Robin Wright and Sean Penn – $61 Million

Even today, it’s not clear whether Sean Penn and Robin Wright are actually split. Okay, that is a bit of an overstatement, but they threatened to do it so many times that no one believed them when they actually did. It all started after Penn divorced Madonna in 1989.

Wright moved in with Penn, and they had two children. But in 1995, they split, only to reconcile and get married in 1996. Then in 2007, they both filed but reconciled again. Then Penn filed in 2009, only to withdraw. In 2010, Wright filed, and the marriage was over in July that year… allegedly.