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
Nutty NamesCan you guess the bizarre baby names Holly Madison and more stars chose for their offspring?
TwinningSisters Jessica and Ashlee Simpson look like twins in an Instagram pic.
Cute OverloadSee Jessica Simpson's latest personal snapshots of her adorable kids Maxwell and Ace.
Famous AuntsSee if you know who these people's famous aunts are.
True LoveStephen Moyer and Anna Paquin share a public kiss and more celebs in love.
Married!Jessica Simpson and Eric Johnson tied the knot in Montecito, Calif. on July 5, 2014.
Happy Fourth!See how the stars are spending their Fourth of July weekend.
Baby Before BrideCheck out which stars had a baby on board before getting hitched!
Family BondingKim Kardashian and Kanye West take North to the museum, plus more celebritots.
Really OverGwyneth Paltrow's rep throws cold water on Chris Martin reconciliation rumors. Plus, more celeb news in the Shortlist.