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
amfAR GalaSee your favorite stars at the amfAR L.A. Inspiration Gala honoring Tom Ford.
Summer WeddingsThe dresses! The rings! The romance! See which celebs tied the knot during the summer of 2014 ...
Ice, Ice BabyLearn more about the beloved baubles belonging to Hayden Panettiere, Kim Kardashian, Olivia Wilde and more celebs.
The Name GameVote on which stars with the same name wore the same look better.
Week In PhotosKendall and Kylie Jenner celebrate DuJour's Fall Issue in New York, plus more of your favorite stars this week in photos.
Diana DishesDiana Ross gushes over son's "perfect" wedding and wishes "love, happiness, and joy" to Evan and Ashlee.
Blond PixiesCheck out Pink, Michelle Williams and more blond pixies we love.
They're Married!Ashlee Simpson and Evan Ross tie the knot at the home of his mom Diana Ross. All the details here...
Wedding DeetsGet all the deets on Ashlee Simpson and Evan Ross' upcoming wedding ...
Sister, SisterVote on Beyonce and Solange Knowles, plus more sisters in a fashion face-off.
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