All six DiCaprio and Scorsese collaborations ranked

Whilst humongous studio productions and superhero franchises dominate the film business globally, only a handful of names can generate worldwide interest and create such buzz around their work that people will flock to the cinema for them. Amongst these, lie Martin Scorsese and Leonardo DiCaprio.

The director and actor have been at the top of their craft for decades and command global recognition for their work. They have collaborated six times, not including the 15-minute short film The Audition, with DiCaprio proving to be one of Scorsese’s favourite actors. Something tells me it’d be a fun exercise to rate these collaborations as their latest Killers of the Flower Moon recently hit cinemas. So, here we go!

6. Shutter Island (2010)– A confused attempt disowned by Scorsese

It’s rare to have a movie as good as Shutter Island ranked as the worst film on a list, but it is even rarer to hear Scorsese regretting a movie he made. But that’s what he did in his recent interview with GQ. A mystery-thriller set in 1954, the film follows DiCaprio’s Deputy US Marshal ‘Teddy’ Daniels, as he visits a psychiatric facility on the Island. DiCaprio’s performance is the movie’s highlight, alongside its mysterious ending that has grown to be loved by a cult following. Though not the most sophisticated attempt by the director, one cannot ignore its gripping intensity and experimental nature.

5. The Aviator (2004)– An ambitious rollercoaster

DiCaprio plays the lead role in Scorsese’s iconic biography of the famous American entrepreneur Howard Hughes. The Aviator is often one of the first movies to be quoted by Scorsese lovers when discussing his filmography and its diversity. The film is also a more ambitious effort by the director, and DiCaprio’s flashy and charismatic acting more than justifies it. The movie was nominated for 11 Academy Awards, including Best Actor and Best Director for the duo.

4. Gangs of New York (2002)– A star-studded period crime drama

This film was the first collaboration between DiCaprio and Scorsese, also featuring Daniel Day-Lewis and Cameron Diaz in important roles. Set in the 19th century, it attempts to present a fictionalised account of life in New York City. DiCaprio plays the role of Amsterdam Vallon, who returns from prison to take revenge on the killer of his father Bill the Butcher (Day-Lewis). It is one of the most riveting works from the master of crime drama himself, whose lower ranking is only due to DiCaprio’s slightly weaker performance in comparison with the other films listed here. However, who’s to blame him for this when he shares the screen with a certain Daniel Day-Lewis?

3. The Departed (2006)– Euphoric thriller with an appealing ensemble

The Departed delivered Scorsese’s long-awaited Best Director Academy Award, which, god knows how, is his only one in the category. The star-studded cast includes DiCaprio, Jack Nicholson, Matt Damon, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga and Alec Baldwin. Nevertheless, DiCaprio shines through in his portrayal of Bill Costigan, who is trying to infiltrate and bust a Boston crime syndicate run by Frank Costello (Nicholson). The film is an edge-of-your-seat thriller, with Dropkick Murphy’s I’m Shipping Up to Boston further heightening the tension that grips the plot throughout. 

2. The Wolf of Wall Street (2013)– DiCaprio’s magnum opus?

All right. Ranking perhaps the most quoted and iconic performance from DiCaprio in the second is probably going to irk many of the fans. But it is a credit to the film at the very top that even sublime and almost perfect performances do not top the list of Scorsese-DiCaprio collaborations. DiCaprio is at his absolute best as he plays the role of Jordon Belfort in this dark comedy that is filled with a lot of dry humour and multiple moments of breaking the fourth wall. The plot goes through the highest of the highs and the lowest of the lows as the viewer is treated to a no-holds-barred, drug-filled, almost unbelievable storyline. 

1. Killers of the Flower Moon (2023)– Scorsese at his narratively ambitious best

Scorsese’s long-awaited collaboration with two of his most frequent partners – DiCaprio and Robert De Niro – is definitely amongst the very best works of the director, sitting comfortably alongside greats such as Taxi Driver, King of Comedy, and Goodfellas. DiCaprio plays Ernest Burkhart, an ambitious and greedy young man who follows the orders of his uncle William King Hale (De Niro) as they try to usurp the wealth of the Osage people through plots of marriage, murders, and bombing. A vibrant, nuanced and haunting adaptation of David Grann’s book Killers of the Flower Moon: The Osage Murders and the Birth of the FBI, the film stands tallest in the list of Scorsese-DiCaprio collaborations.