15 Musicians Who Went Broke

4. Willie Nelson

Ah, Willie Nelson! How can we hate your country-music-singing, pot-smoking ways? Even if you’re not a fan of the man’s music, you have to respect his personality and the way he seems to approach whatever life throws his way with so much humor.

Take, for example, his incredible IRS problems of the early ‘90s. During an audit, the IRS discovered that Willie owed a whopping $30 million in back taxes. The “oversight” was blamed on Willie’s accountants, who had apparently used illegal means to shelter the singer-songwriter’s earnings. At any rate, he paid off the taxman by releasing an album called The IRS Tapes: Who Will Buy My Memories? and also by doing commercials for Taco Bell. Gotta love Willie!

5. MC Hammer

When you look back at the mainstream music that was popular in the early ‘90s, it almost seems like a fever dream. Consider, if you will, MC Hammer’s hit song “U Can’t Touch This,” which was as popular as popular can get, and which would be exceedingly corny by today’s standards. In Hammer’s eyes, the fame and the parachute pants would never end…

But, they did. By the time Hammer released the song “2 Legit 2 Quit,” it was clear that Hammer’s fame would only be fleeting. Still, this didn’t stop him from wasting almost all of his fortune on a massive mansion, cars, and whatever else you can think of. When the record sales dried up and the assets depreciated, Hammer found himself not legit enough to avoid filing for bankruptcy in 1996.

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Everett Collection / Shutterstock.com

Everett Collection / Shutterstock.com

6. Dee Snider

While people often speak of “bubbles” in various industries, few apply the same principle to popular music. Consider, if you will, the popularity of “hair metal” in the 1980s. At the time, it seemed unstoppable, but anyone with a sense of reason should have been able to tell that the “hair metal” bubble would burst eventually.

Sadly, Dee Snider, who was the frontman for Twisted Sister – the band behind “We’re Not Gonna Take It” – didn’t see the forest for the trees. Not wise with his money, Dee’s fortunes rose and then fell with “hair metal” in general, forcing him to file for bankruptcy in the early ‘90s. To his credit, though, Dee has managed to find a second career as a radio host and eccentric media personality.

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