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TheStreet Open House

10 Terrible Financial Choices in Music History

Willie Nelson's tax woes
When you've been on the road as long as Willie Nelson has, even a multimillion-dollar mix-up with Uncle Sam is just another stop along the way. Way back in 1990, the Internal Revenue Service seized most of Nelson's assets and claimed he owed them $32 million in back taxes. Apparently, while Nelson was doing duets with Julio Iglesias and touring around with Johnny Cash, Waylon Jennings and Kris Kristofferson, his accountants were back home doing exactly the opposite of what Nelson was paying them for and not filing his taxes for years at a time.

Instead of grousing about it, Nelson released a double album called The IRS Tapes: Who'll Buy My Memories? for $19.95 and used the proceeds to pay his debts. He also sued Price Waterhouse for steering him into tax shelters that were the equivalent of rice paper umbrellas -- getting a nice settlement out of the deal -- and auctioned off items that were later bought by friends. Nelson shook off the debt about three years later and, aside from the occasional marijuana-related jail stint and charity appeal, has been back on the road ever since.

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