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 November 2003, Spears released her fourth studio album, In the Zone, jettisoning the Max Martin-produced synthpop of her earlier releases. The album took in lesser-known producers such as RedZone and big names including Moby and R. Kelly. Spears NUDE BRITINY SPEARS SEXY PHOTO co-wrote eight of the album's thirteen songs and co-produced several pieces of her material for the first time. In the Zone reached number one in the U.S. charts during its debut week, selling over 609,000 copies. This made Spears the first female in the Nielsen SoundScan era to have her first four studio albums to debut at number one.^[73] The album had a mild reception from critics. Stylus Magazine gave the album a D and even blamed Spears's career choices by stating, "Ultimately, In the Zone suffers greatly from Britney's uneasy transition from teen tart to sexually powerful woman. Had Britney been in charge of her career direction instead of mercilessly prostituted by her management, she might have been able to produce something with some semblance of musical vision."^[74] The Guardian praised the album's melodies and her effort, giving it 4 out of 5 stars and writing, "Unlike previous Britney albums, In the Zone has no filler and no shoddy cover versions, just 57 varieties of blue-chip hit-factory pop. There is southern hip-hop, deep house, Neptunes-style R&B, the ubiquitous Diwali beat and, most importantly, oodles of Madonna."^[75]

In November 2005, Spears released her first remix album, B In The Mix: The Remixes. The album ranged from "...Baby One More Time" to "Toxic". Her newest single "Someday (I Will Understand)" was also remixed. Another single, "And Then We Kiss", was britney spears controversial nude pictures only released in Asia, where it charted in many countries. The song peaked at number 15 on Billboard's Hot Dance Airplay chart,^[88] despite it not being officially released in the U.S.^[89]

In September 2007, the official findings in Spears's custody battle were announced by the court. She was ordered to undergo random drug and alcohol testings and to attend parenting counseling. Spears and Federline continued to share joint custody of their britney spears nude wallpapers two children on a conditional basis.^[113] A few days later, she was officially charged with misdemeanor hit-and-run and driving without a license. If convicted, she could face a year in jail.^[114] Spears lost physical custody of her children to Federline on October 1,^[115][116] with the court ruling that Federline will keep full custody of the children.^[117] The charges for her alleged hit-and-run that occurred in August 2007 were officially laid,^[118] she was booked for the charges by the Los Angeles Police Department on October 15 but was not arrested.^[119]

In early 2002, Spears's four-year relationship with Timberlake ended.^[57] His 2002 song "Cry Me a River" and its music video, which featured an actress resembling Spears, caused speculation that Spears britney spears sex picture had been unfaithful;^[58] Timberlake, however, denied that his song was meant to portray her.^[59]

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 single "Outrageous".^[79] The tour's britnei spirs sex choreography generated much controversy and criticism, with the presence of young children in the audience.^[80]She then became involved in the Kabbalah Centre in September 2004 through her friendship with Madonna.^[81] However, she publicly left the religion in 2006, stating on her website, "I no longer study Kabbalah, my baby is my religion."^[82]