heart of The Revenant, which pits a scrawny frontiersman against harsh, elemental forces. DiCaprio's work is from-the-gut bravado. He claws his way across snowscapes. He plummets from several cliffsides. He's mangled by a mama bear. He foams at the mouth, allowing his golden veneer to sour. The performance is currently entangled in awards buzz, which feels right; it's totally commendable, and dramatically passable. If only the movie were as convincing. -- MP

Leonardo DiCaprio in The Great Gatsby
Warner Bros. Pictures

14. The Great Gatsby (2013)

Few actors have the bone-deep charisma to embody a nearly mythological character who turns up 30 minutes into the film possessing "one of those rare smiles that you may come across four or five times in life, that seemed to believe in you and understand you just as you would like to be understood and believed in." No big deal, that's Leo. While Baz Luhrmann's movie is mostly style over substance, DiCaprio provides depth. You can always feel Gatsby's hollow desperation pulsing beneath his slick facade. Plus, he sounds so good saying "old sport" in his bougie '20s twang we're considering integrating it into our everyday vocabulary. -- AS

Leonardo DiCaprio in Marvin's Room
Miramax Films

13. Marvin's Room (1996)

As Hank, DiCaprio plays the quintessential angsty teen, only one with a few screws loose. It's a complex character to crack. At the beginning of the movie, Hank sets his family's home on fire -- but he's chill about it. As emotions swirl, DiCaprio holds his own against Diane Keaton, Meryl Streep, and the kid from Indian in the Cupboard. One of the actor's rare performances that blooms with compassion. -- MP

Leonardo DiCaprio in Romeo and Juliet
20th Century Fox

12. Romeo + Juliet (1996)

The film that turned DiCaprio into a bona-fide bedroom-poster heartthrob -- a status he would cement in Titanic a year later. As Romeo, DiCaprio brings his twinkly eyed, floppy-haired charisma, shows off an ability to convey deep wells of pent-up longing in a single word, and discovers chemistry with every scene partner (perfect here opposite a wide-eyed, 16-year-old Claire Danes). Few could charm while speaking in iambic pentameter and wearing a Hawaiian shirt. When we lose him, we understand Juliet's plight. -- AS

Leonardo DiCaprio in The Departed
Warner Bros. Pictures

11. The Departed (2006)

Despite winning multiple Oscars, playing on a near-constant loop on cable for the last decade, and somehow giving the Dropkick Murphys a Platinum single, The Departed almost feels underrated. Which is a shame. Don't let your annoying college roommate's affection for it ruin the movie for you -- it's an enormously entertaining crime film. DiCaprio's expert slow-boil performance as undercover cop Billy Costigan is big reason for that and marked a major career step forward; he stood tall against the Scorsese film's many big-name scenery chewers and kept his Boston accent under control. -- DJ 

Leonardo DiCaprio in What's Eating Gilbert Grape
Paramount Pictures

10. What's Eating Gilbert Grape (1993)

DiCaprio earned his first Oscar nod at the ripe young age of 19 for his role as developmentally disabled teen Arnie Grape. In less-skilled hands, Arnie could easily have been an emotionally manipulative Lifetime movie trope, but DiCaprio plays him with remarkable nuance, endowing Arnie with such specific mannerisms and emotional range that you can tell you're watching a once-in-a-generation talent from the movie's first moments. It's not easy to go toe-to-toe with hunky 24-year-old Johnny Depp, but DiCaprio ran away with every scene he was in, prefiguring a career where he would overshadow all manner of A-list scene partners. -- AS

Leonardo DiCaprio in Revolutionary Road
Paramount Pictures

9. Revolutionary Road (2008)

Sometimes, you just want to watch a great actor explode. With Mad Men soaring, maybe we didn't need Sam Mendes' adaptation of the acclaimed Richard Yates novel, but the descent into suburban malaise offered DiCaprio and Kate Winslet the reunion of a lifetime. Their bitter feuds lay waste to ceramic kitchenware. Their looks, bubbling in living portrait after living portrait, scorch harder. Revolutionary Road is stage acting worthy of Broadway. On screen, it's a salvo of in-your-face confrontations, DiCaprio and Winslet pushing themselves to extremes. -- MP

Leonardo DiCaprio in Django Unchained
The Weinstein Company

8. Django Unchained (2012)

Has Leo ever been more detestable? We mean that as a compliment. In his only pure-evil role to date, DiCaprio cribs from the Christoph Waltz school of Tarantino villainy, playing a character whose inner malevolence is cloaked beneath genteel manner. It's a credit to DiCaprio that even with his many scene-chewing monologues and pithy verbal flourishes, there's nothing to like about his sadistic plantation owner Calvin Candie. He really goes balls out with playing against type, harnessing his usual charisma and warping it into something grotesque, all toothy sneers and raw malice. We may cheer when he eventually gets his just desserts ("we will be serving whhhite cake"), but he's still an undeniable treat to watch. -- AS

Leonardo DiCaprio in Shutter Island
Warner Bros. Pictures

7. Shutter Island (2010)

It's difficult to dramatize grief. In his haunted adaptation of Dennis Lehane's pulpy gothic novel, director Martin Scorsese uses visceral horror imagery to convey despair. DiCaprio's terrified mug is the film's spookiest special effect. With every grimace, furrowed brow, and anguished sob, he brings you into the tortured psyche of Edward Daniels, a man who cannot escape his past no matter how hard he tries. It's a carefully modulated performance that helps sell the film's occasionally wonky twists. More than anything, it makes you wish DiCaprio will return to the horror genre in the future. No, The Revenant doesn't count. -- DJ 

Leonardo DiCaprio in Inception
Warner Bros. Pictures

6. Inception (2010)

Inception is known for Christopher Nolan's remarkable directing, sprawling action sequences, an ambitious, sometimes incomprehensible premise. DiCaprio is the movie's totem, making us care about the conscious drama behind the subconscious pyrotechnics. DiCaprio doesn't do a lot of sci-fi popcorn flicks, but here he shows he can handle reams of nonsense exposition and fast-paced action sequences with aplomb. We don't know if that damn top ever stopped spinning, but after his work in Inception, we're more than willing to follow Leo into the abyss. -- AS

Leonardo DiCaprio in Titanic
20th Century Fox

5. Titanic (1997)

Don't let the swooning mother-fueled box-office numbers, Céline Dion radio play, and Tiger Beat coverage fool you: Titanic is tremendous. James Cameron's historical epic was an unsinkable blockbuster because of classic Hollywood romance. Millions in state-of-the-art special effects serviced DiCaprio and Winslet's combustible chemistry, strewn from the pinnacle of luxury to a frozen abyss. DiCaprio rides the edge caricature like Jack Dawson sliding down a bannister. His passion is palpable. His courage is human. He is a real-deal romantic, the last actor with enough star glow to pull off a performance of this magnitude. -- MP

Leonardo DiCaprio in The Aviator
Warner Bros. Pictures

4. The Aviator (2004)

The first of his truly unforgivable Oscar snubs, The Aviator is a tour-de-force historical epic that hinges on DiCaprio as tormented American aviator Howard Hughes, whose mental state stymies grandiose ambitions. DiCaprio loves a good man tormented by internal and external demons, but in this three-hour masterpiece, Martin Scorsese pushes the 30-year-old Leo to bring all of Howard Hughes' many contradictions to life: the swaggering young playboy billionaire, the starlet romancer, the daredevil innovator, and the shrunken madman, unshorn, guzzling milk, pissing in bottles, and muttering "the way of the future" over and over again. It's one of the most harrowing on-screen depictions of how mental illness can wrench a life apart, and one of Leo's unobjectable triumphs. -- AS

once upon a time in hollywood
Sony Pictures

3. Once Upon a Time in Hollywood (2019)

Both riotously funny and achingly melancholy, Once Upon a Time in Hollywood is a movie about an industry in a bloated, strained transition period that perhaps signals a shift in style for director Quentin Tarantino, a Generation X icon approaching his self-styled creative twilight years. While Margot Robbie's Sharon Tate provides historical heft to the material, the friendship between DiCaprio's fictional actor Rick Dalton and Brad Pitt's made-up stuntman Cliff Booth is the core of this dazzling, beguiling epic in miniature, which unfolds over a couple lazy afternoon. The scene where DiCaprio, embarrassed and ashamed after flubbing some lines during a tense taping of a Western TV show, berates himself in his trailer might be the actor's most poignant work. Even at his most ridiculous, you can't help but feel for the guy. -- DJ

Leonardo DiCaprio in Wolf of Wall Street
Warner Bros. Pictures

2. The Wolf of Wall Street (2013)

"There's no nobility in poverty," sneers Jordan Belfort in Martin Scorsese's financial escapade. "I've been a poor man, and I've been a rich man. And I choose rich every fucking time." By finally embracing the most base, profane, and outlandish aspects of his cartoonish public persona, The Wolf of Wall Street finally set DiCaprio free of respectability. It's a performance that lets him play a naive young go-getter, an evil mastermind, and a man who likes a burning candle up his butt. Do you hate him or love him? It really doesn't matter. Both absurdly funny, like in its show-stopping quaalude sequence, and deeply moving, it's the role that made filmgoers in every financial bracket either laugh in recognition or wretch in disgust. Either way, you felt something profound. Forget Oscars; he should've won a Nobel Peace Prize for this one. -- DJ 

Leonardo DiCaprio in Catch Me If You Can
Dreamworks Pictures

1. Catch Me If You Can (2002)

A movie that asks, "What can't Leonardo DiCaprio do?" then answers, with wit, composure, panache: "absolutely nothing." Before he was 19 years old, Frank Abagnale conned his way into millions by impersonating a pilot, a doctor, and a lawyer. Steven Spielberg and DiCaprio, internalizing a full-scoped character study, tap dance through Abagnale's history, reflecting America's many faces in the process. DiCaprio kicked off his rolling relationship with Martin Scorsese at the same time he teamed for his Spielberg one-off. The latter lucked out. Catch Me If You Can is the snowballed DiCaprio. He is a caper ringleader, a romantic (heartbreaking against Amy Adams), a clown -- his faces in the "Do you concur?" sequence alone deserved an Oscar -- and a regular Joe, growing up under the watch of a stern Tom Hanks. There's no better DiCaprio movie because, in the end, Catch Me If You Can is a movie about guys like DiCaprio. -- MP

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