10 Celebrity Millionaires Who Lost It All

10. Willie Nelson

With a country/folk star like Willie Nelson, you would think his financial troubles were more exciting, perhaps something marijuana related. Unfortunately, just the age-old story of never paying your taxes. In 1990, everyone's favorite government agency the IRS seized most of Nelson's assets after it was discovered that his accountants had not been paying his taxes. The original sum was $32 million, although negotiated down to a paltry $6 million. His double album, The IRS Tapes: Who'll Buy My Memories? was released shortly thereafter, with all the profits going to the IRS. Way to turn your debt into something positive. Happy ending: Nelson sued his accountants and was debt free by '93.
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Sarah Frantz hasn't written a bio just yet, but if they had... it would appear here.