9. Toni Braxton
Toni Braxton was one of the best-selling female artists of the 90s, earning her the title of the “Queen of R&B” at the height of her fame. Her song “Un-Break My Heart” even earned her a Grammy award.
She first filed for bankruptcy in 1998 and has blamed it on the insignificant royalties she earned on her first album, and her admittedly out of control spending habits. She filed for bankruptcy again after she had to pull out of her Vegas show because she was diagnosed with microvascular angina, and was told she wouldn’t be able to do long, strenuous shows anymore. Luckily, she’s still pretty popular in Europe and is able to do smaller, private shows for fans to make money.
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