11. Wayne Newton
In spite of being a working entertainer since his high school days, Wayne Newton filed for bankruptcy in 1992. It was reported that he forcibly went into Chapter 11 because of the $20 million that he owed in debts, when he sued NBC for defamation. In 1999, he again went in a financial crisis, with his continual monetary issues. In 2005, Newton was sued by the IRS for over $1.8 million that he owed in penalties and back taxes. Moreover, in 2009, the Michigan airport officials claimed that he had not paid $60,000 for the storage fees of his plane, which was abandoned there for over three years.