Brooke Shields

The actress and supermodel was born in 1965 in New York City. As a result of her early years as a child model and actress, Shields quickly became one of the most recognizable faces in the world by the age of 16. The actress – who says she didn’t lose her virginity until she was 22 years old – dated Michael Jackson in the ’90s, though she called their relationship “asexual.”

Years later, she continues to appear on magazine covers and on screen. Most recently, Shields was featured as part of the now canceled Lipstick Jungle on NBC. The former wife of tennis player Andre Agassi, Shields has been married to television writer Chris Henchy since 2001 and they have two daughters together.