Cyndi Lauper
In the 1980s, Cyndi Lauper was a huge success with colossal hits like Girls Just Want to Have Fun and True Colors. It’s true that girls just want to have fun, but there’s such a thing as too much fun. Following the breakup of her band and an extravagant lifestyle, Cyndi ultimately filed for bankruptcy.
At one point, she was waiting tables in between gigs, but today, she has an estimated net worth of over $50 million from royalties and wise investments. Despite amassing an incredible amount of wealth, Cyndi likes to live below the radar in a modest home (by Hollywood standards) in Connecticut.