One of the great poets of our generation, Biggie Smalls, said it best: "It's like the more money we come across, the more problems we see."

In his case he meant people wanting you for your money, of course -- but sometimes, the trouble comes when you blow through your coin and wind up busted.

Within this list, you'll find the celebs with terrible overspending problems and/or the world's most useless accountants who put them in the red. Some of our selections have since bounced back to their pre-bankruptcy net worth, while others never quite regained their former glory.