Willie Nelson currently has an estimated net worth of $25 million.
In the early 1980s, though, the country icon received one of the highest tax bills in history, after federal investigations found he had invested in a tax shelter that the IRS ruled illegal. Nelson was on the line for $16.7 million.
Although his lawyer negotiated the bill down to $6 million in cash, Nelson still couldn't afford to pay it. Instead, he ignored it, causing the IRS to raid his Texas ranch home and seize his assets — everything but his beloved guitar, which his daughter sent to him in Hawaii — in 1990.
The star made a unique deal with the IRS that some of the revenue from his album, "The IRS Tapes: Who'll Buy My Memories," would go towards his debt. He eventually paid it all off in 1993. Nelson has released multiple albums since, and will be on tour through the first half of 2015.