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In 1999 Jessica relised first album "Sweet Kisses" who had gone double platinum. This album included such singles as "Where You Are" and "I Think I'm In Love With You", which were both big hits. Later they became Simpson's biggest radio hit and was her first release of an uptempo single. Although her debut album sold 2 million copies and 4 million worldwide, sales fell far short of those achieved by Britney Spears and Christina Aguilera, and unlike the two pop princesses, Simpson was not a worldwide household name. After the release of her album Simpson started touring with Ricky Martin and "98 Degrees", a popular boy band at the time.

Simpson recorded a second album "Irresistible", released in summer 2001 on the heels of the title-track first single. "Irresistible" was most popular album throughout her singer career. She has five total album, one remixed ("This Is the Remix") and one Christmas album ("Rejoyce: The Christmas Album").