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Toni Braxton
Grammy Award winner, Tony Braxton, dominated the RnB scene from the ’90s well into the 2000s with her sultry voice and charming personality. Even with most of her songs topping Billboard charts, the singer still managed to file for bankruptcy twice. First in 1998 and the second one 12 years later. The singer successfully managed to pay all her debts, which at one point amounted to close to $50 million, and was forced to surrender rights to 27 of her songs in the process.