Meat Loaf
Meat Loaf was a major success story in the '70s when he released Rocky Horror Picture Show and Bat Out of Hell, but he fell into a financial hole in 1983 and was forced to file bankruptcy. He got caught up in 45 lawsuits, all from major companies, which drained his bank account and crushed his morale. He started to come back a bit in the '90s, but he was ultimately unable to recoup his losses.
50 Cent
In 2015, 50 Cent owed roughly $32.5 million to various outlets. He was behind on taxes, mortgage, and child support. He declared bankruptcy in 2016, and he is still slowly recovering from his financial downfall. Fortunately for him, he is still getting paid regular royalties from his hits in the '90s and early 2000s.
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