Leonardo DiCaprio and Martin Scorsese: How Hollywood’s most dynamic duo made box office billions

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Leonardo DiCaprio and Martin Scorsese are like peanut butter and jelly, salt and pepper, gin and tonic – one of the best cinematic pairings of a lifetime.

Nearly two decades after first working together on the box office hit "Gangs of New York," DiCaprio and Scorsese are joining forces once again for their sixth feature film, "Killers of the Flower Moon," based on the novel by David Grann.

The movie, which is set to premiere in May 2023 at the Cannes Film Festival, also marks the 10th collaboration between Scorsese and his longtime friend, Academy Award-winner Robert De Niro.

And why stop at a sixth feature when a seventh is on the horizon? The Hollywood Reporter confirmed last week DiCaprio and Scorsese will partner up for an adaptation of another Grann nonfiction book, "The Wager: A Tale of Shipwreck, Mutiny, and Murder," through Apple Original Films.

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Leonardo DiCaprio and Martin Scorsese have proven to be one of the best cinematic duos of a lifetime, and will join forces for their seventh feature, "The Wager: A Tale of Shipwreck, Mutiny, and Murder," through Apple Original Films. (Getty Images)

Since 2002, Scorsese and DiCaprio's films have earned multiple Academy Award wins and dozens of nominations in every major ceremony, and grossed more than $1.3 billion at the box office, with their last major movie, "The Wolf of Wall Street," pulling in $392 million alone.

It was De Niro who handpicked DiCaprio to work with him in "This Boy’s Life" in ‘93, and later told his director pal about Leo’s impressive work on set, which eventually led to Scorsese casting him in "Gangs of New York."

De Niro and Scorsese are an easy add to the list of best director-actor duos as well, collaborating on major movies across four decades, some of which are considered the greatest films of all time. 

DiCaprio recalled bumping into the director at a bar in downtown New York after he had finished filming "What's Eating Gilbert Grape," his second film, when he was 18 years old. He told THR he was "sort of paralyzed" upon seeing Scorsese, and stood silently until Marty said: "Hey, kid, I saw your movie. You did a great job. Keep it up." Leo was "blown away" by the encounter.

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Scorsese responded, "I don’t remember that. I remember seeing the film, of course, and Robert De Niro was the one who told me about Leo. He said, ‘I worked with this kid in this film. You should really work with him someday.’ And he doesn’t usually do that."

Robert De Niro first worked with Leonardo DiCaprio on "This Boy's Life" in 1993, and insisted Martin Scorsese look into the actor for future work. The three were pictured in 2010. (Getty Images)

Martin Scorsese poses with Leonardo DiCaprio and Cameron Diaz after a screening of "Gangs of New York" during the 55th Cannes film festival. (Anne-Christine Poujoulat/AFP)

Howard Breuer, CEO of Newsroom PR, told Fox News Digital that the road to Scorsese and DiCaprio’s cinematic success may not have been paved quite as smoothly as it appears.

"Leonardo DiCaprio's starring in all those Scorsese movies may have started with an off-hand comment from De Niro to Scorsese. But these types of partnerships don’t just happen, they involve significant buy-in from the studios and a filmmaker’s other collaborators," Breuer said.

"DiCaprio, coming off ‘Romeo + Juliet’ and ‘Titanic,’ was already a known commodity when Scorsese cast him in their first movie together, ‘Gangs of New York,’ which was a film with a $100 million budget requiring a bankable star with appeal to young people."

"Gangs of New York," a 20-year passion project from Scorsese, was released in 2002 through Harvey Weinstein’s Miramax Films, and also starred Cameron Diaz, Liam Neeson, John C. Reilly and Oscar-winner Daniel Day-Lewis.

Scorsese casting DiCaprio "paid off because the film was a box office success, which is not always a given with a Scorsese film," Breuer added. 

Leonardo DiCaprio and Martin Scorsese celebrated their win for Best Drama Motion Picture for "The Aviator" at a Post Golden Globe party in 2004. (J. Merritt/FilmMagic)

Known for directing "Goodfellas," "Taxi Driver," Raging Bull," and "Casino," Scorsese also had a few box office bombs through the years despite critical acclaim behind his name.

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Regardless, Leo and Marty teamed up again two years later for "The Aviator," where DiCaprio starred as the eccentric and affluent aviation enthusiast, Howard Hughes. The film grossed $214 million on a $110 million budget, and was nominated for 11 Academy Awards, with Cate Blanchett earning a Best Supporting Actress Oscar for her role as Katharine Hepburn.

"It’s interesting, because I have been doing this since I was 13," DiCaprio told IndieWire in 2014. "I am almost about to turn 40, and I am looking back at some of the stuff I’ve gotten to do, and at the center of it is this amazing accidental collaboration that I’ve gotten to have with Marty."

In 2006, Scorsese and DiCaprio paired up for the crime thriller "The Departed," which also starred Mark Wahlberg, Matt Damon, Jack Nicholson, Martin Sheen and Alec Baldwin, and was produced by Brad Pitt.

Earning nearly $300 million at the box office was impressive, but the mob movie also marked Scorsese’s first Academy Award for "Best Director" after seven previous nominations. He received the Oscar from longtime friends George Lucas, Francis Ford Coppola and Steven Spielberg.

Martin Scorsese wins Best Director for "The Departed" with presenters, from left, Francis Ford Coppola, Steven Spielberg and George Lucas at the 79th Annual Academy Awards. (Getty Images)

Leonardo DiCaprio celebrates with Mark Wahlberg after Scorsese won his first Oscar for Best Director for "The Departed" during the 79th Annual Academy Awards in 2007. (Kevin Winter)

DiCaprio and Scorsese partnered for Paramount Pictures' psychological thriller "Shutter Island" in 2010, pulling in a total of $294 million on an $80 million budget, despite widely mixed reviews from film critics and fans alike.

But all was forgiven in 2013 with "The Wolf of Wall Street."

The biographical tale featured DiCaprio as Jordan Belfort, a stockbroker in New York City who thwarted federal officials as he funneled funds through fake businesses and corrupt companies on Wall Street, only to see his sham life come to an end when authorities figured out the scam.

The 180-minute flick also starred Margot Robbie, Jonah Hill, Rob Reiner, Matthew McConaughey and Jon Favreau, and became Scorsese’s biggest release to date, earning almost $400 million globally.

While DiCaprio, Hill and Scorsese were all nominated for Oscars, the film scratched at the Academy Awards and DiCaprio lost Best Actor to McConaughey in "Dallas Buyers Club." However, Leo did earn a Golden Globe for Best Actor.

"You're a risk-taker and a visionary, and as the history of cinema unfolds you'll be regarded as one of the great artists of our time," he told Scorsese while accepting the Globe. "Thank you for your mentorship, and thank you for encouraging me to take risks on this movie."

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Martin Scorsese and Leonardo DiCaprio working on the set of "The Wolf of Wall Street" in Manhattan in 2012.   (Bobby Bank)

Leonardo DiCaprio and Martin Scorsese laugh at a photo call before "The Wolf of Wall Street" world premiere at Cinema Gaumont Opera in Paris, France. (Bertrand Rindoff Petroff)

When DiCaprio finally received the Best Actor Academy Award in 2016 for his role in "The Revenant," he made sure to give another shout out to his director friend.

"I have to thank everyone from the very onset of my career," he told the audience. "Mr. Caton-Jones for casting me in my first film. Mr. Scorsese for teaching me so much about the cinematic art form."

DiCaprio doesn’t take his relationship with Scorsese for granted.

"It’s hard for me to quite articulate or put into words everything that I’ve learned from him," DiCaprio told IndieWire. "These key moments, they’re hard to even reflect on because you sort of have to take a breather and look back and realize how much you’ve actually learned." 

"I’ve grown tremendously as an actor just to be in those moments with him, where he’s giving me the right guidance."

Scorsese was equally grateful for DiCaprio when he told THR in 2013: "Working together reignited my enthusiasm for making pictures. There’s always something more, there’s always more to mine with him. He keeps going deeper and deeper."

While Breuer speculated, "De Niro making a suggestion to Scorsese is a useful piece of Hollywood lore," he added that it takes more than just a meeting of the minds to make movie magic happen.

"It’s not that De Niro couldn’t have made that suggestion to Scorsese," he said of that fateful conversation years ago which sparked the relationship," it’s just that there’s more to it than that."

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