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 
He is sentenced…and is off to the pen to do retirement gangland style.