3. Toni Braxton
Award-winning singer and reality TV star, Toni Braxton has sold more than 40 million records during her career. However, the songstress has had to file or bankruptcy twice, even though she’s made millions. The first filing was in 1998, after she entered into a record deal with LaFace that wasn’t beneficial to her. In 2010, Braxton had to file for bankruptcy a second time, when she suddenly had to cancel her one-woman show in Vegas due to her health (she suffers from lupus). This bankruptcy reportedly left her $50 million in debt. Toni Braxton has since made a comeback with Braxton Family Values, the reality show in which she stars in with her sisters and mother.
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