Jack Nicholson/Whitey Bulger
Martin Scorsese’s The Departed swept the 2007 Academy Awards, winning an Oscar for Best Picture. The film—based on Andrew Lau and Alan Mak’s 2002 Hong Kong film Infernal Affairs—stars Leonardo DiCaprio, Matt Damon, and Jack Nicholson, who plays organized-crime lord Frank Costello, said to be loosely based on James Joseph “Whitey” Bulger. In a life-is-stranger-than-fiction story involving FBI informants, drug trafficking, and racketeering, Bulger seemingly pulled a vanishing act and was the subject of a national manhunt beginning in 1995. He was arrested in 2011 in Santa Monica, Calif., and awaits trial for a string of murders that took place during the 1970s and 1980s.