MC Hammer $33 million 1991, In the early '90s, you couldn't go anywhere without hearing MC Hammer's "U Can't Touch This" or seeing someone wearing his signature parachute pants. Fashion may have moved on, but his album Please Hammer, Don't Hurt 'Em is still one of the best-selling hip-hop albums of all time.Forbes Magazine estimated Hammer's net worth at more than $33 million in 1991. But, just five years later, Hammer—born Stanley Burrell—was reportedly in debt to the tune of $13 million.Hammer filed for bankruptcy in 1996, but today, he says his debt wasn't a matter of losing his head. "No, I lost my heart," he says. "I didn't just take the money and say, 'I want to be a blessing to myself.' I took my money and employed 200 people in my community. I had a payroll of a million dollars a month at times."

Hammer says he's in a good place now. "Some people ask me sometimes, would I go back and change things?" he says. "They are flabbergasted by my answer. My real, true answer is I wouldn't change one thing. I really believe in the butterfly effect. Meaning that if I change one thing, everything else changes. I lose the kids I have now. I lose the relationships I have now. I lose the peace I have now. So I'm very happy with my decision."