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Leonardo DiCaprio's Best Movies: 8 Films That Defined His Career

The eight Leonardo DiCaprio films that defined his career

Among the best actors still performing in Hollywood today is Leonardo DiCaprio. Originally a great young talent, DiCaprio first got nominated for an Oscar at the age of 19. With a run of highly regarded performances in a range of roles, he fulfilled the promise he displayed in his early career. He first developed into a beautiful romantic lead, but he soon moved into historical biopics, crime dramas, and far more.

Despite some huge offers, DiCaprio has never starred in a major motion picture franchise. Rather, he has concentrated on creative stand-alone projects. Working with many outstanding directors including Christopher Nolan, Quentin Tarantino, and Alejandro González Iñárritu has helped him. Martin Scorsese, who has cast DiCaprio in several of his most iconic roles, has been his most often working partner. Working with Paul Thomas Anderson for the first time, DiCaprio is demonstrating his continued eagerness to embrace novel experiences. DiCaprio has learnt to trust his instincts over such a long and successful career.

Eat Gilbert Grape (1993)

Before What's Eating Gilbert Grape, Leonardo DiCaprio had a few little film parts as well as some TV appearances, mostly on The Mickey Mouse Club. Still, What's Eating Gilbert Grape was the first film to reveal DiCaprio's prospective star presence. DiCaprio, who was just 19 years old, received his first Oscar nomination for a drama on coming of age. He portrays Arnold Grape, a young man with a learning handicap who has outlived the terrible prognosis given to him by doctors, but his needs tax his family. Johnny Depp plays the family's provider, brother Gilbert.

Though this falls within the realm of a rural coming-of-age drama, Eating Gilbert Grape is a sentimental drama. The movie's sincere sensibilities really appeals to me, and much of this has to do with the dynamic between Johnny Depp and Leonardo DiCaprio. Often said is that DiCaprio steals the show in What's Eating Gilbert Grape. Though Depp's stoic, austere protagonist should not be discounted so readily, his performance is clearly the highlight of the film.

Romeo + Juliet (1996)

Though it took three years before his next major hit, everyone's attention was on what Leonardo DiCaprio would do following What's Eating Gilbert Grape. DiCaprio assumed one of the most well-known roles in theater history to support his acting credentials, but he gave his Romeo a modern touch in line with Baz Luhrmann's modern interpretation of Shakespeare's great drama. Romeo + Juliet happens on the busy streets of Verona Beach, which resembles the ganglands of Miami, not medieval Italy.

Romeo + Juliet preserves the flowery Elizabethan language while making some tweaks to the drama, mostly to fit Shakespeare's work into a modern environment for a generation grown on MTV. DiCaprio has Shakespeare's beautiful language to play with, but his performance also exudes a tangible vitality that few contemporary readings can ever hope to reach without exacting a rewriting of the play word-by-word. DiCaprio became a young heart-throb right away following Romeo + Juliet, but his performance has real weight.

Titanic from 1997

With Titanic, Leonardo DiCaprio confirmed his reputation as a romantic lead the year Romeo + Juliet was released. He is paired in the historical drama with Kate Winslet as two lovers from disparate social levels boarding the Titanic's fatal maiden voyage across the Atlantic Ocean. Jack and Rose's dreamy romance throughout Titanic is nearly irresistible enough to overlook the approaching catastrophe. Electric chemistry shared by DiCaprio and Winslet helps to make the social divisions of 1912 vivid and modern.

James Cameron strives to add as many period-accurate details as he can since the real Titanic is quite different. Jack and Rose are wholly fictional; some characters are based on actual ship passengers and crew. Though the historical setting gives their love story an inherent sense of tragedy, the actors still have to make them feel real. DiCaprio's performance enabled Titanic to rank among all time highest grossing films. The popularity of the film drove him into a fresh degree of celebrity.

New York's Gangs (2002)

After Titanic, Leonardo DiCaprio chose his next few films very deliberately. Though he proved he was an excellent dramatic actor with a range of roles, he could have easily become typecast as a romantic lead. DiCaprio teamed up with Martin Scorsese for Gangs of New York following working with Steven Spielberg and Danny Boyle. This started the most successful working relationship of his career; he has subsequently replaced Robert De Niro as Scorsese's preferred leading man.

Though bigger hits than Gangs of New York have come from Leonardo DiCaprio and Martin Scorsese's working together, this is where it all started. DiCaprio plays a young gangster who returns to the perilous Five Points borough of New York in search of retribution for the death of his father, so immediately fitting Scorsese's style. Gangs of New York highlight one of DiCaprio's underappreciable acting skills. Though Daniel Day-Lewis steals the show as the eccentric villain Bill the Butcher, he is ready to give his all in supporting parts on occasion.

Start (2010)

Everything viewers have come to expect from Christopher Nolan is found in inception. It uses lots of mind-bending set pieces and a strong dollop of spectacular action to investigate a singular psychological idea. Although it's only the director's one film with Leonardo DiCaprio thus far, it's among his very best. DiCaprio plays Dom Cobb, the leader of a group of corporate thieves who enter the dreams of their targets in order to gather essential data. Joseph Gordon-Levitt and Ken Watanabe in top form support him on an amazing cast.

The enigmatic ending of Inception is the ideal approach to wrap up the enigmatic drama that questions many facets of reality and experience. In this sense, it's comparable to Shutter Island—which also debuted in 2010—but Inception also offers DiCaprio some action scenes. For DiCaprio, this is rare even if the hunt across Mombasa's small streets still feels breathlessly thrilling. Given that this is far more thematically complex and character-oriented than most genre material, it's interesting that DiCaprio pursues this kind of action movie.

The Wolf Of Wall Street 2013

Leonardo DiCaprio has frequently produced his best work during his career when inhabiting real-life inspired roles. The Wolf of Wall Street is no different; the Aviator, J. Edgar, and Catch Me If You Can all let him play morally dubious figures from American history. DiCaprio portrays Jordan Belfort, the notorious stockbroker who led a lavish, extravagant life prior to stock-market manipulation and fraud conviction. Belfort is played by DiCaprio with an ugly arrogance, but he's still appealing and self-righteous enough that people readily buy into his David and Goliath perspective of America's financial institutions.

Among Martin Scorsese's funniest and most entertaining films is The Wolf of Wall Street. Though he isn't particularly known as a comic actor, DiCaprio can be funny when he has to be, as Belfort finds difficult to hold onto reality during a quaalude bender. DiCaprio's magnetic charm is on full show in The Wolf of Wall Street; this humor is only one aspect of that. 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.

Revenants from 2015

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.

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. This riveting drama fit Glass's extraordinary life narrative.

Once Upon A Time In Hollywood (2019)

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. 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.

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