6. Madonna and Guy Ritchie
Settlement Amount: $76 million
In December 2008, pop star Madonna and director Guy Ritchie broke up their marriage of 8 years. Madonna’s representatives confirmed the settlement was between $76-$92 million. Although Ritchie was worth an estimated $45 million at the time and said he wasn’t interested in a substantial portion of his ex-wife’s wealth, the settlement surely wasn’t bad news for the successful director.