Always struggling to step out of the shadow of her more famous sibling, Ashlee Simpson’s life has been a never-ending series of ups and downs. Originally a backup dancer for her sister Jessica’s tours, Simpson first tried to distinguish herself as an actress, playing Cecilia Smith on the WB’s 7th Heaven for two seasons. In 2003, after contributing to the Freaky Friday soundtrack, MTV filmed the making of her first album, Autobiography, for a reality show. Also like sis, she fell in love at work — hooking up with Ryan Cabrera after starring in his video. Thanks to the infectious hit, “Pieces of Me,” the record hit No. 1, but success was tainted by a Saturday Night Live lip-synching snafu in 2004, a booed Orange Bowl performance in ’05, a failed film (Undiscovered) and backlash from stealing Lindsay Lohan’s boyfriend Wilmer Valderrama. I Am Me sold more than 3 million copies and her 2006 stage debut in a London production of Chicago earns rave reviews, but she was plagued by negative nose job coverage and a leaked video of diva behavior at a burger joint. Despite lack of interest in her third record, 2008 was a big year thanks to her marriage to rocker Pete Wentz and the birth of their son, Bronx Mowgli. The last couple of years have been less pleasant as her gig on the ‘09 Melrose Place reboot was shortlived, she divorced in 2011 and called it quits with boyfriend, actor Vincent Piazza, after a year and a half.
Ashlee Simpson Search Results
Katniss FanAshlee Simpson dishes on what her son, Bronx, liked most about visiting her fiance, Evan Ross, on the "Hunger Games" set.
Bachelor BashAdam Levine waves goodbye to the single life in Sin City. Plus, more celeb news in the Shortlist.
Wedding PlannersGet the scoop on Hollywood's leading ladies who are in the midst of planning weddings.
Wild SideFergie and her son are rebels without a cause, plus more celebs with their cute kiddos.
Sunday BestJessica Simpson, Kourtney Kardashian, Beyonce, Gisele and Kendra Wilkinson post Easter Sunday pics on Celebs Gone Social.
New LooksSee plastic surgery before-and-afters for Rose McGowan, Clay Aiken and Farrah Abraham.
Sister SisterJessica Simpson helps Ashlee Simpson toast her engagement to Diana Ross' son ...
Friendly ExesCan you stay friends with an ex? See which stars have translated romance into friendship.
Engagement BlissGet the scoop on Ashlee's new fiance on Replay hosted by Wonderwall's Kirby Kristen.
Wedding BellsAshlee Simpson and Evan Ross are engaged. See her ring ...