DiCaprio Era

Film director Martin Scorsese and actor Leonardo DiCaprio have frequently collaborated, making a total of five feature films and one short film since 2002. The pair's films explore a variety of genres, including crime, thriller, biopic and comedy. Several have been listed on many critics' year-end top ten and best-of-decade lists.

The duo's films have been nominated for thirty-one Academy Awards, winning nine. In 2013, the duo was awarded National Board of Review Spotlight award for career collaboration. Scorsese's work with DiCaprio is considered to be as vital as his work with Robert De Niro.

The pair's relationship is one of the most successful collaborations in film industry, bringing a total of $1.3 billion earnings from their five feature films. DiCaprio called his collaboration with Martin as "accidental" and considered Taxi Driver and Mean Streets as his inspiration of Martin's work. Discussing his collaboration his said, "I am almost about to turn 40, and I am looking back at some of the stuff I’ve gotten to do, and at the center of it is this amazing accidental collaboration that I’ve gotten to have with Marty."Scorsese heard about DiCaprio by De Niro who worked with then 19-years old DiCaprio in This Boy's Life, and suggested his work to Scorsese as "impressive". Describing his first collaboration with Scorsese on Gangs of New York, he said, It was an incredible undertaking.

DiCaprio thanks Scorsese in his acceptance speech at 88th Academy Awards while accepting the Academy Award for Best Actor, saying "I have to thank everyone from the very onset of my career...to Mr. Jones for casting me in my first film to Mr. Scorsese for teaching me so much about the cinematic art form.

2000's

Gangs of New York

In 1999 Scorsese also produced a documentary on Italian filmmakers titled Il Mio Viaggio in Italia, also known as My Voyage to Italy. The documentary foreshadowed the director's next project, the epic Gangs of New York (2002), influenced by (amongst many others) major Italian directors such as Luchino Visconti and filmed in its entirety at Rome's famous Cinecittà film studios.

With a production budget said to be in excess of $100 million, Gangs of New York was Scorsese's biggest and arguably most mainstream venture to date. The film marked the first collaboration between Scorsese and DiCaprio. Director Scorsese initially struggled selling his idea of realizing the film until DiCaprio became interested in playing protagonist Amsterdam Vallon, a young leader of the Irish faction, and thus, Miramax Films got involved with financing the project. The film became one of the success pillars in Leo's career. DiCaprio's acting was well-received but was overshadowed by Daniel Day-Lewis' performance among most critics.

The Aviator

After collaborating in Gangs of New York, the duo worked on 2004 biopic The Aviator. Its centers the life of Howard Hughes (Played by DiCaprio), an aviation pioneer and director of Hell's Angels. The film portrays his life between the late 1920s and late 1940s, during which time Hughes became a successful film producer and an aviation magnate while simultaneously growing more unstable due to severe obsessive–compulsive disorder.

The film was a huge commercial and critical success earning 11-Academy Awards nomination at 77th Academy Awards the most for the ceremony. DiCaprio received his second and first Best Actor nomination.

Roger Ebert of Chicago Sun-Times gave the film four stars out of four and described the film and its subject, Howard Hughes, in these terms: "What a sad man. What brief glory. What an enthralling film...There's a match here between Scorsese and his subject, perhaps because the director's own life journey allows him to see Howard Hughes with insight, sympathy – and, up to a point, with admiration. This is one of the year's best films."

The Departed

The duo's collaboration in 2006 crime-drama The Departed, emerged as one of the most successful films in their careers. DiCaprio played the role of Billy Costigan, a state trooper working undercover in an Irish Mob in Boston. Highly anticipated, the film was released to overwhelmingly positive reviews and became one of the highest-rated wide release films of 2006. Budgeted at US$90 million, it also emerged as DiCaprio and Scorsese's highest-grossing collaboration to date, easily beating The Aviator´s previous record of US$213.7 million.

DiCaprio's performance in The Departed was applauded by critics and earned him a Satellite Award for Best Supporting Actor. The same year, both the Golden Globes and the Screen Actors Guild nominated DiCaprio twice in the Best Actor category (for other being Blood Diamond), however as per Academy rules of "only one nomination" in same category did not get him nominated for Best Actor, but he was nominated for Blood DiamondScorsese won his first Best Director award, after six previous losses. In 2008, The Departed was nominated for AFI's Top 10 Gangster Films list.

 

 

2010's

Shutter Island

2010's Shutter Island sees DiCaprio as a U.S. Marshal Edward "Teddy" Daniels, who is investigating a psychiatric facility located on an island and comes to question his own sanity. Receiving mixed to positive reviews, film was also a financial success. Roger Ebert of the Chicago Sun-Times gave the film 3½ stars out of 4 and wrote "the movie is about: atmosphere, ominous portents, the erosion of Teddy's confidence and even his identity. It's all done with flawless directorial command. Scorsese has fear to evoke, and he does it with many notes."

The Wolf of Wall Street

In 2013, DiCaprio reunited with Scorsese for the film The Wolf of Wall Street, that became Scorsese's highest-grossing film worldwide. The film is based on the memoir of the same name by Jordan Belfort and recounts his career as a stockbroker and the rampant corruption and fraud on Wall Street that led to his downfall. The film was listed on many critics Top Ten lists for the year and the decade and received five Academy Awards nominations.