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Trivia about The Departed :
Jack Nicholson’s Frank Costello is partly based on notorious South Boston gangster Whitey Bulger.
Denis Leary was offered the role of Dignam in this film, but turned it down due to scheduling conflicts with his television show, “Rescue Me” (2004).
Martin Scorsese sent the script to Mel Gibson, offering him an unspecified role. Gibson thought the script was fantastic, but was unable to accept the part because he was starting production on Apocalypto at the time.
As research for his character’s occupation, Matt Damon worked with a Massachusetts State Police unit out of Boston. He accompanied them on routine patrols, participated in a drug raid and was taught proper police procedures like how to pat down a suspect.
Originally, Jack Nicholson turned down his role in the movie, but after a meeting with Martin Scorsese and Leonardo DiCaprio, he was finally convinced to play the role of Frank Costello.
Leonardo DiCaprio was cast in the title role in The Good Shepherd (2006), but he dropped out to play Billy Costigan in this movie. Matt Damon then took the role.
Originally Brad Pitt was cast as Colin Sullivan, but later dropped out. He continued to produce the film under his (and his then wife Jennifer Aniston’s) production company, Plan B.
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