Cyndi Lauper
Back in the ‘80s, it was hard to find a more popular musician than Cyndi Lauper. The singer could no longer have as much fun as she used to after filing for bankruptcy when her band split up. She even had to wait tables and perform in bars to make ends meet. She is now in a better place, but we are sure that it was not easy to get in debt after her success.
Janice Dickinson
Best known for her supermodel career, Janice Dickinson went through a rough patch thanks to her plastic surgery addiction. In 2014, it was revealed that she had a debt of $1 million. She mostly spent this money on cosmetic surgery. She ended up filing for bankruptcy. We hope that she has since learned her lesson and has stopped going under the knife.