Ashlee Simpson

Although Ashlee Simpson is the sister of major league hot commodity Jessica Simpson, the younger Simpson has done her best to carve out her own personal identity. Ashlee performs hard-edged pop rock that has more in common with the sharply crafted teen angst of Avril Lavigne than the sugary pop of sister Jessica. Her first single, "Pieces of Me," appeared on the Freaky Friday soundtrack in 2004. Her 2004 debut album, released at the height of the Jessica Simpson popularity curve, was surprisingly good but any merits of the album were tarnished when, during a live appearance on Saturday Night Live, Simpson's vocal track system screwed up and it became clear she was lip-syncing, prompting Simpson to respond by dancing a now infamous little jig and then stalking off stage. She never owned up to having been caught in the act, and her story ran along the lines of "Acid reflux has swollen my vocal chords and I used a backing track for the very first time to prevent damaging my voice any further." Maybe this public relations disaster was not such a bad thing after all since her 2005 album, I Am Me, was leaps and bounds better than her debut. Things got even better with 2008's Bittersweet World, featuring production and songwriting credits from heavy-hitters (Timbaland, Chad Hugo, Santogold) and a brand new Ashlee (thanks in part to her 2006 nose job and boyfriend Pete Wentz, whom she married in 2008, but especially to a newfound confidence and maturity).