Tarantino and Jackson. Gerwig and Ronan. Scorsese and DiCaprio.
It is a certainty that directors will find performers they jive with, no matter the genre. The latter duo, however, have worked together for the better part of two decades on projects that could not be more different from each other.
Since 2002, Leonardo DiCaprio’s partnership with Martin Scorsese has proven his range as an actor. And while not every one of these collaborations seems to be remembered in the actor’s filmography, that is a mistake. Scorsese’s work with DiCaprio has allowed the actor to take real risks that started at the beginning of his career as a movie star. All of his films with the acclaimed director have brought something to DiCaprio’s longevity, whether it’s obvious or not.
6. Gangs Of New York
Gangs of New York was an ambitious project at almost 3 hours, casting significant actors such as Daniel Day-Lewis, Brendan Gleeson, and Liam Neeson. This film was not a failure by any stretch of the imagination.
DiCaprio plays Amsterdam, a young orphan at the turn of the century in gang-ridden New York City. Immigrants form street gangs such as the one his father, Priest Vallon (Neeson), ran before being killed by the American Native’s leader, Bill the Butcher (Day-Lewis). Amsterdam falls in with Bill only to follow the path of violence to avenge his father. The film was adapted from the non-fiction book by Herbert Asbury about The Five Points and was a precursor for many of Dicaprio’s films. It was the beginning of many true-to-life stories that the actor would pursue.
5. Shutter Island
Scorsese’s neo-noir is generally not thought of as one of the director’s grander pictures. Based on the novel by Dennis Lehane, Shutter Island casts DiCaprio in the role of U.S. Marshal Teddy Daniels, who starts investigating the Ashecliff Hospital for the criminally insane following the disappearance of a patient named Rachel (Emily Mortimer). As Teddy’s investigation heats up, it’s easy to put 2 and 2 together.
But even with a predictable twist, DiCaprio goes to impressive lengths as the central character. He has the responsibility of not just playing one character, but two. The climax of the film reveals that Teddy doesn’t exist. His identity is actually that of Andrew, a patient at the hospital who was confined after he killed his manic-depressive wife. Andrew created Teddy as a way to cope with his guilt. While this turn of events isn’t surprising, DiCaprio still evokes empathy for a tragic character.
4. The Aviator
DiCaprio’s 2004 collaboration with Scorsese marked the beginning of the actor’s long road to the Oscars. By all accounts, The Aviator was a lightning rod for the awards ceremony. The biopic depicts the life and times of Howard Hughes, the famed movie director and aviation genius. Also in the cast were many prominent actors, such as Cate Blanchett, Kate Beckinsale, and Jude Law.
Though DiCaprio did not win the award, it wasn’t for lack of trying. The film spans over two decades, from Hughes’s humble beginnings in the ‘20s to his infamous downward spiral into an eccentric billionaire. DiCaprio certainly deserved any accolades for his performance, but his roles would still be yet to come.
3. The Departed
Adapted from the Hong Kong film, Infernal Affairs, The Departed brings police corruption to South Boston. The organized crime film did not have the reputation of Scorsese’s most notable gangster film, Goodfellas, but weaves a compelling tale with captivating characters. In the film, Scorsese takes on the Irish mob from the perspective of two very similar characters who take different paths in life. Colin (Matt Damon) is in Frank Costello’s (Jack Nicholson) pocket from an early age. Frank is the leader of the Irish mob, and raises Colin to be his mole inside the Boston police department. Billy (DiCaprio) is Colin’s foil. He inversely comes from a criminal background but desires to be in law enforcement. Because of his background, he becomes the primary choice to infiltrate Costello’s racket.
Once again, DiCaprio excels at playing the tragic character. (Warning: Spoilers ensue!) He is unimpeachable in his morals, going as far as to go to prison to maintain his cover. He gets beaten, sees his father figure murdered, and still finds a way to get handcuffs on Colin. He is close to vindication, only to be shot by another mole in the police department. Billy is the heart of the film and sets up DiCpario for some of the best roles of his career.
2. The Wolf of Wall Street
The Wolf of Wall Street cemented DiCaprio as not only a versatile actor but a performer unafraid of any material. Another biopic for the actor-director duo, DiCaprio plays the real-life stock market giant, Jordan Belfort. Founding his firm, Stratton Oakmont, the Wall Streeter went on to commit a myriad of financial crimes during his time as a stockbroker.
The figure’s life was so money-and-drug-filled that it was impossible not to laugh. DiCaprio showed immense talent for comedy as well as dedication to a real-life character. His performance in the film was only superseded by Scorsese’s heartwrenching 2023 true crime story.
1. Killers of the Flower Moon
It takes real dedication to pull off one of the most irredeemable characters in Scorsese’s filmography. Killers of the Flower Moon was adapted from the true crime book of the same name and depicts one of the most harrowing events in American history. Around the time that the Tulsa Race Massacre was happening, there was another culling of a minority group. In Osage County, a number of Indigenous people were killed for their oil money.
While DiCaprio often plays characters with some degree of empathy, this is where that tradition stops. The acclaimed actor plays Ernest Burkhart, a willing pawn in his uncle William Hale’s (Robert De Niro) ploy to take the Osage population’s money through marriage and murder. Ernest may think he’s in love with Mollie (Lily Gladstone) but only pushes the matter at the behest of his uncle. One by one, every one of her family members dies gruesomely as Ernest looks on.
He is fully complicit in these crimes, including poisoning his wife. There is no love to be found for the character here, who is filled to the brim with greed and stupidity. DiCaprio beats every single one of his previous characters, not just in Scorsese films, but in his entire career. It is a thankless role and one that highlights the egregious crimes committed against the indigenous population of the country. While hard for DiCaprio to top, he will probably try in his next Scorsese venture.
