MC Hammer
MC Hammer profited $30 million from his hit single "U Can't Touch This." This massive wealth encouraged Hammer to buy a $1 million house and hired 200 butlers to care for him. He got mixed up in some lofty lawsuits, and he was required to declare bankruptcy in 1996 when it was revealed that he owed the IRS about $13 million. He made his cash back by smartly investing in some promising tech startups, which he revealed in 2011 on The Oprah Winfrey Show.
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