Spears's aunt Sandra Bridges Covington, with whom she had been very close, died of ovarian cancer on January 21, 2007.^[94] Spears then stayed in an off-shore drug rehabilitation facility in Antigua for less than 24 hours on February 16.^[95] 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.^[96] While leaving the facility briefly, she quickly returned on February 22.^[97] 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.^[98] Spears filed for divorce from Federline on November 7, 2006, citing irreconcilable differences and asking for both physical and legal custody of their two children, with visitation rights for Federline.^[99] The following day, Federline filed a response to Spears's divorce petition, seeking physical and legal custody of their children.^[100] American attorney Laura Wasser was hired to represent Spears in the case.^[101] According to a representative for Federline's lawyer, the divorce filing "caught Kevin totally by surprise".^[102] The couple reached a global britney spears sex pictures settlement agreement in March 2007 and their divorce was finalized in July.^[103][104] Throughout 2007, Spears's behavior received heightened media attention, including attacking a paparazzi vehicle with an umbrella.^[105] Spears left the rehabilitation center on March 20 according to her manager, who said she was released after "successfully completing their program."^[106] 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.^[107]

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.^{nude britney spears class="reference">[17]}^[18] 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".^[18] 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.^[19] The album of the same name debuted at number one on the Billboard 200 album charts in January 1999.^[20] 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".^[21] 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".^[22]

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 britney spears sex pictures We Kiss", was only released in Asia, where it charted in many countries. The song peaked at number 15 on Billboard's Hot Dance Airplay chart,^[87] despite it not being officially released in the U.S.^[88]

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 nude britney spears of their two children on a conditional basis.^[111] 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.^[112] Spears lost physical custody of her children to Federline on October 1,^[113][114] with the court ruling that Federline will keep full custody of the children.^[115] The charges for her alleged hit-and-run that occurred in August 2007 were officially laid,^[116] she was booked for the charges by the Los Angeles Police Department on October 15 but was not arrested.^[117]

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".^{brittney spears sex tape id="cite_ref-22" class="reference">[23]} ...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.^[24]

In early 2002, Spears's four-year relationship with Timberlake ended.^[53] His 2002 song "Cry Me a River" and its music video, which featured an actress resembling Spears, nude photos of britney spears caused speculation that Spears had been unfaithful;^[54] Timberlake, however, denied that his song was meant to portray her.^[55]

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 britany spears sex tape 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]