Every Epic Martin Scorsese/Leonardo DiCaprio Movie, Ranked

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YOU COULD PROBABLY count on one hand the amount of auteur film directors that just about anyone you'd ever meet—on the street, at the gym, in a bar, wherever—would know by name. Likewise, in this day and age, there are probably about as many leading actors who could convince someone to see their movie—in a theater or at home—based simply on their name and presence. And it's because they fit so neatly into those two groups that Martin Scorsese and Leonardo DiCaprio have put together what's likely the greatest cinematic partnership in of the last 20 years (and counting).

Scorsese and DiCaprio are back for their first collaboration in ten years with The Killers of the Flower Moon, which also brings the pair together with Scorsese's other muse, the one and only Robert De Niro (DiCaprio and Scorsese have made six films together; De Niro and Scorsese have made 10). Flower Moon, at nearly 3-and-a-half hours long, is a lot of things all at once: a western, a neo-noir, a crime drama, a romance, and an honest telling of what's a true American/indigenous horror story (Lily Gladstone's Flower Moon performance, alongside Scorsese's two leading men, has been hailed as exceptional in early reviews).

It's yet another chapter in the partnership between one of the greatest living actors and perhaps our greatest living director, a partnership that has always pushed the limits of humanity and excess, never limiting themselves to one world or another.

Scorsese and DiCaprio's films, to this point, have contained multitudes, putting both actor and director to the test. All of their work together comes with exceptionally showcased skill from both, films that for just about any other actor or director would classify as their very best. But for our purposes, you know how it goes: something's got to be first, and something's got to be last.

Below, we dive in and offer a complete ranking of every Martin Scorsese and Leonardo DiCaprio movie to date.

BONUS: The Audition (2015)

You probably had no idea, but Martin Scorsese, Robert De Niro, and Leonardo DiCaprio all worked together for a "short film" to promote the opening of Macau's Studio City Casino—with an excessive budget of $70 million—back in 2015.

The Audition was directed by Scorsese and features all three men on-screen, playing exaggerated versions of themselves, with Leo and Bob competing for the top-billed role in the director's next film (for a less-than-two-day shoot, the two actors each received $13 million). It's a funny, self-aware little thing, which Scorsese himself admitted was somewhat difficult to craft, considering he usually works with runtimes sitting around the 3-hour mark (Terence Winter, whom the director worked with on The Wolf of Wall Street, Boardwalk Empire, and Vinyl, wrote the screenplay). We're not going to spoil a surprise, but there's one more major name/face who shows up near the end as well.

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6. The Aviator (2004)

Based on Charles Higham's biography of Howard Hughes, Howard Hughes: The Secret Life, Scorsese and DiCaprio's second collaboration came with 2004's The Aviator. The movie is both their most by-the-books collaboration—it's essentially a traditional biopic of the famed filmmaker/playboy/philanthropist/aerospace engineer Howard Hughes—and also just as interested in details and craft as anything else they ever worked on before.

Scorsese may have first linked up with DiCaprio for Gangs of New York, but you could argue that it was The Aviator, where the duo so perfectly depict Hughes' public bravado and private struggle, where the director really came to realize the full range and potential of his soon-to-be-frequent collaborator. The Aviator was nominated for 11 Academy Awards, winning 5, including Best Supporting Actress for Cate Blanchett.

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5. Gangs of New York (2002)

In Roger Ebert's review of Scorsese's 2002 epic period piece crime drama Gangs of New York, he says that the film "rips up the postcards of American history and reassembles them into a violent, blood-soaked story of our bare-knuckled past." The film, which marked the director's first collaboration with a then-28-year-old DiCaprio, is a revenge tale set around DiCaprio's Amsterdam Vallon, who returns from a stint in prison looking for revenge on the man who killed his father, Bill the Butcher (played with an intense bravado by the always-incredible Daniel Day Lewis).

Gangs is an epic story, tense and long but never boring, and coming with all the attention-to-detail that Scorsese is known for (and that has long been his signature style). As Ebert points out in his review, though, there seems to be a different relationship between the director in this world and the characters in his other worlds: "The characters in Gangs of New York kill because they like to and want to. They are bloodthirsty, and motivated by hate," he wrote. "I think Scorsese liked the heroes of Goodfellas, Casino, and Mean Streets, but I'm not sure he likes this crowd."

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4. Shutter Island (2010)

For as much as people (who don't know what they're talking about) like to say that Scorsese "only makes mob movies," he's got a surprisingly eclectic assortment of genres within his filmography. 2010's Shutter Island—the fourth film Scorsese and DiCaprio made together—is about as close as either have ever come to truly making a horror movie.

And while we probably wouldn't argue this as one of the director's very best (he himself seemed to have mixed feelings about it when reflecting in a recent GQ profile), Shutter Island is about as well-crafted a psychological horror/thriller movie as you can find, complete with a twist ending that will have you re-evaluating everything that came before it. With a cast that also includes Mark Ruffalo, Ben Kingsley, and Michelle Williams, and based on the novel of the same name by Dennis Lehane, Shutter Island kind of just feels like DiCaprio and Scorsese having a little bit of genre fun for once.

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3. The Departed (2005)

Scorsese won his first (and, somehow, only) Best Director Oscar for his work on The Departed, his third collaboration with DiCaprio and a genuine sensation. Based on the 2002 Korean filmInfernal Affairs, The Departed finds DiCaprio as a cop who winds up deep undercover with a Boston crime syndicate (with a ruthless boss played by Jack Nicholson), while Matt Damon is his foil—a criminal raised from his youth by the mob, holed up deep within the Boston police ranks.

While The Departed was the movie to finally win the master director his first Academy Award, it was somewhat dismissed at the time as being a "make-up" win, coming only after he'd been previously passed over time and time again for more deserving work. While he was passed over time and time again for very deserving work, we'd argue against the 'make-up' aspect of things: The Departed is one of the best cops-and-criminals movies you'll ever see, and DiCaprio (along with the rest of the cast) are pitch-perfect. It's hard to have a better time watching a movie than when watching The Departed.

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2. Killers of the Flower Moon (2023)

While The Departed is probably Scorsese and DiCaprio's most thrilling collaboration to date, Killers of the Flower Moon has the most to say. This absolute epic finds a master director and a perfectly-chosen cast operating at the very peak of their powers; the movie is nearly 3.5 hours long, but maintains its intense and compelling nature for every minute of it.

Flower Moon, which brings David Grann's nonfiction book about the 1920s murders of the Osage people of the same name to grisly, horrifying life, doesn't have the same thrill-a-minute nature of The Departed, instead opting for a slow burn crime story where you only realize the sinister scheme unraveling before your very eyes once it's too late. DiCaprio, De Niro, and Lily Gladstone are absolute dynamos in their headlining roles, while late appearances by Jesse Plemons, John Lithgow, and Brendan Fraser are good enough that you'll be talking about them after the credits are rolling.

It's hard to compare a movie like Killers of the Flower Moon that's brand new—and new to our collective minds—with something like The Departed and The Wolf of Wall Street that we've all had the time to sit with and digest for years. But Flower Moon finds one of the greatest directors of all time reckoning with a piece of history that not only tells a grim, angering crime story in and of itself, but in a way explains the history of America in a nutshell. Before it's said and done, Flower Moon could be the #1 movie on this list.

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1. The Wolf of Wall Street (2013)

When it comes to the very best work from both Scorsese as a director/storyteller and DiCaprio as a performer, there's no better showcase than 2013's The Wolf of Wall Street. The movie is ostensibly a biopic of Jordan Belfort, a real life corrupt stock broker/finance bro who defrauded investors and lived a life of rampant excess and debauchery on the way to immense wealth. But it's also a dry satire, a dark comedy, and, in a way, a white collar version of the same type of story Scorsese brings to the screen in maybe his greatest film, Goodfellas.

The Wolf of Wall Street features an all-star cast from top to bottom, including standout work from Jonah Hill, Jon Bernthal, Matthew McConaughey, Kyle Chandler, and the breakthrough role for Margot Robbie. But make no mistake about it—this is Leonardo DiCaprio's movie. He owns it from top to bottom, creating without question the most biting character of his career, delivering his usual great dramatic work in addition to the greatest comedy of his career (one word: Quaaludes).

For all the impressive work that Scorsese and DiCaprio have done together—and we hope there's still much more to come—The Wolf of Wall Street stands tall at the top of the list.

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