6. Willie Nelson
Willie Nelson has had some notable run-ins with the law, in particular because of a certain substance that he has enjoyed using over the years. While fans can chuckle about those stories, there was nothing funny about the amount of money that he owed the IRS by the time 1990 rolled around. Nelson was in debt to the government to the tune of about $16.7 million which the musician not-too-shockingly did not just have sitting in the bank. SEE ALSO: 11 Footballers that went broke (+Photos)
He eventually managed to pay off that debt, in part because of the album entitled The IRS Tapes: Who’ll Buy My Memories?
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