Johnny Cash thought hiding prescription pills inside his guitar case would fool custom officials as he returned to the U.S. after a trip to Mexico in 1965. It didn't work. They were wise to something suspicious going down and searched his luggage to find hundreds of Dexedrine and Equanil tablets.

Later that year, Cash was arrested for trespassing in Starkville, Miss. This arrest led to the song 'Starkville City Jail.' These events were more than enough to fuel his outlaw image, but he gave fans plenty more to talk about during his 45-plus year career. As for famous mug shots, this one isn't bad. He almost looks handsome, and at least they gave him a chair.