MC Hummer

MC Hammer had a 200-person entourage that reportedly cost him $500,000 each month. And he probably needed a large staff for all the housework and maintenance that needed to be done in and around Hammer’s $30 million mansion. In 1990, spending that much money on a house might not have seemed so crazy. According to Forbes magazine, Hammer earned $33 million after his Diamond-selling album “Please Hammer, Don’t Hurt ‘Em” was released.

But it took less than 6 years before he found himself in bankruptcy court, claiming assets of only $9.6 million compared to his debts of $13.7 million. He even owed $500,000 to NFL-star-turned-analyst Deion Sanders. While Hammer has recovered somewhat, the sting of his bankruptcy has lived on. In 2010, Jay-Z mocked Hammer’s financial troubles in Kanye West’s song “So Appalled” which made Hammer release a music video on YouTube in response, featuring a Jay-Z lookalike running away from the devil.