Leonardo DiCaprio Movies Ranked: The 10 Best, From Shutter Island to The Wolf of Wall Street

Leonardo DiCaprio movies have a habit of becoming events. Since his teenage breakthrough in the early 1990s he has chosen projects with unusual care, working again and again with Martin Scorsese and taking on directors such as Steven Spielberg, Christopher Nolan, Quentin Tarantino, James Cameron and Alejandro G. Iñárritu. The result is a filmography with very few throwaway titles, and a career that runs from a heartbreaking supporting role in small-town Iowa to an Academy Award for surviving the American frontier.

Choosing ten is harder for DiCaprio than for almost any actor of his generation, because so many of his films are strong. The ranking leans on the performance itself: how much the role asks of him, how fully he delivers and how much he changes the film around him. When performances feel equally accomplished, the better movie takes the higher spot. The countdown starts at number ten and climbs to the role that shows his gifts most completely.

Leonardo DiCaprio Movies Ranked: Roles, Years and Directors

10. Shutter Island (2010)

Shutter Island, Scorsese's adaptation of the Dennis Lehane novel, opens in 1954 as U.S. Marshal Teddy Daniels and his new partner Chuck Aule, played by Mark Ruffalo, arrive at a hospital for the criminally insane on an island in Boston Harbor. A patient has vanished from a locked room, and the head psychiatrist, Dr. Cawley, played by Ben Kingsley, seems less than eager to help. Teddy, haunted by the war and by his late wife Dolores, played by Michelle Williams, starts to suspect a conspiracy.

Shutter Island is a gothic puzzle box, and DiCaprio plays Teddy with a mounting, migraine-soaked dread that keeps the audience as off balance as he is. The final act reframes everything he has done before it, and his last scene lands with real force. It opens the countdown because the film's twists sometimes overshadow the character work, but it remains a superb psychological thriller and a reminder of how well he and Scorsese bring out the darkness in each other.

9. What's Eating Gilbert Grape (1993)

Lasse Hallström's What's Eating Gilbert Grape is a gentle drama set in Endora, a tiny Iowa town where Gilbert, played by Johnny Depp, holds his family together after his father's death. His responsibilities include his mother, who has not left the house in years, and his younger brother Arnie, played by DiCaprio, an intellectually disabled boy approaching his eighteenth birthday who keeps climbing the town water tower. Juliette Lewis plays Becky, a free-spirited visitor who offers Gilbert a glimpse of a different life.

This was the performance that announced DiCaprio as a serious actor. Arnie is joyful, exhausting and heartbreaking, and DiCaprio plays him with such openness and physical specificity that he never seems to be acting at all. It brought him his first Academy Award nomination, for Best Supporting Actor at the 1994 ceremony. The film is a quiet ensemble piece rather than his showcase, so it ranks ninth, but no early role better explains why directors started lining up to work with him.

8. Once Upon a Time… in Hollywood (2019)

Quentin Tarantino's Once Upon a Time… in Hollywood is set in Los Angeles in 1969, as the old studio system gives way to a new era. DiCaprio plays Rick Dalton, a former star of a television western who is sliding toward guest spots as villains and wondering whether his career is over. Brad Pitt plays Cliff Booth, Rick's laid-back stunt double, driver and closest friend, and Margot Robbie plays Sharon Tate, the rising actress who lives next door on Cielo Drive.

Rick is a nervous, insecure man who drinks too much and cries easily, and DiCaprio finds comedy and tenderness in him. A scene in which Rick blows his lines on set and then rages at himself in his trailer is one of the funniest things he has done, and his conversations with a precocious child co-star are unexpectedly moving. The role earned an Academy Award nomination for Best Actor at the 2020 ceremony. It sits eighth because the film belongs as much to Pitt.

7. Titanic (1997)

James Cameron's Titanic casts DiCaprio as Jack Dawson, a penniless artist who wins a ticket on the doomed ocean liner in a card game. On board he falls for Rose DeWitt Bukater, played by Kate Winslet, an upper-class young woman suffocating in her engagement to the wealthy and controlling Cal Hockley, played by Billy Zane. Their romance plays out across the ship's decks and dining rooms until the iceberg strikes. Kathy Bates plays Molly Brown, and Frances Fisher plays Rose's mother Ruth.

Jack is a simpler character than most on the countdown, but DiCaprio gives him an easy warmth that makes the love story work and turned the film into a cultural phenomenon. His chemistry with Winslet is what audiences remember, and it gives the disaster half of the story its emotional weight. The performance placed him firmly among the biggest stars in the world, and the film remains one of the best romance movies ever made, even if the role asks less of him than the ones above.

6. Catch Me If You Can (2002)

Steven Spielberg's Catch Me If You Can is the true story of Frank Abagnale Jr., a teenager who runs away from his parents' crumbling marriage and becomes a master forger, passing himself off as an airline pilot, a doctor and a lawyer while cashing fake checks across the 1960s. Tom Hanks plays Carl Hanratty, the dogged FBI agent who spends years on his trail, and Christopher Walken plays Frank's father, a charming small businessman whose failures shape everything his son does.

This is DiCaprio at his most effortlessly likable, and the film is pure pleasure from its animated opening titles onward. He plays Frank as a lonely kid in a borrowed uniform, so the con-artist thrills always have a sad undertow. The cat-and-mouse scenes with Hanks are a joy, and his moments with Walken are among the most touching of his career. It ranks in the middle because the role relies on charm more than depth, yet few films show off his star quality so purely.

5. The Revenant (2015)

Alejandro G. Iñárritu's The Revenant sends DiCaprio into the frozen American wilderness of the 1820s as Hugh Glass, a frontier guide with a fur-trapping expedition. After a brutal bear attack leaves him barely alive, the trapper John Fitzgerald, played by Tom Hardy, kills Glass's son Hawk and abandons him in a shallow grave. Glass crawls, limps and claws his way across a vast, snowbound wilderness in pursuit of the man who betrayed him. Domhnall Gleeson plays the expedition's captain and Will Poulter the young trapper Jim Bridger.

The performance is almost wordless, built on breath, pain and sheer determination, and DiCaprio makes survival itself a kind of drama. It finally brought him the Academy Award for Best Actor at the 2016 ceremony, along with the Golden Globe for Best Actor in a drama and a BAFTA. The film sits at number five rather than higher because Glass is a test of endurance more than a rich character, but as a physical commitment nothing else in his career comes close.

4. Killers of the Flower Moon (2023)

Killers of the Flower Moon is Scorsese's account of the murders of Osage people in 1920s Oklahoma after oil was found beneath their land. DiCaprio plays Ernest Burkhart, a weak-willed war veteran who comes to work for his uncle, the cattleman William Hale, played by Robert De Niro. Under Hale's guidance, Ernest marries Mollie, an Osage woman played by Lily Gladstone, as her family members begin dying one by one. Jesse Plemons arrives late in the story as Tom White, the federal investigator sent to find out why.

This is DiCaprio's bravest choice of role. Ernest is not a hero, a charmer or a mastermind but a greedy, dim and pliable man who loves his wife and betrays her anyway, and DiCaprio refuses to make him easier to watch. His scenes with Gladstone are quietly devastating, and the slow rot of his conscience is the film's moral center. A long, demanding watch, it lands fourth because it is the purest character acting he has done, even if the earlier entries are more complete entertainments.

3. Inception (2010)

Christopher Nolan's Inception stars DiCaprio as Dom Cobb, a thief who steals corporate secrets by entering people's dreams. A powerful businessman named Saito, played by Ken Watanabe, offers Cobb a way home to his children if he can do the reverse and plant an idea in a rival heir's mind. Cobb assembles a team that includes his point man Arthur, played by Joseph Gordon-Levitt, the forger Eames, played by Tom Hardy, and a young architect named Ariadne, played by Elliot Page.

The dream heists and folding cities are the selling point, but the film works because DiCaprio grounds it in grief. Cobb is haunted by his dead wife, and the guilt he carries gives every layer of dreaming real stakes. It is a controlled, internal performance in a film built around spectacle, and it showed that he could anchor a high-concept blockbuster as easily as a Scorsese drama. That combination of scale and feeling earns it third place, comfortably ahead of most of his other studio work.

2. The Departed (2006)

In The Departed, Scorsese's Boston crime thriller, DiCaprio plays Billy Costigan, a young police recruit from a troubled family who is sent undercover into the Irish mob run by Frank Costello, played by Jack Nicholson. At the same time, Costello has planted his own man inside the state police: Colin Sullivan, played by Matt Damon. As each side hunts for its rat, the moles race to expose each other before they are exposed themselves. Martin Sheen and Mark Wahlberg play the officers who run Billy's assignment.

Billy is a man coming apart at the seams, and DiCaprio plays him with jittery, sleepless intensity, a raw nerve in every scene. Living a double life under Nicholson's unpredictable gaze, he makes the fear tangible without ever losing the character's decency. The film is one of the great crime thrillers of its decade, and his work, which brought a Screen Actors Guild nomination, is its emotional core. It ranks just behind Belfort only because that role asked him to carry an entire three-hour film alone.

1. The Wolf of Wall Street (2013)

Martin Scorsese's The Wolf of Wall Street follows Jordan Belfort from a junior job on Wall Street to the head of a Long Island brokerage that makes fortunes by pushing worthless penny stocks on ordinary investors. The money funds an empire of drugs, yachts and parties until federal agents close in. Jonah Hill plays Donnie Azoff, Belfort's reckless right-hand man, Margot Robbie plays his second wife Naomi, and Matthew McConaughey turns up early as the mentor who teaches him the culture.

No other DiCaprio performance is this fearless or this funny. He plays Belfort as a motivational speaker and a monster at once, delivering sales-floor sermons with evangelical fire and then throwing himself into physical comedy, most memorably in a drug-addled crawl to his car that plays like a silent-film routine. The role won him a Golden Globe for Best Actor in a comedy or musical and brought Oscar nominations for Best Actor and, as a producer, Best Picture at the 2014 ceremony.

The Scorsese Partnership

No director has shaped DiCaprio's career more than Martin Scorsese. Their collaboration began with Gangs of New York in 2002, in which DiCaprio played a young man seeking revenge against Daniel Day-Lewis's nativist gang leader for his father's death, and it has continued for more than two decades through The Aviator, The Departed, Shutter Island, The Wolf of Wall Street and Killers of the Flower Moon.

Each project has pushed him somewhere new. The Aviator turned him into Howard Hughes and won him the Golden Globe for Best Actor in a drama. The Departed made him a frightened outsider, Shutter Island a broken man, The Wolf of Wall Street a comic grotesque and Killers of the Flower Moon a moral coward. Most of those films appear in the top ten above, and the countdown's top spot belongs to their wildest collaboration.

What Scorsese seems to see in DiCaprio is an actor willing to play weakness. His characters for the director are often liars, addicts or men too frightened to face the truth, and DiCaprio commits to those flaws without asking the audience to forgive them.

Honorable Mentions: More Leonardo DiCaprio Movies to Watch

• This Boy's Life (1993): As Toby, a teenager battling his abusive stepfather, played by Robert De Niro, he showed early on that he could hold the screen opposite a legend.
• The Basketball Diaries (1995): He plays the writer Jim Carroll as a promising high school athlete who spirals into heroin addiction in New York.
• Revolutionary Road (2008): Reunited with Kate Winslet, he plays Frank Wheeler, a suburban husband whose marriage curdles under the weight of unmet dreams.
• The Great Gatsby (2013): Baz Luhrmann's glittering adaptation casts him as Jay Gatsby, the mysterious millionaire throwing parties for a lost love.
• Don't Look Up (2021): As Dr. Randall Mindy, an anxious astronomer warning a distracted world about an incoming comet, he leads a sharp satirical comedy.

Frequently Asked Questions

What is Leonardo DiCaprio's best movie?

The Wolf of Wall Street (2013) takes the top spot for his manic, fearless turn as Jordan Belfort, with The Departed and Inception close behind.

Has Leonardo DiCaprio won an Oscar?

Yes. He won the Academy Award for Best Actor for The Revenant at the 2016 ceremony, after earlier nominations for What's Eating Gilbert Grape, The Aviator, Blood Diamond and The Wolf of Wall Street.

Which Leonardo DiCaprio movies did Martin Scorsese direct?

Gangs of New York, The Aviator, The Departed, Shutter Island, The Wolf of Wall Street and Killers of the Flower Moon.

What was Leonardo DiCaprio's first Oscar nomination?

His first nomination was for Best Supporting Actor as Arnie Grape in What's Eating Gilbert Grape, at the 1994 Academy Awards.

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