3. Sid Vicious
Year Arrested: 1978
This infamous mugshot of the Sex Pistols' bassist has been immortalized as a lasting image of Sid Vicious. Taken a few months after his girlfriend Nancy Spungen was found murdered (which Vicious was arrested for, but not convicted) and after Sid tried to kill himself, the police snatched up the punk rocker after he assaulted Patti Smith's brother after a concert. Sid was sent to Riker's, got out on February 1, OD'd on heroin on February 2, and was found dead on February 3. Sid was so committed to his punk look and image that his alleged suicide note read "Bury me in my leather jacket, jeans and motorcycle boots."