Willie Nelson might be one of the most famous faces in country music, but his celebrity status doesn't make him immune to legal problems. On Sept. 21, 1990, the IRS placed liens on his property totaling $16.7 million.

Ironically, the same year Nelson's 'Born for Trouble' album was released, the IRS ended up seizing most of his assets to satisfy his delinquent tax bill. Nelson later sued his accounting firm, who had involved his money in a tax shelter that turned out to be illegal, causing a downward spiral of penalties and interest when his write-off against that investment was disallowed.

The 'On the Road Again' singer's lawyer successfully negotiated the sum to be lowered to under $6 million, but since Nelson still didn't have the money to satisfy the bill, the IRS took almost everything he owned for auction. He managed to keep his favorite guitar, dubbed Trigger, because his daughter shipped the instrument from his Texas home to Hawaii before the agents arrived at his ranch.

"As long as I got my guitar," he said of the experience, "I'll be fine."

Ultimately, the tunesmith lost virtually everything he had, including his Texas ranch. The property was returned to him, thanks to a generous fan who purchased the ranch on behalf of a group of farmers who promptly gave it back to him, as a gesture of gratitude for his ongoing Farm Aid support.

When Nelson was unable to pay off his substantial debt, in spite of the seizure of all of his property, he released a compilation album, 'The IRS Tapes: Who'll Buy My Memories?,' with the agreement that he would share the proceeds with the IRS.

"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."

Nelson settled his debt with the IRS for an undisclosed amount, and it was considered cleared by 1993.