11. Kurt Cobain
Year Arrested: 1986
Crime: Trespassing, failure to pay, malicious mischief and minor possession.
Even in 1986 Kurt Cobain didn't fit in. As a bullied youth, the 19 year old was caught tagging "Ain't got no how watchamacallit," though the above mugshot was simply for wandering onto the roof of an abandoned building. Cobain's style in the mugshot is simple, but we can already see traces of the grunge era that he would help usher in just a few years later.