Bittersweet World (2008)
Ashley Nicolle Ross (née Simpson; born October 3, 1984), known by the stage name Ashlee Simpson, is an American singer-songwriter and actress. 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. 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 show became a ratings hit, and earned Simpson widespread recognition. Like her sister before her, Simpson became the center of considerable media attention, much of which focused on her relationship with musician Ryan Cabrera.
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 success of the single and her reality show helped propel her debut album, Autobiography (2004), to the top of the Billboard 200 albums chart. The project went on to sell over five million copies worldwide, making it her most successful album to date. Simpson had a leading role in the film Undiscovered (2005), which became a critical and commercial flop. The failure of the film, along with multiple critically panned performances, led to much media scrutiny towards Simpson. Despite this, Simpson’s second studio album, I Am Me (2005), debuted atop the Billboard 200, becoming her second album to do so. The album went on to receive a platinum certification from the Recording Industry Association of America (RIAA).
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. The album differed from the pop-rock sound of her previous efforts, featuring a dance-pop and 1980s themed sound. Bittersweet World (2008) was released to positive critical reception, but saw a decline in sales for Simpson. The effort reached number 4 on the Billboard 200, and went on to sell 126,000 copies by 2009. Simpson announced her engagement to Wentz in April 2008, with the pair wedding the following month. Two weeks after the wedding Simpson announced her pregnancy, thus ending promotion of Bittersweet World. Simpson and Wentz welcomed a son in November 2008. The following year, Simpson joined the main cast of the Melrose Place revamp, though was met with harsh critical reception. She later portrayed Roxie Hart in Chicago on Broadway.
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. She independently released the single "Bat for a Heart" (2012), though it failed to have success. Simpson has since scrapped the album, and focused on her child. She began dating actor Evan Ross in 2013, with the couple marrying in August 2014. Months later the two announced that Simpson was expecting a second child, and in July 2015 she gave birth to a baby girl.