The Departed: Leo’s Leather Belstaff Jacket as Billy Costigan

Leonardo DiCaprio as Billy Costigan in The Departed (2006) Vitals Leonardo DiCaprio as Billy Costigan, undercover Massachusetts State Police trooper Boston, Fall 2006 to Spring 2007 Film: The Departed Release Date: October 6, 2006 Director: Martin Scorsese Costume Designer: Sandy Powell WARNING! Spoilers ahead! Background The Departed was widely released 20 years ago today on October 6, 2006, days after its September 26th premiere at the Ziegfield Theater. William Monahan adapted the material from the 2002 Hong Kong thriller Infernal Affairs, also taking inspiration from real-life Boston crime figures like Winter Hill Gang leader Whitey Bulger and his crooked FBI handler, John Connolly. After six nominations, the prolific Martin Scorsese finally won his first Academy Award for Best Director for The Departed—which was also honored with Best Picture, Best Adapted Screenplay to Monahan, and Best Film Editing to Scorsese’s regular collaborator, Thelma Schoonmaker. This was also Scorsese’s…