8. Mike Tyson: The biting boxer made more than $300 million in his legendary career, but reported a debt of $27 million during a 2003 bankruptcy hearing. 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.