Leonardo DiCaprio’s Best Roles

Leonardo DiCaprio has crafted a career that few actors ever achieve. Starting as a young television actor, he quickly became a teen heartthrob in the 1990s. However, he deliberately moved away from that image, choosing complex and challenging roles that pushed his abilities. He has become one of the most respected actors of his generation, known for his intense performances and his dedication to his craft.

His long-standing collaborations with legendary directors like Martin Scorsese have defined much of his career. DiCaprio consistently seeks out roles that explore the darker and more complicated aspects of human nature. From historical figures and charming con artists to tormented lawmen and vengeful frontiersmen, his filmography is a testament to his incredible range and commitment. This list celebrates fifteen of his most powerful and unforgettable performances.

‘The Revenant’ (2015)

In this grueling survival epic, Leonardo DiCaprio plays Hugh Glass, a frontiersman left for dead after a brutal bear attack. The role is intensely physical, with very little dialogue. Glass must crawl and fight his way through a harsh, frozen wilderness on a quest for revenge against the man who betrayed him and killed his son.

For this performance, DiCaprio finally won the Academy Award for Best Actor. He endured extreme conditions, including freezing temperatures and eating raw bison liver, to fully embody the character’s struggle. The performance is a masterclass in physical acting, conveying immense pain, grief, and determination almost entirely through expression and action.

‘The Wolf of Wall Street’ (2013)

As the corrupt stockbroker Jordan Belfort, Leonardo DiCaprio delivers a performance of pure, chaotic energy. He portrays Belfort’s rise from an ambitious salesman to the leader of a fraudulent empire built on greed and excess. The role required DiCaprio to be charismatic, funny, and utterly depraved, often all in the same scene.

DiCaprio dives headfirst into the character’s hedonistic lifestyle, holding nothing back. The performance is a wild, comedic, and often disturbing look at unchecked ambition. His famous speech to his employees and a scene where he crawls to his car while under the influence of drugs are iconic moments that showcase his fearless commitment to the role.

‘What’s Eating Gilbert Grape’ (1993)

In one of his earliest roles, Leonardo DiCaprio plays Arnie Grape, the severely mentally impaired younger brother of the title character. The performance is incredibly convincing and deeply moving. DiCaprio captures the innocence, frustration, and unpredictable behavior of the character with remarkable sensitivity and accuracy for such a young actor.

The role earned him his first Academy Award nomination and proved he was a serious talent. He spent time at a home for mentally disabled teens to prepare, and his portrayal is full of small, authentic details. It remains one of the most impressive and transformative performances of his entire career.

‘Titanic’ (1997)

As the charming, third-class artist Jack Dawson, Leonardo DiCaprio became a global superstar. He falls in love with the wealthy but constrained Rose DeWitt Bukater aboard the ill-fated ship. Jack represents freedom, passion, and a life outside the rigid rules of high society. DiCaprio’s performance is full of youthful energy and romantic idealism.

His chemistry with co-star Kate Winslet is the heart of the film and a major reason for its phenomenal success. While the role made him a household name and a heartthrob, it also showcased his ability to be a compelling and classic leading man. He carries the epic romance with an effortless and unforgettable charm.

‘The Departed’ (2006)

In this crime thriller, Leonardo DiCaprio plays Billy Costigan, a state trooper who goes deep undercover in the Irish Mob. The role is a tense and paranoid one, as Billy lives in constant fear of being discovered. DiCaprio masterfully portrays the immense psychological toll the assignment takes on his character.

He perfectly captures Billy’s escalating anxiety and crumbling identity as the lines between his real self and his cover begin to blur. It is a raw and nervy performance that anchors the film’s complex plot. He holds his own in a cast of screen legends, delivering a powerful portrayal of a man trapped in an impossible situation.

‘Inception’ (2010)

Leonardo DiCaprio stars as Dom Cobb, a skilled thief who steals information by entering people’s dreams. Cobb is a haunted man, tormented by the memory of his deceased wife, which threatens to sabotage his missions. DiCaprio plays him as a focused professional who is barely holding his personal demons at bay.

The role required DiCaprio to ground a high-concept, complicated plot with a strong emotional core. He portrays Cobb’s intelligence and confidence, but also the deep guilt and sorrow that drive him. His performance makes the film’s complex rules and stunning visuals resonate on a human level.

‘Django Unchained’ (2012)

In a rare villainous turn, Leonardo DiCaprio plays Calvin Candie, a cruel and sadistic plantation owner. Candie is a man of immense privilege who treats human beings as property and entertainment. DiCaprio is terrifying in the role, masking the character’s brutality with a thin ‘Southern charm’ and sophistication.

He fully committed to the character’s evil, famously cutting his hand on glass during a scene and continuing with the take. The performance is shocking and unforgettable, showing a completely different side of his acting abilities. It proved he could be just as compelling playing a monster as he is playing a hero.

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

As fading television star Rick Dalton, Leonardo DiCaprio gives a performance that is both funny and deeply sad. Rick is an insecure actor struggling with his declining career in a changing Hollywood. DiCaprio perfectly captures the character’s anxieties, his moments of self-pity, and his flashes of on-set brilliance.

The role allowed him to play an actor acting, and he does so with incredible skill. A scene where Rick struggles with his lines in his trailer and then gives a powerful performance on set is a highlight. The performance earned him an Academy Award nomination and was a masterful portrayal of a man grappling with his own obsolescence.

‘The Aviator’ (2004)

Leonardo DiCaprio portrays the eccentric and ambitious billionaire Howard Hughes. The film follows Hughes’s life as a filmmaker and aviation pioneer while also chronicling his descent into severe obsessive-compulsive disorder. DiCaprio captures both the grand vision of the public figure and the private torment of the man.

It is a demanding role that spans decades, and DiCaprio’s transformation is remarkable. He shows Hughes’s initial confidence and charisma slowly being eroded by his debilitating mental illness. The performance earned him a Golden Globe Award and an Oscar nomination for his compelling depiction of a brilliant but troubled mind.

‘Catch Me If You Can’ (2002)

In this fun and stylish caper, Leonardo DiCaprio plays Frank Abagnale Jr., a real-life teenage con artist. Frank successfully poses as a pilot, a doctor, and a lawyer, all while forging millions of dollars in checks. DiCaprio perfectly embodies the character’s boyish charm and quick-witted intelligence.

The performance is light and energetic, showcasing DiCaprio’s comedic timing and charisma. He makes Frank’s incredible deceptions believable, but also shows the underlying loneliness of a young man on the run. It’s a highly entertaining performance that proves he can be just as effective in a breezy comedy as in a heavy drama.

‘Blood Diamond’ (2006)

As Danny Archer, a cynical diamond smuggler in war-torn Sierra Leone, Leonardo DiCaprio delivered a tough and gritty performance. Archer is a self-interested mercenary who gets caught up in a quest to find a massive pink diamond. DiCaprio adopted a convincing South African accent and a hardened exterior for the role.

Beneath the character’s tough-guy facade, DiCaprio reveals a man conflicted by the brutal world he operates in. He shows Archer’s gradual shift from pure opportunist to someone with a conscience. The role earned him an Academy Award nomination for his powerful and physically demanding performance.

‘Shutter Island’ (2010)

Leonardo DiCaprio plays U.S. Marshal Teddy Daniels, who is investigating the disappearance of a patient from a hospital for the criminally insane. As the investigation continues, Teddy’s own sanity begins to unravel. DiCaprio gives a performance of intense paranoia and emotional distress.

He keeps the audience guessing about the true nature of his character throughout the film. The role requires him to navigate complex psychological twists and turns, and he does so brilliantly. It is a haunting performance that showcases his ability to portray deep internal conflict and trauma.

‘Gangs of New York’ (2002)

In his first collaboration with Martin Scorsese, Leonardo DiCaprio plays Amsterdam Vallon. After his father is killed in a gang war, Amsterdam returns to the dangerous Five Points neighborhood of New York City seeking revenge. DiCaprio portrays the character’s journey from a vengeful young man to a powerful leader.

The role marked a transition for DiCaprio into more adult, serious roles. He effectively carries the historical epic, showing Amsterdam’s fierce determination and his conflicted feelings as he gets closer to his father’s killer. It was the beginning of one of the most important actor-director partnerships in modern cinema.

‘Revolutionary Road’ (2008)

Reuniting with his ‘Titanic’ co-star Kate Winslet, Leonardo DiCaprio plays Frank Wheeler. Frank is a man trapped in a seemingly perfect 1950s suburban life that he secretly despises. The film is a devastating look at a marriage falling apart under the weight of unfulfilled dreams and societal pressure.

DiCaprio gives a raw and powerful performance, portraying Frank’s frustration, self-loathing, and bursts of anger. He and Winslet have an explosive chemistry, and their arguments are painfully realistic. It is a mature and heartbreaking performance that explores the darker side of the American Dream.

‘Romeo + Juliet’ (1996)

In this modern, stylized adaptation of Shakespeare’s play, Leonardo DiCaprio plays the iconic role of Romeo. He brought a youthful passion and angst to the character that connected with a new generation of audiences. Despite the modern setting, he handles the classic Shakespearean dialogue with skill.

The role cemented his status as a leading man and a teen idol. His portrayal of the star-crossed lover is full of raw emotion, capturing both the dizzying heights of first love and the depths of tragic despair. It remains a defining performance of his early career.

Which Leonardo DiCaprio role do you believe stands above the rest as his greatest achievement?