Willie Nelson

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Willie Nelson's run-in with the tax man almost cost him everything he owned.
Corbis Images

Known for his hair, music and his outlaw demeanor, Willie Nelson seems an unlikely candidate for having one of the largest unpaid tax bills of any individual in U.S. history.

In 1990, the IRS seized Nelson's assets owing to some $32 million in unpaid taxes, though that number was later reduced. Nelson was never accused of fraud, but rather simply nonpayment -- albeit a very large nonpayment.

Nelson's assets were auctioned off to pay his debt. He also released a double album, The IRS Tapes: Who'll Buy My Memories?, with all the proceeds going to the IRS.

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