Martin Scorsese and Leonardo DiCaprio films, ranked

Martin Scorsese is a filmmaker who clearly has a cast of favorites, as there are quite a few who have worked with him on more than one film. If you look at the actors he usually casts in lead roles, none have proven as prolific as Robert DeNiro, particularly from 1973 to 1995, when Scorsese directed eight different films. In 2019 there was a ninth (The Irishman) and a 10th feature film collaboration with Killer of the Flower Moonwhich premiered at the Cannes Film Festival in May 2023.

On the subject Killer of the Flower Moonthis film is notable for featuring Scorsese’s other favorite leading man: Leonardo DiCaprio. For at least the first 13 years of the 21st century, DiCaprio was Scorsese’s most popular actor and was something of a 21st-century De Niro for Scorsese. Killer of the Flower Moon will be DiCaprio’s sixth feature film with Scorsese and their first film together in ten years. To celebrate the upcoming release, here are the other captivating films the two have worked on together, listed below, from worst to best.


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5 Shutter Island (2010)

Leonardo DiCaprio in Shutter Island
Image via Paramount

It feels a little hard to call shutter Island the “worst” of all the films Martin Scorsese and Leonardo DiCaprio have made together, but unfortunately something has to take last place. That shouldn’t mean at all shutter Island is a bad movie because it works quite well as a dark psychological thriller/mystery film. It begins with a US Marshal investigating the disappearance of a patient from a high-security psychiatric facility, only to evolve over time into something far more complex.

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It’s a solid film and tells its story relatively well, but Scorsese feels a bit out of his element when he makes a thriller with heavy mystery elements (other psychological dramas/thrillers of his have fared better, such as taxi driver and – probably – The king of comedy). Likewise, DiCaprio’s overall performance is pretty good, but he’s managed to shine better as a lead actor at other points in his career, including in various other films he’s made with Scorsese.

4 “The Aviator” (2004)

Leonardo DiCaprio as Howard Hughes in The Aviator.
Image via Miramax Films

Of all the films that Martin Scorsese has directed Leonardo DiCaprio, there’s a case for it the aviator is their most ambitious and perhaps also the least likely to garner mass appeal. It is a nearly three-hour biopic that tells the dramatic life story of Howard Hughesfocusing in particular on his life between 1927 and 1947.

To say that Hughes accomplished and went through a lot during this period of his life would be a massive understatement considering he was a film producer/director, a business tycoon, and a veteran pilot. His life has also been problematic as he has had numerous relationships, been involved in some controversial events and also struggled with severe OCD. the aviator It may seem like an overstatement, but Scorsese’s directing consistently impresses, and the role of Hughes kept DiCaprio busy as an actor and helped him further hone his acting skills while moving away from “just” being the guy where he came from titanic.

3 Gangs of New York (2002)

DiCaprio gangs of New York

Criminal Organizations of New York is an inconsistent film, but at best it’s honestly a suspenseful and very compelling film. It’s an epic historical crime thriller that surpasses previous Scorsese films Goodfellas And casino When it comes to scope (though maybe not quality), it’s set in the crime-ridden Five Points neighborhood of New York in the 1860s. Narratively, it revolves around rival gangs in the area and follows DiCaprio’s character as the protagonist, who wants revenge on Bill the Butcher for killing his father.

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DiCaprio might be at the top of the list, but it’s true Daniel Day-Lewis’ The performance as Bill the Butcher remains the most memorable aspect of the film (apart from its impressive scale and attention to detail when it comes to the film’s appearance and atmosphere). The villainess of his character – and the way Day-Lewis portrays him – adds significant value to the film, while DiCaprio can’t help but feel like he’s taking a backseat at times, though he may have had more time overall the canvas has. Still, a young DiCaprio is solid here Criminal Organizations of New York is ultimately a better Martin Scorsese film than a Leonardo DiCaprio film, if that makes sense.

2 “The Dead” (2006)

the late leonardo dicaprio billy0

A crime/thriller that is as violent as it is often profane The departed portrays Martin Scorsese as a director at his most energetic and Leonardo DiCaprio as an actor at (almost) his loudest. The Best Picture winner is a remake of the 2002 Hong Kong film Infernal AffairsBoth cases involve the conspiracy of a criminal gang sending one of their own undercover cops to the police force, and the police sending an undercover cop to infiltrate the same gang.

As expected, this eventually leads to an intense game of cat and mouse, with each undercover cop desperately trying to uncover the other’s identity. The departed sees DiCaprio in the role of the undercover cop, bringing an edgy energy to the film and acting alongside the greats Jack Nicholson, who does a wonderful job of being the mafia boss of the infiltrated gang. It’s a dramatic and often intense film that rivals the best of Scorsese and DiCaprio’s respective works.

1 “The Wolf of Wall Street” (2013)

Leonardo DiCaprio in The Wolf of Wall Street
Image via Paramount Pictures

The Wolf of Wall Street even manages to top it The departed when it comes to profanity, and it contains a lot more debauchery, drug use and salacious content. Before Killer of the Flower MoonIt was also the longest film Scorsese and DiCaprio had made together, running at just under three hours. While the fast pace, direct content, and long running time make the film a little taxing to watch, it uses various excesses to comment…well, the excesses and greed that come with the relentless pursuit of more money, regardless of the cost.

The film sheds light on white-collar crime, which is destructive in a different way than the types of crimes typically seen in other Scorsese crime films where the actual victim count is higher. Lives are still being harmed here and society as a whole is being made worse by the main character’s actions Jordan Belfort and his associates, but the punishment is ultimately lesser, and as the cynical ending shows, people still look up to him and want to be him. It’s a somber, sometimes funny, and always compelling look at greed and the economic system that tends to incentivize despite the high cost it can inflict on people living their lives without significant wealth.

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Dustin Huang

Dustin Huang is a 24ssports U.S. News Reporter based in London. His focus is on U.S. politics and the environment. He has covered climate change extensively, as well as healthcare and crime. Dustin Huang joined 24ssports in 2021 from the Daily Express and previously worked for Chemist and Druggist and the Jewish Chronicle. He is a graduate of Cambridge University. Languages: English. You can get in touch with me by emailing:

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