4. MC Hammer
Virtually everyone remembers how huge MC Hammer was in the 1980s and 1990s. His oversized pants and electrifying dance moves were quite entertaining, but it wasn’t enough to keep him out of debt. Hammer was giving a significant portion of his money to friends and family, which left him with nearly nothing. The rapper also had to pay his entourage, which consisted of about 200 people. He even had to borrow $500,000 for his friend, athlete Deion Sanders. MC Hammer filed for bankruptcy in 1996, admitting that he didn’t have the money to support his lavish lifestyle. As part of his comeback, he has attempted to create WireDoo, his own search engine.
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