46. Lil Kim

Lots has changed about rap star Lil Kim over the years she's been on the music scene. The most dramatic of the changes has been to her physical appearance; thanks to years of cosmetic surgery, she's now completely unrecognizable compared to how she looked just ten years ago. Her financial situation is unrecognizable when compared to her best years, too.

Kim's tax issues aren't as bad as some we've seen on this list, but any debt is bad when you don't have the means to pay it. She owed $1m to the IRS, and also failed to pay the legal team she'd contracted to defend her against the charges. She's not yet gone bankrupt, but if she doesn't find a way to pay the money soon, it's hard to imagine how she'll find another way around the problem. Perhaps a new album will do the trick - if she can afford to record it.

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