Every Martin Scorsese & Leonardo DiCaprio Movie Ranked

Legendary director Martin Scorsese has worked with Leonardo DiCaprio on six movies over the last 23 years, and these titles are all impressive works of cinema. The two Oscar-winning icons first collaborated in 2002’s Gangs of New York, which entered production less than a decade after DiCaprio’s noteworthy performances in What’s Eating Gilbert Grape, Romeo + Juliet, and Titanic. Scorsese’s most recent film starring DiCaprio is 2023’s Killers of the Flower Moon. Their seventh joint venture will be an upcoming movie about organized crime in Hawaii, which is slated to star DiCaprio alongside Dwayne Johnson and Emily Blunt. Additionally, DiCaprio will headline Scorsese’s The Devil in the White City film adaptation. Scorsese and DiCaprio are both remarkable talents in the film industry who have build a successful working relationship. As the duo’s next collaboration gears up, fans should take the opportunity to watch every Scorsese and DiCaprio film.

Ranked from worst to best, these are all of Scorsese’s movies featuring DiCaprio.

6) The Wolf of Wall Street

Scorsese cast DiCaprio as real-life stock-broker-turned fraudster Jordan Belfort in 2013’s The Wolf of Wall Street, based on Belfort’s memoir of the same name. The film chronicles Belfort’s criminal exploits as he grows more and more corrupt over time. DiCaprio delivers an exceptional performance alongside a stacked supporting cast including Margot Robbie, Jonah Hill, and Matthew McConaughey. However, The Wolf of Wall Street‘s star power doesn’t prevent its plot from dragging after the midway point of its three-hour run time.

As he has done before in his career, Scorsese succeeds in spotlighting the despicable measures the rich and powerful will take to gain more money and power, however, it’s difficult to remain invested in Belfort’s story all the way through, and at times it feels like the movie’s overall message gets lost in all of the antics. Although it’s far from Scorsese’s best, The Wolf of Wall Street should impress anyone who enjoys a quintessential DiCaprio masterclass.

5) The Aviator

DiCaprio teamed up with Scorsese for the second time in 2004’s The Aviator, starring as filmmaker and aerospace engineer Howard Hughes in the biopic. Based on Charles Higham’s book Howard Hughes: The Secret Life, The Aviator details Hughes’ professional accomplishments in aviation and entertainment, as well as his many personal relationships. DiCaprio leads the movie with a layered interpretation of the real-life figure, supported by Cate Blanchett’s portrayal of Katharine Hepburn and Kate Beckinsale’s rendition of Ava Gardner.

The Aviator‘s narrative is satisfyingly compelling and well-directed, even though it doesn’t reach the heights of Scorsese’s other masterpieces. Nonetheless, The Aviator makes a worthwhile viewing thanks to its splendid cast, detailed visuals and set design, and intricate plot.

4) Gangs of New York

Scorsese and DiCaprio’s first collaboration is arguably the filmmaker’s most underrated project. Gangs of New York takes inspiration from Herbert Asbury’s 1927 nonfiction book The Gangs of New York: An Informal History of the Underworld, focusing on the various gang rivalries in 19th-century New York City. In Scorsese’s movie, DiCaprio’s lead character, Amsterdam Vallon, returns to the Five Points area to exact revenge for his father’s murderer Bill “The Butcher” Cutting (Daniel Day-Lewis).

Gangs of New York is a gripping and gritty period drama with fantastic character portrayals across the board. DiCaprio expertly communicates Amsterdam’s thirst for vengeance, while Day-Lewis serves as a convincing mustache-twirling villain. Although close to three hours long, Gangs of New York never grows stale, as its heart-pounding tension and fight sequences easily keep audiences engaged.

[RELATED – Robert De Niro Really Hit Leonardo DiCaprio Filming Killers of the Flower Moon]

3) Killers of the Flower Moon

Killers of the Flower Moon, Scorsese’s newest movie, adapts David Grann’s 2017 novel with incredible attention to detail. The story, based on true events, centers on the recurring murders of Osage Nation members in 1920s Oklahoma after the discovery of oil led many wealth-seeking white Americans to settle on the land. DiCaprio’s interpretation of Ernest Burkhart and Robert De Niro’s portrayal of his uncle William Hale are each brilliant in their own right, however, it’s Lilly Gladstone’s career-defining performance as Ernest’s wife and Osage member Mollie Burkhart that defines Killers of the Flower Moon. While the film’s nearly three-and-a-half-hour run time slightly exceeds the story’s demand, Killers of the Flower Moon presents an important subject in a compelling manner. The movie’s depiction of America’s relationship with its Indigenous population is harrowing, especially given that many of Killers of the Flower Moon‘s themes still resonate in modern times. Thus, Killers of the Flower Moon is poised to movie audiences for decades to come.

2) Shutter Island

Scorsese delivered a riveting spectacle with his 2010 psychological thriller Shutter Island. Based on Dennis Lehane’s novel of the same title, the film stars DiCaprio as U.S. marshal Teddy Daniels, who, along with his partner Chuck Aule (Mark Ruffalo), is sent to investigate the disappearance of a psychiatric hospital patient on a remote Boston Harbor island in the 1950s.

Saturated with a deliciously eerie atmosphere and tantalizing horror elements throughout, Shutter Island is a breathtaking first-time viewing. The movie’s astonishing plot twist inspires numerous replays of Shutter Island, as its masterful details cannot be absorbed all at once. Moreover, DiCaprio forms a fantastic on-screen duo with Ruffalo. The star’s portrayal of Teddy’s declining grip on reality as the case drags on is a fascinating terror on its own. All in all, it’s difficult to find a Scorsese movie that delivers the chills and exhilaration of Shutter Island.

1) The Departed

Scorsese and DiCaprio’s greatest joint achievement is none other than 2006’s The Departed. An English-language remake of the 2002 Hong Kong film Infernal Affairs, Scorsese’s version takes place in Boston, where DiCaprio’s young police recruit Billy Costigan is tasked with infiltrating local mob boss Frank Costello’s (Jack Nicholson) empire. Although Scorsese has directed numerous other gangster thrillers, The Departed sets itself apart from the rest thanks to its heart-pounding narrative filled with twists and turns.

An Oscar winner for Best Director and Best Picture in 2007, The Departed remains one of Scorsese’s best masterpieces. DiCaprio’s top-notch performance pairs well with the impressive portrayals of Nicholson and the rest of the cast, while William Monahan’s captivating screenplay never loses its luster. Complete with a flawlessly executed shock of an ending, The Departed simply cannot be beat.

What’s your favorite collaboration between Scorsese and DiCaprio? Let us know in the comments below!