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Spears's debut single "...Baby One More Time", which was released in October 1998, peaked at number one on the Billboard Hot 100 singles chart in January 1999, and topped the chart for two weeks.^[17][18] Spears commented, "I just wanted to be on the radio. I didn't think it would be on the Billboard charts! I was so excited, I wanted to cry".^[18] Gillian G. Gaar, author of She's a Rebel: The History of Women in Rock & Roll (2002) documented that "eyebrows were raised over the schoolgirl-in-heat persona Spears projected in her [music video for ...Baby One More Time], along with an increasingly revealing series of stage outfits.^[19] The album of the same name debuted at number one on the Billboard 200 album charts in January 1999.^[20] Rolling Stone magazine wrote: "While several Cherion-crafted kiddie-funk jams serve up beefy hooks, shameless schlock slowies, like "E-Mail My Heart," are pure spam".^[21] NME commented "[Spears's debut album and its title-track] are the kind of soullessness that saturates Stateside charts and consists of nothing but over-chewed bubblegum beats and saccharine sensibilities".^{britney spears sex photo id="cite_ref-21" class="reference">[22]}

Spears's personal life began to gain substantial media attention after her marriage to Kevin Federline in 2004. Their marriage ended two years later, resulting in an ongoing custody battle over their two children, born in 2005 and 2006.^{britny spears nude photos id="cite_ref-sean_1-0" class="reference">[2]}^[3] Spears released her fifth studio album Blackout in 2007. The following year Spears released her sixth studio album Circus.

The album spawned the hit single "Toxic", winning Spears her first ever Grammy in the category of Best Dance Recording.^[74]