Tom Petty
Tom Petty declared bankruptcy in 1979. He wasn't broke; the stint was just a legal paly to get himself out of an exploitative contract with a record label that refused to pay him due to internal debt. They pocketed 100% of the cash that he earned for them (which was millions) while claiming that they were deeply in debt and needed a bailout. Petty filed for bankruptcy to get the attention of the IRS and the Better Business Bureau. He ended up winning the case, shutting down the label, and claiming all of his lost profits.
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