Few actor-director collaborations have been as iconic as the one between Leonardo DiCaprio and Martin Scorsese. Since they first worked together in 2002, the duo has crafted a series of films that have captivated audiences and solidified their status as Hollywood’s creative powerhouses. Interestingly, all 7 movie collaborations have grossed above $150 million at the Box Office.
Leonardo DiCaprio and Martin Scorsese have worked in a wide range of genres, from gritty crime dramas to psychological thrillers. The octogenarian filmmaker has generally earned a reputation for collaboration with several actors. For a working relationship spanning over two decades, these are the 7 times Leonardo DiCaprio collaborated with Martin Scorsese on the big screen.
2002: Gangs of New York
Martin Scorsese’s epic historical drama Gangs of New York was the filmmaker’s first work with Leonardo DiCaprio. In the movie, DiCaprio played Amsterdam Gallon, a young Irish immigrant seeking revenge for his father’s (Liam Neeson) murder. His father, Priest Vallon was killed by the ruthless gang leader William “Bill the Butcher” Cutting (Daniel Day-Lewis), after the gang battle for supremacy over mid-19th-century New York’s Five Points.
Amsterdam, who witnessed his father’s death, is sent to an orphanage on Blackwell’s Island. After returning to the neighborhood as an adult, Amsterdam infiltrates Bill the Butcher’s gang to avenge his father’s death. Gangs of New York was a critical and commercial success. Besides receiving 10 nominations at the 75th Academy Awards, it grossed $193.8 million against its $97-100 million production budget.
2004: The Aviator
Interestingly, Leonardo DiCaprio’s next feature film was another collaboration with Martin Scorsese. The Aviator, released two years after The Gangs of New York, was another epic biographical drama. Leonardo DiCaprio led the star-studded cast in The Aviator, portraying Howard Hughes. As its protagonist, The Aviator chronicles Howard Hughes’ life from the late 1920s through the 1940s.
It journeys through his achievements in filmmaking and aviation and his increasingly debilitating struggle with obsessive-compulsive disorder (OCD). Leonardo DiCaprio received an Academy Award nomination for Best Actor for his performance. Although a moderate Box Office success, The Aviator received generally positive reviews. It grossed $213.7 million against a $110 million budget.
2006: The Departed
Having found a working relationship that worked for them, Leonardo DiCaprio and Martin Scorsese teamed up again for their third collaboration with the 2006 The Departed. Again, it was DiCaprio’s third consecutive feature film, which Scorsese coincidentally directed. In the crime thriller, Leonardo DiCaprio played Trooper William “Billy” Costigan Jr., an undercover cop assigned to infiltrate the Irish-American mob in Boston. Costigan’s main task is to gain the trust of the mob’s ruthless leader, Francis “Frank” Costello (Jack Nicholson).
As Costigan delves deeper into the mob, he faces extreme pressure, constantly risking exposure. At the same time, Costello has planted a mole, Staff Sergeant Colin Sullivan (Matt Damon), within the police department. As always, Leonardo DiCaprio delivered yet another stellar performance. Martin Scorsese’s The Departed grossed $291.5 million against a production budget of $90 million. The movie also starred Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, and Alec Baldwin.
2010: Shutter Island
The Martin Scorsese-directed Shutter Island was based on Dennis Lehane’s 2003 novel. Leonardo DiCaprio played U.S. Marshal Edward “Teddy” Daniels in Shutter Island. Teddy is sent to investigate the disappearance of a patient from a mental institution. As the story unfolds, Teddy grapples with his traumatic past and begins to question reality. Shutter Island’s twist in the end, makes it one of Hollywood’s most shocking plot twists of the 21st century. Shutter Island was another collaborative success, grossing $294 million against a production budget of $80 million.
2013: The Wolf of Wall Street
The Wolf of Wall Street is one of Leonardo DiCaprio’s most popular and successful films. In the movie, DiCaprio portrayed Jordan Belfort, a stockbroker who rises to tremendous wealth and power through corrupt practices and fraudulent schemes. The movie chronicles his extravagant lifestyle, characterized by greed, excess, and hedonism, and his inevitable downfall.
Belfort’s journey highlights Wall Street’s moral and ethical pitfalls during the 1990s financial boom. DiCaprio co-starred alongside notable actors such as Jonah Hill, Margot Robbie, Matthew McConaughey, and Kyle Chandler. The Wolf of Wall Street grossed $406.9 million at the Box Office against a budget of $100 million.
2015: The Audition
The Audition isn’t a feature-length movie but a short comedy film. In the 16-minute film, DiCaprio and Robert De Niro audition for the same role. The short film is created as a comedy that sees DiCaprio and De Niro try to convince Martin Scorsese to cast them in a new film. Despite their stellar auditions, Scorsese invites Brad Pitt to audition for the role. Accepting their losses, DiCaprio and De Niro enjoy their evening in Japan. Although not a movie, it is a testament to Leonardo DiCaprio and Martin Scorsese’s long-standing relationship and collaboration.
2023: Killers of the Flower Moon
Eight years later, Leonardo DiCaprio and Martin Scorsese reconnected to collaborate in the epic Western crime drama Killers of the Flower Moon. In the movie, DiCaprio portrayed Ernest Burkhart, a World War I veteran. DiCaprio’s character is a nephew of Robert De Niro’s William Hale Character. With the film set in the 1920s, Killers of the Flower Moon explores the Osage Nation murders, where members of the Osage tribe were killed for their oil wealth.
Ernest Burkhart becomes embroiled in the conspiracy surrounding these crimes. He’s torn between his loyalty to his family and his love for an Osage woman, Mollie (portrayed by Lily Gladstone). Since they collaborated in 2002, Killers of the Flower Moon has been their least successful movie. It grossed $157 million against a $200–215 million production budget. Besides these Leonardo DiCaprio and Martin Scorsese collaborations, Scorsese has also worked on several successful screenplays.
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