Best films starring Leonardo DiCaprio and directed by Martin Scorsese

Leonardo DiCaprio and Martin Scorsese are reuniting once again for their seventh feature film together.

The actor is to star in frequent collaborator Scorsese’s new Naval drama The Wager based on David Grann novel The Wager: A Tale Of Shipwreck, Mutiny and Murder.

The book is set in the 1740s and is about two groups of sailors who were stranded in South America.

The first group of survivors were from a British ship and they were hailed heroes after turning on an island in Patagonia, but six months later another vessel was discovered off the coast of Chile with three men onboard who accused the other group of being mutineers.

A trial was later set up to discover the truth about what happened.

The project will follow the pair’s latest film project Killers Of The Flower Moon which is expected to debut at the Cannes Film Festival in France in 2023.

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The Wager will be DiCaprio and Scorsese’s seventh feature film collaboration following the release of The Wolf of Wall Street in 2013.

The pair also worked on a short film together, The Audition, in 2015.

Scorcese and DiCaprio have worked together on a number of multi-award-winning flicks, including the likes of The Departed, Gangs Of New York and The Aviator.

But what is their greatest film of all? We rank their six feature film projects to see which comes out on top…

6. Killers of the Flower Moon

Much like The Wager, upcoming flick Killers of the Flower Moon has also been made for Apple and is based on another book by David Grann titled Killers of the Flower Moon: The Osage Murders and the Birth of the FBI.

The novel is set in 1920s Oklahoma and focuses on a series of murders in the Osage Nation committed after oil was discovered on tribal land.

The film was first confirmed in 2018 with Robert DeNiro joining the picture alongside Jesse Plemons, Lily Gladstone and Brendan Fraser the following year.

Production was due to begin in 2020 but was postponed due to the coronavirus pandemic, and ultimately began in 2021.

As well as being the sixth collaboration between Scorcese and DiCaprio, this will be the 10th time Scorcese and DeNiro will join forces after working on the likes of Taxi Driver, Raging Bull, Goodfellas, Cape Fear, and The Irishman.

5. Shutter Island

Plunging viewers back into the gloomy days of film noir, 2010’s Shutter Island follows DiCaprio in the role of US Marshal Edward ‘Teddy’ Daniels, who is investigating a psychiatric facility located on a remote island.

After being stuck on the island due to an impending storm, he comes to question his own sanity.

The film also stars the likes of Mark Ruffalo, Ben Kingsley, Michelle Williams, Max Von Sydow, and Patricia Clarkson.

Shutter Island originally received mixed to positive reviews, with Roger Ebert of the Chicago Sun-Times giving the film three and a half stars out of four

He said: ‘The movie is about: atmosphere, ominous portents, the erosion of Teddy’s confidence and even his identity.

‘It’s all done with flawless directorial command. Scorsese has fear to evoke, and he does it with many notes.’

4. The Aviator

An emotional rollercoaster by every definition of the term, 2004 film The Aviator was the second time DiCaprio and Scorcese joined forces and arguably one of their most successful.

Released in 2004, biopic The Aviator sees DiCaprio as aviation pioneer and filmmaker Howard Hughes.

The film follows Hughes’ life between the late 1920s and late 1940s, during which time he became a successful film producer and an aviation magnate while simultaneously growing more unstable due to severe obsessive-compulsive disorder (OCD).

The film became a huge success, earning 11 Oscar nominations at the 77th Academy Awards – the most for the ceremony that year.

This included a best picture nomination, a best director nomination for Scorsese, and a best actor nomination for DiCaprio, his first in the lead actor category.

Roger Ebert gave the film four stars out of four, saying: ‘What a sad man. What brief glory. What an enthralling film.’

He continued: ‘There’s a match here between Scorsese and his subject, perhaps because the director’s own life journey allows him to see Howard Hughes with insight, sympathy – and, up to a point, with admiration.

‘This is one of the year’s best films.’

3. The Wolf of Wall Street

You can barely watch 10 minutes of The Wolf of Wall Street’s 180-minute run time without coming across an iconic scene.

And the black comedy biopic has gone down in history as a modern classic and a must-watch for all film fans.

In the 2013 release based on the memoir of the same name, the latest from the duo, DiCaprio plays Jordan Belfort as he recounts Belfort’s career as a stockbroker and the corruption and fraud on Wall Street that led to his eventual downfall.

The film was listed on many critics’ top ten lists for both the year and the decade and became Scorsese’s highest-grossing film worldwide.

The Wolf of Wall Street received five Academy Awards nominations, including best picture and best director for Scorsese.

DiCaprio won a Golden Globe Award For best actor – musical or comedy for his performance as Belfort and received his third best actor Oscar nomination.

2. Gangs of New York

Scorcese and DiCaprio first joined forces on epic historical drama Gangs of New York.

The film follows 1999 documentary Il Mio Viaggio in Italia, produced by Scorcese about Italian filmmakers.

The project foreshadowed Gangs of New York which was influenced by Italian directors such as Luchino Visconti and filmed in its entirety at Rome’s famous Cinecittà film studios.

The film is set in 1862, when a long-running Catholic-Protestant feud erupts into violence, just as an Irish immigrant group is protesting against the threat of conscription.

DiCaprio appears in the film as Amsterdam Vallon who returns to the Five Points area of New York City seeking revenge against Bill the Butcher, played by Daniel Day-Lewis, his father’s killer.

Scorsese reportedly initially struggled selling his idea of the film until DiCaprio became interested in playing protagonist Amsterdam Vallon, and the film went on to become a box office success.

1. The Departed

very film collaboration between Scorcese and DiCaprio is a strong contender for the number one spot, but The Departed is a true stand-out gem in both of the film icons’ filmographies.

Crime drama The Departed was eagerly anticipated following the release of Gangs of New York, and it certainly did not disappoint becoming one of the most successful films in their respective careers.

DiCaprio played the role of Billy Costigan, a state trooper working undercover in the Irish Mob in Boston.

Following its release, it received overwhelmingly positive reviews and became one of the highest-rated wide-release films of 2006.

DiCaprio’s performance in The Departed was applauded by critics and earned him a Satellite Award for best supporting actor.

Scorsese won his first best director Oscar for The Departed, after six previous losses in the category; the film also took home best picture.

It received four Oscars at the 79th Academy Awards, including adapted screenplay, and best film editing.

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Stevie Flavio
Film Writer


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