Sean Penn – Madonna | Then
It may be a challenge to wrap your head around this one. Sean Penn and Madonna used to be married. Although the marriage was short-lived, we still have a lot of feelings about it. These mega stars were married from 1985 to 1989. Because Madonna and Sean Penn are so unbelievably famous, the press got out of control with them. Penn was actually arrested for assaulting a photographer on a film set. Penn had to spend 33 days in jail (he was sentenced to 60 days!).