There’s an old saying that it’s easy to make a million dollars in the music business, but it’s hard to hold on to one dollar. These country stars found that out the hard way when they ended up having to declare bankruptcy.

The country singers who have gone bankrupt include some all-time legends. Willie Nelson‘s money troubles in the early ’90s have been well-documented; the IRS seized and auctioned off many of his assets, and he ended up recording an album that he admitted was purely to pay off his debts.

He’s not the only legend to go broke. Several of the country stars on our list had decades-long careers that earned them big money, but wound up with little to show for it.

Many of the country stars who have declared bankruptcy did so because of poor advice from financial advisors. Investments that went bad are another reason, while some country stars suffered career setbacks that altered their finances.

Disputes with a manager or other business associates also drove some of these stars into bankruptcy, and let’s face it, some people just aren’t that good at handling money. Just because you hand someone a big chunk of cash, that doesn’t mean they know what to do with it, as some country stars found out first-hand.

Scroll through the pictures below to see which country stars have gone bankrupt over the years.

Sterling Whitaker is a Senior Writer and Senior Editor for Taste of Country. He focuses on celebrity real estate, as well as coverage of Yellowstone and related shows like 1883 and 1923. He’s interviewed cast members including Cole Hauser, Kelly Reilly, Sam Elliott and Harrison Ford, and Whitaker is also known for his in-depth interviews with country legends including Don Henley, Rodney Crowell, Trace Adkins, Ronnie Milsap, Ricky Skaggs and more.