Estimated settlement: $49 million

Model Heather Mills married former Beatle Paul McCartney in 2002. McCartney reportedly said no to Mills' offer of a prenuptial agreement. In 2006, the couple split and things got nasty: Heather accused Paul of drug use and abuse flying back and forth. Mills initially sought more than $250 million from McCartney, citing needs such as $25 million to buy a home in London, $6 million for a home in New York, $1 million per year for vacations, $250,000 for clothing, $80,000 for wine, and $60,000 for equestrian activities.