15: MC Hammer
The Grammy-winning artist MC Hammer was worth around $33 million at the peak of his career. Considering the fact that he was reportedly spending $500,000 a month on his 200-person staff, no amount of money would have been enough. The inevitable, bankruptcy, was only a matter of time. His other spends included the $10 million mortgage loan on his mansion, maintenance for 17 luxury cars and acquisition and care of a massive race course with 21 racehorses.
When the rapper went burst in 1996, he claimed $1 million in assets and $10 million in debt. As per the latest reports, it seems he has bounced back now and is taking control of his life. He is getting active back in the music industry and has produced few albums as well as ventured into starting his own company.