As long as there's been music, there have been musicians who get into trouble with the law.
Entries Beginning with W
Wendy O' Williams was arrested after a show and charged with assaulting a police officer. She claimed that she decked the police officer in self-defense after she felt that she was groped.
In addition to losing much of his properties, Nelson recorded an album ("The IRS Tapes: Who'll Buy My Memories") solely to pay back his past due taxes and fines, nearly $16 million by some accounts. (He's also been busted for marijuana and hallucinogenic mushroom possession.)
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