Britney Spears posing nude - black and white

In 2006, Spears guest-starred on the Will & Grace episode "Buy, Buy Baby" as a closeted lesbian. Her performance drew criticism from conservative Christian groups.^[90] Spears announced her second pregnancy in May 2006 during an appearance on The Late Show with David Letterman.^[91] She also appeared on Dateline the next month to discuss tabloid rumors about an impending divorce, and motherhood. She addressed an incident which occurred in February when photos revealed her driving with her son unrestrained in her lap,^[92] explaining, "I see a bunch of photographers and I’m scared and I want to get out of the situation... They’re coming up BRITTNEY SPEARS NUDE PHOTOS on the sides of the car which is a scary situation for me… so I get my baby out of the car and I go home."^[93] The month following the televised interview, Spears posed nude for the August 2006 cover of Harper's Bazaar.^[94][95] Just two days before Sean's first birthday, Spears gave birth to her second son, Jayden James Federline on September 12 in Los Angeles.^[7]

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 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] britney spears : sex pics 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 Britney Spears Porn Photos 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 and Canadian musician-singer Sarah McLachlan, respectively.^[40]