1. Tom Cruise
Tom Cruise has a thing for his leading ladies. From 1983 to 1985, he dated his Risky Business co-star Rebecca DeMornay. He dated Cher briefly in 1985. Cruise married actress Mimi Rogers in 1987, and they divorced in 1990.
On the set of Days of Thunder, Tom fell in love with Nicole Kidman. They were married from 1990 to 2001. While he was filming Vanilla Sky, he fell in love with actress Penelope Cruz. Unfortunately, their relationship ended in 2004. In April of 2005, he met Katie Holmes. Their whirlwind marriage lasted from November of 2006 to July of 2012.