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Sullivan was then offered a solo recording contract with J, which in 2008 released her debut single, "Need U Bad." Featuring and co-produced by Missy Elliott, the song topped Billboard's R&B/hip-hop chart. Fearless, her debut album, featuring productions by Salaam Remi and Stargate, among others, was issued that September. It topped the R&B/hip-hop chart and crossed over to reach number six on the Billboard 200, aided by "Bust Your Windows" and "Lions, Tigers & Bears" -- both of which went into the Top Ten of the R&B chart. Sullivan followed it up in November 2010 with Love Me Back, previewed with "Holding You Down (Goin' in Circles)," yet another Top Ten R&B/hip-hop hit.
Despite an impressive total of 11 Grammy nominations for her work as a vocalist and songwriter, Sullivan was frustrated with the industry and announced in 2011 that she was leaving it. However, she was eventually drawn back. In 2014, "Dumb" (featuring Meek Mill), "Forever Don't Last," and "Mascara" were released as the first singles from her third album, Reality Show. The set was issued the following January and led to three more Grammy nominations, including one for Best R&B Album. Sullivan continued to assist other artists, as heard on Frank Ocean's Endless, Mali Music's The Transition of Mali, and Mary J. Blige's Strength of a Woman. In 2017, she and Bryson Tiller contributed "Insecure" to Issa Rae's HBO series of the same title. ~ Jason Birchmeier