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Britney Spears's castmates on the show included Justin Timberlake and Joshua Chasez (who later became members of the pop band NSYNC), Keri Russell (star of the TV show Felicity) and Christina Aguilera, also a pop singer. Spears dated Timberlake for about five years.

In common with a number of other popular female figures in show business, Britney Spears' private life has attracted considerable media attention. Her situation illustrates a common tension between publicity and privacy: while an increased "profile" can carry with it the loss of certain liberties many of the rest of us take for granted, the trafficking of personal revelations is nevertheless widely considered to be an effective marketing strategy in many areas of popular culture. Indeed, some people feel that Ms. Spears has brought on this kind of public attention by cultivating, in her early years at least, a chaste, God-fearing and "wholesome" image somewhat at odds not only with the traditional pressures, temptations and opportunities of "pop 'n' roll" but with the increasingly sexualized content of her own songs. Regardless of where the responsibility for the gossip industry surrounding the pop star lies, Ms. Spears' public response has been to repeatedly express regret and resentment at the intrusive media coverage.

Britney Spears's first album on Jive Records, ...Baby One More Time, debuted in the number 1 spot on the Billboard Charts in early 1999, and also topped the charts in the UK. The single of the same name was also a number 1 hit in many countries, and was accompanied by a music video in which Spears wore a school-girl outfit and danced through a high-school corridor. Her followup album, Oops I Did It Again, also debuted at number 1 and was a similarly huge hit.