12. Toni Braxton
Toni Braxton has had some massive radio hits during her career. She has also been one of many in the music business to learn that money earned is not always money earned. SEE ALSO: 15 celebrity strippers you NEVER knew (With Pictures)
Braxton was forced to file for bankruptcy in 1998 because of that reality and also because she admittedly spent more than she should have at that time of her life. She filed for bankruptcy a second time in 2010, but she has since shown that some life lessons are hard learned. Reality television series Braxton Family Values helped get Braxton back on her feet, and she purchased a mansion in January 2014. Spend wisely, ma’am.
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