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One of Ms. Spears best friends, Jenny, was in the unsuccessful girl-group Innosence. Ms. Spears was a former member of the group, but left and debuted as a solo-artist before the band released their first record. One of her closest friends is Felicia Culotta, her assistant.

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.

While young girls seldom address this debate in the same terms as their parents, many are divided on whether they consider Britney Spears appealing, especially in the light of more recent developments in her career.