Willie Netson

Country music legend 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 managed to settle the debt by releasing a compilation album called “The IRS Tapes: Who’ll Buy My Memories?” He shared the revenue with the Feds. The singer was able to keep his head up throughou the ordeal. “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.”