Forget Turtle and Johnny Drama. MC Hammer had an entourage for the ages: a 200-person crew that reportedly cost him $500,000 every month. To be fair, who else was going to wash all of those Hammer pants? Not to mention there was probably a lot of housework to be done in Hammer’s $30 million mansion. Back in 1990, spending that much cash on a house might not have seemed so crazy. According to Forbes, Hammer pulled in $33 million after his Diamond-selling album Please Hammer, Don’t Hurt ‘Em was released. It only took six years before he found himself in bankruptcy court claiming assets of $9.6 million compared to debts of $13.7 million. He even owed $500,000 to NFL-star-turned-analyst Deion “Prime Time” Sanders. While Hammer has recovered to, among others things, help start a new search engine called WireDoo, the sting of his bankruptcy lives on. In 2010, the most lopsided beef in rap history played out when Jay-Z joked about Hammer’s financial troubles on Kanye West’s song “So Appalled,” prompting Hammer to release a music video on YouTube featuring a Jay-Z lookalike running away from the Devil.
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