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 nude britney spears 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.^{brittney spears sex tape 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]

Spears's personal life began to gain substantial media attention after her marriage to Kevin Federline in 2004. Their marriage ended two years later, resulting in an ongoing custody battle over their two children, born in 2005 and 2006.^{nude britney spears class="reference">[2]}^[3] Spears released her fifth studio album Blackout in 2007. The following year Spears began recording her sixth studio album Circus.

The album spawned the hit single "Toxic", brittney spears sex tape winning Spears her first ever Grammy in the category of Best Dance Recording.^[74]

The album's lead single of the same name broke the record for most radio station additions in a single day, and quickly became a top ten hit in the U.S. and other countries.^[42] The same nude photos of britney spears year, Spears launched her first world tour, the "Oops!... I Did It Again World Tour". During the tour, she made a stop in New York for the 2000 MTV Video Music Awards. As part of her performance, she ripped off a black suit to reveal a provocative nude-colored and crystal-adorned outfit that generated much controversy.^[43] Spears earned two Billboard Music Awards for Oops!... I Did It Again.^[44]

The music video for "...Baby One More Time" and Spears's appearance on the cover of Rolling Stone magazine also established her as an international sex symbol, garnering controversy over the influence of her public image on teenage girls.^{britany spears sex tape class="reference">[1]}

The release of Spears's fifth album, Blackout, was rescheduled to October 30, 2007 rather than November 13, 2007 due to online leaks.^[118]^{britney spears oops class="reference">[119]} Blackout debuted at number two on the U.S. Billboard 200.,^[120] making Spears the only female music artist to have her first five albums go to number one and two. It was fairly well received by critics.^[121] As of June 2008, there have been 3.1 million digital downloads of the songs and remixes from the album in the United States.^[122] Rolling Stone gave the album 3.5 out of 5 stars.^[123] Allmusic also rated the album 3.5 out of 5 stars, calling Blackout "coherent and entertaining" and stating that "it holds together better than any of her other records".^[124] Blackout's lead single, "Gimme More" leaked on the internet on August 30.^[118] The song, which was Spears's first produced by Danja, peaked at number three on Billboard's Hot 100 on October 3, making it her most successful single in the U.S. since her debut, "...Baby One More Time".^[125][126] Spears's highly anticipated performance of "Gimme More" at the 2007 MTV Video Music Awards was panned.^{[127][128][129]} The BBC stated that "her performance would go down in the history books as being one of the worst to grace the MTV Awards",^[130] and The Times noted that "Spears was out of synch as she lip-synched and at times just stopped singing altogether".^[131] Despite the criticism on her performance,^[132] the single has achieved worldwide success.^{[133][134][135]} The second single, "Piece of Me", was certified platinum in the US.^[136]