All 6 Martin Scorsese and Leonardo DiCaprio Movies, Ranked

Martin Scorsese is a filmmaker who clearly has a roster of favorite actors, seeing as there's a decent number who've collaborated with him on more than one movie. When going by the actors he usually casts in leading roles, no one's proven to be as prolific as Robert De Niro, particularly from 1973 to 1995, when Scorsese directed him in eight different movies. Indeed, De Niro might be Scorsese's most consistent collaborator, and their careers have become closely related to each other.

However, Scorsese has another favorite leading actor: Leonardo DiCaprio. At least for the first 13 years of the 21st century, DiCaprio was Scorsese's most favored actor, and has been something of a 21st-century De Niro for Scorsese. Killers of the Flower Moon was DiCaprio's sixth feature film with Scorsese and their first together in 10 years. DiCaprio and Scorsese have produced several major modern classics—five of their six films have received Best Picture nominations. And while they all rank highly in their respective filmographies, some are undoubtedly better than others.

6 'Shutter Island' (2010)

The worst of the best

It feels a little harsh to call Shutter Island the "worst" of all the movies Martin Scorsese and Leonardo DiCaprio have made together, but unfortunately, something has to take the bottom spot. In no way should that imply that Shutter Island is a bad movie because, as a dark psychological thriller/mystery movie, it works pretty well. It begins with a U.S. Marshal investigating the disappearance of a patient from a high-security psychiatric facility, only to morph into something much more complex as it goes along.

Shutter Island is solid and tells its story relatively well, but Scorsese does feel somewhat out of his element, making a thriller with strong mystery elements—other psychological dramas/thrillers of his have fared better, such as Taxi Driver and The King of Comedy. Similarly, DiCaprio's performance is pretty good overall, but he's shone brighter as a lead actor at other points in his career, including in various other films he's done with Scorsese. Shutter Island excels as a quasi-horror thriller, even if it feels slightly off as a Scorsese-DiCaprio vehicle.

Shutter Island

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5 'The Aviator' (2004)

DiCaprio's tour-de-force

Of all the movies Martin Scorsese has directed Leonardo DiCaprio in, there's an argument to be made that The Aviator is their most ambitious, and also maybe the one that was least likely to have mass appeal. It's a biopic that runs close to three hours in length, telling the dramatic life story of Howard Hughes, focusing particularly on his life between the years 1927 and 1947.

To say Hughes accomplished and went through a great deal throughout this time in his life would be a massive understatement, considering he was a film producer/director, a business magnate, and a skilled pilot. His life was also troubled, as he had numerous relationships, was involved in some controversial events, and also dealt with severe OCD. The Aviator might feel a tad overlong, but Scorsese's direction impresses throughout. The film, however, is mainly a showcase for DiCaprio, who delivers one of his finest performances, throwing himself entirely to the role and deepening his acting skills as he moved away from "just" being the guy from Titanic.

The Aviator

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4 'Gangs of New York' (2002)

Daniel Day-Lewis steals the show

Gangs of New York is an uneven movie, sure, but at its best, it's honestly a thrilling and very engaging watch. It's a historical crime epic that surpasses earlier Scorsese movies like Goodfellas and Casino when it comes to scale, though perhaps not quality. It takes place in the 1860s in the crime-infested New York City neighborhood of Five Points and revolves around warring gangs in the area. At the center of the action is DiCaprio's character, who seeks revenge against Bill the Butcher for killing his father.

DiCaprio may be top-billed, but it's Daniel Day-Lewis' performance as Bill the Butcher that remains the film's most memorable aspect beyond its impressive scale and attention to detail when it comes to the film's look and feel. The viciousness of his character and Day-Lewis' raw, ball-to-the-wall portrayal considerably elevates the movie, while DiCaprio can't help but feel like he takes a backseat at times, even if he might have more screen time overall. Still, a young DiCaprio is solid here, though Gangs of New York is ultimately a better Martin Scorsese movie than it is a Leonardo DiCaprio movie if that makes sense.

Gangs of New York

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3 'The Departed' (2006)

Scorsese's ticket to the Oscar stage

A crime/thriller movie that's as violent as it is frequently profane, The Departed represents Martin Scorsese at his most energetic as a director and Leonardo DiCaprio at his loudest as an actor. The 2007 Best Picture winner, a remake of Hong Kong's 2002 film Infernal Affairs, centers on a criminal gang sending one of their own undercover within the police force and the police sending an undercover cop to infiltrate the same gang. As expected, this eventually results in an intense game of cat and mouse, with each undercover person trying desperately to uncover the identity of the other.

The Departed sees DiCaprio playing the role of the undercover cop, bringing a nervous energy to the film and acting alongside the great Jack Nicholson, who hams it up wonderfully as the violent and ruthless mob boss Frank Costello. It's a dramatic and often intense movie, embracing the genre's grit and producing an unforgiving, often cruel story that remains enthralling throughout. Scorsese finally won the Best Director Oscar for his work here, ensuring The Departed's reputation as one of the best within both Scorsese and DiCaprio's respective bodies of work.

The Departed

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2 'Killers of the Flower Moon' (2023)

Scorsese and DiCaprio's latest masterpiece

Martin Scorsese, Leonardo DiCaprio, and Robert De Niro. Those three names in succession should be enough to make plenty of people interested in Killers of the Flower Moon, which sees Scorsese collaborating with his two favorite actors for the same feature film. All three are in top form here, as is Lily Gladstone, who plays the third lead, with the film's story revolving around a series of numerous murders committed against the Osage people during the 1920s in Oklahoma.

Killers of the Flower Moon tells an unsettling narrative about a series of atrocities that were able to extend for a horrifically long amount of time. The runtime is long, but it uses 3+ hours to drive home the enormity of the real-life events and the countless troubling implications that arose from such things happening. Killers of the Flower Moon is the most upsetting and hardest to watch of all the DiCaprio-Scorsese collaborations, but it also stands as one of their best. DiCaprio excels as a type of character he's seldom played before, while Scorsese is in fine form as a director who recently turned 80 yet is showing no signs of slowing down creatively.

Killers of the Flower Moon

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1 'The Wolf of Wall Street' (2013)

A profane ode to excess

The Wolf of Wall Street manages to top even The Departed when it comes to profanity, and it contains a great deal more debauchery, drug use, and racy content to boot. Before Killers of the Flower Moon, it also stood as the longest film Scorsese and DiCaprio had made together, with a runtime of three hours. The fast pace, in-your-face content, and long runtime do make the film a little exhausting to watch, but it uses various excesses to comment on... well, the excesses and greed that come with the relentless pursuit of more money, no matter the cost.

The film sheds light on white-collar crime, which is destructive in a different way from the sorts of crimes usually featured in other Scorsese crime movies where the literal body count is higher. Lives are still damaged and society is worse off because of Jordan Belfort and his associates, but the punishment is ultimately lighter, and as the cynical ending shows, people still look up to him and want to be him. The Wolf of Wall Street is a dark, often funny, and always compelling look at greed and the economic system that tends to incentivize it despite the hefty cost it can have to people who live their lives without considerable wealth.

The Wolf of Wall Street

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NEXT: Martin Scorsese's Best Cameos, Ranked

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