Liz Phair

When MTV’s Newlyweds: Nick and Jessica went off the air in 2005, Jessica Simpson had the world in the palm of her hands.

The addictive show became a pop culture phenomenon, thanks in large part to Simpson’s ditzy but endearing persona. Whether it was not knowing that “Chicken of the Sea” was a metaphor, thinking Buffalo wings actually came from buffaloes or blaming her inability to hit a golf ball on her Mae West-like features, Simpson’s simple but good-natured demeanor – to say nothing of her covergirl looks – allowed her to become a bona fide superstar while launching legions of reality show wannabes and copycats. Her then-current album, In This Skin, sold 5 million copies worldwide making it her best-selling record of all time, and she landed plum acting roles like Daisy Duke in The Dukes of Hazzard (2005). After divorcing Nick Lachey less than a year after the end of their reality show, there was nothing holding Simpson back anymore. She seemed poised to become a true double-threat, joining the likes of J-Lo, Beyonce and Cher as an A-lister on both the silver screen and airwaves.

By 2008, however, she was hanging by a thread. Thanks to poor performances and modest box office returns, Simpson’s Hollywood career was deader than David Caruso’s. Her music career, meanwhile, was also on life support – threatening to go the way of her show, marriage and sister post-SNL. So she did what many artists have tried to do: reinvent herself in order to stay relevant.

With the release of her first (and to date, only) country album, 2008’s Do You Know, she was certainly able to reinvent herself. Unfortunately, it also killed off her music career, forcing her to reinvent herself yet again — this time as an ultimately successful fashion maven.