Ordinarily a fairly savvy businesswoman -- especially considering she started her Maverick record label with
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
, her "British" children's book
The English Roses
, her directorial debut
Filth and Wisdom
album and her affected English accent -- you marry a guy who directs heist movies like
Lock, Stock and Two Smoking Barrels
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.