Janet Damita Jo Jackson (born May 16, 1966) is an American singer, songwriter, dancer, and actress. Known for sonically innovative, socially conscious and sexually provocative records, and elaborate stage shows, she has been a prominent figure in popular culture for over thirty years. The youngest child of the Jackson family, she began her career with the variety television series The Jacksons in 1976 and went on to appear in other television shows throughout the 1970s and early 1980s, including Good Times and Fame. After signing a recording contract with A&M Records in 1982, she became a pop icon following the release of her third studio album Control (1986).

Jackson began recording her ninth studio album, 20 Y.O., in 2005. She recorded with producers Dupri, Jam and Lewis for several months during the following year. The album's title was a reference to the two decades since the release of her breakthrough album Control, representing the album's "celebration of the joyful liberation and history-making musical style."  To promote the album, Jackson appeared in various magazines, and performed on the Today Show and Billboard Awards. Jackson's Us Weekly cover, revealing her slim figure after heavy media focus was placed on her fluctuations in weight, became the magazine's best-selling issue in history. 20 Y.O. was released in September 2006 and debuted at number two on the Billboard 200. The album received mixed reviews, with multiple critics chastising the production and involvement of Jermaine Dupri. Rolling Stone disagreed with the album's reference to Control, saying "If we were her, we wouldn't make the comparison."  Jackson's airplay and music channel blacklist remained persistent, massively affecting her chart performance and exposure. However, lead single "Call on Me", which featured rapper Nelly, peaked at number twenty-five on the Hot 100, number one on the Hot R&B/Hip-Hop Songs chart, and number six in the United Kingdom. The video for the album's second single, "So Excited", was directed by Joseph Kahn and portrayed Jackson's clothes disappearing through a complex dance routine.  20 Y.O. was certified platinum by the RIAA and sold 1.2 million worldwide, also receiving a Grammy nomination for Best Contemporary R&B Album. After the album's release, Dupri was condemned for his production and misguidance of the album, and subsequently was removed from his position at Virgin Records. Slant Magazine stated, "After promising a return to Janet's dance-pop origins, [Dupri] opted to aim for urban audiences, a colossal mistake that cost Dupri his job and, probably, Janet her deal with Virgin."  Jackson was ranked the seventh richest woman in the entertainment industry by Forbes, having amassed a fortune of over $150 million. In 2007, she starred opposite Tyler Perry as a psychotherapist in the film Why Did I Get Married?. It became her third consecutive film to open at number one at the box office, grossing $60 million in total. Jackson's performance was praised for its "soft authority", though also described as "charming, yet bland".

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Jackson was ranked the seventh richest woman in the entertainment industry by Forbes,