21. Willie Nelson

You can be one of the biggest country music stars of all time, and you can sell millions of records for six decades, but if you insist on stiffing the IRS on their share of the profits it's bound to catch up with you in the end. Nelson's fortune was huge, but so was the bill that he was racking up to the taxman in the background. When it hit $16.7m, the IRS decided they were no longer going to wait for Nelson to pay up, and came looking for him with a vengeance.

Nelson paid what he owed by releasing a new album - the cheekily-titled 'The IRS Tapes,' which settled at least some of the bill. The remainder came out of his own pocket, and as a result, he doesn't quite live the same lavish lifestyle he enjoyed beforehand. Given that he still generates big sales figures every year, though, we imagine it won't be too long before his accounts are topped up again.

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