Unfortunately for MC Hammer, his music career has been overshadowed by his terrible business acumen. But truth be told, he didn't have much talent in the music department either. At Hammer's height of fame, he was worth about $30 million but was spending far more on his lavish lifestyle, which reportedly consisted of a 200-person entourage, costing him $500,000 per month! In 1996, he filed for bankruptcy when he was $13 million in debt. But story's not over yet. In 2011, the IRS alleged that Hammer still owed just over $700,00 in back-taxes. Although Hammer claimed on Twitter that he had paid all his debts and that he even got a receipt. I should hope so. MC Hammer, you joined our list of repeat offenders.