James "Whitey" Bulger, the notorious Boston crime boss who was serving a life sentence in prison and who also served as an informant to the FBI, died on Tuesday at the age of 89. His story has inspired a handful of gangster characters across film and TV, including one direct adaptation of his life story.
"The Departed" (2006)
Jack Nicholson's role as mob boss Frank Costello in Martin Scorsese's Boston gangster drama "The Departed" is very loosely based on Whitey Bulger, though Scorsese's film is actually a remake of the Hong Kong film "Infernal Affairs" from 2002.
"Brotherhood" (2006 - 2008)
Jason Isaacs and Jason Clarke played two Irish-American brothers, one a crime lord and the other a politician, in a drama inspired by the relationship between Whitey Bulger and his brother Billy. "Brotherhood," however, is set in Providence, Rhode Island as opposed to Boston.
"The Blacklist" (2013-present)
NBC's drama starring James Spader as the country's most notorious criminal Raymond "Red" Reddington was inspired by Whitey Bulger's capture and his relationship as an informant to the FBI. Spader's portrayal, though, may have a bit more Hannibal Lecter in him than Whitey Bulger.
"Ray Donovan" (2013)
James Woods portrayed a Bulger-esque Boston crime boss named Sully Sullivan in the first season of the Showtime drama "Ray Donovan." Woods donned a wicked Boston accent opposite Steven Bauer before meeting an untimely end at the hands of a double crosser.
"Whitey: United States of America vs. James J. Bulger" (2014)
Joe Berlinger's documentary captured the trial of Whitey Bulger to use as a springboard to make a broader point about corruption within law enforcement. He examines the extent of Bulger's close-ties and relationship with the FBI and the Department of Justice as an informant.
"Black Mass" (2015)
Director Scott Cooper finally brought the true story of Whitey Bulger to the screen in the 2015 drama "Black Mass." Cooper recruited Johnny Depp to give a vampiric performance as the ruthless mob boss, with his character's thin hair, heavy makeup and massive forehead doing some heavy lifting.