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'Gangs of New York' -

DiCaprio and Scorsese first worked together on 2002's 'Gangs of New York.'

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'Gangs of New York' -

The director first heard of DiCaprio in the 1993 film 'This Boy’s Life.' It also starred Robert De Niro, who told Scorsese about the young actor’s potential.

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'Gangs of New York' -

'Gangs of New York' had been in production for around 25 years. DiCaprio wanted to work with the director, and knew that Scorsese wanted to finish the film once and for all.

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'Gangs of New York' -

“It was an incredible undertaking,” DiCaprio said. In the film, he played the son of a gang member, who returns to New York to avenge his father’s death.

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'The Aviator' - After 'Gangs,' DiCaprio focused on 2004's 'The Aviator,' a biopic about business magnate Howard Hughes. The actor initially developed the film with director Michael Mann.

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'The Aviator' - However, Mann chose to direct 'Ali' instead, leaving DiCaprio with John Logan’s script. The actor didn’t give up, and reached out to Scorsese to complete the project.

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'The Aviator' -

“I had always shied away from the Howard Hughes story,” Scorsese said. “Spielberg wanted to make it [...] But this was the story of Howard Hughes I hadn’t seen.”

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'The Aviator' - With Scorsese directing, and DiCaprio in the lead role, 'The Aviator' was a hit. It won five Oscars, and DiCaprio called it the “next level of collaboration.”

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'The Departed' -

Scorsese felt burnt out after these two epic films. “I had had it with 'The Aviator,' in a good way, because I made a spectacle. I just wanted to do a street war,” he said. So in comes 'The Departed.'

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'The Departed' - The 2006 film is about an undercover policeman (played by DiCaprio), who tries to outsmart a member of the Irish Mob (played by Matt Damon).

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'The Departed' -

“It was a film that didn’t give a damn about anything,” Scorsese said. DiCaprio called the film “the pinnacle of something you’d get offered” as an actor.

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'The Departed' - The director also said he stopped “caring” about winning awards at the time. Ironically, 'The Departed' won four Oscars.

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'Shutter Island' - Four years later, DiCaprio and Scorsese returned with thriller film 'Shutter Island.' The film is based on the novel of the same name by Dennis Lehane.

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'Shutter Island' - The duo got attached to the film in 2007, just one year after 'The Departed' was released.

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'Shutter Island' - In 'Shutter Island,' DiCaprio plays Teddy Daniels, a man who investigates the disappearance of a murderer from a mental hospital.

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'Shutter Island' - Scorsese worked on 'The Wolf of Wall Street' before 'Shutter Island. However, he could not get financing from studios at the time.

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'The Wolf of Wall Street' - Production for this hit film started back in 2007, when DiCaprio beat Brad Pitt for rights to the blockbuster. Scorsese was a natural pick to direct.

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'The Wolf of Wall Street' - The 2013 film is a biopic about Jordan Belfort, a former stockbroker who broke the law with his corrupt stock-market manipulation.

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'The Wolf of Wall Street' - The film grossed nearly US$400 million worldwide, and made multiple year-end lists.

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'The Wolf of Wall Street' -

“It’s about the American dream and the corruption of that dream [...] Putting this culture up on screen is something I’ve wanted to do for a long time,” DiCaprio described.

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'The Audition' - DiCaprio and Scorsese scaled things down for their next collab: the 2015 short film 'The Audition.'

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'The Audition' - The short film has an all-star cast, featuring DiCaprio, Brad Pitt, Robert De Niro, and Scorsese himself.

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'The Audition' - The actors play themselves, traveling through Asia to compete for a role in Scorsese’s next film.

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'The Audition' - The film was made in partnership with the Studio City Macau Resort in China. It has not seen a commercial release.

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More new projects -

In addition to 2023's 'Killers of the Flower Moon,' DiCaprio is also set to star in Scorsese's 'Roosevelt,' about President Theodore Roosevelt, and 'The Wager: A Tale of Shipwreck, Mutiny, and Murder' (also based on a book by David Grann).

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