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Her breakout came following her appearance on the reality show Newlyweds: Nick and Jessica (2003–05), which focused on her sister Jessica and her then-husband Nick Lachey.While working on her debut studio album, Simpson became the star of her own spin-off reality series, The Ashlee Simpson Show (2004–05).In 2006, Simpson began a relationship with Fall Out Boy member Pete Wentz, which gained much media attention.Following her appearance as Roxie Hart in the West End production of Chicago, Simpson announced that she had begun working on her third studio album.Two weeks after the wedding Simpson announced her pregnancy, thus ending promotion of Bittersweet World. The following year, Simpson joined the main cast of the Melrose Place revamp, which was met with harsh critical reception.She later portrayed Roxie Hart in Chicago on Broadway.Despite this, Simpson's second studio album, I Am Me (2005), debuted atop the Billboard 200, becoming her second album to do so.

Simpson's debut single, "Pieces of Me" (2004), became a top five hit in the United States, and topped the Billboard Mainstream Top 40 chart based on radio airplay.

The younger sister of pop singer and actress Jessica Simpson, Ashlee began appearing in television commercials at the age of 15.

She later pursued a career as an actress, and had a recurring role on the family drama 7th Heaven.

Simpson announced her separation from Wentz in 2011, citing irreconcilable differences.

Despite having taken time to focus on being a mother, Simpson announced a fourth studio album that same year.

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