50 Cent
In 2015, rapper 50 Cent owed more than 50 cents in payment. In fact, it was around more like $32.5 million to be paid to various outlets. He was a mess when it came to taxes, house payments, and supporting his child. He filed for bankruptcy in 2016, and he is still slowly recovering from his downfall. Luckily for him, he is still getting regular royalties from his singles in the 1990s and early aughts.
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