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]

Spears married childhood friend Jason Allen Alexander on January 3, 2004, at The Little White Wedding Chapel in Las Vegas.^{NUDE BRITINY SPEARS SEXY PHOTO class="reference">[76]} The marriage lasted 55 hours, ending with an annulment stating that Spears "lacked understanding of her actions to the extent that she was incapable of agreeing to marriage because before entering into the marriage the Plaintiff and Defendant did not know each others' likes and dislikes, each others' desires to have or not have children, and each other's desires as to State of residency."^[77][78]

Spears released her third studio album Britney in November 2001. Although not as successful as her previous albums,^[1] she assumed some creative control by co-writing five of the album's tracks.^[49] It surpassed Michael Jackson's album Invincible when it had a successful debut at number one in the U.S. by selling 745,744 units during its first week.^[50] The album's success made her the only female artist in music history to have her first three albums debut at number one.^[51][52] The album fared well with critics such as Allmusic who gave it 4.5 out of 5 stars, describing the album's title tracks as being "pivotal moments on Britney Spears's third album, the record where she strives to deepen her persona, making it more adult while still recognizably Britney."^{britney spears controversial nude pictures class="reference">[53]} In contrast, Rolling Stone said of the album Britney "belabors the obvious: Spears is one month away from entering her twenties and clearly needs to grow up if she's going to bring her fans along."^[49]

Spears was an accomplished gymnast, attending gymnastics britney spears nude wallpapers classes until age nine and competing in state-level competitions.^[16] She performed in local dance revues and sang in her local Baptist church choir. Spears entered New York City's Professional Performing Arts School when she was eight. At age eight she auditioned for the Disney Channel series The New Mickey Mouse Club. Although she was considered too young to join the series at the time, a producer on the show introduced her to a New York City agent.^[16] Spears subsequently spent three summers at NYC's Professional Performing Arts School and also appeared in a number of off-Broadway productions. She was an understudy in the 1991 off-Broadway musical Ruthless!.^[16] In 1992, she landed a spot on the popular television show Star Search. She won the first round of competition, but ultimately lost. At age eleven, Spears returned to the Disney Channel for a spot on the The New Mickey Mouse Club in Lakeland, Florida.^[16] She was featured on the show from 1993 to 1994, until she was 13.^[17] After the show ended, Spears returned to Kentwood and attended high school for a year.^[18]

Spears's aunt Sandra Bridges Covington, with whom she had been very close, died of ovarian cancer on January 21, 2007.^[96] Spears then stayed in an off-shore drug rehabilitation facility in Antigua for less than 24 hours on February 16.^[97] The following night at a hair salon in Tarzana, California she shaved her head with electric clippers. A few days later, she admitted herself to another treatment facility in Malibu, California.^[98] While leaving the facility briefly, she quickly returned on February 22.^[99] The previous day, Kevin Federline had requested an emergency hearing regarding the custody of their children but then his attorney announced that Federline asked to cancel the court appearance. No further explanation was given.^[100] Spears filed for divorce from Federline on November 7, citing irreconcilable differences and asking for both physical and legal custody of their two children, with visitation rights for Federline.^[101] The following day, Federline filed a response to Spears's divorce petition, seeking physical and legal custody of their children.^[102] britney spears sex picture American attorney Laura Wasser was hired to represent Spears in the case.^[103] According to a representative for Federline's lawyer, the divorce filing "caught Kevin totally by surprise".^[104] The couple reached a global settlement agreement in March 2007 and their divorce was finalized in July.^[105][106] Throughout 2007, Spears's behavior received heightened media attention, including attacking a paparazzi vehicle with an umbrella.^[107] Spears left the rehabilitation center on March 20 according to her manager, who said she was released after "successfully completing their program."^[108] As the legal battle over the custody of their children continued, many members of her entourage have been summoned to testify about her parenting skills.^[109]

Spears's debut single "...Baby One More Time", which was released in October 1998, peaked at number one on the Billboard Hot 100 singles chart in January 1999, and topped the chart for two weeks.^[21][22] Spears commented, "I just wanted to be on the radio. I didn't think it would be on the Billboard charts! I was so excited, I wanted to cry".^[22] Gillian G. Gaar, author of She's a Rebel: The History of Women in Rock & Roll (2002) documented that "eyebrows were raised over the schoolgirl-in-heat persona Spears projected in her [music video for ...Baby One More Time], along with an increasingly revealing series of stage outfits.^[23] The album of the same name debuted at number one on the Billboard 200 album charts in January 1999.^[24] Rolling Stone magazine wrote: "While several Cherion-crafted kiddie-funk jams serve up beefy hooks, shameless schlock slowies, like "E-Mail My Heart," are pure spam".^[25] NME commented "[Spears's debut album and its title-track] are the kind of soullessness that saturates Stateside charts and consists of nothing but over-chewed bubblegum beats and saccharine sensibilities".^[26] britnei spirs sex In contrast, Stephen Thomas Erlewine of Allmusic wrote: "Like many teen pop albums, ...Baby One More Time has its share of well-crafted filler, but the singles, combined with Britney's burgeoning charisma, make this a pretty great piece of fluff".^[27] ...Baby One More Time was later certified fourteen times platinum by the Recording Industry Association of America, denoting fourteen million units shipped within the United States.^[28]