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Ranking Martin Scorsese/Leonardo DiCaprio Films 1-5

I've been a movie enthusiast my whole life and been writing movie reviews for over 15 years.


Since 2002, acclaimed director Martin Scorsese and global superstar Leonardo DiCaprio (now both Oscar Winners, Scorsese for The Departed and DiCaprio for The Revenant) have worked together for five movies, and none of them are under 2 hours and 10 minutes (Shutter Island being the shortest at a “mere” 138 minutes). This is not meant to be a complaint. There are stretches when each of these films feels like they should be trimmed a little, but in all honestly, I’m glad it’s all there because any student of film could learn things with each successive viewing of a Scorsese film.

At least that’s what I’ve heard from students of film.

Martin Scorsese and Leonardo DiCaprio are scheduled to make the film Killers of the Flower Moon sometime in 2021 (hopefully). Until that comes out (hopefully), here are all five of their collaborations ranked.

Please vote for your favorite at the end of the list.


1) The Departed (2006)

Oscar Wins-

  • Best Picture
  • Best Director (Martin Scorsese)
  • Best Adapted Screenplay (William Monaghan)
  • Best Editing (Thelma Schoonmaker)

Oscar Nominations

  • Best Supporting Actor (Mark Wahlberg)

Martin Scorsese finally got his Best Director Oscar for 2006’s Oscar winning Best Picture. It’s the Oscar he should have gotten for Raging Bull…or Goodfellas, but better late than never. Directing an all-star cast with William Monahan’s Oscar Winning screenplay, Scorsese makes the audience sweat blood with desperation as all the characters are practicing some form of deception.

Leonardo DiCaprio performance as Billy Costigan is a study in inner torment, though of the major stars, I rank his performance as third best behind Matt Damon’s scumbag cop and Jack Nicholson’s scenery gnawing Frank Costello.

Why It’s Ranked First

The Departed is the leanest of the Scorsese/DiCaprio collaborations as I think most would agree the other four movies on this list have minor issues with bloat. Seeing all those stars onscreen with Baw-stun accents in varying degrees of success (Matt Damon’s feels the least forced, probably because he’s from that area) is worth a watch on its own. Sure, the only female character of importance in the entire movie feels like a function of the plot instead of an actual person, but hopefully that’s forgiven.

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2) The Wolf of Wall Street (2013)

Oscar Wins- None

Oscar Nominations

  • Best Actor (Leonardo DiCaprio)
  • Best Supporting Actor (Jonah Hill)
  • Best Director (Martin Scorsese)
  • Best Adapted Screenplay (Terence Winter)
  • Best Picture

Simplified, the movie is two and half hours of men behaving terribly and getting really rich doing so. Led by DiCaprio’s Jordan Belfort, most of the cast is drug addled, misogynistic and avaricious to an extreme I hadn’t seen on film for a while. You don’t condone their behavior, but while you’re watching it you kind of wish you were part of it. It’s the highest of highs, but the comedown is an extremely hard crash. As in a plane, or a Lamborghini.

DiCaprio’s best performance in a Scorsese film. It’s a coked-up, no brakes, adrenaline rush for most of the movie’s running time but DiCaprio never lets us lose sight that there’s a human being underneath the druggy haze. Granted, it’s not a particularly likable human being most of us would want to spend any time with unless we were being paid to, but a human being nonetheless. DiCaprio doesn’t need to sell us this pen.

Why It’s Ranked Second

Wolf’s final act is the fall after the rise. It’s no surprise that what follows is less than what precedes it. It doesn’t make it a worse movie, just a less energized one, which the viewer definitely feels after the two-hour mark.


3) The Aviator (2004)

Oscar Wins

  • Best Supporting Actress (Cate Blanchett)
  • Best Editing (Thelma Schoonmaker)
  • Best Art Direction (Dante Ferretti, Francesca Lo Schiavo)
  • Best Cinematography (Robert Richardson)
  • Costume Design (Sandy Powell)

Oscar Nominations

  • Best Picture
  • Best Director (Martin Scorsese)
  • Best Supporting Actor (Alan Alda)
  • Best Actor (DiCaprio)
  • Best Original Screenplay (John Logan)
  • Sound Mixing (Tom Fleischman, Petur Hliddal)

The Aviator made Scorsese consider retirement after all the struggles with the studio and budget overruns. Good thing he didn’t. This Howard Hughes biopic has Leonardo “way of the future” DiCaprio looking nothing like Howard Hughes but capturing his spirit perfectly. It’s got huge stars in small parts along with cameos from other Scorsese projects which helps during the movie’s ebbs and flows.

DiCaprio’s showiest acting role to date before he grunted his way to an Oscar for The Revenant and well-deserving of an Oscar nom. It’s inside out acting as Leo shows us Hughes’ inner battles while never feeling like he’s acting for effect. There’s a solid case to be made that he deserved the Best Actor Oscar more than Jamie Foxx did that year. I would agree.

Why It’s Ranked Third

It’s the most uneven of the Scorsese-DiCaprio movies. There are some scenes that just go on way too long along with scenes of perfect cinema (the flight). You leave the movie thinking The Aviator is very good, but just misses greatness.


4) Gangs of New York (2002)

Oscar Wins - None

Oscar Nominations

  • Best Picture
  • Best Actor (Daniel Day-Lewis)
  • Best Director (Scorsese)
  • Best Original Screenplay
  • Best Cinematography (Michael Ballhaus)
  • Best Art Direction/Set Direction (Dante Ferretti, Francesca Lo Schiavo)
  • Best Costume Design (Sandy Powell)
  • Best Film Editing (Thelma Schoonmaker)
  • Best Sound
  • Best Song

Martin Scorsese’s passion project took years before it finally hit the screen but as you watch the movie, you wonder what Scorsese had to compromise to finally get it made. The movie looks beautifully grimy at times, but after the credits roll it feels like a triumph of set decoration over story. The generic DiCaprio-Cameron Diaz-Henry Thomas love triangle feels pulled out of another movie.

DiCaprio’s Amsterdam Vallon is his weakest performance in a Scorsese movie, but it’s not really his fault. Amsterdam really isn’t given anything but a pretty basic storyline. DiCaprio’s accent is all over the place and he physically seems too slight to be intimidating. It doesn’t help that Daniel Day-Lewis blows him off the screen with his pit bull of a performance as Bill the Butcher.

Why It’s Ranked Fourth

Aside from its production design and various sweeping overhead shots, Gangs of New York feels less epic than it looks. After over a year of postproduction which caused a delay in its release, it should have been a slam dunk, but it ends up being a polite golf clap. Sorry for the mixed sports metaphors.

Don't set the island on fire.

Don't set the island on fire.

5) Shutter Island (2010)

Nominated for jack. Based on the novel by Dennis Lehane, Scorsese “lighter” fare after winning the Oscar is entertaining an entertaining enough parlor trick, but even its fans would agree that it feels way too long and would have greatly benefited from trimming 20 minutes. Even if you can guess the movie’s main twist(s), you’re diverted for the most part as it’s rarely boring. It’s fun to see respected actors like Ben Kingsley and Max Von Sydow acting to the cheap seats.

DiCaprio does some pretty stellar work as a man just trying to do his job in extreme circumstances and never realizing what he’s up against. Teddy Daniels moves from a WTH character to a W…T…F by the end credits. DiCaprio’s scenes with Mark Ruffalo have an unexpected comic bite.

Why It’s Ranked Last

Scorsese’s follow up to The Departed isn’t endeavoring for any awards, just trying to entertain. As stated before, it’s the only Scorsese/DiCaprio movie that feels longer than it needs to be. You’re never bored, but you’re also never taken away.


Since most of you are staying at home, you’ve got 16-20 hours to kill. Revisit some of these movies you might have not seen in a while and maybe in 2021 Killers Of The Flower Moon will be released for lucky number six.


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