Despite being one of the most successful country artists of all time, Willie Nelson found himself in deep trouble with the IRS for not paying taxes. In 1990, his property — including a golf course and recording studio — was seized across six states. The singer hilariously struck a deal with the government and recorded the album The IRS Tapes: Who’ll Buy My Memories to pay off his $16 million debt. While it didn't cover the full amount, it made a dent, and he paid it all off later.
Willie told Rolling Stone, "Mentally, it was a breeze. They didn’t bother me, they didn’t come out and confiscate anything other than that first day, and they didn’t show up at every gig and demand money. I appreciated that. And we teamed up and put out a record."