The Stunning Amount Of Money Willie Nelson Owed The Government

Tax season looms over three hundred million Americans each year, puckishly elbowing and daring us to see just how many wrong turns we can take within the labyrinthian H&R Block website before we send up a red flag at the IRS and have our minimum wages maximum garnished. Still, the upshot of never being a one-percenter is that the government can't repossess what we never owned in the first place.

For the rich and famous, however, there's a lot more to lose. Take Willie Nelson, for example. In 1990, the music icon found himself at odds with the Internal Revenue Service to the tune of more money than you will ever even find yourself tangentially connected to. Nelson, who came into life as a delightful old codger at a relatively young age, apparently had some fun with it, with Rolling Stone reporting that he would, over the course of the IRS investigation, park his bus outside of their offices and sign autographs between interrogations.

Still, all the glass-pipe-is-half-full attitude in the world couldn't undo the fact that Willie Nelson was deep in the hole. How far? By the IRS's reckoning, around $32 million. After a seizure of his assets, the bill was brought to a more manageable $16.7 million. On the up side, the singer apparently knew that there was trouble a-brewin', and had sent his guitar, Trigger, to the Hawaiian islands to keep it out of the hands of the Man.

By February of 1993, Nelson and the IRS came to a gentleman's agreement and settled the debt for $9 million. Willie apparently took every job he could find to pay this off: he appeared in a Taco Bell commercial, a tax prep service advertisement, and released an acoustic album titled "The IRS Tapes: Who'll Buy My Memories." In the end, he claimed that the ordeal wasn't as stressful as it could have been, which, to be fair, is probably what you'd say too if the U.S. government technically owned you and you were really, really high.