1953 Boston Police - James "Whitey" Bulger
His early mug shots attest to a certain brooding criminal sexiness. Whitey Bulger, the inspiration for Martin Scorsese’s The Departed, was arrested in Santa Monica earlier this month. The 82 year-old mobster ran Boston’s south side for decades and was responsible for dozens of gangland killings. Jack Nicholson portrayed him in the movie.
The Gay Highwaymen 