Leonardo DiCaprio is one of the most acclaimed and successful actors of his generation. Over his nearly three decade career, he has delivered powerful, nuanced performances in a wide range of films, working with many of the greatest directors in the business. From his early breakout roles to his more recent prestige pictures, DiCaprio has demonstrated his incredible talent and versatility.
In this extensive blog post, I will rank what I consider to be the 27 best Leonardo DiCaprio movies. This was an extremely difficult list to compile, as DiCaprio has been a part of so many fantastic films throughout his career. But after much deliberation, here is my ranking of DiCaprio’s greatest cinematic achievements.
27. Critters 3 (1991)
We start the list with DiCaprio’s inauspicious film debut. The third installment in the low-budget comedy horror series, Critters 3 is a mostly forgettable B-movie. A young Leo appears as Josh, the stepson of an unscrupulous landlord who gets attacked by the titular alien creatures.
While the movie itself is nothing special, DiCaprio demonstrates some early acting chops, proving to be a charismatic screen presence even in a small role. It’s fascinating to see him at the very beginning of his career in a cheap direct-to-video flick like this. Little did anyone know he would go on to be one of the biggest movie stars in the world.
26. The Man in the Iron Mask (1998)
In this literary adaptation, DiCaprio takes on dual roles as the cruel King Louis XIV and his secret twin brother Philippe. While DiCaprio gives a solid performance, especially as the sympathetic Philippe, the movie around him is a bit of a mess.
An uneven script and some questionable directorial choices result in a film that never quite gels. However, it’s still interesting to see DiCaprio take on a period piece and play against type as a villain, something he would do to much greater success later in his career. The lavish costumes and production design are also impressive.
25. The Beach (2000)
Following the monumental success of Titanic, The Beach was DiCaprio’s first major starring role. Directed by Danny Boyle, the film sees Leo as an American tourist who discovers a secret island paradise off the coast of Thailand.
While the movie has some visually striking moments, the muddled story and uneven tone prevent it from being fully successful. DiCaprio’s character is not particularly likable or compelling, which makes it difficult to fully invest in his journey. It’s an ambitious misfire, but a misfire nonetheless. The Beach showed DiCaprio trying to subvert his heartthrob image, but he wouldn’t fully succeed in that endeavor for a few more years.
24. Body of Lies (2008)
Ridley Scott’s Body of Lies is a solid if unremarkable entry in the post-9/11 espionage thriller genre. DiCaprio stars as a CIA operative working in the Middle East who grows disillusioned with the moral ambiguity of his work.
It’s a well-crafted, gripping film with strong performances from DiCaprio and Russell Crowe. However, it covers a lot of the same thematic territory as other, better movies. DiCaprio is good as always, but his character feels a bit underwritten. Body of Lies is a perfectly watchable political thriller, but it doesn’t reach the heights of DiCaprio and Scott’s best work.
23. J. Edgar (2011)
Clint Eastwood’s biopic of controversial FBI director J. Edgar Hoover features another transformative performance from DiCaprio. Under heavy old age makeup, he portrays Hoover over multiple decades as he builds the FBI into a formidable organization while battling his own repressed homosexuality.
It’s an ambitious, well-acted film that doesn’t quite come together in the end. The nonlinear structure and sprawling timeline make it feel disjointed at times. And the screenplay never really gets under Hoover’s skin to understand what made him tick. Still, DiCaprio’s total commitment to the role is impressive, proving yet again what a chameleonic performer he can be.
22. Total Eclipse (1995)
In one of his first leading roles, DiCaprio portrays the French poet Arthur Rimbaud opposite David Thewlis as Paul Verlaine. It’s a challenging, provocative film about the tempestuous real-life love affair between the two men.
DiCaprio fully commits to the part, fearlessly depicting Rimbaud’s rebelliousness, sexuality, and ultimate self-destruction. It’s not an easy film to watch, but it showcases DiCaprio’s willingness to take on daring, unconventional projects even early in his career. While not entirely successful, Total Eclipse hinted at the depths DiCaprio would plumb in his later work.
21. The Quick and the Dead (1995)
Sam Raimi’s stylized Western was a change of pace for DiCaprio, allowing him to show off a tougher, more macho side as a young gunslinger known as “The Kid.” Starring alongside Sharon Stone and Gene Hackman, DiCaprio more than holds his own.
The Quick and the Dead is a slick, entertaining shoot-em-up with Raimi’s signature flair. DiCaprio seems to be having a blast playing a cocky, roguish cowboy, a far cry from the sensitive roles that defined his early career. While the movie is pretty slight overall, it’s still a fun, action-packed showcase for DiCaprio’s star power.
20. The Aviator (2004)
Martin Scorsese’s epic biopic of Howard Hughes allowed DiCaprio to sink his teeth into a meaty, challenging role. As the brilliant but troubled Hughes, DiCaprio depicts his rise as a filmmaker and aviation pioneer, as well as his struggles with mental illness.
It’s a huge, ambitious film that doesn’t always work, but DiCaprio is never less than fully committed. He captures Hughes’ charm, intelligence, and slow descent into paranoia and isolation. The lavish period detail and Scorsese’s kinetic direction make for a visually dazzling film, even if the script is a bit bloated. The Aviator was the first of many fruitful collaborations between DiCaprio and Scorsese.
19. The Basketball Diaries (1995)
One of DiCaprio’s best early roles was as real-life poet and musician Jim Carroll in The Basketball Diaries. Based on Carroll’s memoir, the film follows his teenage years as a star basketball player who descends into drug addiction.
It’s a harrowing, emotionally raw performance from DiCaprio. He fearlessly portrays Carroll’s downward spiral, as well as his eventual path to redemption. The Basketball Diaries is a gritty, uncompromising film that doesn’t shy away from the ugly realities of addiction. DiCaprio’s searing work is a major reason why it’s so effective.
18. Blood Diamond (2006)
Edward Zwick’s action drama stars DiCaprio as Danny Archer, a South African mercenary and diamond smuggler. Over the course of the film, he has a crisis of conscience as he faces the human cost of the illegal diamond trade.
It’s a physically and emotionally demanding role, requiring DiCaprio to adopt a convincing Zimbabwean accent. He brings his usual intensity to the part, as Archer gradually transforms from a cynical opportunist to a man seeking redemption. Blood Diamond can be heavy-handed at times, but DiCaprio’s performance grounds the film in a flawed but relatable protagonist.
17. Marvin’s Room (1996)
This underseen family drama gave DiCaprio a chance to show his softer side. He plays Hank, a troubled teenager who is sent to live with his estranged aunt (Diane Keaton) and terminally ill father (Hume Cronyn).
As the angry, emotionally damaged Hank, DiCaprio delivers a heartbreaking performance. He captures the character’s pain and vulnerability, as well as his gradual bond with his aunt and father. Marvin’s Room is a quiet, moving film that showcases DiCaprio’s range as an actor. It’s a shame more people haven’t seen this lovely little movie.
16. Revolutionary Road (2008)
DiCaprio reunited with his Titanic co-star Kate Winslet for this bleak drama about a 1950s couple whose marriage is disintegrating. As Frank Wheeler, DiCaprio plays a man who feels trapped and disillusioned by the conventions of suburban life.
It’s a devastating portrait of a toxic relationship, with both DiCaprio and Winslet delivering raw, emotionally honest performances. DiCaprio captures Frank’s simmering resentment and growing desperation as his dreams slowly die. Revolutionary Road is a difficult film to watch at times, but it’s a powerful showcase for its two lead actors.
15. Inception (2010)
Christopher Nolan’s mind-bending sci-fi thriller stars DiCaprio as Cobb, a professional thief who steals secrets from people’s dreams. Over the course of the film, Cobb assembles a team for one last job that will hopefully allow him to finally return home to his children.
Inception is a stunningly ambitious film, full of dazzling visuals and narrative trickery. At the center of it all is DiCaprio’s grounded, emotional performance. He brings a sense of real stakes to the film’s high-concept premise, as Cobb grapples with guilt over his wife’s death. Inception is a true original, and DiCaprio’s layered work is crucial to its success.
14. Shutter Island (2010)
Martin Scorsese’s twisty psychological thriller stars DiCaprio as Teddy Daniels, a U.S. Marshal investigating a disappearance at a remote mental hospital. As the mystery deepens, Teddy begins to question his own sanity.
It’s a juicy, scenery-chewing role for DiCaprio, and he fully commits to Teddy’s unraveling mental state. He captures the character’s mounting paranoia and confusion, as well as his tragic backstory. Shutter Island is a pulpy, stylish mind-bender with a killer twist ending. DiCaprio’s intense performance keeps you guessing until the very end.
13. The Departed (2006)
DiCaprio scored his third Oscar nomination for his work in Martin Scorsese’s crime epic The Departed. He stars as Billy Costigan, a young cop who goes undercover to infiltrate the Irish mob in Boston.
It’s a meaty, complex role that requires DiCaprio to constantly switch between different identities and allegiances. He captures Billy’s internal conflict and growing sense of isolation, as he loses himself in his undercover persona. The Departed is a masterfully crafted thriller with an incredible ensemble cast. DiCaprio more than holds his own opposite heavy hitters like Jack Nicholson and Matt Damon.
12. Catch Me If You Can (2002)
In Steven Spielberg’s breezy caper film, DiCaprio stars as real-life con artist Frank Abagnale Jr. The movie follows Frank’s exploits as he successfully impersonates a pilot, doctor, and lawyer, all while staying one step ahead of the FBI.
It’s a charming, lighthearted performance from DiCaprio, who brings his natural charisma to the role. He makes Frank a likable rogue, even as his deceptions become increasingly audacious. Catch Me If You Can is a fun, stylish romp that allows DiCaprio to show off his comedic chops. It’s one of his most purely enjoyable performances.
11. Django Unchained (2012)
Quentin Tarantino’s revisionist Western stars DiCaprio as Calvin Candie, a sadistic plantation owner who forces his slaves to fight to the death for his amusement. It’s a truly despicable character, and DiCaprio tears into the role with gusto.
With his thick Southern drawl and oily charm, DiCaprio makes Candie a memorably loathsome villain. He’s both charismatic and utterly repellent, a man who sees his slaves as nothing more than property. Django Unchained is a wild, bloody revenge fantasy, and DiCaprio’s go-for-broke performance is one of its many highlights.
10. The Revenant (2015)
Alejandro González Iñárritu’s grueling survival epic features DiCaprio as Hugh Glass, a frontiersman who is left for dead after being mauled by a bear. The movie follows Glass as he treks through the wilderness, seeking revenge on the men who abandoned him.
It’s an intensely physical performance from DiCaprio, who endures all manner of hardships throughout the film. He crawls, limps, and grunts his way through the harsh landscape, conveying Glass’ determination and sheer force of will. The Revenant is a punishing, visually stunning film that pushed DiCaprio to his limits. His raw, committed work finally won him a long-overdue Oscar.
9. Gangs of New York (2002)
Martin Scorsese’s sprawling historical epic stars DiCaprio as Amsterdam Vallon, a young man seeking revenge against the vicious gang leader (Daniel Day-Lewis) who killed his father. Over the course of the film, Amsterdam infiltrates the gang and plots his vengeance.
It’s a tricky role, requiring DiCaprio to hold his own opposite the ferocious Day-Lewis. He more than rises to the challenge, capturing Amsterdam’s burning desire for justice as well as his growing moral compromise. Gangs of New York is a flawed but fascinating film, with DiCaprio providing its emotional center.
8. The Wolf of Wall Street (2013)
In his fifth collaboration with Martin Scorsese, DiCaprio stars as Jordan Belfort, a stockbroker who makes a fortune through fraudulent schemes and flagrant corruption. The movie chronicles Belfort’s rise and fall, as well as his debauched lifestyle.
It’s a big, showy performance from DiCaprio, who fully embodies Belfort’s manic energy and unrestrained greed. He delivers Belfort’s profane, fast-talking monologues with gusto, making him a strangely charismatic figure even as his behavior becomes increasingly reprehensible. The Wolf of Wall Street is a wild, exhilarating ride, and DiCaprio is its raging heart and soul.
7. What’s Eating Gilbert Grape (1993)
In one of his earliest and most acclaimed roles, DiCaprio stars as Arnie Grape, a mentally disabled teenager being cared for by his older brother Gilbert (Johnny Depp). It’s a sensitive, nuanced performance that avoids any hint of caricature.
DiCaprio fully inhabits Arnie’s childlike innocence and unbridled enthusiasm, as well as his occasional frustration and sadness. He brings a real sense of humanity to the character, making him more than just a simple plot device. What’s Eating Gilbert Grape is a tender, bittersweet film, and DiCaprio’s heartbreaking work is a big reason why.
6. The Aviator (2004)
Yes, The Aviator appears twice on this list. That’s because DiCaprio’s performance as Howard Hughes is so good it deserves to be recognized twice. As mentioned earlier, it’s a physically and emotionally demanding role that requires DiCaprio to depict Hughes’ slow descent into mental illness.
But what’s even more impressive is how DiCaprio captures Hughes’ brilliance and charisma in the early scenes. He shows us the man’s genius and ambition, before the crippling phobias and obsessions take over. It’s a towering performance that anchors Scorsese’s sprawling biopic.
5. Titanic (1997)
The movie that made DiCaprio a global superstar remains one of his most iconic roles. As Jack Dawson, the charming artist who falls in love with aristocrat Rose DeWitt Bukater (Kate Winslet) aboard the doomed ship, DiCaprio is the epitome of old-school Hollywood glamour.
With his tousled hair and megawatt smile, DiCaprio is the perfect romantic lead. But he also brings a real sense of depth and vulnerability to Jack, making him more than just a dashing hero. Titanic is a grand, sweeping epic, and DiCaprio’s star-making performance is a huge part of its enduring appeal.
4. The Departed (2006)
DiCaprio’s work in The Departed is so good it also deserves a second mention. As undercover cop Billy Costigan, DiCaprio delivers a performance of simmering intensity and barely concealed anguish.
Watching Billy slowly unravel as the pressure of his double life takes its toll is both riveting and heartbreaking. DiCaprio navigates the character’s moral ambiguity with ease, making us empathize with his plight even as he crosses ethical lines. It’s a tour-de-force performance that ranks among his very best.
3. Once Upon a Time in Hollywood (2019)
Quentin Tarantino’s love letter to 1960s Hollywood features DiCaprio as Rick Dalton, a fading TV star struggling to stay relevant in a changing industry. It’s a more subdued performance than we’re used to seeing from DiCaprio, but no less effective.
As Dalton, DiCaprio captures the insecurity and vulnerability of an actor facing the twilight of his career. He brings a real sense of pathos to the character, making us feel for this flawed, sometimes pathetic man. But he also shows Dalton’s inherent decency and loyalty, particularly in his scenes with his longtime stunt double Cliff Booth (Brad Pitt).
Once Upon a Time in Hollywood is a sprawling, meandering film that divided audiences. But DiCaprio’s nuanced, tragicomic performance is one of its undeniable highlights. It’s a reminder of just how versatile and compelling he can be, even in a relatively low-key role.
2. Inception (2010)
Inception is a true cinematic achievement, a mind-bending thriller that operates on multiple levels of reality. At the heart of it all is DiCaprio’s performance as Cobb, the haunted dream thief desperate for a chance at redemption.
What makes the performance so impressive is how DiCaprio grounds the film’s high-concept premise in real emotion. Even as the plot twists and turns, we never lose sight of Cobb’s pain and longing. DiCaprio brings a sense of gravity to the character, making us feel the weight of his choices and the depth of his regret.
In a film full of dazzling visuals and narrative trickery, it’s DiCaprio’s deeply human performance that resonates the most. Inception is a true original, and DiCaprio is a big reason why it works so well.
1. The Wolf of Wall Street (2013)
DiCaprio’s performance as Jordan Belfort is a true tour-de-force, a manic, high-wire act that ranks as one of the greatest in modern cinema.
From the moment he appears on screen, DiCaprio is a force of nature. He fully embodies Belfort’s unrestrained greed and hedonism, delivering his profane monologues with a kind of deranged gusto. It’s a physical, all-consuming performance that required DiCaprio to go to some dark and twisted places.
The Wolf of Wall Street is a wild, exhilarating ride, and DiCaprio is its raging, unstoppable center. It’s the kind of performance that comes along once in a generation, a true masterclass in acting. Love him or hate him, you can’t take your eyes off him.
Conclusion
There you have it, my ranking of the 27 best Leonardo DiCaprio movies. As you can see, the man has had an incredible career, working with some of the greatest directors of all time and delivering one iconic performance after another.
What’s most impressive about DiCaprio is his versatility. He can play the charming romantic lead, the tortured antihero, the despicable villain, and everything in between. He fully commits to every role, disappearing into the character and making us forget we’re watching one of the most famous actors in the world.
