April 14, 2021 Willie Nelson – The country star known as the Red-Headed Stranger acquired a whopper of a tax bill in 1990. His bill of $16.7 million was negotiated down to $6 million by Nelson's lawyers — but Nelson could not pay $6 million, either. The IRS raided his home in November of 1990, taking virtually everything except his favorite guitar named Trigger. Nelson has perhaps the most unusual IRS settlement deal ever. He issued an album called "The IRS Tapes: Who'll Buy My Memories?" and split the proceeds with the IRS. The agency picked up only $3.6 million from album sales, suggesting that it may be hard to generate great album sales with "IRS" in the title.