Profession: Actress

Child star in the '80s turned THE chick every teenage boy in America wanted to smash in the early '90s (and some non-teenagers, sickos!), Milano captured the attention of the tissues of a generation of young men with a series of films (Casualties of Love: The Long Island Lolita Story, Embrace the Vampire, Deadly Sins,and the Skinemax classic, Poison Ivy II: Lily) designed to propel her career far beyond the PG confines of her definitive role as Samantha on the iconic Who's the Boss? Watching Milano's career unfold was like watching the cute, pretty little girl you knew in elementary school become a hot as shit badass teenage chick who you knew knew all the tricks. And everyone loves that girl. Especially in the right car on the dark night. Who's got the keys to the jeep?