American original Willie Nelson was a pioneer of the “outlaw country” movement of the 1960s and ’70s, but the ’80s saw the singer become a real outlaw — in the eyes of the IRS. For much of the decade, Nelson funneled his income into a tax shelter later deemed illegal by the agency. His tax bill totaled $16.7 million and forced the government to seize his assets in 1990, including his Texas ranch. Nelson eventually helped settle the debt by releasing a compilation album The IRS Tapes: Who’ll Buy My Memories?, the revenue from which he shared with the feds. The singer, however, was able to keep his head up throughout, saying, “I had a lot of things I owned, I needed to get rid of,” he said. “I had a lot of people around and needed to back off and stop supporting half the world so I could stop and look at my situation. It’s given me time to take inventory.”