In late 1999, Spears appeared on the sitcom Sabrina, the Teenage Witch and performed the song "(You Drive Me) Crazy"; this cameo was a cross-promotion for the film Drive Me Crazy, which starred Sabrina's Melissa Joan Hart and was named after the song.^[38]

June 2002 saw the opening of Spears's restaurant, Nyla, in New York City, which served Louisianan and Italian cuisine. However, she was pulled out of the business venture in britney spears controversial nude pictures November as a result of debts and management issues. Nyla officially closed in 2003.^[20] In the same year, Limp Bizkit frontman Fred Durst confirmed that he was in a relationship with Spears. Durst was also hired to help write and produce tracks for her album In the Zone, which were eventually scrapped.^[60]

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 NUDE BRITINY SPEARS SEXY PHOTO 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 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 britney spears controversial nude pictures 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] 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] britney spears nude wallpapers 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]

In July 2004, Spears announced her engagement to Kevin Federline, three months after they met. Federline had recently been in a relationship with actress Shar Jackson, who was eight months pregnant with their second child.^{britney spears sex picture class="reference">[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]

In March 1999, Tamara Conniff of Entertainment News Wire reported: "Only a few years ago, Spears was a Mouseketeer on the Disney Channel's "Mickey Mouse Club." Now, she's a 17-year-old pop superstar with a No. 1 album, a double-platinum single and britnei spirs sex a provocative video in heavy rotation on MTV. Spears' debut album and its title track, "... Baby One More Time," have taken the music world by storm".^[29] Spears commented, "My main goal is just to make good music...And since I am so young, I can grow as an artist each time and hopefully be a legend or something, like Madonna".^[29] By April 1999, Spears was described as "the Reigning Princess of Pop" by the Orlando Sentinel.^[30]