Willie Nelson

Troubled Willie
Unfortunately, Nelson's accounting acumen was not as accomplished as his mastery of music. In 1990, the IRS slapped him with a bill of unpaid back taxes amounting to $16.7 million. The government seized most of his assets, but the country legend kept on strumming. In 1992, he released The IRS Tapes: Who Will Buy My Memories to help pay off his tax debts.