April 15 is a feared day for many, as it marks the deadline for filing your annual income taxes to the Internal Revenue Service. (If this is news to you, feel free to finish reading this later while you scramble to find your W2.)
Paying taxes as a rock star can be difficult, as you usually have dozens of different income streams, spend most of your time on the road and can’t often keep track of your own payroll (or, you know, what month it is). Sometimes it helps to move to a tax-free foreign country, like David Bowie (who moved to Switzerland), the Rolling Stones (France) and Cat Stevens (Brazil).
Though it seems like you could avoid the burden forever, the IRS tends to catch up with everybody. When that happens, they’re either prosecuted (like Method Man, who was arrested and charged with tax evasion based on the $33,000 he owed to Uncle Sam) or else you have to come up with a pretty inventive way to come up with the cash.
Take country-music icon Willie Nelson, who through either ignorance or unwillingness never bothered to pay his taxes over his hugely successful career. When the IRS caught up with him in 1997, they handed him a bill for $16.7 million. Unable to pay the government, Nelson quickly released the double album The IRS Tapes: Who’ll Buy My Memories? and sold off most of his possessions. He managed to pay it off after settling for an undisclosed amount, and luckily many of the items auctioned off were purchased by friends of his, so he was able to recover most everything.
Nelson was perhaps taking a cue from Jerry Lee Lewis, who in 1984 was face-to-face with a prison term for the $560,000 he owed in unpaid taxes. In order to avoid hard time, Lewis did what any desperate rock star would do: He set up a phone number that allowed callers to hear the Killer tell stories from his childhood for the price of $2.75 per minute. It was lucrative enough to get him out of a jam.
While Lewis managed to avoid doing time, rock legend Chuck Berry wasn’t so lucky. In 1979, the government decided that the man who invented rock and roll owed them $200,000 in unpaid taxes. It was the third time the government had told him to pay up, so Berry pleaded guilty to tax evasion, spent four months in jail and put forth 1,000 hours of community service.
That was a walk in the park compared to Ron Isley, who thought that declaring bankruptcy would allow him to sidestep doing time. Not so, as the founder of the Isley Brothers spent 37 months behind bars in a federal prison in Terre Haute, Indiana, for tax evasion. Even then, he might have gotten off easy, as the maximum sentence he could have faced was 26 years.