Leonardo DiCaprio’s Career: From ‘Critters 3’ to ‘Killers of the Flower Moon’

Leonardo DiCaprio is a figure who needs little introduction, a true titan of modern cinema who has managed the rare feat of evolving from a teen heartthrob into one of the most respected and powerful actors of his generation. His career is defined by his intense dedication to his craft, his strategic choice of complex roles, and his celebrated collaborations with some of the world’s greatest directors. From his early days as a promising young talent to his status as an Academy Award-winning leading man, DiCaprio has consistently challenged himself and his audiences.

Beyond his on-screen work, DiCaprio has also become a prominent and passionate advocate for environmental causes, using his immense platform to raise awareness about climate change and conservation. This commitment often intertwines with his film projects, adding another layer to a career built on purpose and prestige. His journey is a masterclass in navigating the demands of Hollywood stardom while maintaining artistic integrity, securing his place as a cinematic icon.

‘Critters 3’ (1991)

Leonardo DiCaprio made his feature film debut in this direct-to-video horror-comedy. In the film, a family returning from a road trip unknowingly brings a litter of the furry, carnivorous alien creatures back to their Los Angeles apartment building. DiCaprio played Josh, the young stepson of the building’s corrupt landlord.

It was a humble beginning for an actor who would go on to become a global superstar. The role was a small part of his early work as a child actor in television and commercials, but it holds the distinction of being his very first step into the world of film.

‘This Boy’s Life’ (1993)

In his first major leading role, Leonardo DiCaprio played the real-life author Tobias “Toby” Wolff. The biographical drama is based on Wolff’s memoir and chronicles his volatile relationship with his abusive and tyrannical stepfather, Dwight Hansen, played by Robert De Niro.

DiCaprio’s performance was a revelation, earning him widespread critical acclaim for his ability to hold his own opposite a screen legend like De Niro. He powerfully conveyed the mix of rebellion, vulnerability, and resilience of a young man trying to survive in a toxic environment, signaling the arrival of a major dramatic talent.

‘What’s Eating Gilbert Grape’ (1993)

Leonardo DiCaprio gave a stunning breakthrough performance as Arnie Grape, the severely mentally impaired younger brother of the title character. The film follows the life of a young man in a small town who is responsible for caring for Arnie and his morbidly obese mother.

For his incredibly convincing and touching portrayal, DiCaprio received his first Academy Award and Golden Globe nominations. He spent time at a home for mentally disabled teens to research the role, and his performance was so realistic that many audience members believed the actor himself had a mental disability.

‘The Basketball Diaries’ (1995)

Leonardo DiCaprio starred as the teenage author and musician Jim Carroll in this biographical drama based on Carroll’s memoir of the same name. The film chronicles his descent from a promising high school basketball star to a heroin addict on the streets of New York City.

The role was another showcase for DiCaprio’s fearless intensity as a young actor. He fully committed to the harrowing depiction of addiction, delivering a raw and visceral performance that further cemented his reputation for taking on dark and challenging material.

‘The Quick and the Dead’ (1995)

In this stylish Western directed by Sam Raimi, Leonardo DiCaprio played Fee “The Kid” Herod. He is the cocky, fast-drawing son of the ruthless outlaw who rules the town and is hosting a deadly gunslinging competition. The Kid enters the tournament hoping to finally earn his father’s respect.

This supporting role allowed DiCaprio to work with established stars like Sharon Stone and Gene Hackman and showed his versatility in a more traditional genre film. He brought a youthful charm and arrogance to the character, making him a memorable part of the ensemble.

‘Total Eclipse’ (1995)

Leonardo DiCaprio portrayed the brilliant and volatile 19th-century French poet Arthur Rimbaud. The film focuses on the passionate, destructive, and scandalous affair between the teenage Rimbaud and the older, married poet Paul Verlaine.

This was another demanding and unconventional choice for the young actor, further demonstrating his attraction to complex, often unlikeable characters. His performance captured the wild, rebellious spirit of the poetic genius, and he once again proved he was unafraid of controversial roles.

‘Romeo + Juliet’ (1996)

Leonardo DiCaprio took on the iconic role of Romeo Montague in Baz Luhrmann’s frenetic, modern-day adaptation of the classic Shakespearean tragedy. Set in the fictional “Verona Beach,” the film retains Shakespeare’s original dialogue while placing the story in a contemporary, stylized world of gangs and gun violence.

The film was a massive international hit that launched DiCaprio into the stratosphere of fame, officially making him a global teen idol. His passionate and charismatic performance as the star-crossed lover cemented his status as a bankable Hollywood leading man.

‘Marvin’s Room’ (1996)

In this family drama, Leonardo DiCaprio played Hank Lacker, a troubled and rebellious teenager who has been committed to a mental institution for burning down his family’s house. The film centers on two estranged sisters who are forced to reconnect when one is diagnosed with leukemia.

Acting alongside a powerhouse cast that included Meryl Streep, Diane Keaton, and Robert De Niro, DiCaprio once again proved his dramatic abilities. He gave a powerful and sensitive performance as the angry and misunderstood young man at the heart of the family’s dysfunction.

‘Titanic’ (1997)

In one of the most iconic roles in film history, Leonardo DiCaprio starred as Jack Dawson, a poor, third-class artist who wins a ticket onto the maiden voyage of the RMS Titanic. Aboard the ship, he falls in love with Rose DeWitt Bukater, a young woman from a wealthy family who is unhappily engaged to a domineering millionaire.

The film, directed by James Cameron, became a cultural phenomenon and, at the time, the highest-grossing movie ever made. It solidified DiCaprio’s status as a global superstar and a romantic leading man, and “Leo-Mania” swept the globe.

‘The Man in the Iron Mask’ (1998)

Leonardo DiCaprio took on the challenge of a dual role in this historical adventure. He played both the cruel and arrogant King Louis XIV of France and his secret twin brother, Philippe, who has been imprisoned his entire life to hide his existence. The aging Three Musketeers plot to replace the evil king with his gentle brother.

Released in the wake of his ‘Titanic’ fame, the film was a commercial success. It showcased DiCaprio’s ability to portray both a hissable villain and a sympathetic hero within the same movie, demonstrating his impressive range.

‘Celebrity’ (1998)

In this Woody Allen film, Leonardo DiCaprio made a memorable cameo appearance as Brandon Darrow. The movie follows a journalist through a series of misadventures in the world of the rich and famous. DiCaprio’s character is a spoiled, out-of-control young movie star.

His role was a very self-aware parody of the mega-fame he was experiencing at the time. He fearlessly portrayed the worst stereotypes of a young celebrity, trashing a hotel room and demonstrating a willingness to poke fun at his own public image.

‘The Beach’ (2000)

Leonardo DiCaprio starred as Richard, a young American backpacker looking for adventure in Thailand. He comes into possession of a map that supposedly leads to a secret, idyllic island paradise, and he sets off to find this hidden community, only to discover that paradise has a dark side.

This was a highly anticipated film and marked a conscious effort by DiCaprio to move into more complex and adult-oriented roles. The movie explores themes of utopianism, corruption, and the loss of innocence.

‘Don’s Plum’ (2001)

This low-budget, black-and-white independent film was shot in the mid-1990s as a largely improvised project between DiCaprio and his friends, including Tobey Maguire and Kevin Connolly. The film consists of a group of young friends meeting at their regular diner spot to talk about their lives over one night.

The film became the subject of a major controversy and lawsuit. DiCaprio and Maguire blocked its release in the United States and Canada, arguing that they had only intended it to be an acting exercise and that it was never meant to be a commercial feature film.

‘Gangs of New York’ (2002)

This film marked the beginning of one of modern cinema’s most important collaborations, pairing Leonardo DiCaprio with legendary director Martin Scorsese for the first time. Set in the 1860s, the epic historical drama follows Amsterdam Vallon, a young man who returns to the violent Five Points neighborhood of New York City to seek revenge on the ruthless gang leader who murdered his father.

This role was a crucial turning point in DiCaprio’s career. It signaled his full transition from teen idol to a serious, respected adult actor and began a creative partnership with Scorsese that would redefine his career and produce some of his finest work.

‘Catch Me If You Can’ (2002)

In this breezy and entertaining caper directed by Steven Spielberg, Leonardo DiCaprio played the real-life con artist Frank Abagnale Jr. The film chronicles Frank’s incredible story of successfully impersonating a Pan Am pilot, a doctor, and a lawyer, all while being pursued by a determined FBI agent.

DiCaprio’s charming and energetic performance was highly praised, earning him a Golden Globe nomination. He perfectly captured the fun and adventure of Frank’s exploits while also conveying the underlying loneliness and desperation of a young man on the run.

‘The Aviator’ (2004)

Reuniting with Martin Scorsese, Leonardo DiCaprio delivered a powerful performance as the visionary and deeply troubled billionaire Howard Hughes. The biographical drama charts several decades of Hughes’s life, from his career as a successful filmmaker and daring aviation pioneer to his descent into crippling obsessive-compulsive disorder and isolation.

For his stunning and transformative portrayal, DiCaprio won the Golden Globe for Best Actor and received his second Academy Award nomination. The role required him to show both Hughes’s commanding public persona and his tortured private existence, and it was a tour-de-force performance.

‘The Departed’ (2006)

In his third collaboration with Martin Scorsese, Leonardo DiCaprio starred as William “Billy” Costigan. He is a young Massachusetts state trooper who goes deep undercover to infiltrate the inner circle of a ruthless Irish Mob boss, played by Jack Nicholson.

DiCaprio gave a raw and intense performance, masterfully conveying the immense psychological stress and constant fear of a man living a double life where one wrong move means death. The film was a critical and commercial smash hit, finally winning Scorsese the Academy Award for Best Director.

‘Blood Diamond’ (2006)

Leonardo DiCaprio played Danny Archer, a cynical and resourceful white Rhodesian gunrunner and diamond smuggler in war-torn 1990s Sierra Leone. He becomes involved with a local fisherman who has found a massive, rare diamond that could be his ticket out of Africa.

For his gritty and committed performance, which required mastering a difficult South African accent, DiCaprio received another Academy Award nomination. The role showcased his ability to excel as a morally ambiguous anti-hero and brought attention to the real-world issue of conflict diamonds.

‘The 11th Hour’ (2007)

Leonardo DiCaprio served as the narrator and producer of this feature-length documentary about the environmental crises facing the planet. The film features interviews with dozens of scientists, politicians, and activists who discuss the state of the natural world and the urgent need for action.

This project was a clear and powerful demonstration of DiCaprio’s off-screen passion for environmentalism. He used his celebrity and resources to create a film that aimed to educate audiences and inspire change, a cause he would continue to champion throughout his career.

‘Body of Lies’ (2008)

In this spy thriller from director Ridley Scott, Leonardo DiCaprio played Roger Ferris, a brilliant CIA operative on the ground in the Middle East. He is hunting a major terrorist leader but finds his efforts complicated by his tense relationship with his superior back in the United States.

DiCaprio delivered a solid and believable performance as the capable but increasingly world-weary agent. The role continued his trend of starring in intelligent, complex thrillers that explore the moral gray areas of modern geopolitics.

‘Revolutionary Road’ (2008)

This film marked the highly anticipated reunion of Leonardo DiCaprio and his ‘Titanic’ co-star Kate Winslet. They played Frank and April Wheeler, a seemingly perfect young couple living in a Connecticut suburb in the 1950s whose marriage and dreams are slowly disintegrating under the pressure of conformity.

The movie is a devastating portrait of a relationship falling apart. DiCaprio and Winslet’s performances were praised for their raw, unflinching honesty, and DiCaprio earned another Golden Globe nomination for his portrayal of a man trapped between his desires and his perceived responsibilities.

‘Shutter Island’ (2010)

In his fourth collaboration with Martin Scorsese, Leonardo DiCaprio starred as U.S. Marshal Edward “Teddy” Daniels. He and his new partner travel to a remote island hospital for the criminally insane to investigate the impossible disappearance of a patient.

DiCaprio gives a harrowing and intense performance in this twisting psychological thriller. He masterfully portrays Teddy’s unraveling mental state as the investigation delves deeper into the mysteries of the island and the traumas of his own past.

‘IMAX Hubble’ (2010)

Leonardo DiCaprio lent his famous voice to narrate this IMAX 3D documentary. The film follows the astronauts of the Space Shuttle Atlantis on their mission to perform maintenance and repairs on the Hubble Space Telescope.

This was another example of DiCaprio using his platform to support scientific and educational projects. His narration helped to make the wonders of space and the importance of scientific exploration accessible to a wide audience.

‘Inception’ (2010)

Leonardo DiCaprio starred as Dom Cobb in this mind-bending science fiction blockbuster written and directed by Christopher Nolan. Cobb is a professional thief who specializes in “extraction,” stealing secrets from deep within a person’s subconscious during a dream state. He is offered a chance at redemption if he can pull off the impossible: “inception,” planting an idea into someone’s mind.

The film was a global phenomenon, praised for its originality and complexity. DiCaprio’s performance provided the emotional anchor for the high-concept story, portraying Cobb as a haunted and tormented man whose personal stakes were the heart of the film.

‘J. Edgar’ (2011)

In this biographical drama directed by Clint Eastwood, Leonardo DiCaprio took on the monumental role of J. Edgar Hoover. The film chronicles Hoover’s long and controversial career as the first and most powerful director of the Federal Bureau of Investigation (FBI).

DiCaprio underwent a significant physical transformation for the role, using prosthetics to portray Hoover over several decades. His complex and nuanced performance captured the man’s ambition, his secrets, and his iron grip on American power, earning him more award nominations.

‘Django Unchained’ (2012)

In a shocking and brilliant departure, Leonardo DiCaprio played his first true villain in this Quentin Tarantino Western. He portrayed “Monsieur” Calvin J. Candie, the charming but monstrously cruel and sadistic owner of a Mississippi plantation called Candyland.

DiCaprio’s terrifying performance was one of the most talked-about aspects of the film, earning him a Golden Globe nomination. He fully committed to the character’s depravity, famously cutting his hand on glass during a scene but never breaking character, creating one of cinema’s most memorable modern villains.

‘The Great Gatsby’ (2013)

Reuniting with director Baz Luhrmann, Leonardo DiCaprio took on the iconic literary role of Jay Gatsby. This lavish and stylized adaptation of F. Scott Fitzgerald’s classic novel tells the story of the mysterious and fabulously wealthy millionaire who throws extravagant parties in the hope of reuniting with the love of his life.

DiCaprio perfectly embodied the character’s immense charisma, his romantic obsession, and the deep vulnerability hidden beneath his glamorous facade. His performance was praised for capturing the very essence of one of American literature’s most famous figures.

‘The Wolf of Wall Street’ (2013)

In his fifth film with Martin Scorsese, Leonardo DiCaprio gave a tour-de-force performance as the real-life stockbroker Jordan Belfort. The film is a debaucherous black comedy that chronicles Belfort’s meteoric rise as a wealthy and corrupt Wall Street tycoon and his subsequent fall from grace.

DiCaprio’s portrayal of Belfort was fearless, hilarious, and utterly unapologetic, diving headfirst into the character’s hedonistic and excessive lifestyle. For his incredible comedic and dramatic performance, he won the Golden Globe for Best Actor.

‘The Revenant’ (2015)

Leonardo DiCaprio starred as the legendary 19th-century frontiersman Hugh Glass. The film tells the incredible survival story of Glass, who, after being brutally mauled by a bear and left for dead by his companions, endures an unimaginably perilous journey through the harsh winter wilderness to seek revenge.

The role was physically and emotionally grueling, requiring DiCaprio to endure freezing conditions and perform intense physical stunts. His deeply committed performance, which features very little dialogue, finally earned him his long-awaited and well-deserved Academy Award for Best Actor.

‘The Audition’ (2015)

In this short film, which was a high-concept advertisement for a new casino resort, Leonardo DiCaprio starred as a fictionalized version of himself. Directed by Martin Scorsese, the comedic short follows DiCaprio and Robert De Niro as they arrive at the casino and discover they are both competing for the same role in Scorsese’s next movie.

The film playfully pits the two legendary Scorsese collaborators against each other. It was a fun, lighthearted project that showcased the close relationship between the three cinematic giants.

‘Before the Flood’ (2016)

In this feature-length documentary, Leonardo DiCaprio travels the globe to witness firsthand the devastating effects of climate change. As a UN Messenger of Peace, he meets with scientists, world leaders, and activists to discuss the problem and explore potential solutions.

This was his most significant and personal environmental project to date. He used his global fame and access to create a powerful and comprehensive call to action, urging audiences to confront the reality of the climate crisis.

‘Once Upon a Time… in Hollywood’ (2019)

Leonardo DiCaprio starred as Rick Dalton, a fading television Western star in 1969 Hollywood. He and his stunt double, played by Brad Pitt, struggle to navigate the changing industry and find their place in a world that seems to be leaving them behind. This was his second film with director Quentin Tarantino.

DiCaprio earned another Academy Award nomination for his funny, vulnerable, and deeply poignant performance. He masterfully captured the anxiety, insecurity, and quiet desperation of an aging actor terrified of becoming a has-been.

‘Ice on Fire’ (2019)

Continuing his work as an environmental advocate, Leonardo DiCaprio served as the narrator for this HBO documentary. Unlike many climate change films that focus on the problem, this movie explores the many innovative solutions that could potentially reverse the crisis.

The film highlights the work of scientists and visionaries who are developing ways to reduce carbon in the atmosphere. DiCaprio’s involvement helped to bring a message of hope and possibility to the climate conversation.

‘Don’t Look Up’ (2021)

In this satirical black comedy, Leonardo DiCaprio played Dr. Randall Mindy, a mild-mannered astronomer who, along with his student, discovers a massive comet on a direct collision course with Earth. They embark on a frantic media tour to warn a world that is too distracted by politics and social media to care about its impending doom.

The film served as a direct allegory for the climate change crisis. DiCaprio’s performance as the increasingly panicked and exasperated scientist perfectly blended his acting career with his passionate real-world advocacy.

‘Killers of the Flower Moon’ (2023)

In his most recent collaboration with Martin Scorsese, Leonardo DiCaprio played Ernest Burkhart. The film is based on the true story of the serial murders of wealthy members of the Osage Nation in Oklahoma in the 1920s after oil was discovered on their land. Burkhart is a World War I veteran who marries an Osage woman and gets drawn into the criminal schemes of his powerful and manipulative uncle.

DiCaprio delivered a complex and unflinching performance as a weak-willed and morally compromised man caught between his love for his family and his complicity in horrific crimes. The role was praised as one of his most challenging and mature, showcasing a man who is not a hero or a villain, but a troubling portrait of human weakness.

From teen heartthrob to cinematic titan, let us know which Leonardo DiCaprio role you believe best defines his incredible career in the comments.