Willie Nelson
Even if you don’t listen to country music religiously, you definitely know who Willie Nelson is. For the two or three of you who don’t, Willie Nelson is a legendary country singer who’s been in the game for centuries now. Since he’s been singing and touring for so long, he should have a couple hundred million in the bank by now, right?
That might have been true had he not neglected to pay his taxes. He got slapped with a $16.7 million bill and had to work twice as hard to dig himself out of debt. Thankfully, his lawyer helped him get out of trouble, and his album The IRS Tapes: Who’ll Buy My Memories helped him escape bankruptcy.