5. Toni Braxton
The songstress has had money problems since the 90s and has actually filed for bankruptcy twice. Braxton declared bankruptcy in 1998 because she was in debt for $3.9 million. Her personal possessions were sold including her awards, to pay back the IRS. Then, Braxton filed again in 2010 and it was announced that she may be close to $50 million in debt. Maybe her reality show will help her pay back the government. We think she needs some counseling or she might end up back on the list of celebs who blew their fortune yet again.
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