DiCaprio played Josh in ‘Critters 3’ in 1991.
Rotten Tomatoes score: 0%
This straight-to-video movie was actually DiCaprio’s first credited appearance in a film ever, so not a particularly good start to his career, critically speaking. This was the third installment of the “Critters” franchise, if you can call it that.
In 2000, he played Richard in ‘The Beach.’
Rotten Tomatoes score: 20%
Danny Boyle’s movie is actually treated pretty harshly. It may not be a perfect film by any means, but it’s an intriguing story about a young man travelling to a solitary paradise on a beach in Thailand. There are surely enough good points here to make this 20% score feel unfair, one of them being the presence of Tilda Swinton.
He played Arthur Rimbaud in 1995’s ‘Total Eclipse.’
Rotten Tomatoes score: 25%
David Thewlis, best known for playing Remus Lupin in the “Harry Potter” film series, plays the mentor and older lover of DiCaprio’s young poet Arthur Rimbaud in this film about a forbidden romance.
In 1998, he played King Louis and Philippe in ‘The Man in the Iron Mask.’
Rotten Tomatoes score: 33%
This was a star-studded cast back in the 1990s, featuring Jeremy Irons, Gérard Depardieu, John Malkovich, and Gabriel Byrne playing the four musketeers. DiCaprio takes on dual roles as King Louis XIV and his imprisoned twin brother, Philippe.
He was credited as ‘1st Guy’ in 1992’s ‘Poison Ivy.’
Rotten Tomatoes score: 36%
DiCaprio only appears briefly in this film about a seductive teen, named Ivy and played by Drew Barrymore, scheming her way into a rich family.
DiCaprio played Brandon in Woody Allen’s ‘Celebrity’ in 1998,
Rotten Tomatoes score: 40%
DiCaprio plays Brandon Darrow, a teen heartthrob who Kenneth Branagh’s Lee encounters along his journey as a celebrity journalist. As usual with Woody Allen’s movies, there’s a wealth of stars featured, including Judy Davis, Winona Ryder, and Charlize Theron. Oh, and Donald Trump cameos as himself, too.
He took on the titular role in 2011’s ‘J. Edgar.’
Rotten Tomatoes score: 43%
This biopic was one of those projects that was in development for years and had various directors and actors attached to star in the movie. Eventually, the titanic names of Clint Eastwood and Leonardo DiCaprio combined to finally make the film a reality.
In 1995, DiCaprio played Jim Carroll in ‘The Basketball Diaries.’
Rotten Tomatoes score: 45%
Early comparisons between Timothee Chalamet and Leonardo DiCaprio may have started here. Chalamet played a teenager with a serious drug addiction in “Beautiful Boy,” while way back in 1995, DiCaprio did the same. He plays a teen who dreams of becoming a basketball star, only to fall into addiction.
In 2013, he gave us his version of Jay Gatsby in ‘The Great Gatsby.’
Rotten Tomatoes score: 48%
There have been many versions of F. Scott Fitzgerald’s seminal book, including one starring Robert Redford as Gatsby, but this is the most lavish of them all. DiCaprio dons pink suits to a killer soundtrack and spectacular, Oscar-winning production and costume design.
He played Roger Ferris in 2008’s ‘Body of Lies.’
Rotten Tomatoes score: 55%
DiCaprio teamed up with Hollywood powerhouses Russell Crowe (costar) and Ridley Scott (director) for this thriller in which DiCaprio plays a CIA agent hunting a terrorist in Jordan.
In 1995’s ‘The Quick and the Dead,’ he played Kid.
Rotten Tomatoes score: 57%
Starring Sharon Stone as The Lady, a killer gunslinger, and Gene Hackman as Herod, the man she seeks to get revenge on, this was DiCaprio’s first and only western up until “Django Unchained.” He beat out Sam Rockwell to the role of The Kid, a young boy trying to impress Herod.
He was Oscar-nominated for playing Danny Archer in 2006’s ‘Blood Diamond.’
Rotten Tomatoes score: 63%
DiCaprio earned an Oscar nomination for best actor for this complex film following vastly different people all tied together by a priceless blood diamond. Considering this film was nominated for five Oscars, its Rotten Tomatoes score of 63% seems pretty harsh.
In 2008’s ‘Revolutionary Road,’ he played Frank.
Rotten Tomatoes score: 67%
DiCaprio reunited with his “Titanic” costar Kate Winslet for this drama based on Richard Yates’ book of the same name, and it earned three Oscar nominations. While DiCaprio and Winslet were left out by the Academy, costar Michael Shannon earned his first Oscar nomination in this claustrophoic, often violent film.
He played Teddy Daniels in Martin Scorsese’s ‘Shutter Island’ in 2010.
Rotten Tomatoes score: 68%
Martin Scorsese’s twisty, horror-tinged thriller surely deserves more than the 68% it has been given by Rotten Tomatoes. It’s a gripping, dark mystery that keeps you thinking about it long after the credits roll, and supporting actors Ben Kingsley and Mark Ruffalo match DiCaprio for excellence.
He gave us his version of Romeo in Baz Luhrmann’s ‘Romeo + Juliet’ in 1996.
Rotten Tomatoes score: 72%
Coming out a year before “Titanic,” Baz Luhrmann’s “Romeo + Juliet” cemented DiCaprio as a complete heartthrob in this exciting update of Shakespeare’s play. People will be dressing up as DiCaprio’s Romeo at costume parties for decades to come.
He played Amsterdam Vallon in Scorsese’s 2002 movie ‘Gangs of New York.’
Rotten Tomatoes score: 73%
Truthfully, DiCaprio is outshone here by costar Daniel Day-Lewis, who plays Bill the Butcher and earned an Oscar nomination for doing so. Day-Lewis’ old-timey New York accent is frighteningly good, while DiCaprio’s Irish accent is often a little shaky. However, the movie earned 10 Oscar nominations for a reason — it’s excellent.
He played Toby in ‘This Boy’s Life’ in 1993.
Rotten Tomatoes score: 76%
While DiCaprio and Robert De Niro will be reuniting for Martin Scorsese’s upcoming “Killers of the Flower Moon,” “This Boy’s Life” was the first time the two titans of acting costarred together. De Niro plays DiCaprio’s abusive stepfather in this 1950s-set film.
DiCaprio won the best actor Oscar for playing Hugh Glass in 2015’s ‘The Revenant.’
Rotten Tomatoes score: 78%
While DiCaprio’s performance in this movie is not even his best, this is the film that finally won him his Oscar. He puts himself through the mill in Alejandro G. Iñárritu’s brutal film, which has stunning, Oscar-winning cinematography — but it’s Tom Hardy who steals the show as the movie’s villain.
He teamed up with Scorsese again to play Jordan Belfort in 2013’s ‘The Wolf of Wall Street,’ and was Oscar-nominated for it.
Rotten Tomatoes score: 79%
This is DiCaprio at his finest. A stunning, full-throttled and no-less-physical performance than the one in “The Revenant,” DiCaprio manages to make Scorsese’s three and a half hour movie feel half that time. Jonah Hill helps, too. DiCaprio and Hill were both Oscar-nominated for this.
In 1996, he played Hank in ‘Marvin’s Room.’
Rotten Tomatoes score: 84%
DiCaprio x Streep. DiCaprio has worked with some of the best actors and actresses in Hollywood, and his 1995 collaboration with Meryl Streep and Diane Keaton is actually one of his most under-appreciated films. Keaton received an Academy Award nomination for her role.
He was Oscar-nominated for playing Rick Dalton in Quentin Tarantino’s ‘Once Upon a Time in Hollywood.’
Directed by Quentin Tarantino. Sony Pictures ReleasingRotten Tomatoes score: 85%
This was DiCaprio’s first film since he won his Oscar for “The Revenant,” and he followed it up by earning another Oscar nomination for this movie.
In this instant classic by Quentin Tarantino, DiCaprio pairs with Brad Pitt to make one of the decade’s best on screen duos. DiCaprio plays a fading television star trying to claw back success in golden-age Hollywood, and Pitt plays his stunt double.
In 2004, he was Oscar-nominated for playing Howard Hughes in Scorsese’s ‘The Aviator.’
Rotten Tomatoes score: 85%
This was the second collaboration between Scorsese and DiCaprio following “Gangs of New York,” and this time DiCaprio was nominated for an Oscar. In fact, the film, a biopic about Howard Hughes, was nominated for 11 Oscars, including best picture and best director, and won five. Cate Blanchett took home a statue for playing Katharine Hepburn.
In 2010, he teamed up with Christopher Nolan to play Dom Cobb in ‘Inception.’
Rotten Tomatoes score: 87%
Every Christopher Nolan film seems to be a complete masterpiece, so it’s no wonder that DiCaprio was quick to team up with Nolan. “Inception,” even by Nolan’s incredibly high standards, stands out as one of the British director’s very best, too.
He played Calvin Candie in Tarantino’s 2012 movie ‘Django Unchained.’
Rotten Tomatoes score: 87%
This was the first time DiCaprio starred in a Tarantino film. He played Calvin Candie — the Mississipian plantation owner who the titular Django tries to free his wife from.
DiCaprio is excellent as the scenery-chewing villain, and the now-infamous dining room table scene in which DiCaprio cut his hand open but still continued acting (the take is in the film) proves why.
In 1997, he took on the now-iconic role of Jack Dawson in James Cameron’s ‘Titanic.’
Rotten Tomatoes score: 89%
There’s little to say about “Titanic” that hasn’t already been said, but the 11-time Oscar-winning juggernaut of a movie launched DiCaprio into stardom and confirmed him as Hollywood’s pretty boy heartthrob, a label DiCaprio worked hard to throw off through his varied filmography.
He earned his first Oscar nomination for playing Arnie Grape in 1993’s ‘What’s Eating Gilbert Grape.’
Rotten Tomatoes score: 90%
This was only DiCaprio’s fourth feature film, yet he was still nominated for the best supporting actor Oscar for playing Arnie Grape, the titular character’s mentally-impaired younger brother. And DiCaprio really is sublime here — it’s probably still the best performance he has ever given.
He starred as Billy Costigan in Scorsese’s 2006 masterpiece ‘The Departed.’
Rotten Tomatoes score: 91%
A remake of the 2002 Hong Kong movie “Infernal Affairs,” Scorsese’s thriller sees DiCaprio (an undercover cop) and Matt Damon (a mole in the police) trying to find each other before the other one does. This cat-and-mouse movie is one of Scorsese’s very best, and DiCaprio and Damon are joined by an excellent supporting cast including Jack Nicholson, Alec Baldwin, Vera Farmiga, Martin Sheen, and a very sweary (and Oscar nominated) Mark Wahlberg.
In 2002, he teamed up with Steven Spielberg and Tom Hanks to play Frank Abagnale Jr. in ‘Catch Me If You Can’ — his best-reviewed film.
Rotten Tomatoes score: 96%
Considering the fact that DiCaprio’s filmography includes films like “Titanic,” “The Wolf of Wall Street,” “Inception,” and “Django Unchained,” it may seem suprising that “Catch Me If You Can” is his top rated film ever. Steven Spielberg’s movie blends a variety of genres and sees Tom Hanks as the FBI agent trying to track down DiCaprio’s con-artist Frank Abagnale Jr. Guillermo Del Toro agrees with Rotten Tomatoes verdict, too, calling it the most underrated movie ever made.
