Madonna
Ordinarily a fairly savvy businesswoman -- especially considering she started her Maverick record label with Time Warner ( TWX) almost 20 years ago before that was a thing to do -- Madonna's one major blunder came during her marriage to Guy Ritchie, which was filled with them.

Forget her and Ritchie's heavy ordnance of a film Swept Away, her "British" children's book The English Roses, her directorial debut Filth and Wisdom, her American Life album and her affected English accent -- you marry a guy who directs heist movies like Lock, Stock and Two Smoking Barrels and Snatch for a living and you don't sign a prenuptial agreement?

Madonna was worth $500 million during her marriage to Ritchie and, while the director didn't clean her out when their marriage dissolved in 2008, the $75 million he reportedly got was a nice parting gift.

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