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
Starbucks PickupRosie has a new girlfriend; plus, Vanessa's PDA and more romance news ...
Broken EngagementStay calm, everyone: Alcide is single. Find out who else is in Splitville in the Romance Report ...
Family NuptialsAshlee Simpson talks about her upcoming fashion line at the Herve Leger Max Azria Show in NYC's Fashion Week.
Young MomsFrom Hilary Duff to Ashlee Simpson, The Daily Beast rounds up Hollywood's youngest moms.
Summer ShowsConcerts don't just have stars on stage! Check out the celebs you might be next to in line for merch.
Parental PassionKate Hudson puckers up in London; plus, Leo and Blake, Emma Watson, and more romance news ...
Young & PregnantBrenda Song is having Trace Cyrus' baby! See more young celeb moms.
Week in PhotosSofia Vergara parties in New York, plus more of your favorite celebs this week in photos.
Week in PhotosSelena Gomez shines on stage, plus more celebs this week in photos.
Hair FaceoffWho has better blond curls: Beyonce or Taylor Swift? Vote now on the best celeb hair!