Year Arrested: 1995

Crime: Sexual abuse.

Up until 1995, Tupac certainly had his run-ins with the law, including shooting a cop in the ass, but this is by far his most stylish mugshot. Stemming from a 1993 sexual abuse charge, this was the mugshot taken before Pac went to jail for 11 months. In a rugged bomber jacket, Tupac looked defiant of what awaited him.