Madonna and Sean Penn, 1985

Do you remember Madonna and Sean Penn were once married? It seems like it was in another universe! Madonna’s career was on an intense upswing in 1984, as she had just released her self-titled debut album and was quickly becoming known the world over for her vogue-worthy fashion and self-sufficient attitude. In 1985, she met actor Sean Penn who, like Madonna, was becoming one of the biggest icons in American film history. 

They met on the set of the singer’s “Material Girl” music video. On Madonna’s 27th birthday, the two wed in a clifftop mansion in Malibu, CA. While these remarkable newlyweds may have been known as Hollywood’s dream couple, it didn’t take long for this match to fall from grace. Rumors of immense jealousy and abuse started to swirl, and in 1989 the couple filed for divorce. Years later Madonna would confess there was absolutely no abuse in their marriage, but she nor Penn ever explained the actual reason for the breakup.