All 7 Scorsese & DiCaprio Films Ranked

Martin Scorsese is one of the greatest directors of all time and has a filmography that most could only dream of. He became a household name by collaborating with Robert De Niro on films like Taxi Driver and Raging Bull.

However, it’s his collaboration with Leonardo DiCaprio that has kept his long career going. They have made some truly iconic films together that will stand the test of time. Here’s my personal ranking of the films directed by Martin Scorsese that star Leonardo DiCaprio:

7. The Audition

Leonardo DiCaprio and Robert De Niro in The Audition — Leonardo DiCaprio and Robert De Niro in *The Audition*

This looks like a Scorsese short film starring his two leading men, but it’s really a glorified, extremely expensive commercial for a pair of Asian casinos. The premise is fun enough with DiCaprio and De Niro competing for the lead in Scorsese’s next film; we even get an appearance from Brad Pitt. However, it isn’t memorable like Scorsese’s other films and can only be found in very low quality on YouTube; I feel like there’s a good reason for that.

6. The Aviator

Leonardo DiCaprio as Howard Hughes in The Aviator — Leonardo DiCaprio as Howard Hughes in *The Aviator*

This film being low on my list doesn’t mean I think it’s a bad film. However, the way Scorsese tells the story of Howard Hughes’ life is very difficult to follow. At times it feels like we’re jumping forward or backward without much warning, which is confusing at times. That being said, the production design is top notch and DiCaprio gives it his all with his performance as Howard Hughes. Unfortunately, he was a little overshadowed by the brilliant Cate Blanchett as Katharine Hepburn (who has 25 minutes of screen time and won Best Supporting Actress for it).

5. The Wolf of Wall Street

Leonardo DiCaprio as Jordan Belfort in The Wolf of Wall Street — Leonardo DiCaprio as Jordan Belfort in *The Wolf of Wall Street*

This was the first Scorsese film that I saw in theaters, and 10 years ago I thought it was a wild ride. After rewatching it for this ranking, it didn’t excite me the same way it did when I was 20 years old. I found the sex and drugs too gratuitous this time around, along with every other word being the F-word. DiCaprio still gives a great performance and has great chemistry with Margot Robbie, Jonah Hill, and the scene-stealing Matthew McConaughey. It’s definitely a film to watch, but maybe not as rewatchable as other Scorsese films.

4. Shutter Island

Leonardo DiCaprio as U.S. Marshall Edward “Teddy” Daniels in Shutter Island — Leonardo DiCaprio as U.S. Marshall Edward “Teddy” Daniels in *Shutter Island*

This is a Scorsese film that demands a rewatch, mainly in part due to the big twist that will have you looking for clues throughout your next viewing. DiCaprio pairs up with Mark Ruffalo this time around as U.S. Marshalls investigating the disappearance of a hospital patient; the two work very well together and have a nice back-and-forth with their characters. Shutter Island is the closest Scorsese has gotten to making a horror film; I can’t say much more about this one without spoiling it but it’s a solid film on this list.

3. Gangs of New York

Leonardo DiCaprio as Amsterdam Vallon and Daniel Day-Lewis as Bill the Butcher in Gangs of New York

While this film isn’t at the top of my list, it might be my favorite one. Scorsese captures 19th-century New York beautifully, from the set pieces to costumes. It also helps when you pair DiCaprio with arguably the greatest actor of all time, Daniel Day-Lewis. He chews the scenery every second he’s on-screen and is both menacing and fatherly to DiCaprio’s Amsterdam. The supporting cast features a plethora of talented actors, from Cameron Diaz to Liam Neeson. It’s violent, funny, and emotional all at once and it’s one I look forward to watching again.

2. The Departed

Leonardo DiCaprio as Trooper William “Billy” Costigan Jr. and Jack Nicholson as Francis “Frank” Costello in Avengers: Endgame

This is the Scorsese film almost anyone should know/recognize, especially since it finally earned him an Academy Award for Best Director. The Departed is essentially a remake of the 2002 film Infernal Affairs, but Scorsese puts his own stamp on it so it stands on its own. DiCaprio, Matt Damon, Jack Nicholson, and Mark Wahlberg all bring their A-game to this film, Boston accents and all. It’s a brutal thriller that will keep you on the edge of your seat until the credits begin to roll.

1. Killers of the Flower Moon

Lily Gladstone as Molly Burkhart, Robert De Niro as William King Hale, and Leonardo DiCaprio as Ernest Burkhart in Killers of the Flower Moon

Scorsese’s latest film might honestly be his best work to date; it’s a towering Western epic that keeps you captivated for the entire 3½ hours. DiCaprio gives a tremendous performance as Ernest Burkhart, a WWI veteran who comes to live with his uncle William (Robert De Niro) in Oklahoma. He goes toe-to-toe with De Niro, who gives his best performance in years as the calculating Hale. But it’s DiCaprio’s chemistry with Lily Gladstone that’s the heart of the film; Gladstone blows you away with her performance. I can see this being a true frontrunner for several Academy Awards and I’m thankful for Scorsese sharing Osage/Native American culture with the world.