SEAN PENN AND MADONNA

Out of all the guys that got romantically involved with Madonna, there are a few that stood out: Warren Beatty, Lenny Kravitz, Tupac, and Guy Ritchie. One of the relationships that stood out was when The Crazy For You singer also got crazy for actor Sean Penn. It was in the mid-’80s when they met each other on the set of the singer’s Material Girl music video. They started off as friends and eventually blossomed into a relationship. After dating for six months, the renowned singer and Mystic River actor wed in August 1985 on her 27th birthday.

The following year, they two starred together in the adventure comedy Shanghai Surprise. Much to our surprise, Madonna and Sean split after only four years of marriage. Whatever their reason was, whether money management problems or other personal issues, we still believe they were an attractive couple. Madonna is 5 feet 4 inches while Sean stands four inches taller than her.