Martin Scorsese is considered to be one of the greatest directors of all time. Since the 60s, he has been creating brilliant work that is not only critically acclaimed and loved by audiences all around, but quite literally changed the face of cinema. His films are masterpieces and Scorsese is truly a genius. With all of this being said, you can only imagine how incredible his films are when you have one of the greatest actors in the business, Leonardo DiCaprio starring in them. Leonardo DiCaprio started acting at a young age and got one of his first leading roles in a film at the age of 18 when he was cast as Tobias in This Boy’s Life where he got to work alongside the great Meryl Streep and Scorsese’s long time collaborator and muse Robert De Niro.
Both Scorsese and DiCaprio are Academy Award winners and the definition of great directing and acting. Their first collaboration was in 2002 on the crime/drama Gangs of New York and since then have gone on to release four other films together including The Aviator, The Departed, Shutter Island, and The Wolf of Wall Street. Currently, the two are working on an American Western crime/drama film titled Killers of the Flower Moon, which is set to release sometime in 2022. While we eagerly await their future collaborations, here are Leonardo DiCaprio and Martin Scorsese’s five collaborations, ranked.
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5 Shutter Island
Shutter Island is the fourth project DiCaprio and Scorsese worked on together. Released in 2010, this film follows U.S. Marshall Teddy Daniels (DiCaprio) and his partner Chuck (played by Mark Ruffalo) as they head to Ashecliffe Hospital, an insane asylum, where they attempt to find a murderer who escaped from the institution. This movie is a rollercoaster, and the mind games both DiCaprio and Scorsese are able to play with the audience are so unique compared to all of their other collaborations. Interestingly, Shutter Island is the only film out of all five of the duo’s movies together that wasn’t nominated for Best Picture at the Academy Awards.
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4 Gangs of New York
This 2002 crime/drama that stars Leonardo DiCaprio, Daniel Day-Lewis, and Cameron Diaz is the first film DiCaprio and Scorsese ever made together. Gangs of New York was an instant success as it is a reflection of what a brilliant director Scorsese is, and it includes great performances from all the actors involved. Although the film didn’t take home any Oscars, it was nominated in nine categories including Best Actor, Best Director, and Best Picture. Another long-standing collaboration Scorsese has is with film editor Thelma Schoonmaker. She has done incredible work with Scorsese and has edited so many of his films including Goodfellas, Casino, Raging Bull, and Gangs of New York.
3 The Aviator
The Aviator follows the true story of Howard Hughes, the brilliant and ambitious, yet troubled, public figure, Hollywood director, and aviator. At its core, this film is best remembered for the incredible performances by Leonardo DiCaprio, who stars as Howard Hughes, and Cate Blanchett who gives an unforgettable portrayal of Katherine Hepburn. Blanchett’s performance was so praised, she even won the Academy Award that year for Best Supporting Actress. In addition to this Oscar win, The Aviator also won in the categories of Best Cinematography, Best Costume Design, and Best Film Editing for Thelma Schoonmaker.
2 The Departed
The Departed is a fan favorite and definitely one of Martin Scorsese’s best works. The film follows an undercover cop, Billy Costigan (Leonardo DiCaprio) who is trying to get information on a mob leader and infiltrate his work in Boston. Meanwhile, Frank Costello, the mob leader played by the great Jack Nicholson, has one of his men Colin Sullivan (Matt Damon) pose as a cop to infiltrate the police department and help keep Costello’s business running. The Departed involves family, crime, and drama, everything Scorsese does best. This film was an especially important milestone in the director’s career as it won him his first-ever Academy Award for Best Director.
1 The Wolf of Wall Street
Leonardo DiCaprio gives arguably the best performance of his career as Jordan Belfort in The Wolf of Wall Street. While this film deals with dark subjects from addiction to theft and an unimaginable number of scandals it is also incredibly entertaining and comedic. What makes The Wolf of Wall Street so great is DiCaprio’s ability to completely embody the wild and unpredictable essence of Jordan Belfort. The over-the-top lifestyle he is able to maintain throughout the film makes it so hard to believe that Jordan Belfort is a real person and that the three-hour film is based on his life before getting arrested for money laundering and securities fraud. DiCaprio was nominated for Best Actor in 2014 at the Academy Awards, but lost to Matthew McConaughey, which some consider being one of the biggest Oscar snubs. Jonah Hill and Margot Robbie also give great performances as Donnie Azoff, Jordan’s best friend and associate, and Naomi Lapaglia, Jordan’s ex-wife, respectively.
