Ashlee Simpson-Ross

Pop singer and occasional actress Ashlee Simpson-Wentz emerged from the shadow of her superstar pop singing sister Jessica, thanks to the success of her 2004 album Autobiography, and its catchy single "Pieces of Me." Considered the "edgier" of the two sisters, her questionably authentic rock 'n' roll persona provided an alternative to her blonde Southern belle sister, though the pair were both managed by their Svengali-like father Joe Simpson, who utilized reality television to bolster both their careers. While Simpson-Wentz enjoyed a few top singles, she endured perpetual heartache at the hands of the media; first, over a highly publicized lip-synching snafu on live television, then relentless taunting over a nose job, a film flop, her marriage and bizarrely-named first son, and a short-lived stint on the remake of "Melrose Place" (The CW, 2009-10), from which she was unceremoniously let go. Simpson-Wentz managed to avenge some of her detractors when she offered well-received runs on the New York and London stages in the musical "Chicago," which was considerably lower on the fame scale than a pop music career but possibly better suited to a young woman whose initial talent had actually been as a dancer.