MC Hammer
MC Hammer netted $30 million from his hit single "U Can't Touch This." This explosion of wealth encouraged Hammer to purchase a $1 million mansion and hired 200 servants to take care of him. He got caught up in several expensive lawsuits, and he was forced to declare bankruptcy in 1996 when it was found that he owed the government $13 million. He made his money back by investing in Silicon Valley tech startups, which he revealed on The Oprah Winfrey Show in 2011.