Fugitive gangster Whitey Bulger snuck into 'The Departed' to critique Jack Nicholson’s portrayal

Gregory Wakeman
Whitey Bulger apparently had huge issues with Jack Nicholson's performance in The Departed (Image by Warner Bros)

A new book on infamous Boston gangster Whitey Bulger has revealed that the criminal went to see The Departed as a fugitive, and critiqued Jack Nicholson’s performance throughout.

Authors Casey Sherman and Dave Wedge told this story to The Hollywood Reporter to mark the release of Hunting Whitey: The Inside Story of the Capture & Killing of America’s Most Wanted Crime Boss. 

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Bulger was particularly interested in Martin Scorsese’s Oscar winning gangster film as Nicholson’s portrayal of Frank Costello was heavily inspired by his life.

According to Sherman, “Bulger was spotted in the movie theater by a Sheriff's deputy who happened to be from Boston. He told us in an interview that Bulger shook his head in disgust many times while watching Jack Nicholson's fictional version of him on the big screen.”

Former mob boss and fugitive James "Whitey" Bulger, who was arrested in Santa Monica, California on June 22, 2011 along with his longtime girlfriend Catherine Greig, is seen in a booking mug photo released to Reuters on August 1, 2011. Bulger fled Boston in late 1994 after receiving a tip from a corrupt FBI agent that federal charges were pending. Greig joined him a short time later and has been charged with harboring Bulger as a fugitive. REUTERS/U.S. Marshals Service/U.S. Department of Justice/Handout (UNITED STATES - Tags: CRIME LAW HEADSHOT) FOR EDITORIAL USE ONLY. NOT FOR SALE FOR MARKETING OR ADVERTISING CAMPAIGNS. THIS IMAGE HAS BEEN SUPPLIED BY A THIRD PARTY. IT IS DISTRIBUTED, EXACTLY AS RECEIVED BY REUTERS, AS A SERVICE TO CLIENTS

“Bulger was armed and the Sheriff's deputy was not. By the time the cop retrieved his service weapon, Whitey Bulger was gone.”

Despite Bulger’s criticisms, The Departed went on to be both a critical and financial success for Scorsese, winning four Oscars at the 79th Academy Awards, including Best Picture, Best Director, Best Adapted Screenplay, and Best Film Editing

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Clearly Bulger was a hard man to be please, as he was just as critical about Black Mass, the 2015 gangster film that was actually based on his life and criminal antics.

Sherman and Wedge read various letters where he “voiced his anger for the filmmakers behind the Whitey biopic Black Mass.”

Bulger, who was murdered in prison in 2018 while servicing two consecutive life sentences, had originally “refused to cooperate with the production because Depp’s character ratted out both his friends and gangland rivals.”