Cyndi Lauper
Lauper started her career with several grand failures. Her first album with the band Blue Angel flopped massively, and her manager sued her for $80,000. Lauper was forced to file bankruptcy in 1981. She recovered after she released her hit solo album She's So Unusual, and she went on to become a Grammy-winning artist and inspiration to many.
Aaron Carter
Aaron Carter was once a major pop star, but his fall from fame pushed him so far away from the limelight that he wasn't able to pay his bills. "When I turned 18, I got hit with all those taxes. I filed a Chapter 7 bankruptcy last year; now I'm already over $100,000 in debt," said Aaron Carter in a 2018 interview with Esquire. Recently, Carter has been able to recoup his losses, and he released an album that did fairly well.
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