He's one of the rare Hollywood actors whose magazine heartthrob status did nothing to keep him away from awards season prestige. He's also one of the few Hollywood actors to really pick and choose his projects, never busying himself up too much and always considering who he's working with. He's Leonardo DiCaprio, and safe to say, you've heard of him before.
Named after the Italian painter Leonardo da Vinci because his mother felt him kick during her pregnancy while looking at a da Vinci painting in Italy, DiCaprio grew up working class poor in Los Angeles neighborhoods like Echo Park and Los Feliz. He began his acting career in the 1980s, working on children's shows and in TV commercials for Kraft cheese and Bubble Yum. His first big break was on the TV sitcom Parenthood (based on the 1989 movie), and later had another recurring gig on the show Growing Pains as homeless boy Luke Brower. In 1991, DiCaprio made his film debut in the horror-comedy Critters 3. It's not quite "the rest is history," but safe to say it's the movies where DiCaprio became widely known.
Before his Oscar victory in 2016, Leonardo DiCaprio was considered one of the finest-ever actors to have never won an Academy Award. Now, he's just one of the finest-ever actors, period, enjoying a career where quality and collaboration take precedence. For proof of that, here's 32 of the greatest movies with Leonardo DiCaprio.
32. The Beach (2000)
Directed by Danny Boyle and based on the book by Alex Garland, The Beach follows an American backpacker (Leonardo DiCaprio) who seeks to discover an urban legend: a pristine, secluded beach in Thailand, free from tourists and civilization. While Boyle's film version was panned by critics as a weak adaptation of a book hailed as seminal for Generation X, DiCaprio still earned high marks for his performance as someone whose idealism morphs into a nightmare.
31. Don's Plum (2001)
It's the movie Leonardo DiCaprio doesn't want you to see. (At least if you're in the U.S. or Canada.) Written and directed by R.D. Robb, this heavily improvised indie drama follows a group of young adults – played by Leonardio DiCaprio, Tobey Maguire, and Buffy the Vampire Slayer's Amber Benson among others – who meet late one Saturday night at an L.A. diner. While a weekly ritual among the men of the group, their fates take a turn when their female dates for the night change all their lives forever. A legal dispute between the producers and the actors, who thought they had signed on for a short film rather than a full-length feature, has made the movie legally unavailable in North America. So, we're not saying you should go see it, because we can't. But if somehow you come across it, it's worth saying just to say you've seen it.
30. Before the Flood (2016)
Leonardo DiCaprio puts his activist money where his mouth is in Before the Flood, a 2016 call-to-action documentary with major subjects ranging from President Barack Obama to Pope Francis to even Elon Musk. (At the time, Musk was a firm believer in climate change.) A comprehensive look at both the widespread effects of climate change as well as the harm of climate change denial, Before the Flood follows DiCaprio as he personally meets with scientists, activists, and world leaders. Though not the most acclaimed of DiCaprio's doc work, the actor's prominent place in the feature demonstrates his commitment to the cause. Behind the scenes, the filmmakers showed their commitment to climate advocacy by paying a voluntary carbon tax.
29. Hubble 3D (2010)
One of several documentaries narrated by Leonardo DiCaprio, Hubble 3D takes advantage of IMAX film technology to take audiences on an eye-opening journey through space via the Hubble Space Telescope. The documentary is essentially a showcase of the Hubble Space Telescope and the many discoveries mankind has made about our universe directly because of it. While Hubble 3D is a mere 43 minutes long, DiCaprio's dignified narration lends a graceful feeling to the experience.
28. Critters 3 (1991)
Just before Leonardo DiCaprio became a household name, a then-17-year-old DiCaprio made his film debut (albeit direct-to-video) in the schlocky horror comedy Critters 3, the third in the Critters film series. DiCaprio has a minor role as Josh, a teenager who helps the main characters – including another teenager named Annie, played by Aimee Brooks – fight the bizarre monsters. Critters 3 is far from the level of prestige DiCaprio would eventually be known for, but it's hard not to see portents of his bright future ahead.
27. The 11th Hour (2007)
Leonardo DiCaprio's environmental activism takes center stage in The 11th Hour, a 2007 documentary about humanity's collective challenges due to climate change. As both producer and narrator, DiCaprio gives impassioned warnings about what's coming for us all while offering solutions through conservation, green technology, and greater social responsibility. While overshadowed by Al Gore's more prolific An Inconvenient Truth, released a year earlier, The 11th Hour is an equally moving and stirring call-to-action doc.
26. This Boy's Life (1993)
Based on the memoir by Tobias Wolff, This Boy's Life is a coming-of-age drama that follows young Toby Wolff (Leonardo DiCaprio) who grows up in a household ruled by his abusive stepfather (Robert De Niro) in 1950s Washington state. The first of several notable collaborations between De Niro and DiCaprio, This Boy's Life rises above its paint-by-numbers storytelling through the sheer magnitude of its actors' performances, especially coming from an exceedingly young DiCaprio.
25. Ice on Fire (2019)
Even after Leonardo DiCaprio won his Oscar in 2016, he never stopped caring about the planet. In 2019, the actor produced and narrated another climate documentary, this time focusing on emerging technologies that strive (and successively) reduce carbon in the atmosphere, which just might be key to permanently reversing climate change. Ice on Fire received a standing ovation at the Cannes Film Festival in 2019 and for good reason: It's the first time in a long time that's made us feel hopeful that tomorrow is still assured.
24. Marvin's Room (1996)
Leonardo DiCaprio only plays a supporting role in the 1996 drama Marvin's Room, but he still makes the most of it in a tremendously layered performance. Most of the film centers on the tensions between two adult sisters, played by Meryl Streep and Diane Keaton, whose father (Hume Cronyn) is ill and now Keaton's character Bessie is diagnosed with leukemia and may need a bone marrow transplant. The estranged sisters reunite under difficult circumstances. DiCaprio's rebellious Hank doesn't make anything easier, being a teen delinquent himself.
23. Don't Look Up (2021)
After years of legitimate climate advocacy, Leonardo DiCaprio teamed with director Adam McKay to play an astronomer, Dr. Randall Mindy, who becomes desperate to warn the world of an incoming disastrous asteroid only to be met with skepticism, denial, and even mockery. Though Don't Look Up didn't light up movie critics, who collectively found the movie as clumsy in its social commentary, DiCaprio still pulls his weight in a leading role that finds a lot of humor in being totally hopeless. In a lot of ways, Don't Look Up sees DiCaprio play someone close to himself, as Dr. Mindy becomes a celebrity but can't seem to get the right message across.
22. The Man in the Iron Mask (1998)
An adaptation of the final chapter of Alexandre Dumas' serialized 1847 novel The Vicomte of Bragelonne: Ten Years Later, Leonardo DiCaprio does double duty as both King Louis XIV and his twin brother Philippe – aka, the titular man in the iron mask. A Three Musketeers movie, The Man in the Iron Mask sees the three now-middle-aged swashbucklers reunite for one last benevolent job: to overthrow King Louis XIV and install his imprisoned brother as the new king of France. The Man in the Iron Mask isn't quite a modern classic, but its box office success indicated that audiences were absolutely drawn to DiCaprio. Even if he is wearing an iron mask literally half the time.
21. J. Edgar (2011)
Although J. Edgar falls short of expectations – being a biopic of founding FBI director J. Edgar Hoover directed by Clint Eastwood – a predictably strong Leonardo DiCaprio makes it a worthwhile cursory glance. Also a de facto origin story of the FBI, DiCaprio towers in his role as a historical figure that sees the ineptitude of a system and seeks to tighten it (not to mention make it a thousand times more evil) but can't keep his own life together. Although J. Edgar didn't gather any consideration for the Oscars, DiCaprio was nominated for Best Actor at the Golden Globes and landed in the National Board of Review's list of 2011's top ten best movies.
20. Celebrity (1998)
Just as Leonardo DiCaprio was minted as Hollywood's premier leading man, the actor appeared in Woody Allen's intended treatise on the toxicity of fame and modern day celebrity worship in his 1998 comedy-drama, Celebrity. While Kenneth Branagh takes lead in the role of a divorced writer who becomes a rookie celebrity journalist, DiCaprio plays a satirical version of himself in Brandon Darrow, a self-absorbed movie star in the throes of being Hollywood's number-one new man. Celebrity is far from Woody Allen at his peak, but DiCaprio is quite fun to watch as a flamboyant, debaucherous male movie star who epitomizes how hollow Hollywood can be.
19. Revolutionary Road (2008)
Some 11 years after Titanic, Kate Winslet and Leonardo DiCaprio reunited for Sam Mendes' Revolutionary Road. Based on Richard Yates' celebrated 1961 novel, the film follows a married couple in 1950s Connecticut who find themselves disillusioned with their idyllic American lifestyle and start yearning for more. Or at least, something different. While a movie about well-off middle class suburbanites didn't scan too well in the thick of the financial crisis, both DiCaprio and Winslet give powerful performances in this handsome rendition of Yates' work.
18. The Revenant (2015)
It's the movie that won Leonardo DiCaprio his coveted Oscar for Best Actor. While there's dispute whether it's a movie actually deserving of that prize, there's no turning back the clock. And certainly, DiCaprio has never looked more beaten and battered than in Alejandro González Iñárritu's The Revenant. Based on Michael Punke's 2002 novel, itself inspired by the experiences of frontiersman Hugh Glass, The Revenant follows 19th century fur trapper Hugh Glass who is attacked by a bear and later left for dead by his company in the frigid, snowy winter of what is currently the American Dakotas. DiCaprio's Glass fights for survival while seeking revenge against the man (Tom Hardy) who betrayed him and killed his son. Specific choices aside, The Revenant is an impressive feat of filmmaking with DiCaprio looking absolutely grody.
17. The Basketball Diaries (1995)
It's maybe one of the most emotionally distressful movies in Leonardo DiCaprio's entire filmography, even if the pain of Jim Caroll's addictions doesn't compare to getting mauled by a bear. Based on Caroll's autobiographical novel of the same name, DiCaprio plays the author whose life begins as a promising varsity high school athlete before it collapses due to substance abuse. Although critics weren't enamored by The Basketball Diaries – including the late Roger Ebert, who gave it a scathing review – the movie has cultivated some goodwill as another early exhibition of DiCaprio and his maturing talent.
16. Body of Lies (2008)
Leonardo DiCaprio in a movie directed by Ridley Scott should feel, I don't know, big. Unfortunately, Body of Lies isn't quite so epic. All told, it's a paint-by-numbers spy thriller. Still, DiCaprio asserts his leading male dominance opposite Russell Crowe in a dadcore picture fully mired in the miasma of the War on Terror. DiCaprio plays a CIA agent, Roger Ferris, who works tirelessly to capture an elusive terrorist while warring with his own boss (Crowe). As predictable as Body of Lies can be, the overall direction by Scott and red-hot performances by DiCaprio and Crowe make Body of Lies, truthfully, a pretty good time.
15. Romeo + Juliet (1996)
If you had a "cool" English teacher in high school, there's a nonzero chance you've seen Baz Luhrmann's Romeo + Juliet. While its contemporary SoCal setting with mostly faithful dialogue is, on the face, totally off-putting, DiCaprio and co-star Claire Danes are irresistible as they – and everyone around them – recite the Bard's words wearing tank tops and pointing guns. Luhrman's typically ostentatious style is on full, gleeful display, his sense of color and excess giving the most familiar play in the world a fresh coat of paint.
14. The Quick and the Dead (1995)
The dusty old Western genre gets a whole new spin under Sam Raimi, for his 1995 revenge pic The Quick and the Dead shoots faster than a loaded Smith & Wesson. Sharon Stone takes charge as "The Lady," a young woman (real name Ellen) who strolls into a frontier town ruled by her father's killer, an outlaw named John Herod (Gene Hackman). As Ellen enters a gunfighter tournament sponsored by Herod, she befriends a cocky young stud who calls himself "The Kid" (DiCaprio). While DiCaprio isn't the true hero of this story, The Quick and the Dead is a rollicking gunslinger picture buoyed by Raimi's signature direction and camerawork. And DiCaprio is hard to ignore as he chews up every scene with confidence and boyish charm.
13. The Great Gatsby (2013)
Baz Luhrmann's style, consisting of cranked-up excess and intentional anachronisms, definitely isn't for everyone. But few can argue that the director doesn't have it. Adapting what is widely considered to be one of the single greatest novels in American literature – F. Scott Fitzgerald's The Great Gatsby – Luhrmann's lavish rendition sees Leonardo DiCaprio suit up as enigmatic millionaire Jay Gatsby, whose many parties feel like the center of the universe. Take umbrage with the movie's plastic aesthetics or Jay-Z needledrops (which, again, are not careless) all you want. But when Leo hands you a cocktail, it's hard not to feel fireworks.
12. Shutter Island (2010)
In 2010, Leonardo DiCaprio was really haunted by dreams. In the same year he blew up the box office with Inception, DiCaprio also appeared in Martin Scorsese's trippy psychological thriller Shutter Island. Based on Dennis Lehane's 2003 novel, the movie sees DiCaprio play a U.S. Marshal who comes to the mysterious Shutter Island to investigate the whereabouts of a patient at a psychiatric facility. Whether you anticipate the movie's wild twist ending or not, Shutter Island is a formidable effort by both DiCaprio and Scorsese, whose dalliance with pulpy scares proves they're not always in the business of high-level prestige.
11. The Aviator (2004)
For Martin Scorsese's The Aviator, Leonardo DiCaprio fills the white tennis shoes of Howard Hughes, the prominent 20th century industrialist, pilot, and filmmaker who once epitomized wealth and the playboy lifestyle. In Scorsese's epic biopic, DiCaprio's interpretation of Hughes proves Hollywood bigwigs wrong when his costly aviation picture Hell's Angels becomes a rousing success. This is only the beginning of Hughes' time in the limelight, as the film chronicles his rollercoaster decade marked by high-profile romances with actresses, rivalries with aerospace competitors, and accusations of war profiteering. While The Aviator tends to get overlooked in the filmographies of both Scorsese and DiCaprio, this second collaboration between the two truly soars.
10. Django Unchained (2012)
Leonardo DiCaprio plays the most despicable villain in modern movie history in Quentin Tarantino's mesmerizing revenge Western Django Unchained. While Jamie Foxx struts the screen as the ultra-cool Django Freeman, standing opposite him is DiCaprio as Calvin J. Candie, an affluent Mississippi plantation owner who delights in the abuse of his slaves. It's popular trivia that DiCaprio cut his hand for real during one of his monologues, and kept on performing and staying in character while actually tearing out shards of glass from his hand. While DiCaprio mysteriously didn't get so much of an Oscar nomination, he did earn praise in the press (as did the movie overall) as well as a Golden Globe nomination for Best Supporting Actor.
9. The Departed (2006)
Martin Scorsese's remake of Andrew Lau and Alan Mak's Infernal Affairs, which transports its story of cops infiltrating gangsters and vice versa from Hong Kong to Boston, marked the third collaboration between Scorsese and Leonardo DiCaprio. The star plays the central role of Billy, an undercover cop who infiltrates the inner circle of Irish mob boss Frank Costello (Jack Nicholson). Though Scorsese scholars insist The Departed isn't Scorsese's best and maybe not the movie the director should have won Best Director for, it's foolish to dismiss it. It's easily one of the best movies of the decade, being a sweeping (and at times, unexpectedly hilarious) gangster epic eclipsed only by another movie: Scorsese's own Gangs of New York.
8. What's Eating Gilbert Grape (1993)
The movie that launched a young 19-year-old Leonardo DiCaprio to fame, What's Eating Gilbert Grape still remains one of the actor's finest movies of his long and prolific career. The film stars Johnny Depp as the titular Gilbert Grape, a grocery store clerk who feels stuck in his mid-20s as he cares for his morbidly obese mother (played by the late Darlene Cates) and his mentally disabled brother Arnie, played by DiCaprio. DiCaprio's performance as the sympathetic Arnie drew lots of attention for DiCaprio, including Academy Award and Golden Globe nominations. What's Eating Gilbert Grape can often feel like typical Hollywood schmaltz, but DiCaprio is really something as Arnie, disappearing in the part enough to make you forget he's now a truly matured movie star.
7. Catch Me If You Can (2002)
Steven Spielberg's stylish caper Catch Me If You Can, in which Leonardo DiCaprio plays real-life con artist Frank Abagnale Jr., is at times hilarious, other times a touch sad, but altogether a handsome dalliance through a rapidly changing America in the mid-20th century. DiCaprio's Abagnale is a serial liar whose silver tongue lets him get away with just about anything. That includes avoiding arrest by FBI agent Carl Hanratty (Tom Hanks) who relentlessly pursues Abagnale for years. Though Hanratty wants nothing more than Abagnale behind bars, the movie sees the men come to a place of mutual understanding, which lends their story a dash of unexpected sweetness. Catch Me If You Can is an especially disarming movie from Spielberg, and DiCaprio is a big part of the movie's appeal.
6. Gangs of New York (2002)
In this 21st century giant of American cinema, Leonardo DiCaprio plays the vengeful son of Irish Catholic immigrants with a vendetta against a gangster, William Poole, aka "Bill the Butcher" (Daniel Day-Lewis) for the murder of his father in 1860s New York. As the Civil War looms in the background, DiCaprio's blood hunt against a rapidly changing New York encapsulates the mythology of a nation refined by conflict. While a stunning recreation of Gilded Age New York, the movie's release over a year after 9/11 imbued it with significance that's simply hard to put into words. The history of New York may not be pretty, nor is it clean. But that's what makes it the envy of the world, and Gangs of New York is a moving tribute.
5. Killers of the Flower Moon (2023)
In his sixth film with director Martin Scorsese, Leonardo DiCaprio proved the two men still have an infinite well to draw from, and plenty to say about America as they know it. Based on David Grann's 2017 true crime book about the Osage murders, Killers of the Flower Moon sees DiCaprio as real-life Ernest Burkhart, a World War I veteran and husband to an Osage woman (Lily Gladstone) with ties to the murders of prominent Osage Nation members after they discover oil on their own tribal land. In this engrossing three-and-a-half-hour epic, DiCaprio gives a layered performance that illustrates Ernest’s conflict and complicity in a horrendous crime that, truth be told, is nothing more American in spirit.
4. Inception (2010)
Director Christopher Nolan was no stranger to having box office hits before 2010, with his films like Following drawing cult buzz and his Batman movies becoming global hits. But with his trippy 2010 sci-fi Inception, which follows a team pull off an important heist in the dreamscape of a corporate executive (Cillian Murphy), Nolan became minted as a true Hollywood auteur who doesn't need comic book IP to sell tickets. It may have helped that Inception packed a stellar cast led by Leonardo DiCaprio, whose leading man Cobb takes on one last albeit risky job to see his family again. Inception is maybe the platonic ideal of a Hollywood blockbuster: a cool, confident, and most of all original picture that knows how to balance smarts with vibes.
3. Once Upon a Time In… Hollywood (2019)
Quentin Tarantino's heavenly reimagining of Hollywood in 1969 makes that time and place the place to be. It also plays out a bittersweet ending to the utterly horrific murder of actress Sharon Tate at the hands of the Manson Family, an incident that Tarantino makes clear was the end of Hollywood as anyone knew it. In Tarantino's alternate timeline, there exists Rick Dalton (Leonardo DiCaprio), a once prominent film star who is now fading in TV. DiCaprio's Rick Dalton is talented but insecure, a man desperate to be told he's not yesterday's news. While Rick's best friend and chauffeur Cliff Booth (Brad Pitt) slowly becomes the real main character, DiCaprio's Rick Dalton is why this Hollywood fairy tale even gets told at all.
2. The Wolf of Wall Street (2013)
The movie spawned a million memes, but Martin Scorsese's damning biopic of Jordan Belfort is nothing to laugh at. (Even when it's actually freaking funny.) An exceedingly imposing Leonardo DiCaprio stars as Belfort, the charismatic and calculating Wall Street broker whose aggressive style and machismo gets him on the fast track to a high life, only for all of it to come crashing down through investment fraud and money laundering. Through Belfort's rise and fall, Scorsese and DiCaprio – whose performance as Belfort really is something to behold – meditate on the intoxicating allure of the American dream, even going so far to posit that maybe Belfort might be onto something. But the thing about dreams is that eventually, you wake up.
1. Titanic (1997)
The era-defining romance of the century, James Cameron's seismic picture Titanic just has it all. That includes Leonardo DiCaprio as nomad artist Jack, who falls in love with high society gal Rose (Kate Winslet) while aboard the ill-fated ocean liner thought to be invincible. Besides the monumental technical achievements of Titanic, the movie works because of Winslet and DiCaprio, whose roles embody young love and the tragedy of it ending far too soon. You're free to argue that DiCaprio has put on better performances until your face is as blue as Jack in the Atlantic Ocean. But there's simply no movie of DiCaprio's that's bigger than Titanic.
