Every Leonardo DiCaprio And Martin Scorsese Movie Ranked

After filming the 1993 biographical drama "This Boy's Life," actor Robert De Niro approached his frequent collaborator, filmmaker Martin Scorsese, to share his positive experience working with a young and unknown Leonardo DiCaprio. According to Scorsese in a GQ interview, this remark stood out to him, since it was rare for De Niro to endorse another actor so openly. Still, it was a few more years before Scorsese and DiCaprio ever worked together, but when they finally did, a new collaborative partnership was born. By then, DiCaprio had begun to establish a name for himself in the industry with his notable performances in "Romeo + Juliet" and "Titanic." However, it was his work with Scorsese that catapulted him to a new level of prestige and recognition.

Together, the duo created some of the most iconic films of all time, racking up several award nominations, wins, and millions in earnings. But what exactly is it about the two creative forces that allow them to complement each other so well? For one, they gravitate toward the same type of material, specifically character studies on deeply flawed protagonists with themes of crime, morality, or obsession. Although these staples are recurring in their collaborative work, the two remain adaptable, exploring a wide range of genres and approaching each story with a specific intention. But despite their consistent acclaim, not all of their films are created equally. Thus, we take on the task of ranking every Leonardo DiCaprio and Martin Scorsese movie from the least to the best.

The 2002 historical drama "Gangs of New York" is by no means a bad film, but when compared to Martin Scorsese and Leonardo DiCaprio's other work, it ends up being the weakest out of the bunch. The film follows a 19th-century New York City gang rivalry through the perspective of a young Irish immigrant (DiCaprio) seeking revenge on the gang leader (Daniel Day-Lewis) who killed his father (Liam Neeson).

"Gangs of New York" is Scorsese and DiCaprio's first film together, so perhaps the unfamiliarity of this initial meeting of minds has something to do with the film falling short of expectations. While DiCaprio provides a strong performance alongside the standout Day-Lewis, and Scorsese delivers atmospheric grit and historical authenticity with his direction, the over-the-top end result was poorly received by many viewers.

Look to Reddit discourses and Rotten Tomato reviewers who blame the film's perceived failures on the desperation to create something more commercially mainstream, leading Scorsese astray with a disjointed narrative and disappointing payoff. One Reddit user writes, "The film doesn't seem to know if it wants to be a revenge story, gangster movie, a historical drama, or an epic. It's bloated with themes [that] aren't really explored to any depth."

One of Martin Scorsese's most admirable talents as a filmmaker is his ability to infuse his distinctive style into any genre. There's no better example of this than his 2010 psychological thriller "Shutter Island." Although this genre wasn't unfamiliar territory for Scorsese, as evidenced in films like "Taxi Driver" and "Cape Fear," "Shutter Island" ventured into a notably more eerie and surreal direction. In the film, a U.S. Marshal (Leonardo DiCaprio) investigates the mysterious disappearance of a patient from a mental institution on a remote island. As the investigation unfolds, he's confronted with his own delusions and past traumas that leave audiences guessing until the very end.

An overwhelming majority found the twists clever and the psychological suspense gripping, making this Scorsese's second-highest-grossing movie of all time. However, there remains a vocal chunk of critics who are critical of Scorsese's genre work and believe he does best when he sticks to his drama and crime flicks. Simultaneously, critics have scrutinized DiCaprio's performance, accusing him of trying too hard. "Beneath the Robert Mitchum mannerisms and carefully cultivated Boston accent . . . DiCaprio still seems like a pudding-faced little boy, alternately sullen and giddy, a little too eager to be loved," writes Dana Stevens for Slate. Ultimately, this slightly lower ranking comes down to nitpicking, often necessary when assessing Scorsese and DiCaprio's widely celebrated collaborations.

When considering Martin Scorsese's best biographical films, titles like "Raging Bull" and "The Wolf of Wall Street" are likely to come to mind, with "The Aviator" often slipping under the radar. This is precisely why the 2004 film finds itself squarely in the middle. It doesn't achieve the level of memorability that would make it overrated, nor does it earn the remarkable status of being underrated. Nevertheless, it remains worthy of appreciation for its cinematic spectacle.

Based on the eccentric life of aviation pioneer and filmmaker Howard Hughes, played by Leonardo DiCaprio, the film benefits from its compelling subject matter. However, it's worth noting the film tends to stay within the safer territory of Scorsese's usual risk-taking and adventurous filmmaking. Of course, this is not to discount the overall impressive efforts of Scorsese and, in particular, DiCaprio. Portraying a real-life figure is a formidable task, and capturing the depth of Hughes' frequently unstable character presented a unique challenge. Luckily, DiCaprio pulled it off with an exceptional performance that stood out as the film's most significant highlight.

The 2006 crime thriller "The Departed" perfectly exemplifies Martin Scorsese's raw, gritty realism at its finest. While Scorsese is no stranger to Academy Award nominations, it's remarkable that "The Departed" is the only one of his films to win best picture and best director awards, along with best adapted screenplay and best editing – the latter credit going to another one of his frequent collaborators, Thelma Schoonmaker. Anyone who's seen the film knows these awards are more than well-deserved.

Adapted from the 2002 Hong Kong film "Infernal Affairs," the gangster detective flick follows a cat-and-mouse chase between an undercover cop (Leonardo DiCaprio) infiltrating an Irish gang and a mole (Matt Damon) within the police force working for that same mob. It's a tale of clashing cultures and class conflicts that keep audiences on edge with its palpable sense of tension and unexpected twists. Even among a stacked cast of notable names, DiCaprio continues to radiate brilliance under Scorsese's guidance. Taking all of this into account, "The Departed" is a valid contender as Scorsese's best film of the decade and has rightfully been hailed as a contemporary classic.

Martin Scorsese's 2013 biopic "The Wolf of Wall Street" is by far his most commercially successful film, earning more than $392 million at the worldwide box office. The film's high energy and dark comedy make for one of Scorsese's most fascinating character studies and one of Leonardo DiCaprio's most provocative performances. Inspired by the life of Wall Street stockbroker Jordan Belfort (DiCaprio) and his 2007 memoir of the same name, "The Wolf of Wall Street" gives a satirical look into the unhinged spirit of late-stage capitalism. It's an adrenaline-inducing cautionary tale about what happens when one is driven solely by greed and ego, which DiCaprio embodies with convincing fervor.

Although the film's shocking and offensive nature likely attracted many to the story, it has also faced significant backlash for its perceived glorification of Belfort's unsavory behavior and undermining of real-life victims of his financial crimes. However, this was never enough to do any real damage to the film's overall reception. One could argue that good art is inherently divisive. On the other side of that coin, Joel M. Cohen, a former Assistant United States Attorney who prosecuted Belfort, conveyed the opposing viewpoint plainly in his piece for The New York Times, stating, "That might be art, but it's wrong."

Six years in the making and nine years after Martin Scorsese and Leonardo DiCaprio's last collaboration, the historical epic "Killers of the Flower Moon" finally hit theaters in fall 2023 to widespread praise and an impressive $23 million opening weekend at the box office. It's the first film to unite both of Scorsese's recurring stars, DiCaprio and Robert De Niro, which is cause for further celebration among Scorsese admirers.

After the discovery of oil on tribal territory in the Osage Nation in Oklahoma, a string of mysterious homicides begin to occur, ordered by a reserve deputy sheriff, William King Hale (De Niro), who is looking to claim all the wealth for himself. Hale ropes his nephew Ernest (DiCaprio) into his scheme by convincing him to marry Mollie (Lily Gladstone), an Osage woman whose family has lucrative headrights to the oil fortune. What unfolds is a moving tale of betrayal and tragedy that pays tribute to its real-life inspiration. Even with a three-and-a-half hour runtime, the film maintains engagement with its captivating performances, thoughtful pacing, and harrowing themes of corruption, exploitation, and intergenerational trauma, making "Killers of the Flower Moon" one of Scorsese's most necessary stories to date.