If directors manage to forge a strong working relationship with one movie star, they’re lucky. Martin Scorsese is so prolific that he has close collaborations with two A-listers: Robert De Niro and Leonardo DiCaprio. Scorsese and De Niro’s first collaboration, Mean Streets, deserves an honorable mention. They went on to top themselves, but the reckless Johnny Boy was a great character in that movie, especially when he was contrasted with Harvey Keitel’s more well-behaved Charlie.
Scorsese is currently working on his first movie to feature both De Niro and DiCaprio, titled Killers of the Flower Moon. It’s about a series of murders in Osage County, Oklahoma in the early 1920s. Tonally, it could be a western slasher noir.
De Niro: Taxi Driver (1976)
Martin Scorsese’s neo-noir masterpiece Taxi Driver perfectly captured Watergate-era paranoia with the story of a Vietnam War veteran with PTSD and insomnia who goes on a brutal vigilante crusade on the crime-ridden streets of New York.
De Niro stars as Travis Bickle, a cabbie who witness crime and corruption on every street corner in New York and eventually decides to take up arms and handle it himself.
DiCaprio: Gangs Of New York (2002)
Possibly Scorsese’s most ambitious movie epic to date, Gangs of New York chronicles the birth of America through the lens of gangland warfare in the early days of Manhattan.
Daniel Day-Lewis stars as Bill the Butcher. In the prologue, Bill kills the leader of a rival gang and declares Five Points to be his gang’s territory. Little does he know, the orphaned son of the gang leader he killed will grow up to become Amsterdam Vallon, played by Leonardo DiCaprio, who vows revenge against Bill.
De Niro: Raging Bull (1980)
Scorsese was hesitant to make a movie about boxer Jake LaMotta when Robert De Niro brought the story to him because he had no interest in sports movies, but De Niro was so passionate about the role that he convinced him it would be more of a harrowing human drama than a sports movie.
De Niro was deservingly awarded an Oscar for his shocking, warts-and-all portrayal of LaMotta’s violent rage. He packed on muscle to play LaMotta at the height of his boxing career, then gained even more weight to play LaMotta at the end of his life.
DiCaprio: The Aviator (2004)
Howard Hughes is one of the most fascinating figures to get a Scorsese-helmed profile on the big screen. Eccentric to a fault, Hughes was a record-setting pilot, a celebrated filmmaker, and a wealthy investor with untold riches to his name.
DiCaprio’s portrayal of Hughes in The Aviator would’ve been a shoo-in for the Academy Award for Best Actor if it hadn’t been the same year as Jamie Foxx’s revelatory turn as Ray Charles.
De Niro: The King Of Comedy (1982)
Easily Scorsese’s most underrated film, The King of Comedy is a cynical indictment of the emptiness of fame – which both Scorsese and De Niro were feeling after Raging Bull catapulted them to varying degrees of stardom.
De Niro plays aspiring standup comic Rupert Pupkin, who resorts to crime to make it in Hollywood after his delusions of a friendship with late-night host Jerry Langford are shattered.
DiCaprio: The Departed (2006)
Scorsese’s English-language remake of Infernal Affairs, The Departed, is an intense cat-and-mouse thriller in which the cat and mouse are both looking for each other. Leonardo DiCaprio plays Billy Costigan, an undercover cop who infiltrates Frank Costello’s mob to find out which cops he’s got on his payroll.
Matt Damon, meanwhile, plays Colin Sullivan, one of Costello’s police moles who’s trying to learn the identity of the undercover cop in Costello’s organization.
De Niro: Goodfellas (1990)
This was De Niro’s first – and, so far, only – collaboration with Scorsese in which he didn’t play the lead role. The lead role in Goodfellas is Henry Hill, played by Ray Liotta. His lifelong goal is to be a mobster, then he finds himself woefully unprepared for the dirty work that comes with being a gangster.
De Niro plays Jimmy Conway, a seasoned mobster and one of Henry’s mentors. They plot the Lufthansa heist together and share the secret of Billy Batts’ murder. The character was based on Jimmy Burke.
DiCaprio: Shutter Island (2010)
Scorsese has dipped into the horror genre once with each of his closest collaborators. He remade Cape Fear in 1991 with Robert De Niro playing the role of sadistic killer Max Cady, first made iconic by Robert Mitchum.
Then, in 2010, he adapted Shutter Island with Leonardo DiCaprio in the lead role as U.S. Marshal Teddy Daniels, who’s been sent to investigate the escape of a mental patient at a mysterious asylum on an island, or so it seems. This movie is notable for its harrowing plot twist followed by a haunting ambiguous ending.
De Niro: The Irishman (2019)
Scorsese and De Niro had wanted to tell the story of Frank Sheeran for years but had to wait for technology to catch up with their vision. Sheeran sits in a nursing home at the end of his life in the framing narrative of The Irishman, taking the audience through his entire life with occasionally distracting digital de-aging.
De Niro brought a great amount of pathos to Sheeran – who claimed to be responsible for the unsolved murder of union boss Jimmy Hoffa – and it was a surprise when he was snubbed for a Best Actor nomination.
DiCaprio: The Wolf Of Wall Street (2013)
The most popular DiCaprio/Scorsese collaboration is The Wolf of Wall Street, a three-hour epic with a more complex true crime story than Goodfellas and even raunchier hard-R antics than The Hangover.
DiCaprio plays Jordan Belfort, a stockbroker who conned millions of dollars out of honest working people to build an empire that came crashing down in a federal investigation. The film has been read as both a glorification of Belfort’s criminal lifestyle and a sharp satire of it.