Willie Nelson has been the opposite of broke for the past 20 years, but for a three year span between 1990 and 1993, Nelson was in deep trouble financially. The notorious pot smoking country star owed $16 million to the IRS and went completely bankrupt.This story has a happy ending. Willie Nelson released an album that was called “The IRS Tapes: Who’ll Buy My Memories”. It sold enough copies to the point where Willie was able to pay off all of his debt in just that three year span. Nelson is doing just fine for himself now, still traveling the world singing music and advocating for the legalization of marijuana.