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In April 1999, Spears posed for the cover of Rolling Stone magazine, shot by photographer David LaChapelle.^[31] Spears commented, "It was so much fun!...I loved the idea of me holding Tinky Winky and talking on the phone!"^[32] Geoff Boucher of The Los Angeles Times reported, "there was no mistaking the titillation factor in the recent Spears cover story and accompanying photos in the April 15 issue of Rolling Stone, which sent eyebrows arching throughout the music industry, where several executives half-jokingly called it "child pornography."^[33] Similarly, an editorial review from Iowa State Daily commented, "a distinction should be drawn between the cute teeny-boppers in cool outfits who make the boys and girls buy records by the truckload and the exploitation of a minor by her parents, her record company and the media... Pictures like these are only barely legal when taken by private citizens. But when Rolling Stone does it, it's just good business".^[34] Gillian G. Gaar reported, "The American Family Association charged that the pictures, which showed Spears in push-up bras and a minuscule pair of shorts with "Baby" in rhinestones britney spears nude paparazzi photos on the bottom, presented a "disturbing mix of childhood innocence and adult sexuality" and asked that all "God-loving Americans" boycott stores carrying her albums".^[23] More controversy arose when Spears declared that she would "remain a virgin until marriage".^[35] This pledge has been questioned due to her apparently sexual relationship with fellow pop singer Justin Timberlake.^[36][37]

In December 1999, she won four Billboard Music Awards, including Female Artist of the Year. A month later, she took home the Favorite Pop/Rock New Artist award at the American Music Awards.^[39] At the 2000 Grammy Awards, Spears received two nominations in the categories of Best New Artist and Best Female Pop Vocal Performance for ...Baby One More Time, but lost to American singer Christina Aguilera britney spears oops photos and Canadian musician-singer Sarah McLachlan, respectively.^[40]

In July 2004, Spears announced her engagement to Kevin Federline, three months after they met. Federline had britney spears porno pics recently been in a relationship with actress Shar Jackson, who was eight months pregnant with their second child.^[83] These initial stages were chronicled in Spears's first reality show Britney & Kevin: Chaotic, which aired on UPN in May and June 2005.^[84] On the night of September 18, Spears married Federline in a surprise, non-denominational ceremony at a residence in Studio City, California, filing legal papers on October 6.^[85][86] After the marriage, Spears announced via her website that she would be taking another career break to start a family. She gave birth to her first child, Sean Preston Federline, on September 14, 2005 in Santa Monica, California by a scheduled caesarean section.^[6]