MC Hammer

In 1990, MC Hammer‘s net worth was an estimated 33 million. Six years later, the rapper filed for bankruptcy with at least 10 million in debt. During an interview with Oprah, Hammer told her that his bankruptcy was filed because he employed over 200 people every month. To this day, he still owes the IRS some back taxes and is Hollywood’s poster child of what not to do with your savings.