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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 britny spears nude photos Me Crazy, which starred Sabrina's Melissa Joan Hart and was named after the song.^[34] 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.^[35]

June 2002 saw the opening of Spears's restaurant, www.briney spears.com Nyla, in New York City, which served Louisianan and Italian cuisine. However, she was pulled out of the business venture in November as a result of debts and management issues. Nyla officially closed in 2003.^[16] 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.^[56]

Months after her Las Vegas marriage, Spears embarked on The Onyx Hotel Tour, which was canceled in June, after Spears injured her knee during the filming of the video for the Britney Spears Porn Photos single "Outrageous".^[78] The tour's choreography generated much controversy and criticism, with the presence of young children in the audience.^[79] She then became involved in the Kabbalah Centre in September 2004 through her friendship with Madonna.^[80] However, she publicly left the religion in 2006, stating on her website, "I no longer study Kabbalah, my baby is my religion."^[81]