6. Sinbad
Comedian Sinbad (born David Adkins) made appearances on shows like The Redd Foxx Show, A Different World, and The Cosby Show during the 80s and early 90s. He also had his own show, The Sinbad Show, a variety of comedy specials, and a few film roles.
Despite his success, he had a problem with paying his fair share of taxes. In 2007, he was placed in the Top 10 of the 250 worst tax debtors for the state of California for owing the state $2.5 million in personal income tax. In 2009, he filed for Chapter 7 bankruptcy, which is the type that requires you to liquidate all your assets.
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