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
Angie, Au NaturelAngelina Jolie models without makeup in Louis Vuitton's new ads, plus more stars shilling.
Rebound RomanceAshlee Simpson is spied cuddling up to a new man. Get the details!
Week in PhotosMatthew McConaughey and Camila Alves go to the LA Film Festival, plus more celebs this week in photos.
GOOP gets SocialGwyneth Paltrow joins Facebook and Twitter, plus more celeb news in the Shortlist.
Cloak and DaggerLeo and Blake go covert; plus, Ashlee and Pete, Courteney and David, and more in the Romance Report ...
Popping BackAshlee Simpson says she's ripe for a comeback in the pop music world.
Lavish NuptialsUse the power of Bing to see which stars had the most extravagant weddings.
Week In PhotosKim Kardashian visits "The Wendy Williams Show," plus more in this week in photos.
Fashion FumblesWho face-planted in the style sweepstakes?
Sexy SiblingsHot runs in the family. See the Kardashians, the Afflecks, the Gyllenhaals and more.