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T-Pain

See Pictures of Celebrities Who Are Poor Today
Image Source: Wikipedia

With a long name such as Faheem Rasheed Rajm, this American rapper and songwriter decided on the stage name T-Pain to make it easier to pronounce his name. He went from $40 million to nothing and had to borrow money to buy burgers for his kids, and that was in his own words. But he bounced back, and after years of singing, he is worth $10 million, but that could have been much more was it not for bad management.