The 8 Leonardo DiCaprio Movies That Defined His Career

July 31, 2024, 6:30 p.m.

Movies

The 8 Leonardo DiCaprio Movies That Defined His Career

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Summary DiCaprio's early career includes some outstanding romantic dramas.

His collaboration with Martin Scorsese and work with other great directors like Christopher Nolan and Quentin Tarantino shows his dedication to interesting standalone projects.

DiCaprio shines in roles based on real-life figures, delivering award-winning performances in movies like The Revenant.

Leonardo DiCaprio is one of the greatest actors currently working in Hollywood, and there are a few key movies which have helped cement his reputation. DiCaprio started out as a prodigious young talent, earning his first Oscar nomination at the age of 19. He delivered on the promise that he showed in his early career with a string of critically acclaimed performances in a variety of roles. First, he became a handsome romantic lead, but he soon transitioned into crime dramas, historical biopics and much more.

DiCaprio has never appeared in a major movie franchise, despite some big offers. Instead, he has focused on interesting standalone projects. This has helped him work with plenty of great directors, including Christopher Nolan, Quentin Tarantino and Alejandro González Iñárritu. His most frequent collaborator has been Martin Scorsese, who has given DiCaprio many of his most memorable roles. DiCaprio is set to work with Paul Thomas Anderson for the first time, showing that he is still willing to take on new experiences. With such a long and successful career, DiCaprio has learned to trust his instincts.

Related Martin Scorsese’s New Movie Is A Big First For Leonardo DiCaprio - And A Major Challenge DiCaprio & Scorsese will team up for their seventh feature collaboration on a long-awaited Frank Sinatra biopic, which already poses a major concern.

1 What's Eating Gilbert Grape (1993)

Arnold Grape

Leonardo DiCaprio had a couple of minor film roles before What's Eating Gilbert Grape, as well as some TV appearances, notably on The Mickey Mouse Club. However, What's Eating Gilbert Grape was the movie that first announced DiCaprio's arrival as a star in the making. DiCaprio was just 19-years-old when he scored his first Oscar nomination for the coming-of-age drama. He plays Arnold Grape, a young man with a learning disability who has outlived the grim prognosis given to him by doctors, but his needs place a strain on his family. Johnny Depp plays his brother Gilbert, the provider of the family.

DiCaprio was just 19-years-old when he scored his first Oscar nomination for the coming-of-age drama.

What's Eating Gilbert Grape is a sentimental drama, but this comes with the territory of being a rural coming-of-age drama. It's hard not to be won over by the movie's earnest sensibilities, and a lot of this has to do with the dynamic between Johnny Depp and Leonardo DiCaprio. It's often been said that DiCaprio steals the show in What's Eating Gilbert Grape. His performance is undoubtedly the highlight of the movie, but Depp's steady, stoic protagonist should not be discounted so easily.

2 Romeo + Juliet (1996)

Romeo Montague

All eyes were on what Leonardo DiCaprio would do next after What's Eating Gilbert Grape, but it took three years before his next big hit. As a way of bolstering his acting credentials, DiCaprio took on one of the most famous roles in the history of theater, but he brought a contemporary touch to his Romeo in keeping with Baz Luhrmann's modern retelling of Shakespeare's classic drama. Rather than medieval Italy, Romeo + Juliet takes place on the hectic streets of Verona Beach, which looks like the ganglands of Miami.

DiCaprio became a young heart-throb instantly after Romeo + Juliet, but his performance has genuine substance.

Romeo + Juliet makes some changes to the play, mostly to fit Shakespeare's work into a modern setting for a generation raised on MTV, but it keeps the flowery Elizabethan prose. This means that DiCaprio has Shakespeare's gorgeous language to play with, but his performance also radiates a palpable vitality that few modern interpretations can ever hope to achieve without rewriting the play word-by-word. DiCaprio became a young heart-throb instantly after Romeo + Juliet, but his performance has genuine substance.

3 Titanic (1997)

Jack Dawson

Leonardo DiCaprio cemented his reputation as a romantic lead the year after Romeo + Juliet with Titanic. The historical drama pairs him up with Kate Winslet as two lovers from different social classes who board the Titanic's fateful maiden voyage across the Atlantic Ocean. Throughout Titanic, Jack and Rose's dreamy romance is almost captivating enough to ignore the impending doom. DiCaprio and Winslet share electric chemistry, helping to make the social divisions of 1912 feel vivid and contemporary.

DiCaprio and Winslet share electric chemistry, helping to make the social divisions of 1912 feel vivid and contemporary.

The true story behind Titanic is remarkable, and James Cameron does his best to inject as many period-accurate details as he can. Some characters are based on real passengers and crew from the ship, but Jack and Rose are entirely fictional. The historical context lends their love story an inherent sense of tragedy, but it's still up to the actors to make them feel real. DiCaprio's performance helped Titanic become the highest-grossing movie of all time. The movie's success propelled him to a new level of stardom.

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4 Gangs Of New York (2002)

Amsterdam Vallon

Leonardo DiCaprio chose his next few projects carefully after Titanic. He could easily have become typecast as a romantic lead, but he proved that he was an outstanding dramatic actor with a variety of different roles. After working with Steven Spielberg and Danny Boyle, DiCaprio teamed up with Martin Scorsese for Gangs of New York. This kicked off the most beneficial working relationship of his career, and he has since taken over from Robert De Niro as Scorsese's go-to leading man.

After working with Steven Spielberg and Danny Boyle, DiCaprio teamed up with Martin Scorsese for Gangs of New York.

Leonardo DiCaprio and Martin Scorsese's collaboration has produced bigger hits than Gangs of New York, but this is where it all began. DiCaprio fits into Scorsese's style immediately, as he plays a young gangster who returns to the dangerous Five Points borough of New York to seek revenge for his father's death. Gangs of New York shows off one of DiCaprio's underrated traits as an actor. He's willing to give his all in supporting roles from time to time, and he delivers a great performance while Daniel Day-Lewis steals the show as the eccentric villain Bill the Butcher.

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5 Inception (2010)

Dom Cobb

Inception Where to Watch stream

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buy Not available Not available Not available *Availability in US Director Christopher Nolan Release Date July 16, 2010 Cast Tom Hardy , elliot page , Joseph Gordon-Levitt , Cillian Murphy , Ken Watanabe , Marion Cotillard , Leonardo DiCaprio

Inception is everything that audiences have come to expect from Christopher Nolan. It explores a unique psychological concept using plenty of mind-bending set pieces and a heavy dollop of jaw-dropping action. It's the only time the director has worked with Leonardo DiCaprio so far, but it's one of his very best movies. DiCaprio stars as Dom Cobb, the leader of a group of corporate thieves who infiltrate the dreams of their targets to extract vital information. He is supported by an impressive cast which includes Joseph Gordon-Levitt and Ken Watanabe in top form.

It's telling that this is the type of action movie DiCaprio goes in for, since it's much more thematically complex and character-focused than most genre fodder.

Inception's enigmatic ending is the perfect way to close out the mysterious drama, which questions the nature of reality and experience in many ways. It's similar to Shutter Island in this regard, which also came out in 2010, but Inception also gives DiCaprio a few action scenes. This is a rarity for DiCaprio, although the chase through the narrow streets of Mombasa still feels breathlessly exciting. It's telling that this is the type of action movie DiCaprio goes in for, since it's much more thematically complex and character-focused than most genre fodder.

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6 The Wolf Of Wall Street (2013)

Jordan Belfort

Throughout his career, Leonardo DiCaprio has often delivered his best work when playing characters based on real life. The Aviator, J. Edgar and Catch Me If You Can all allow him to play morally dubious figures from American history, and The Wolf of Wall Street is no different. DiCaprio plays Jordan Belfort, the infamous stockbroker who lived a lavish, excessive lifestyle before being convicted of fraud and stock-market manipulation. DiCaprio plays Belfort with an ugly arrogance, but he's still charming and self-righteous enough that people easily buy into his David and Goliath view of America's financial institutions.

DiCaprio isn't necessarily known as a comedic actor, but he can be hilarious when he needs to be.

The Wolf of Wall Street is one of Martin Scorsese's funniest and most entertaining movies. DiCaprio isn't necessarily known as a comedic actor, but he can be hilarious when he needs to be, like when Belfort is struggling to maintain his grip on reality during a quaalude bender. This humor is just one part of DiCaprio's magnetic charisma, which is on full blast in The Wolf of Wall Street. The reason some people have misinterpreted the movie as aspirational or glorifying Belfort's lifestyle is partly because DiCaprio and the rest of the cast are so fun to spend time with.

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7 The Revenant (2015)

Hugh Glass

Leonardo DiCaprio was nominated for an Oscar four times before The Revenant, and each time he had to hear someone else's name being read out at the ceremony. In truth, he could have earned even more nominations for movies like Titanic and Shutter Island, so it felt long overdue when he finally won Best Actor for his performance as Hugh Glass. The Revenant gives DiCaprio a platform to do what he does best, with so much of the movie's success hinging on the qualities of his performance. Naturally, he delivers the goods, and he deserves each of the awards he won.

Leonardo DiCaprio was nominated for an Oscar four times before The Revenant, and each time he had to hear someone else's name being read out at the ceremony.

Alejandro González Iñárritu's Western survival drama tells the real-life story of a fur trapper who was abandoned by his colleagues and left for dead after a vicious bear attack. Initial reactions to the movie were colored by the stories that emerged from The Revenant's troubled production, with the cast and crew forced to endure freezing conditions and extensive reshoots. After a few years, The Revenant can now be judged on its merits, and it has held up well. It's a gripping drama worthy of Glass' remarkable life story.

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8 Once Upon A Time In Hollywood (2019)

Rick Dalton

Leonardo DiCaprio had worked with Quentin Tarantino before Once Upon a Time in Hollywood, but he only had a supporting role in Django Unchained. Once Upon a Time in Hollywood puts DiCaprio center stage, and he produces one of his most emotional and personal performances. DiCaprio plays Rick Dalton, an aging actor struggling to cling on to his relevance as Hollywood changes rapidly all around him. He finds some solace in his friendship with his stunt double Cliff Booth, as the two men find their fates tied to one another.

Once Upon a Time in Hollywood is a story about the dying embers of Old Hollywood, so Tarantino needed the kinds of actors who could evoke the same movie star magic of the era.

Once Upon a Time in Hollywood is a story about the dying embers of Old Hollywood, so Tarantino needed the kinds of actors who could evoke the same movie star magic of the era. While other directors might want their actors to disappear into their roles, it's important to maintain the impact of having Leonardo DiCaprio and Brad Pitt on screen together. DiCaprio gets chances to roleplay as Steve McQueen and an old Western star at different points. Once Upon a Time in Hollywood is much more than just a victory lap for DiCaprio, however. He also provides the emotional heart of the story.