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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.

The sexual iconography of Britney Spears once again became a topic of debate as a result of her 2003 semi-nude photo spread for the men's magazine, Esquire. Prompted by this, Playboy reportedly offered the star over a million dollars to pose nude for their magazine. It is believed that Spears is still deciding whether to accept the offer.

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.