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The Man in Black was busted in October 1965 when U.S. Customs agents found hundreds of pep pills and tranquilizers in his luggage.
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The Doors vocalist was photographed following a 1970 conviction for exposing himself during a concert performance in Miami the prior year.
The Rolling Stones singer was arrested on a narcotics charge following a police raid at bandmate Keith Richards’s English home.
Frank Sinatra was arrested by the Bergen County, New Jersey sheriff in 1938 and charged with carrying on with a married woman (yes, you could get popped for that back then).