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In early 2002, Spears's four-year relationship with Timberlake ended.^[111] His 2002 song "Cry Me a River" and its music video, nude britney spears which featured an actress resembling Spears, caused speculation that Spears had been unfaithful;^[112] Timberlake, however, denied that his song was meant to portray her.^[113]

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.^[27] britney spears sex 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.^[28]

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 November as a result of debts and management issues. britney sprears sex tape 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.^[95]