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. Troubled times: Jessica's headlining gig at VH1's Divas Live in 2004 sank the franchise like a battleship. The only reason to laugh at her role in "Dukes of Hazzard" were tabloid reports she let Johnny Knoxville tag and bag it. Simpson's refusal to open up to the media about her split from Lachey cast her as the villain by default, and without the public on her side, her first post-divorce album shifted less units than her line of weaves. Oh, and it was rumored that she was dumped via text message by Maroon 5's Adam Levine. Hooking up with America's Quarterback Tony Romo and going country have done nothing to help. Bailout plan: Some things in the pop economy can't and shouldn't be saved. The Fed let Lehman sink because ... well, it wasn't that important. Sorry Jessica, but whether it's a bull market, a bear market or even a pink wig market, you were always a distant third anyway.
Evan Agostini / Associated Press
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