Ranked: The Unbeatable Martin Scorsese & Leonardo DiCaprio Movie Collabs

Over the past two decades, the esteemed filmmaker Martin Scorsese has partnered with Leonardo DiCaprio in six movies, each a cinematic masterpiece. Their first joint project was the 2002 film “Gangs of New York,” which began production just under a decade after DiCaprio’s standout performances in “What’s Eating Gilbert Grape,” “Romeo + Juliet,” and “Titanic.” Scorsese’s latest film featuring DiCaprio is the 2023 release “Killers of the Flower Moon.” Their upcoming collaboration includes a movie about organized crime in Hawaii, set to star DiCaprio alongside Dwayne Johnson and Emily Blunt. Additionally, DiCaprio will lead the cast for Scorsese’s adaptation of “The Devil in the White City.” With their impressive track record in the film industry, these two Oscar-winning icons have built a fruitful working relationship. As their next project gets underway, fans should take the chance to watch every movie they’ve made together.

Ranked from worst to best, these are all of Scorsese’s movies featuring DiCaprio.

6) The Wolf of Wall Street

In 2013, Scorsese chose DiCaprio to portray Jordan Belfort, a real-life fraudster who transformed into a stockbroker, in “The Wolf of Wall Street.” This film is adapted from Belfort’s autobiography and follows his increasing corruption as the story unfolds. DiCaprio gives an outstanding performance alongside a talented ensemble including Margot Robbie, Jonah Hill, and Matthew McConaughey. Unfortunately, despite its impressive cast, “The Wolf of Wall Street” loses momentum somewhat after reaching its halfway point in its three-hour duration.

In his career, just as he’s done before, Scorsese effectively exposes the reprehensible actions the wealthy and powerful will resort to in order to amass more wealth and power. However, it can be challenging to stay engaged with Belfort’s story throughout, and at times, the movie’s central message seems to get overshadowed by the excessive antics. Despite being not among Scorsese’s finest works, The Wolf of Wall Street is sure to captivate anyone who appreciates a top-notch performance by DiCaprio.

5) The Aviator

In 2004, Leonardo DiCaprio collaborated once more with Martin Scorsese in the biopic “The Aviator.” He played the role of Howard Hughes, a filmmaker and aerospace engineer, whose life was chronicled in the film. The storyline was adapted from Charles Higham’s book “Howard Hughes: The Secret Life.” The movie showcases Hughes’ significant achievements in both aviation and entertainment industries, as well as his intricate personal relationships. In this production, DiCaprio delivers a nuanced portrayal of the real-life character, with Cate Blanchett bringing Katharine Hepburn to life on screen and Kate Beckinsale embodying Ava Gardner.

The storyline of “The Aviator” is captivatingly engaging and skillfully executed, although it doesn’t quite match the greatness of Scorsese’s other iconic works. Despite this, the film remains a valuable watch due to its impressive cast, meticulous visuals and set design, and intricate storyline.

4) Gangs of New York

Scorsese and DiCaprio’s initial collaboration is often considered one of Scorsese’s lesser-known masterpieces. The film, titled “Gangs of New York,” draws inspiration from the 1927 nonfiction book by Herbert Asbury, entitled “The Gangs of New York: An Informal History of the Underworld.” This cinematic creation delves into the fierce rivalries among gangs in 19th-century New York City. In Scorsese’s film, DiCaprio portrays the main character, Amsterdam Vallon, who returns to the Five Points district seeking vengeance for his father’s killer, Bill “The Butcher” Cutting (Daniel Day-Lewis).

Scorsese and DiCaprio’s debut project together is often overlooked but deserves more recognition as one of Scorsese’s most exceptional works. The movie, known as “Gangs of New York,” takes its inspiration from the 1927 nonfiction book by Herbert Asbury titled “The Gangs of New York: An Informal History of the Underworld.” This film explores the intense rivalries among gangs in 19th-century New York City. DiCaprio’s character, Amsterdam Vallon, in Scorsese’s movie, is portrayed as seeking revenge for his father’s murderer, Bill “The Butcher” Cutting (Daniel Day-Lewis), after returning to the Five Points district.

The movie “Gangs of New York” is an intense and raw period film that showcases remarkable character depictions all around. Leonardo DiCaprio skillfully conveys Amsterdam’s desire for retribution, while Daniel Day-Lewis convincingly plays the role of a sinister villain with a twirled mustache. Despite its nearly three-hour running time, “Gangs of New York” never becomes tedious, as it maintains audience interest through its pulse-pounding tension and action sequences.

3) Killers of the Flower Moon

Martin Scorsese’s latest film, “Killers of the Flower Moon,” brings David Grann’s 2017 novel to life with remarkable precision. The plot, inspired by real events, focuses on a series of murders in the 1920s Oklahoma that targeted members of the Osage Nation following the discovery of oil, attracting many greedy white Americans to the land. Leonardo DiCaprio and Robert De Niro deliver outstanding performances as Ernest Burkhart and his uncle William Hale, respectively, but it’s Lilly Gladstone’s standout portrayal of Ernest’s wife Mollie Burkhart, an Osage member, that truly embodies the essence of “Killers of the Flower Moon.” Although the film’s almost three-and-a-half-hour duration is slightly longer than necessary, “Killers of the Flower Moon” effectively addresses a significant topic in an engaging way. The film’s portrayal of America’s history with its Indigenous population is chilling, and its themes are strikingly relevant even today. Therefore, “Killers of the Flower Moon” promises to captivate moviegoers for years to come.

2) Shutter Island

In 2010, Scorsese crafted an engaging, suspenseful drama titled Shutter Island, adapted from Dennis Lehane’s book by the same name. The film features Leonardo DiCaprio as U.S. Marshal Teddy Daniels and Mark Ruffalo as his partner Chuck Aule. They are dispatched to a secluded psychiatric hospital on an island in Boston Harbor during the 1950s to investigate the mysterious disappearance of one of its patients.

Immersed in a captivatingly unsettling ambiance with horror elements subtly woven throughout, “Shutter Island” offers an unforgettable viewing experience for first-timers. The movie’s surprising plot twist keeps drawing viewers back to rewatch “Shutter Island“, as its intricate details demand multiple viewings to fully appreciate them. Additionally, DiCaprio and Ruffalo make a stellar on-screen pairing. DiCaprio’s portrayal of Teddy’s deteriorating grasp on reality as the story unfolds is a chilling spectacle in itself. In summary, it’s challenging to find a Scorsese film that matches the chills and excitement provided by “Shutter Island“.

1) The Departed

Martin Scorsese and Leonardo DiCaprio’s most notable collaboration is none other than the 2006 film “The Departed”. This is a remake of the 2002 Hong Kong movie “Infernal Affairs”, but set in Boston. In this film, DiCaprio plays Billy Costigan, a young police officer who’s given the challenging task of infiltrating the criminal empire of Frank Costello, portrayed by Jack Nicholson. Although Scorsese has directed many other gangster movies, “The Departed” stands out because of its gripping plot full of unexpected twists and turns.

2007 saw Martin Scorsese’s film “The Departed” win both Best Director and Best Picture at the Oscars, solidifying its status as one of his finest works. Leonardo DiCaprio delivers an outstanding performance that complements the stellar portrayals by Nicholson and the rest of the cast. The screenplay penned by William Monahan keeps audiences entranced with its captivating narrative. To top it off, the movie’s unexpected climax is executed brilliantly, making “The Departed” a tough act to follow in the crime thriller genre.

2025-03-11 22:14