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10_3_09_ash029950

Ashlee Simpson

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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.
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Ashlee Simpson
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Evan Ross, Ashlee Simpson
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Evan Ross and Ashlee Simpson
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Evan Ross, Ashlee Simpson
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Evan Ross, Ashlee Simpson, Jagger Ross
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Ashlee Simpson, Ziggy Blu Ross
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Ashlee Simpson, Pete Wentz, 2008 MTV VMAs
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Ashlee Simpson, Evan Ross
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Ashlee Simpson, Colin Egglesfield, Katie Cassidy, Laura Leighton, Thomas Calabro, Stephanie Jacobsen, Shaun Sipos, Jessica Lucas, Michael Rady, Melrose Place
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Ashlee Simpson
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Ashlee Simpson, Evan Ross
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Ashlee Simpson, 7th Heaven
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Evan Ross, Ashlee Simpson
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Jessica Simpson, Eric Johnson, Evan Ross, Ashlee Simpson
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Jessica Simpson, sister Ashlee Simpson
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Jessica Simpson, daughter Maxwell Drew Johnson, sister Ashlee Simpson
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Pregnant Ashlee Simpson
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Ashlee Simpson shows off her growing baby bump on a family lunch outing in LA
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Ashlee Simpson, husband Evan Ross
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Ashlee Simpson, husband Evan Ross
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Ashlee Simpson, husband Evan Ross
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Ashlee Simpson, Evan Ross
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Ashlee Simpson, husband Evan Ross, daughter Jagger
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Evan Ross, Ashlee Simpson
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Evan Ross, Ashlee Simpson
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Evan Ross And Ashlee Simpson Ross
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Ashlee Simpson, husband Evan Ross
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Ashlee Simpson, Evan Ross, daughter Jagger
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Ashlee Simpson: Related Content

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    Ashlee Simpson and Evan Ross announce pregnancy Ashlee Simpson and Evan Ross announced their pregnancy in matching Instagram posts. Apr. 30, 2020 Share Tweet
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    Ashlee Simpson and Evan Ross share a smooch, plus more pics you have to see this week! See the best photos of your favorite stars at events and out and about this week. May. 24, 2019 Share Tweet
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    In the latest Shortlist: Britney Spears is ready to take back her life, plus Mischa Barton, Kiefer Sutherland, Sienna Miller, Ashlee Simpson, and more Jul. 22, 2009 Share Tweet
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    Will Ashlee Simpson cut an album of Michael Jackson hits? Plus Mel Gibson, Jerry Seinfeld, Heidi Montag, Rihanna, George Clooney, and more. Jul. 10, 2009 Share Tweet
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    In the latest Shortlist: Ashlee Simpson takes on Michelle Trachtenberg, plus Christina Ricci, the Jonas Brothers, Audrina Patridge and Chris Pine, and more. Jun. 3, 2009 Share Tweet
  • Lindsay Lohan
    Lindsay Lohan, Victoria Beckham, Ashlee Simpson Wentz and more rock the bandage dress, one of Elle.com's "It" styles for Spring. Check 'em out. Apr. 22, 2009 Share Tweet
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