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. There was a ninth in 2019 (The Irishman), and a 10th feature film collaboration with Killers of the Flower Moon, which had its premiere at the Cannes Film Festival in May 2023.
On the topic of Killers of the Flower Moon, that film is notable for featuring Scorsese’s other 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 will be DiCaprio’s sixth feature film with Scorsese, and their first together in 10 years. In celebration of its upcoming wide release, here are the other compelling films the two have worked on together, ranked below from worst to best.
Updated October 19, 2023, by Jeremy Urquhart:
Martin Scorsese and Leonardo DiCaprio are something of a cinematic match made in heaven, with 2023’s Killers of the Flower Moon – now getting a wide release – being another successful collaboration. And of the various Martin Scorsese Leonardo DiCaprio team-ups, all are worth watching, albeit it’s easy to suggest that some are even greater than others. What matters most is that the pair bring out the best in each other, and here’s hoping a planned seventh feature film collaboration between Scorsese and DiCaprio turns out well, too.
6 ‘Shutter Island’ (2010)
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.
It’s a solid film, 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 – arguably – The King of Comedy). Similarly, DiCaprio’s performance is pretty good overall, but he’s managed to shine brighter as a lead actor at other points in his career, including in various other films he’s done with Scorsese.
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5 ‘The Aviator’ (2004)
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 a troubled one, as he had numerous relationships, was involved in some controversial events, and also dealt with having severe OCD. The Aviator might feel a tad overlong, but Scorsese’s direction impresses throughout, and playing Hughes gave DiCaprio a great deal to do as an actor, further helping him deepen his acting skills as he moved away from “just” being the guy from Titanic.
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4 ‘Gangs of New York’ (2002)
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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), taking place in the 1860s in the crime-infested New York City neighborhood of Five Points. Narratively, it revolves around warring gangs in the area, and follows DiCaprio’s character – seeking revenge against Bill the Butcher for killing his father – as the protagonist.
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 the way Day-Lewis portrays him – elevates the movie considerably, 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.
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3 ‘The Departed’ (2006)
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 (just about) his loudest as an actor. This Best Picture winner serves as a remake of the 2002 Hong Kong film Infernal Affairs, with both having plots that center 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 mob boss of the gang being infiltrated. It’s a dramatic and often intense movie, and right up there with the best within both Scorsese and DiCaprio’s respective bodies of work.
2 ‘Killers of the Flower Moon’ (2023)
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 one another one of the leads here alongside the aforementioned actors, 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. It’s the most upsetting and hardest to watch of all the DiCaprio + Scorsese collaborations, but also stands as one of their best, with the former excelling as a type of character he’s seldom played before, and the latter in fine form as a director who recently turned 80, yet is showing no signs of slowing down creatively.
1 ‘The Wolf of Wall Street’ (2013)
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, having a runtime right on 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. Here, lives are still damaged and society as a whole is made worse by the actions of lead character 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. It’s a dark, sometimes 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.
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