10. Cyndi Lauper: The True Colors singer was not seeing green during some early career struggles — filing for bankruptcy in 1981, after her group Blue Angel disbanded and was sued by their manager — but put herself on the map just two years later with her enduring pop anthem, Girls Just Wanna Have Fun. 12. MC Hammer: U Can’t Touch This was clearly not written about Hammer’s bankroll: the Bay Area-based rapper reported a debt of more than $13.7 million during a 1996 bankruptcy court hearing, less than seven years after the release of his multi-Platinum selling album, Please Hammer Don’t Hurt ‘Em.