Willie Nelson
Even those who don’t like country music will know who Willie Nelson is! As someone who has been making music since 1956, you’d think he has a few extra dollars to his name. However, when he got into trouble with the IRS, he ended up with a $16.7 million tax bill!
Luckily, with a talented lawyer and an album named ‘The IRS Tapes: Who’ll Buy My Memories?’ he eventually managed to get out of debt, but he definitely doesn’t live the life he was so used to in the past.
Cyndi Lauper
Cyndi Lauper was a massive hit in the 1980s, with hits such as ‘Girls Just Want to Have Fun.’ However, Lauper hasn’t always been able to have fun after she found herself having to declare bankruptcy after her first band broke up.
The singer found herself waiting tables and performing in bars, just to try and earn a living. Sure, she may be doing better now, but it was a tough pill to swallow when she ended up in so much debt.