Leonardo DiCaprio’s 35-Film Career: From ‘Critters 3’ to ‘Killers of the Flower Moon’
Leonardo DiCaprio has built a remarkable and varied filmography over more than three decades. From his early days as a child actor to his current status as a global movie star and acclaimed performer, his career is a journey through different genres and increasingly complex roles. He has worked with some of the most celebrated directors in cinema, consistently delivering performances that capture attention and drive conversation.
His path shows a clear progression from a teen heartthrob to a serious dramatic actor, willing to take on challenging and often unconventional parts. This evolution is marked by collaborations with legendary filmmakers, a commitment to environmental advocacy through his documentary work, and an impressive collection of awards and nominations. DiCaprio’s body of work reflects a deliberate and thoughtful approach to his craft, making him one of the most respected actors of his generation.
Critters 3 (1991)
Leonardo DiCaprio’s first movie role was in the direct-to-video horror sequel ‘Critters 3’. He played Josh, the stepson of a greedy landlord who finds his apartment building under attack by the small, furry alien creatures. It was a humble beginning for an actor who would later become one of Hollywood’s biggest stars.
The film itself is a campy creature feature, typical of the early ’90s horror scene. While it might not be a highlight on his resume, his appearance in the movie is a fun piece of trivia for his followers. It marked his entry into feature films before he moved on to more significant and artistically fulfilling projects.
This Boy’s Life (1993)
In this biographical drama, DiCaprio delivered a powerful performance as Tobias ‘Toby’ Wolff, a rebellious teenager in the 1950s. The film is based on the real-life memoirs of the author, detailing his difficult relationship with an abusive stepfather, Dwight Hansen, played by Robert De Niro.
DiCaprio was chosen for the role by De Niro himself from a pool of hundreds of young actors. His portrayal of Toby’s struggle and resilience in the face of emotional and physical turmoil was praised by critics. The film established him as a serious young actor with immense potential and a commanding screen presence.
What’s Eating Gilbert Grape (1993)
DiCaprio’s role as Arnie Grape, the mentally impaired younger brother of Gilbert, played by Johnny Depp, earned him widespread critical acclaim. To prepare for the part, he spent time at a home for children with developmental disabilities, carefully observing their mannerisms to create an authentic and touching character.
His performance was so convincing that many viewers believed the actor himself had a mental disability. For this role, he received his first Academy Award and Golden Globe nominations, which was a huge achievement for a teenage actor. The film showed his remarkable talent and his ability to completely transform for a role.
The Basketball Diaries (1995)
Based on the autobiographical book by Jim Carroll, this film features DiCaprio as a promising high school basketball player and writer whose life spirals into heroin addiction. The movie offers a raw and unflinching look at the destructive nature of drug use on the streets of New York City.
DiCaprio’s portrayal of Jim’s descent and eventual struggle for recovery was intense and gripping. He captured the character’s vulnerability and desperation with a performance that was both disturbing and moving. The film also features Mark Wahlberg in an early supporting role.
The Quick and the Dead (1995)
In this stylish Western directed by Sam Raimi, DiCaprio played the role of Fee ‘The Kid’ Herod. The character is the arrogant, fast-drawing son of the ruthless outlaw John Herod, played by Gene Hackman. The Kid participates in a deadly gunfighting tournament to earn his father’s respect.
DiCaprio brought a youthful energy and charm to the role, standing out in a cast that also included Sharon Stone and Russell Crowe. Though his screen time is limited, his confident performance as the ambitious gunslinger was memorable and added a unique dynamic to the film.
Total Eclipse (1995)
DiCaprio took on the challenging role of the brilliant and rebellious 19th-century French poet Arthur Rimbaud in this biographical drama. The film explores his passionate and destructive relationship with the older poet Paul Verlaine, played by David Thewlis.
He portrayed Rimbaud as a magnetic and volatile young genius, capturing the poet’s defiant spirit. The film was noted for its frank depiction of their love affair and its exploration of artistic creation and self-destruction. It was another example of DiCaprio’s willingness to take on complex and unconventional roles.
Romeo + Juliet (1996)
Baz Luhrmann’s modern adaptation of Shakespeare’s classic play cast DiCaprio as Romeo Montague. Set in a stylized, contemporary Verona Beach, the film retained the original Shakespearean dialogue but placed the story in a world of gang violence, fast cars, and modern fashion.
DiCaprio’s performance as the passionate and impulsive Romeo, alongside Claire Danes as Juliet, made him a global teen idol. The film’s energetic visuals and his romantic portrayal resonated with a younger audience, turning a classic tragedy into a modern pop culture event.
Marvin’s Room (1996)
In this family drama, DiCaprio played Hank, a troubled and rebellious teenager who is committed to a mental institution. The film revolves around two estranged sisters, played by Meryl Streep and Diane Keaton, who are forced to reconnect when one is diagnosed with leukemia.
DiCaprio’s character is the son of Streep’s character, and his anger and emotional turmoil are a central part of the family’s dysfunction. He delivered a strong performance alongside a veteran cast, holding his own and providing a raw, emotional core to the story.
Titanic (1997)
Playing the role of Jack Dawson, a poor artist who wins a third-class ticket on the doomed RMS Titanic, catapulted DiCaprio to international superstardom. The epic romance and disaster film, directed by James Cameron, became one of the highest-grossing movies of all time.
His on-screen chemistry with Kate Winslet, who played the wealthy socialite Rose DeWitt Bukater, created one of cinema’s most iconic love stories. The film’s massive success cemented his status as a leading man and a global phenomenon, though he famously did not receive an Oscar nomination for the role.
The Man in the Iron Mask (1998)
In this historical adventure film, DiCaprio took on a dual role, playing both the cruel and arrogant King Louis XIV of France and his secret, kind-hearted twin brother, Philippe. The story follows the legendary Three Musketeers as they attempt to replace the tyrannical king with his twin.
This was his first film after the massive success of ‘Titanic’, and it gave him the opportunity to play both a hero and a villain in the same movie. The film was a commercial success, further solidifying his position as a major box office draw.
Celebrity (1998)
DiCaprio made a brief but memorable appearance in Woody Allen’s black-and-white film ‘Celebrity’. He played Brandon Darrow, a self-absorbed and out-of-control young movie star who leads a life of excess and bad behavior.
His role was a satirical take on the nature of fame, showing a wilder side that contrasted with his romantic image from ‘Titanic’. Even in a small part, he made an impression, showcasing his versatility and willingness to play against type.
The Beach (2000)
In this adventure drama directed by Danny Boyle, DiCaprio starred as Richard, a young American backpacker in Thailand who is searching for an authentic, off-the-grid experience. He discovers a map to a legendary, hidden island paradise and sets off to find it.
The film explores themes of utopia, disillusionment, and the darker side of human nature when a perfect community begins to fall apart. DiCaprio’s character goes on a psychological journey from idealism to paranoia, and the film became a cult favorite for many travelers.
Don’s Plum (2001)
This black-and-white independent film was shot in the mid-90s but faced a delayed and limited release due to legal disputes with its stars, DiCaprio and Tobey Maguire. The largely improvised film features a group of young adults having conversations at a diner over one night.
DiCaprio and Maguire stated they had agreed to participate in a short film as a favor, not a feature-length production, and successfully blocked its release in the US and Canada. The film shows a raw, unfiltered side of the actors, and its controversial history has made it a curious piece of their filmographies.
Gangs of New York (2002)
This marked DiCaprio’s first collaboration with director Martin Scorsese. In the historical epic set in the violent Five Points neighborhood of 1860s New York City, DiCaprio played Amsterdam Vallon, a young Irish immigrant seeking revenge against the powerful gang leader who killed his father.
To prepare for the role, DiCaprio underwent extensive training in 19th-century fighting styles. His performance as the driven and conflicted Amsterdam was a key part of the film’s gritty portrayal of a formative period in American history.
Catch Me If You Can (2002)
In this biographical crime film directed by Steven Spielberg, DiCaprio played Frank Abagnale Jr., a real-life con artist who successfully posed as a pilot, doctor, and lawyer before his 19th birthday. The film follows the cat-and-mouse chase between Frank and the FBI agent, played by Tom Hanks, who is determined to catch him.
DiCaprio’s charming and energetic performance captured the charisma that allowed Frank to pull off his incredible deceptions. The film was both a critical and commercial success, showcasing a lighter, more playful side of his acting abilities.
The Aviator (2004)
In his second collaboration with Martin Scorsese, DiCaprio portrayed the eccentric and visionary billionaire Howard Hughes. The biographical drama follows Hughes’s life from the late 1920s to the late 1940s, covering his career as a film producer and aviation pioneer, as well as his struggles with severe obsessive-compulsive disorder.
DiCaprio’s detailed and deeply researched performance earned him his first Academy Award nomination for Best Actor. He masterfully depicted both the public genius and the private torment of Hughes, capturing his descent into isolation and mental illness.
The Departed (2006)
This critically acclaimed crime thriller, and DiCaprio’s third film with Martin Scorsese, saw him play William ‘Billy’ Costigan, an undercover state trooper who infiltrates an Irish Mob crew in Boston. The film’s plot involves a parallel story of a mob mole, played by Matt Damon, who has infiltrated the police force.
DiCaprio’s portrayal of Billy’s intense stress and deteriorating mental state as he lives a dangerous double life was highly praised. The film won the Academy Award for Best Picture, and his performance is often cited as one of the best of his career.
Blood Diamond (2006)
Set during the Sierra Leone Civil War, this political thriller stars DiCaprio as Danny Archer, a cynical and resourceful diamond smuggler from Zimbabwe. He becomes involved with a fisherman, played by Djimon Hounsou, who has discovered a rare pink diamond.
DiCaprio adopted a convincing South African accent for the role and delivered a powerful performance that highlighted the brutal human cost of the conflict diamond trade. He received an Academy Award nomination for Best Actor for his work in the film.
The 11th Hour (2007)
DiCaprio co-wrote, produced, and narrated this documentary about the state of the natural environment. The film explores the grave problems facing the planet, such as global warming, deforestation, and mass species extinction.
Featuring interviews with over 50 politicians, scientists, and environmental activists, the film serves as a call to action for humanity to address climate change. It marked a significant step in DiCaprio’s public advocacy for environmental issues, using his platform to raise awareness about a cause he is passionate about.
Body of Lies (2008)
In this spy thriller directed by Ridley Scott, DiCaprio played Roger Ferris, a CIA operative on the ground in the Middle East trying to track down a high-level terrorist. He works with his manipulative boss, played by Russell Crowe, who gives him commands from Washington D.C.
DiCaprio portrayed the physical and psychological toll of intelligence work in a dangerous environment. The film is a tense and complex look at modern espionage and the moral compromises involved.
Revolutionary Road (2008)
This film reunited DiCaprio with his ‘Titanic’ co-star Kate Winslet. They play Frank and April Wheeler, a seemingly perfect couple living in a 1950s Connecticut suburb who find themselves trapped in a life of conformity and unfulfilled dreams.
The movie is a powerful and heartbreaking examination of a marriage falling apart and the death of the American Dream. Both DiCaprio and Winslet received critical acclaim for their raw and emotionally devastating performances, which explored the bitterness and desperation lurking beneath a picture-perfect surface.
Shutter Island (2010)
In his fourth collaboration with Martin Scorsese, DiCaprio starred as U.S. Marshal Teddy Daniels. In this psychological thriller, Teddy and his new partner, played by Mark Ruffalo, travel to a remote hospital for the criminally insane to investigate the disappearance of a patient.
The film is filled with suspense and paranoia, and DiCaprio’s character becomes increasingly unraveled as he uncovers disturbing secrets about the island and confronts his own past. The movie’s shocking twist ending left audiences questioning everything they had seen.
Hubble (2010)
DiCaprio served as the narrator for this IMAX 3D documentary about the Hubble Space Telescope. The film takes viewers on a journey through distant galaxies and showcases stunning images of the universe.
The documentary also follows the astronauts of the Space Shuttle Atlantis on their mission to perform vital repairs and upgrades to the telescope. DiCaprio’s narration guides the audience through the wonders of space and the importance of this scientific instrument.
Inception (2010)
In this mind-bending science fiction film from director Christopher Nolan, DiCaprio played Dom Cobb, a skilled thief who steals information by entering people’s dreams. He is offered a chance to have his criminal record erased in exchange for performing the seemingly impossible task of ‘inception’ – planting an idea into a target’s subconscious.
The film was celebrated for its originality, complex narrative, and stunning visual effects. DiCaprio’s performance as the haunted and conflicted Cobb, who is trying to find his way back to his children, anchored the film’s emotional core.
J. Edgar (2011)
Directed by Clint Eastwood, this biographical drama saw DiCaprio take on the role of J. Edgar Hoover, the powerful and controversial first director of the Federal Bureau of Investigation. The film spans nearly 50 years of Hoover’s life, from his rise to power to his later years.
DiCaprio underwent significant physical transformation with the help of prosthetics and makeup to portray Hoover as an older man. He captured the complex and secretive nature of a public figure who wielded immense power while hiding personal secrets.
Django Unchained (2012)
In this Quentin Tarantino-directed Western, DiCaprio played his first true villain role as Calvin J. Candie, a ruthless and charismatic plantation owner in pre-Civil War Mississippi. He is the cruel master of Candyland, where he forces his slaves to fight to the death.
DiCaprio’s performance was both charming and terrifying, and he famously injured his hand during a scene where he slammed it on a table, but continued with the take. He received a Golden Globe nomination for his chilling portrayal of the sadistic slave owner.
The Great Gatsby (2013)
DiCaprio took on the iconic literary role of Jay Gatsby in Baz Luhrmann’s lavish adaptation of F. Scott Fitzgerald’s classic novel. The film brings the roaring twenties to life with a modern soundtrack and dazzling visual style.
He portrayed the mysterious and endlessly optimistic millionaire who throws extravagant parties in the hope of reuniting with his lost love, Daisy Buchanan. His performance captured both the glamour and the deep-seated loneliness of the character.
The Wolf of Wall Street (2013)
In his fifth film with Martin Scorsese, DiCaprio played Jordan Belfort, a real-life stockbroker who engaged in massive corruption and fraud on Wall Street in the 1990s. The film is a dark comedy that depicts a world of extreme greed, debauchery, and excess.
DiCaprio’s energetic and uninhibited performance was widely praised and earned him a Golden Globe for Best Actor. The film was both celebrated and criticized for its unapologetic portrayal of financial crimes and a hedonistic lifestyle.
The Revenant (2015)
This survival drama finally earned DiCaprio his first Academy Award for Best Actor. He played Hugh Glass, a real-life frontiersman in the 1820s who is left for dead by his companions after being mauled by a bear. The film follows his grueling journey of survival and revenge through the harsh wilderness.
The production was famously difficult, with DiCaprio enduring freezing conditions and performing physically demanding scenes, including eating raw bison liver. His performance was a testament to his dedication and commitment as an actor.
The Audition (2015)
This short film, directed by Martin Scorsese, was created as a promotional piece for the Studio City and City of Dreams casinos in Macau and Manila. DiCaprio and Robert De Niro play fictionalized versions of themselves, competing for the same role in Scorsese’s next film.
The short is a humorous look at the rivalry between two of Scorsese’s most frequent collaborators. It also features Brad Pitt and is a rare comedic turn for all involved.
Before the Flood (2016)
In his second major environmental documentary, DiCaprio again served as a producer and on-screen guide. The film follows him as he travels to five continents and the Arctic to witness the effects of climate change firsthand.
He speaks with scientists, world leaders, and activists to understand the challenges and potential solutions to this global crisis. The documentary aimed to make the issue of climate change accessible and urgent for a wide audience.
Once Upon a Time in Hollywood (2019)
In Quentin Tarantino’s ninth film, DiCaprio played Rick Dalton, a fictional, aging television actor who struggles to find his place in a rapidly changing Hollywood in 1969. His best friend and stunt double, Cliff Booth, is played by Brad Pitt.
DiCaprio’s performance captured the insecurity and desperation of an actor facing his own fading relevance. The role was both humorous and poignant, and it earned him another Academy Award nomination for Best Actor.
Ice on Fire (2019)
Continuing his work as an environmental advocate, DiCaprio produced and narrated this HBO documentary. The film focuses on the potential solutions to reverse the effects of climate change, looking at innovative science and technologies.
Unlike some earlier environmental films that focused on the problems, ‘Ice on Fire’ offers a more hopeful message. It explores methods that could potentially reduce carbon in the atmosphere and stabilize the climate.
Don’t Look Up (2021)
This satirical science fiction film cast DiCaprio as Dr. Randall Mindy, an astronomer who, along with his student played by Jennifer Lawrence, discovers a comet on a direct collision course with Earth. They embark on a media tour to warn a distracted and disbelieving world.
The film serves as an allegory for the climate crisis and the public’s and media’s inability to seriously address existential threats. DiCaprio’s performance as the anxious and increasingly exasperated scientist was a central part of the film’s dark humor and social commentary.
Killers of the Flower Moon (2023)
In his latest collaboration with Martin Scorsese, DiCaprio stars as Ernest Burkhart. The film is based on the true story of the Osage Nation murders in the 1920s, after oil was discovered on their land in Oklahoma. Burkhart is a white man married to an Osage woman, played by Lily Gladstone, who becomes entangled in a series of brutal crimes orchestrated by his uncle, a powerful local cattleman played by Robert De Niro.
The film is a gripping crime saga that explores a dark chapter in American history. DiCaprio’s portrayal of the morally conflicted Ernest, caught between love for his wife and loyalty to his greedy family, is a complex and powerful performance.
Which Leonardo DiCaprio performance do you believe is his absolute best? Let me know your pick in the comments below.