On Feb. 2, 1993, Willie Nelson settled a $16.7 million tax bill with the IRS — one of the most high-profile tax cases in music history.

The trouble began when the IRS decided that tax shelters his accountants had set up were not valid. Though his lawyer negotiated the massive bill and penalties down to $6 million, the government still seized much of Nelson's property and sold it at auction.

Fortunately, much of the property was bought by friends and supporters who gave it right back to him. Nelson then released an album titled The IRS Tapes: Who Will Buy My Memories? It's not generally remembered as his finest project, but the profits also helped him get back on his feet. The country music legend settled his debt for an undisclosed amount, and paid it off by 1993.

"We try to work with taxpayers," the IRS explained of the unusual agreement. "And if we have to come up with some creative payment plan, that’s what we’re going to do, because it’s in everyone’s best interest."

In 2006, Nelson poked fun at his tax troubles in a hilarious commercial for H&R Block, which aired during Super Bowl XXXVIII.

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