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 starring in them: Leonardo DiCaprio

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 five other films together, including The Aviator, The Departed, Shutter Island, and The Wolf of Wall Street. After considerable time apart, the pair reunited for their latest project, the recently released Killers of The Flower Moon, a true epic lauded by the critics. With talk of another collaboration on the horizon, with The Wager confirmed as the pair's next film, let's rank every movie the pair have created together.

Update October 23, 2023: In honor of the release of Killers of the Flower Moon, this list has been updated to include it and also where you can stream all of DiCaprio and Scorsese's collaborations.

6 Shutter Island (2010)

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.

Shutter Island 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. With Killers of the Flower Moon already generating Oscar attention, if it secures a Best Picture nomination that will mean Shutter Island will be the only film out of the duo's movies together that wasn't nominated for Best Picture at the Academy Awards.

Stream on Paramount+

5 Gangs of New York (2002)

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.

Despite being their first collaboration, it is clear from the beginning that DiCaprio and Scorsese work well together. Scorsese certainly helps DiCaprio grow as an actor, while DiCaprio gives Scorsese's film a larger commercial appeal to general audiences.

Stream on Max

4 The Aviator (2004)

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 that 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. Yet DiCaprio should not be overlooked, and the actor fully commits himself to the legendary figure.

Stream on Paramount+

3 The Departed (2006)

The Departed is certainly one of Martin Scorsese's and Leonardo DiCarpio's best works both together and within their filmograpies. 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 a significant milestone in the director's career as it won him his first-ever Academy Award for Best Director. DiCaprio's performance is a major factor in the movie's success and his final scene is certainly one audiences still remember.

Rent on Prime Video, AppleTV+, or Vudu

2 The Wolf of Wall Street (2013)

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 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 for Dallas Buyers Club, which some consider to be 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. Yet it is DiCaprio that is the one everyone remembers, and this might be his defining role.

Stream on Netflix and Paramount+

1 Killers of the Flower Moon (2023)

After a decade-long hiatus, the partnership of Leo and Marty reconvened following the vast riches enjoyed after the release of The Wolf of Wall Street in 2013. Reuniting for 2023's eagerly-awaited Killers of the Flower Moon, the screen adaptation of David Grann's compelling, best-selling novel of the same name, naturally, the anticipation around its release was sky-high. Having received its World Premiere at Cannes in May 2023, garnering a gushing critical response, the October theatrical release was understandably longed for by not just cinephiles but also casual movie fans. The film is a milestone as it marks the first time that Scorsese has directed a movie starring his two most iconic leading stars: DiCaprio and Robert DeNiro.

After hitting the big screen for public consumption, there was a resounding outpouring of commendation for the feature, which tells the true story of members of the Osage Nation in 1920s America who fall victim to a string of mysterious homicidal attacks. Leonardo DiCaprio, Robert De Niro, and the utterly spellbinding newcomer in Lily Gladstone take center stage in this chilling, sensationally shot masterpiece that has the right to be atop the pile as far as the pair's collaborations are concerned. While it is early, there is a strong chance Killers of the Flower Moon will be a major awards contender.

Killers of the Flower Moon is currently playing in theaters and will be streamed on AppleTV+ at a later date.