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MC Hammer
In the early ’90s, no artist came close to MC Hammer’s popularity. By 1991, the rapper had won two Grammys and was worth an estimated $33 million. With all the money trickling in from record deals and brand endorsements, MC Hammer bought a large mansion and employed a massive entourage of groupies that accompanied him everywhere he went. It only took five years of extravagant spending, and before he knew it, the rapper found himself filing for bankruptcy with debts amounting to $13 million.