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Like Paul Rudd or Jennifer Aniston who would follow, Leonardo DiCaprio got his start in the business befitting all future megastars: Starring in a godawful horror movie. 1991’s Critters 3 was DiCaprio’s rite of passage, followed by a bit part in Poison Ivy the next year — and that about ended his association with the genre. By 1993, DiCaprio was applying his striking cherubic looks to dramatic features like This Boy’s Life and breakthrough What’s Eating Gilbert Grape, in which he shared the screen with already-established heartthrob Johnny Depp. Romeo + Juliet made Bill Shakespeare palatable for the mid-’90s teenybopper set, which set the stage for world-storming Titanic, which won all the awards, made all the money and fashioned DiCaprio as a legend in his own time.
Not to rest on his laurels like on a haphazard dresser floating in the ocean, DiCaprio spent the immediate post-Titanic years seeking only to work with the best directors on edgy material, even as they were in their creative doldrums: Woody Allen with Celebrity, and Danny Boyle with The Beach. The viscerally negative reaction to Beach was enough to get DiCaprio to seemingly pull a disappearing act for what seemed like ages in the pre-Internet world. In reality, not even three years had passed when he re-appeared in Gangs of New York, igniting a rich De Niro-esque relationship with Martin Scorsese that would pay dividends with The Aviator, The Departed, Shutter Island, The Wolf of Wall Street and now Killers of the Flower Moon.
Beyond his conservation efforts (resulting in documentaries like Ice on Fire and Before the Flood), which have kept him from acting, DiCaprio maintains his brand and allure by making each screen performance a major event, going years between narrative films and working only with the biggest-name directors out there: Clint Eastwood (J. Edgar), Christopher Nolan (Inception), Alejandro González Iñárritu (The Revenant, for which he won the Best Actor Oscar) and Quentin Tarantino (Once Upon a Time in Hollywood).
Read on to see Leonardo DiCaprio’s 10 best movies, and see the entire list at Rotten Tomatoes.
10. Marvin's Room (1996)
Tomatometer: 84%
Audience Score: 63%
Synopsis: Bessie (Diane Keaton) and Lee (Meryl Streep) are sisters who have remained apart for nearly 20 years due to radically different personalities and life paths. Bessie remained in Florida to care for their ill, bed-ridden father (Hume Cronyn), and Lee moved to Ohio to marry and have a family. But Bessie's doctor (Robert De Niro) has informed her she has leukemia and needs a bone marrow transplant. Bessie's prognosis and Lee's troubled son (Leonardo DiCaprio) create an unexpected family reunion.
Critics Consensus: Marvin's Room rises above the pack of dysfunctional family dramas thanks to an impeccable cast that includes Meryl Streep, Diane Keaton and Leonardo DiCaprio.
Starring: Meryl Streep, Leonardo DiCaprio, Diane Keaton, Robert De Niro
Directed By: Jerry Zaks
9. Once Upon A Time In Hollywood (2019)
Tomatometer: 85%
Audience Score: 70%
Synopsis: Actor Rick Dalton gained fame and fortune by starring in a 1950s television Western, but is now struggling to find meaningful work in a Hollywood that he doesn't recognize anymore. He spends most of his time drinking and palling around with Cliff Booth, his easygoing best friend and longtime stunt double. Rick also happens to live next door to Roman Polanski and Sharon Tate -- the filmmaker and budding actress whose futures will forever be altered by members of the Manson Family.
Critics Consensus: Thrillingly unrestrained yet solidly crafted, Once Upon a Time in Hollywood tempers Tarantino's provocative impulses with the clarity of a mature filmmaker's vision.
Starring: Leonardo DiCaprio, Brad Pitt, Margot Robbie, Kurt Russell
Directed By: Quentin Tarantino
8. The Aviator (2004)
Tomatometer: 86%
Audience Score: 79%
Synopsis: Billionaire and aviation tycoon Howard Hughes (Leonardo DiCaprio) is a successful public figure: a director of big-budget Hollywood films such as Hell's Angels, a passionate lover of Hollywood leading ladies Katharine Hepburn (Cate Blanchett) and Ava Gardner (Kate Beckinsale), and an aviation pioneer who helps build TWA into a major airline. But in private, Hughes remains tormented, suffering from paralyzing phobias and depression. The higher he rises, the farther has to fall.
Critics Consensus: With a rich sense of period detail, The Aviator succeeds thanks to typically assured direction from Martin Scorsese and a strong performance from Leonardo DiCaprio, who charts Howard Hughes' descent from eccentric billionaire to reclusive madman.
Starring: Leonardo DiCaprio, Cate Blanchett, Kate Beckinsale, John C. Reilly
Directed By: Martin Scorsese
7. Titanic (1997)
Tomatometer: 88%
Audience Score: 69%
Synopsis: James Cameron's Titanic is an epic, action-packed romance set against the ill-fated maiden voyage of the R.M.S. Titanic; the pride and joy of the White Star Line and, at the time, the largest moving object ever built. She was the most luxurious liner of her era -- the "ship of dreams" -- which ultimately carried over 1,500 people to their death in the ice cold waters of the North Atlantic in the early hours of April 15, 1912.
Critics Consensus: A mostly unqualified triumph for James Cameron, who offers a dizzying blend of spectacular visuals and old-fashioned melodrama.
Starring: Leonardo DiCaprio, Kate Winslet, Billy Zane, Kathy Bates
Directed By: James Cameron
6. Django Unchained (2012)
Tomatometer: 87%
Audience Score: 92%
Synopsis: Two years before the Civil War, Django (Jamie Foxx), a slave, finds himself accompanying an unorthodox German bounty hunter named Dr. King Schultz (Christoph Waltz) on a mission to capture the vicious Brittle brothers. Their mission successful, Schultz frees Django, and together they hunt the South's most-wanted criminals. Their travels take them to the infamous plantation of shady Calvin Candie (Leonardo DiCaprio), where Django's long-lost wife (Kerry Washington) is still a slave.
Critics Consensus: Bold, bloody, and stylistically daring, Django Unchained is another incendiary masterpiece from Quentin Tarantino
Starring: Jamie Foxx, Christoph Waltz, Leonardo DiCaprio, Samuel L. Jackson
Directed By: Quentin Tarantino
5. Inception (2010)
Tomatometer: 87%
Audience Score: 91%
Synopsis: Dom Cobb (Leonardo DiCaprio) is a thief with the rare ability to enter people's dreams and steal their secrets from their subconscious. His skill has made him a hot commodity in the world of corporate espionage but has also cost him everything he loves. Cobb gets a chance at redemption when he is offered a seemingly impossible task: Plant an idea in someone's mind. If he succeeds, it will be the perfect crime, but a dangerous enemy anticipates Cobb's every move.
Critics Consensus: Smart, innovative, and thrilling, Inception is that rare summer blockbuster that succeeds viscerally as well as intellectually.
Starring: Leonardo DiCaprio, Joseph Gordon-Levitt, Elliot Page, Tom Hardy
Directed By: Christopher Nolan
4. What's Eating Gilbert Grape (1993)
Tomatometer: 90%
Audience Score: 89%
Synopsis: Gilbert Grape (Johnny Depp) is a small-town young man with a lot of responsibility. Chief among his concerns are his mother (Darlene Cates), who is so overweight that she can't leave the house, and his mentally impaired younger brother, Arnie (Leonardo DiCaprio), who has a knack for finding trouble. Settled into a job at a grocery store and an ongoing affair with local woman Betty Carver (Mary Steenburgen), Gilbert finally has his life shaken up by the free-spirited Becky (Juliette Lewis).
Critics Consensus: It's sentimental and somewhat predictable, but those are small complaints, given the tender atmosphere and moving performances at the heart of What's Eating Gilbert Grape.
Starring: Johnny Depp, Juliette Lewis, Mary Steenburgen, Leonardo DiCaprio
Directed By: Lasse Hallström
Directed By: Lasse Hallström
3. The Departed (2006)
Tomatometer: 91%
Audience Score: 94%
Synopsis: South Boston cop Billy Costigan (Leonardo DiCaprio) goes under cover to infiltrate the organization of gangland chief Frank Costello (Jack Nicholson). As Billy gains the mobster's trust, a career criminal named Colin Sullivan (Matt Damon) infiltrates the police department and reports on its activities to his syndicate bosses. When both organizations learn they have a mole in their midst, Billy and Colin must figure out each other's identities to save their own lives.
Critics Consensus: Featuring outstanding work from an excellent cast, The Departed is a thoroughly engrossing gangster drama with the gritty authenticity and soupy morality we come to expect from Martin Scorsese.
Starring: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg
Directed By: Martin Scorsese
2. Killers of the Flower Moon (2023)
Tomatometer: 94%
Synopsis: Based on David Grann's broadly lauded best-selling book, "Killers of the Flower Moon" is set in 1920s Oklahoma and depicts the serial murder of members of the oil-wealthy Osage Nation, a string of brutal crimes that came to be known as the Reign of Terror.
Critics Consensus: Enormous in runtime, theme, and achievement, Killers of the Flower Moon is a sobering appraisal of America's relationship with Indigenous peoples and yet another artistic zenith for Martin Scorsese and his collaborators.
Director: Martin Scorsese
Starring: Leonardo DiCaprio, Robert De Niro, Lily Gladstone
1. Catch Me If You Can (2002)
Tomatometer: 96%
Audience Score: 89%
Synopsis: Frank Abagnale, Jr. (Leonardo DiCaprio) worked as a doctor, a lawyer, and as a co-pilot for a major airline -- all before his 18th birthday. A master of deception, he was also a brilliant forger, whose skill gave him his first real claim to fame: At the age of 17, Frank Abagnale, Jr. became the most successful bank robber in the history of the U.S. FBI Agent Carl Hanratty (Tom Hanks) makes it his prime mission to capture Frank and bring him to justice, but Frank is always one step ahead of him.
Critics Consensus: With help from a strong performance by Leonardo DiCaprio as real-life wunderkind con artist Frank Abagnale, Steven Spielberg crafts a film that's stylish, breezily entertaining, and surprisingly sweet.
Starring: Leonardo DiCaprio, Tom Hanks, Christopher Walken, Martin Sheen
Directed By: Steven Spielberg
