Jack Nicholson's Mob Boss in 'The Departed' Was Based on These Real-Life Gangsters

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Jack Nicholson's Mob Boss in 'The Departed' Was Based on These Real-Life Gangsters
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The Big Picture When directing movies, particularly his crime stories, Martin Scorsese strives for authenticity. What makes Mean Streets, Goodfellas, and The Wolf of Wall Street so intoxicating is the documentary-like coverage that Scorsese presents these illicit underworlds. By the same token, Scorsese's gritty realism underlines the brutality and fatalism of organized crime. As much as he glorifies crime, he'll always be sure to show the inevitable horror that awaits its participants.

Release Date October 5, 2006 Director Martin Scorsese Cast Leonardo DiCaprio , Matt Damon , Jack Nicholson , Mark Wahlberg , Martin Sheen , Ray Winstone Runtime 150 mins Main Genre Crime Writers William Monahan , Alan Mak , Felix Chong Studio Warner Bros. Pictures Expand What Is 'The Departed' About? Being set in Boston, Massachusetts, The Departed, a remake of the Hong Kong police thriller, Infernal Affairs, differs from Scorsese's oeuvre.

Frank Costello Was Modeled After Boston's Most Notorious Criminal, Whitey Bulger Close For Boston natives and organized crime historians, Costello's character description, a menacing Irish gangster with moles inside federal offices, sounds quite familiar. James "Whitey" Bulger, the head of the Winter Hill Gang in South Boston and the most infamous criminal from the area, was a loose inspiration for Nicholson's character.

If Costello is a stand-in for Bulger, then Damon's Sullivan is an avatar for John Connolly. Nicholson's Costello was a father figure to Sullivan as a youth. The film identifies the inextricable bond that would form between Sullivan and Costello. Even after joining the Special Investigations Unit, Sullivan still answers to his old boss he reported to while on the streets of Boston.

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