Over more than 20 years, DiCaprio and Scorsese have delighted filmgoers with masterclass performances and acclaimed directional efforts. With varied roles such as a real-life mentally troubled billionaire, a psychologically complex undercover cop, and a dim-witted greedy veteran, DiCaprio has brought Scorsese films to life with committed and impressive performances. While all the roles DiCaprio has played for Scorsese have something special to offer, some were more compelling than others, and a select few stood as some of the most acclaimed of all time.

6 Teddy Daniels

Shutter Island (2010)

Leonardo DiCaprio’s character of Teddy Daniels in Shutter Island was a deeply sad case that became more nuanced and interesting upon multiple viewers. The Shutter Island ending revealed that Teddy was a patient at a psychiatric facility with a loose grip on reality who deluded himself into believing he was a US marshal investigating the disappearance of a patient on the island. DiCaprio’s performance was complex and layered, as the subtlety of the movie’s mysteries gradually unraveled in this gripping Martin Scorsese thriller.

While Teddy, also known as Patient 67 Andrew Leaddis, was not as compelling as the best characters DiCaprio has portrayed for Scorsese, it remained a top-tier performance that expertly captured the mental anguished and buried trauma of Teddy. An example of an unreliable perspective, watching Teddy’s confidence in his own sense of identity crumble as Shutter Island progressed was as harrowing as it was fearsome. Teddy was a unique Scorsese protagonist full of depth and intrigue, and the fact that he ranked bottom of the list of Scorsese’s DiCaprio protagonists was a testament to the strength of the director’s characters.

5 Amsterdam Vallon

Gangs of New York (2002)

The first of Leonardo DiCaprio and Martin Scorsese’s collaborations together, it appeared the director saw something special in the actor after his performance in Gangs of New York. DiCaprio played Amsterdam Vallon, who returned to Five Points New York to seek revenge against Bill the Butcher, the man who killed his father. An epic tale of religious factions, gang violence, and vengeance, DiCaprio delivered a compelling performance that captured the emotional turmoil, personal loss, and desire for justice of Vallon.

However, while DiCaprio gave his all to the role of Vallon his performance cannot compete with the masterclass method acting of Daniel Day-Lewis as the antagonist Bill the Butcher. The most villainous character in Scorsese’s filmography, Bill the Butcher was the most watchable part of Gangs of New York and in the process, Day-Lewis unwittingly upstaged DiCaprio’s less compelling role. Gangs of New York stood as a testament to an untold aspect of American history, but in DiCaprio’s later work for Scorsese, he would deliver much more absorbing characters.

4 Howard Hughes

The Aviator (2004)

In Martin Scorsese’s The Aviator, Leonardo DiCaprio expertly tracked the famed engineer, film producer, and pilot, Howard Hughes from an eccentric billionaire into a reclusive and deranged maniac. Based on a real-life figure, DiCaprio lost himself in the role of Hughes and was nominated for an Academy Award for Best Actor for his performance. In a masterclass of acting, DiCaprio captured the awe-inspiring highs of Hughes’ life and the gut-wrenchingly sad nature of his later years suffering from obsessive-compulsive disorder, increasing paranoia, and troubling panic attacks.

While Scorsese and DiCaprio’s working relationship began with Gangs of New York, it was in The Aviator that the true potential of their creative partnership fully came to the forefront. DiCaprio was always an actor capable of delivering committed and spellbinding performances and, with Scorsese, he found a director who recognized and exploited his potential as both a bankable Hollywood leading man and a character actor of great skill. The role of Howard Hughes was a challenging and rewarding endeavor that helped transform the public perception of DiCaprio from being a good actor to one of the best working today.

3 Ernest Burkhart

Killers of the Flower Moon (2023)

Leonardo DiCaprio stepped outside of his acting comfort zone to play the dim-witted and morally questionable Ernest Burkhart in Martin Scorsese’s Killers of the Moon. Depicting the real-life murders of Osage of Native American Osage Nation , DiCaprio abandoned his charismatic leading man persona to portray a man easily led into committing horrible acts, poisoning his wife, and assisting in stealing Osage Nation ' wealth from oil discovered on tribal land. As Burkhart, DiCaprio demonstrated his skill for playing a much darker character, who appeared so simple-minded that he remained oddly sympathetic as he carried out unspeakable wrongs.

While there’s an argument DiCaprio was too old for the part of Burkhart and should have played a different role in Killers of the Flower Moon, he managed to capture the complexity and sinister implications of his marriage to Mollie, played by Lily Gladstone, with nuanced depth and a careful vulnerability. Burkhart’s unquestioned loyalty to his uncle William King Hale, played by Robert De Niro, and willingness to hurt the people he loved to satisfy his greed, provided DiCaprio an opportunity to reveal a new facet to his performance repertoire. Burkhart stood as a unique entry among DiCaprio’s Scorsese characters.

2 Billy Costigan

The Departed (2006)

The undercover cop Billy Costigan from Martin Scorsese’s The Departed was a tragic figure from start to finish. Played by Leonardo DiCaprio, Costigan had a complex history with family ties to criminal behavior and the boss of the Irish Mob Frank Costello, which made him the perfect candidate to infiltrate his criminal syndicate. A thrilling game of cat and mouse between Costigan and a criminal police mole named Collin Sullivan, The Departed blurred the lines between perceived and hidden identity, and, to accurately capture the difficult entanglements of Costigan’s life, DiCaprio needed to deliver one of his best performances.

Despite being a remake of the Hong Kong film Infernal Affairs, The Departed became a uniquely American tragedy that won Best Picture at the Academy Awards. Propped up by an incredible performance by DiCaprio, Costigan struggled to maintain his moral fortitude as he descended into his criminal alter ego and was forced to reckon with a fractured and split personality. DiCaprio’s role as Costigan represented an important moment in his career and showcased his ability to tackle characters with a disted and fragmented sense of self.

1 Jordan Belfort

The Wolf of Wall Street (2013)

The grand excesses of The Wolf of Wall Street protagonist Jordan Belfort stood to capture the best of Leonardo DiCaprio and Martin Scorsese’s fruitful creative collaboration together. In his fifth movie for the acclaimed director, DiCaprio as Belfort encapsulated the exploitative, greedy, and self-centered nature of modern capitalism in an explicit feature that remained as compelling as it was profane. DiCaprio gave his all to portraying this real-life con artist and, in the process, was allowed to showcase both his skills as a dramatic actor and expert comedic timing in an unusually amusing Scorsese epic.

DiCaprio appeared to relish the opportunity of playing such a morally questionable character who had no qualms about ripping people off, indulging in excessive drug use, and engaging in shady money practices. Through Belfort, both DiCaprio and Scorsese highlighted that there was no limit to the potential extremity of the characters in their films together, and that, even with a role as over-the-top as Belfort, DiCaprio would always deliver a committed portrayal. While it would be hard to top this DiCaprio performance in a Scorsese movie, there will surely be more interesting roles ahead in the pair’s acclaimed partnership.