Examining DiCaprio’s Performances Throughout the Years

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Leonardo DiCaprio is an Oscar-winning actor and producer who – after beginning his career in the early 1990s – received critical acclaim in 1993 for his performance in What’s Eating Gilbert Grape . He later reached worldwide acclaim with his roles in Romeo + Juliet (1996) and Titanic (1997). Throughout his career, DiCaprio has received nominations for several prestigious awards, including Golden Globes, Academy Awards, SAG, and BAFTA awards. Most recently, he starred in Martin Scorsese’s Killers of the Flower Moon, a film nominated for ten Academy Awards. Here’s a look at some of DiCaprio’s performances throughout the years, ranked from worst to best. 

DiCaprio’s performances were ranked according to the following criteria: Critic and audience reviews, box office earnings, and how big of a role DiCaprio played in the film. For the purposes of the article, we took the average of the critics’ and audience scores on Rotten Tomatoes to determine the score for each movie. According to Rotten Tomatoes, the movies with the highest scores overall are Catch Me If You Can and The Departed, while the movies that grossed the most money were Titanic (658.8M) followed by Inception (292.6M). Some movies – like Don’t Look Up – had significant drops in earnings due to the COVID-19 pandemic, which was taken into account when creating the rankings. With that in mind, let’s count down Leo’s performances!

29. Don’s Plum (2001)

Photo Credit: Polo Pictures Entertainment.

In Don’s Plum (2001), DiCaprio plays a young twenty-something on a night out with friends. The film centers on said group of friends throughout its 90-minute run, all while being highly improvised and yielding little to no plot. In a 1999 lawsuit, DiCaprio and one of the film’s other stars – Tobey Maguire – sued its director, saying they never agreed to do a feature film. Instead, they thought they were signing on to do a short film. The lawsuit, which DiCaprio and Maguire won, blocked the film’s release in the U.S. and Canada.

28. Total Eclipse (1995)

Photo Credit: FIT Productions.

In Total Eclipse, DiCaprio plays a young, hopeful poet in a secret, forbidden relationship with his mentor, played by David Thewlis. The film only grossed around 340k at the box office after its release, ensuring it flew under the radar.

27. Celebrity (1998)

Photo Credit: Sweetland Films.

Directed by Woody Allen, Celebrity follows an entertainment journalist as he immerses himself in the glitzy lifestyle of celebrity media coverage. Despite its star-studded cast, including DiCaprio, Kenneth Branagh, Winona Ryder, Hank Azaria, Melanie Griffith, and Charlize Theron, Celebrity received poor reviews and was considered a box-office bomb.

26. The Beach (2000)

Photo Credit: Fox.

In The Beach, DiCaprio plays a young man backpacking through Thailand in search of adventure. Throughout his travels, his character might find more than he bargained for. With a 21% on Rotten Tomatoes, critics think this is one you can miss, calling it “unfocused and muddled.”

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25. The Basketball Diaries (1995)

Photo Credit: New Line Cinema.

In The Basketball Diaries, DiCaprio stars as a high school basketball star who develops a drug addiction to help cope with the pressures put on him by his mother, coaches, and teammates. The critics’ consensus for The Basketball Diaries states, “Despite its young leading man’s heroic efforts to hold it all together, a muddled message prevents the movie from being anything more than a cautionary tale.”

24. The Man in the Iron Mask (1998)

Photo Credit: MGM.

In Randall Wallace’s directorial debut, DiCaprio stars as King Louis XIV, the primary antagonist during the Franco-Dutch war. The film focuses on reunifying the four musketeers, who band together to stop the king. While the movie itself is fictional, the events portrayed within are loosely based on historical events.

23. J. Edgar (2011)

Photo Credit: Imagine Entertainment.

In J. Edgar, DiCaprio takes on the titular role of the infamous head of the FBI. An excellent display of character work from DiCaprio, the film struggles in terms of story structure and production value.

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22. The Quick and the Dead (1995)

Photo Credit: Sony Pictures.

The Quick and the Dead follows a gunslinging competition in a small desert town, in which DiCaprio plays the son of a man who enters the contest. At the time of filming, DiCaprio was only 21 years old.

21. Body of Lies (2008)

Photo Credit: Warner Bros.

In this spy thriller, DiCaprio plays CIA agent Roger Ferris, tasked with tracking a high-ranking terrorist across the Middle East. One critic described Body of Lies as a story “rising above the mediocrity of its storyline thanks largely to its ensemble cast.”

20. Blood Diamond (2006)

Photo Credit: Lonely Film Productions.

Blood Diamond follows DiCaprio as a mercenary hunting for blood diamonds during the civil wars of Sierra Leone. While Blood Diamond only has a critic score of 63%, it has an audience score of 90%. The audience likes this one!

19. Revolutionary Road (2008)

Photo Credit: Dreamworks.

Based on the novel by Richard Yates, Revolutionary Road reteams DiCaprio and Kate Winslet, their first collaboration since Titanic. In the film, they star as a young couple living in suburbia who try to balance their relationship problems while trying to raise their children.

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18. The Great Gatsby (2013)

Photo Credit: Warner Bros.

Based on F. Scott Fitzgerald’s classic novel, The Great Gatsby, tells the story of Jay Gatsby (DiCaprio), a self-made billionaire. The film focuses heavily on the “American Dream” and how wealth and exuberance became coveted throughout the “Roaring Twenties.”

17. Don’t Look Up (2021)

Photo Credit: Hyperobject Industries.

In this satirical outing from Adam McKay, DiCaprio plays Dr. Randall Mindy, an astronomer trying to warn the nation of the planet’s impending climate doom. Don’t Look Up was released during the COVID-19 pandemic and only spent two weeks in theaters before being released on Netflix.

16. This Boy’s Life (1993)

Photo Credit: Warner Bros.

In This Boy’s Life, young boy Toby (DiCaprio) and his mother move to Seattle, where his mother gets remarried to an abusive man (Robert De Niro). The movie chronicles the abuse Toby faces and how he plans to escape for a better life. Per critics, this movie is often referenced as DiCaprio’s breakout performance.

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15. Gangs of New York (2002)

Photo Credit: Miramax Films.

The first collaboration between DiCaprio and esteemed director Martin Scorsese, Gangs of New York, follows DiCaprio as a young Irish immigrant seeking revenge against his father’s killer. Scorsese spent nearly two decades developing the film based on the real Catholic-Protestant feuds of the mid-1800s.

14. Marvin’s Room (1996)

Photo Credit: Miramax.

The second collaboration between DiCaprio and co-star Robert DeNiro, Marvin’s Life, is a film about complicated familial relationships and how they shape us. In this movie, an estranged woman and her wayward son (DiCaprio) return home to care for her dying father.

13. Romeo + Juliet (1996)

Photo Credit: Twentieth Century Fox.

Based on the seminal play by William Shakespeare, Baz Luhrmann’s adaptation features a modern take on the old classic. In Luhrmann’s version, rather than star-crossed lovers from fair Verona, DiCaprio and Claire Danes—Romeo and Juliet, respectively—hail from rival gangs in a city called Verona Beach. The overall premise of the story remains the same, featuring the good ’ole sidekicks and a forbidden love story.

12. Shutter Island (2010)

Photo Credit: Paramount Pictures.

Based on the novel by Dennis Lehane, Shutter Island follows two U.S. marshals as they are sent to a remote island asylum to investigate an inmate’s escape. The film grossed $128 million worldwide and had an average audience score of 77%.

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11. Killers of the Flower Moon (2023)

Photo Credit: Apple Studios.

The latest collaboration between DiCaprio and Scorsese, Killers of the Flower Moon, depicts the brutal mistreatment and murder of many members of the Osage Nation tribe. In the film, DiCaprio plays Ernest Burkhart, a settler who marries an Osage woman in an attempt to gain access to her land and oil.

10. Once Upon a Time in Hollywood (2019)

Photo Credit: Columbia Pictures.

Based in 1969 Los Angeles, Once Upon a Time in Hollywood follows an aging actor and his stunt double as the duo try to figure out where their stagnant careers after their long-running Western ends. DiCaprio stars as prolific actor Rick Dalton, who is struggling to hold onto a career in Hollywood after a few unsuccessful turns.

9. The Revenant (2015)

Photo Credit: Twentieth Century Fox.

The Revenant is the film that finally won DiCaprio his long-awaited Oscar. Based in 1820’s South Dakota, the movie follows DiCaprio as frontiersman Hugh Glass, who was left for dead by his fellow travelers after being mauled by a bear.

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8. The Aviator (2004)

Photo Credit: Miramax Films.

The Aviator is a biopic about the life of legendary aviator Howard Hughes. The film depicts Hughes’ life and career from 1927 to 1947 when he became an aviation tycoon and began working as a Hollywood producer.

7. Django Unchained (2012)

Photo Credit: The Weinstein Company.

DiCaprio plays the film’s primary antagonist, enslaver Calvin J. Candie, in Django Unchained. The film follows Jaime Foxx, a formerly enslaved man, as he tries to rescue his wife from her captor (DiCaprio).

6. The Wolf of Wall Street (2013)

Photo Credit: Red Granite Pictures.

The Wolf of Wall Street tells the tale of wealthy stockbroker Jordan Belfort and depicts his rise and fall from Wall Street. Money, fame, exuberant wealth, and the lengths people go to ascertain it are recurring themes throughout the movie.

5. Inception (2010)

Photo Credit: Syncopy.

In Inception, DiCaprio plays Dom Cobb, a thief who extracts information from people via their dreams. Many critics call Inception an intellectual masterpiece, and the film is often ranked in the top 10 of DiCaprio’s performances.

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4. What’s Eating Gilbert Grape (1993)

Photo Credit: Paramount Pictures.

What’s Eating Gilbert Grape is the story of a young man forced to care for his mother and autistic young brother (played by DiCaprio). DiCaprio received his first-ever Academy Award and Golden Globe nominations for his performance in the film.

3. Titanic (1997)

Photo Credit: Paramount Pictures.

Directed by James Cameron, Titanic is an epic romance set aboard the ship of the same name. DiCaprio plays Jack Dawson, the love interest in Kate Winslet’s Rose, marking the first of several onscreen partnerships between the two actors.

2. The Departed (2006)

Photo Credit: Warner Bros.

Starring alongside Jack Nicholson, Matt Damon, and Mark Wahlberg, DiCaprio plays a Boston cop responsible for infiltrating an Irish gang in The Departed. With a superb cast, one critic calls The Departed “one of the best crime dramas ever made.”

1. Catch Me if You Can (2002)

Photo Credit: Dreamworks Pictures.

Starring alongside Tom Hanks, DiCaprio plays elusive con man Frank Abagnale, who spends most of the film eluding capture by Hanks’ no-nonsense Carl Hanratty. The most popular film in DiCaprio’s filmography, Catch Me If You Can, has a critics score of 96% and an audience score of 89%. With an average score of 92.5%, this movie is DiCaprio’s highest-scoring movie of all and grossed $352 million worldwide. It’s definitely worth a watch!

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Photo Credit: Vertigo Films.

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Photo Credit: 20th Century Fox Television.

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