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That same year, Ashlee recorded a song titled "Christmas Past, Present, and Future" for the holiday album School's Out!

Christmas; the song was later re-released on Radio Disney Jingle Jams following Simpson's musical breakthrough.

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).

The effort reached number 4 on the Billboard 200, and went on to sell 126,000 copies by 2009.Despite having taken time to focus on being a mother, Simpson announced a fourth studio album that same year.She independently released the single "Bat for a Heart" (2012), though it failed to have success.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.The album differed from the pop-rock sound of her previous efforts, featuring a dance-pop and 1980s themed sound.

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