Just as Robert De Niro once served as Martin Scorsese's cinematic alter ego, so too has Leonardo DiCaprio become the director's muse for the 21st century. Their partnership, spanning over two decades and six feature films, represents one of modern cinema's most electrifying collaborations. Each project has seen DiCaprio delve deeper into complex, often morally ambiguous characters, guided by Scorsese's unparalleled vision and kinetic energy. To rank their films is not to diminish any, for even their "lowest" collaboration still stands as a monumental achievement. Rather, it is to trace an arc of evolving artistry, from ambitious beginnings to profound masterworks.
Here, we chronicle their extraordinary joint ventures, from least to most impactful:
6. Gangs of New York (2002)
Their inaugural collaboration was a sprawling, visceral epic set in the brutal streets of 1860s Five Points, New York. Gangs of New York is a film of immense ambition, a historical canvas painted with blood, mud, and the burgeoning spirit of a nation. DiCaprio plays Amsterdam Vallon, an Irish immigrant seeking revenge on Bill "The Butcher" Cutting (Daniel Day-Lewis), the nativist gang leader who murdered his father.
While visually stunning and brimming with Scorsese's signature historical detail, Gangs occasionally feels weighed down by its own grandeur. DiCaprio delivers a compelling performance, his youthful intensity perfectly suiting the raw determination of Amsterdam. However, he is often eclipsed by the towering, almost mythical presence of Day-Lewis, whose Bill the Butcher is a performance for the ages. It's a foundational film in their partnership, demonstrating their shared capacity for epic storytelling, but it's perhaps the one where DiCaprio hadn't yet fully synchronized with the specific rhythms of a Scorsese protagonist. It’s an extraordinary film by any measure, but in the context of their shared oeuvre, it stands as the ambitious, slightly less refined genesis.
5. Shutter Island (2010)
A sharp departure from the historical epics and crime dramas, Shutter Island plunges viewers into a gothic, psychological thriller. DiCaprio stars as U.S. Marshal Teddy Daniels, investigating the disappearance of a patient from a remote asylum for the criminally insane. From the moment Teddy steps onto the storm-battered island, the film drips with an oppressive atmosphere of dread and paranoia, masterfully crafted by Scorsese.
DiCaprio's performance here is a tour de force of simmering intensity and growing madness. As the lines between reality and delusion blur, he navigates a labyrinth of suspicion, his face a canvas of confusion, anger, and mounting despair. Scorsese, ever the genre chameleon, embraces the tropes of classic noir and horror, using unsettling imagery, disorienting editing, and a thunderous score to keep the audience, and Teddy, on edge. While perhaps not as thematically rich or expansive as some of their other works, Shutter Island is a meticulously constructed, deeply unsettling experience that showcases DiCaprio's ability to carry an entire film on the weight of his psychological unraveling. It's a masterclass in mood and suspense, a testament to their versatility.
4. The Aviator (2004)
Following Gangs, Scorsese and DiCaprio re-teamed for another lavish biopic, this time focusing on the eccentric, visionary, and ultimately tragic life of Howard Hughes. The Aviator is an ode to a bygone era of Hollywood glamour and technological ambition, tracking Hughes's rise as a filmmaker and aviation pioneer, all while grappling with his debilitating obsessive-compulsive disorder.
DiCaprio's portrayal of Hughes is remarkable. He captures the dazzling charisma, the entrepreneurial genius, and the escalating paranoia with stunning nuance. We see the sparkle in his eye as he pushes boundaries, and the agony of his mind as it turns against him. Scorsese, in turn, matches the film's grandeur with breathtaking cinematography that evokes the Technicolor hues of old Hollywood and spectacular aerial sequences. The Aviator is an epic character study, a tragic exploration of genius undone by mental illness, and a deeply felt portrait of a man consumed by his own creations. It earned DiCaprio his second Oscar nomination and solidified his place as Scorsese's leading man for complex, larger-than-life figures.
3. The Wolf of Wall Street (2013)
If The Aviator was an exploration of ambition and its psychological costs, The Wolf of Wall Street is an unbridled, darkly comedic descent into hedonistic excess and moral decay. DiCaprio delivers perhaps his most audacious and unrestrained performance as Jordan Belfort, the real-life stockbroker who amassed a fortune through fraud and indulged in every imaginable vice.
The film is a three-hour rollercoaster of drugs, sex, and reckless abandon, fueled by DiCaprio's manic energy. He fully embodies Belfort's grotesque charm, his ability to captivate and corrupt, making his downward spiral both hilarious and horrifying. Scorsese, in turn, directs with an exhilarating, almost punk-rock urgency, employing fast-paced editing, direct addresses to the camera, and an electrifying soundtrack. It's a dizzying, unapologetic exposé of unchecked capitalism and human gluttony, forcing the audience to confront the allure of depravity while simultaneously condemning it. DiCaprio's performance here is a fearless act of physical and emotional comedy, proving his range extended far beyond brooding intensity.
2. The Departed (2006)
Finally bringing Martin Scorsese his long-overdue Academy Award for Best Director, The Departed is a taut, thrilling, and supremely satisfying crime drama. A remake of the Hong Kong film Infernal Affairs, it pits DiCaprio as Billy Costigan, an undercover state trooper infiltrating the Irish mob, against Matt Damon's Colin Sullivan, a mole for the mob within the police department.
The film is a masterclass in suspense, with both men living double lives, constantly on the verge of exposure. DiCaprio's performance as Billy is a raw nerve, a man tearing himself apart under the psychological strain of his deception. He embodies the paranoia, the anger, and the desperation of a man losing his identity in a moral quagmire. Surrounded by an all-star cast (Jack Nicholson, Mark Wahlberg, Vera Farmiga), DiCaprio still manages to anchor the film with his intense portrayal of internal conflict. Scorsese's direction is razor-sharp, delivering visceral action sequences and expertly ratcheting up the tension to its explosive, unforgettable climax. It's a perfect melding of thrilling narrative, powerful performances, and iconic direction – a modern crime classic.
1. Killers of the Flower Moon (2023)
Their most recent collaboration is also, arguably, their most profound and resonant. Killers of the Flower Moon is a sprawling, meditative true-crime epic based on the murders of wealthy Osage Nation members in 1920s Oklahoma. DiCaprio plays Ernest Burkhart, a simple-minded World War I veteran drawn into the insidious plot orchestrated by his uncle, William Hale (Robert De Niro), to inherit the Osage's oil wealth.
This film sees DiCaprio at his most subdued and complex. Ernest is not a charismatic villain or a tortured hero, but a man of weak will, easily manipulated, whose genuine affection for his Osage wife, Mollie (Lily Gladstone), conflicts with his complicity in her family's destruction. It's a performance devoid of grandstanding, instead relying on quiet internal turmoil and the horrifying banality of evil. Scorsese, in his most mature and deliberate work, foregrounds the Osage perspective, painting a devastating portrait of systemic racism and greed. The film's measured pace allows the full weight of the tragedy to sink in, culminating in a deeply emotional and ultimately chilling reflection on historical injustice. Killers of the Flower Moon is a testament to the enduring power of their collaboration, demonstrating a willingness to tackle uncomfortable truths with nuance and immense cinematic craft. It feels like the culmination of their journey together, a masterpiece of quiet devastation and moral reckoning.
From the ambitious historical sweep of Gangs to the devastating intimacy of Killers, the partnership between Leonardo DiCaprio and Martin Scorsese has continually pushed the boundaries of cinematic storytelling. DiCaprio's evolution from a promising young actor to a powerhouse capable of embodying incredible range has been significantly shaped by Scorsese's demanding vision. In turn, Scorsese has found in DiCaprio a muse capable of translating his most complex characters to the screen with unwavering commitment. Their filmography together is not just a collection of great movies, but a living testament to the transformative power of a truly symbiotic artistic collaboration.
