Jessica Simpson

Glory days: In 1999, Simpson was the fresh-faced, big-voiced virgin alternative to pop princess Spears and the original Good Girl Gone Bad Aguilera. Unfortunately for Jess, America is a two-party system, so her label's attempts to sex up her image looked set to make her the teen-pop bubble's first casualty. Still, an impending deflowering from Nick Lachey made her the envy of millions of girls, women and sexually confused teen boys. "Newlyweds," the last ditch effort to save the couple's careers, proved an unlikely pop culture phenomenon and jump-started her career to multi-platinum sales, sellout tours, prime-time variety shows and endorsement deals galore. At last, she was America's sweetheart with a heart of gold, straw for brains and Lachey in the background making jokes for more oral gratification.