Year Arrested: 1969

Crime: Heroin possession.

By 1969 Jimi Hendrix's wardrobe was at its peak levels of insanity and awesomeness. Imagine the knowing smirks airport security must have given each other when he strolled up at the Toronto airport. After finding a small bag of H in his luggage, Jimi's trippy gear was on full display in the ensuing mugshot. But joke was on the po-po; the charge against Hendrix was dropped after he convinced the judge that a fan had slipped the drugs into his bag.