Martin Scorsese and Leonardo DiCaprio

"[5] In 1999, Scorsese produced a documentary on Italian filmmakers titled Il Mio Viaggio in Italia, also known as My Voyage to Italy.

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.

Scorsese initially struggled selling his idea of the film until DiCaprio became interested in playing protagonist Amsterdam Vallon, a young leader of the Irish faction.

[13] The film received positive reviews and was a box office success, bolstering DiCaprio's reputation as one of Hollywood's preeminent talents.

The film was a huge commercial and critical success, earning 11 Oscar nominations at the 77th Academy Awards (the most for the ceremony that year).

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.

DiCaprio played the role of Billy Costigan, a state trooper working undercover in the Irish Mob in Boston.

Shutter Island originally received mixed to positive reviews, but was a financial success, and throughout the years became a cult classic.

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.

In October 2018, it was announced that DiCaprio and Scorsese were re-teaming for a film adaptation of David Grann's Killers of the Flower Moon, about the Osage Indian murders.

[31] The film gained universal critical acclaim, ended up in many best of year and best of decade lists, and received ten Academy Awards nominations, including Best Picture, Best Director for Scorsese, and Best Actress for Lily Gladstone.