T-Boz

One of the three members of R&B/hip hop girl-group TLC. The groups’s third album sold over 11 million copies. The singing trio was immensely popular and made plenty of money. Unfortunately their earnings were not enough to pay for their huge bills. T-Boz filed for bankruptcy in 1995 and in 2011.

Toni Braxton

Toni Braxton declared bankruptcy in 1998 and 2010 after a huge $20,000 American Express bill and monthly expenses of around $43,000. Fortunately she could put her bad days behind as she is back on track with an estimated net worth of $10 million.