In the ‘70s, when Martin Scorsese made his name with New Hollywood classics like Mean Streets and Taxi Driver, Robert De Niro became inextricably attached to the director’s filmmaking. This iconic actor-director pairing united for such acclaimed gems as Raging Bull, Casino, and The Irishman. But around the turn of the 21st century, Scorsese began working with a new go-to leading man: Leonardo DiCaprio.
Scorsese’s latest movie, the true-crime western noir Killers of the Flower Moon, will be his first directorial effort to star both DiCaprio and De Niro. Over the course of his two-decade working relationship with Scorsese, DiCaprio has starred in five of his movies, breathing life into some unforgettable characters (both fictional and true-to-life).
5 Amsterdam Vallon (Gangs Of New York)
Released in 2002 to warm reviews and moderate box office success, Gangs of New York is one of Scorsese’s most ambitious movies. The director set out to visualize how modern America came to be with a complicated story involving Irish immigrants, freed slaves, and a Catholic-Protestant feud. DiCaprio stars as Amsterdam Vallon, a young gangster seeking revenge against Bill “the Butcher” Cutting for the murder of his father.
This human story and relatable motivation draw the audience in and keep the movie grounded against the vast backdrop of America’s origin story. A young DiCaprio managed to hold his own opposite Daniel Day-Lewis as Bill the Butcher, but he’s ultimately overshadowed by Day-Lewis’ typically unforgettable performance.
4 Billy Costigan (The Departed)
When Scorsese accepted the Academy Award for Best Director for his work on the fast-paced crime thriller The Departed, he joked that it was his first movie with a real plot. Scorsese usually helms character studies about a personal journey undergone by a morally dubious antihero. In The Departed’s more traditional narrative, DiCaprio plays a true Hollywood hero that the audience can root for.
An English-language remake of the action-packed Hong Kong classic Infernal Affairs, The Departed stars DiCaprio as an undercover cop infiltrating the Irish mob to figure out which of his colleagues has infiltrated the police force on behalf of that mob. At the same time, that very same police mole, played by Matt Damon, is trying to figure out who the undercover cop is. The Departed is a cat-and-mouse thriller in which the cat and mouse are chasing each other.
3 Jordan Belfort (The Wolf Of Wall Street)
From Gangs of New York to The Departed to Shutter Island, most of DiCaprio’s starring vehicles in the Scorsese canon are somber dramatic pieces. But that tone didn’t feel right for the story of Jordan Belfort. The accounts of orgies and drug binges in Belfort’s memoir, The Wolf of Wall Street, were closer to The Hangover than Goodfellas. Sopranos writer Terence Winter imbued his script with a pitch-black sense of humor, and DiCaprio knocked every comedic delivery out of the park.
DiCaprio gave one of his funniest performances in The Wolf of Wall Street, charming audiences so much that the movie was accused of glorifying Belfort’s criminal lifestyle. But the excess is so excessive that it has to be seen as satirical. DiCaprio plays Belfort as a modern-day Caligula – the ruler of a corrupt empire addicted to sex, drugs, and wealth.
2 Teddy Daniels / Andrew Laeddis (Shutter Island)
Along with his ‘90s remake of Cape Fear, Shutter Island is one of Scorsese’s only horror films. The opening scenes of Shutter Island, adapted from the novel of the same name by Dennis Lehane, introduce DiCaprio as a U.S. Marshal who’s been sent to a mental institution on a remote island to investigate the disappearance of a patient. But from the offset, it’s clear that nothing is what it seems.
Scorsese doesn’t just keep the audience guessing; he keeps DiCaprio’s character guessing. The whole movie rests on DiCaprio’s performance as he drifts in and out of reality and learns all the shocking twists at the same time as the viewer. This is the best kind of protagonist for a psychological thriller. As DiCaprio slowly peels back the layers of his deeply disturbed character, the audience gets a haunting insight into his troubled psychology.
1 Howard Hughes (The Aviator)
Scorsese beat a couple of other directors to the punch with a Howard Hughes biopic. Hughes is one of the most fascinatingly eccentric figures in American history, and this complicated magnate needed the combined efforts of a master filmmaker and an incredible actor to do him justice as a movie character.
DiCaprio’s erratic performance in The Aviator does just that. He shares impeccable chemistry with his co-stars, like Cate Blanchett as Katharine Hepburn and John C. Reilly as Noah Dietrich, and commands the screen solo when Hughes closes himself off from society and spends extended sequences of the movie alone. It’s not easy to bring brooding nuance to a guy who pees in milk bottles.
In The Aviator, DiCaprio painted a rounded, in-depth portrait of Hughes. His performance doesn’t just focus on the sensationalist aspects like his uncut fingernails; he shows all sides of this historical icon. DiCaprio would’ve been a shoo-in for Best Actor for The Aviator if it hadn’t been released in the same year Jamie Foxx played Ray Charles.
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