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In 2001, she released her third studio album Britney and expanded her brand, playing the starring role in the film Crossroads. She assumed creative control of her fourth studio album, In the Zone (2003), which yielded chart-topping singles "Me Against the Music", "Toxic" and "Everytime". After the release of two compilation albums, Spears experienced personal struggles and her career went into hiatus. Her fifth studio album, Blackout, was released in 2007 and despite receiving little promotion, it spawned hits "Gimme More" and "Piece of Me". In 2008, her erratic behavior and hospitalizations caused her to be placed in a conservatorship. The same year, her sixth studio album Circus was released, with the global chart-topping lead single "Womanizer". She embarked on her highest-grossing global concert tour, The Circus Starring Britney Spears, in 2009. Her seventh studio album Femme Fatale, released in 2011, has become the first of her albums to yield three top ten singles in the United States.

Spears has sold over 100 million records worldwide. According to the Recording Industry Association of America (RIAA), she is the eighth top-selling female artist in the United States, with 33 million certified albums. Spears is also recognized as the best-selling female artist of the first decade of the 21st century, as well as the fifth overall. She was ranked the 8th Artist of the 2000s by Billboard. In June 2010, Spears was ranked sixth on Forbes list of the 100 Most Powerful and Influential celebrities in the world; she is also the third most mentioned musician on the internet, according to Forbes.

Britney Jean Spears was born on December 2, 1981, the second child of Lynne Irene (née Bridges) and James Parnell Spears. She is of English heritage through her maternal grandmother, who was born in London, and of distant Maltese descent. Her siblings are Bryan James and Jamie Lynn. At age three, she started to attend dance lessons in her hometown of Kentwood, Louisiana, and was selected to perform a solo at the annual recital. During her childhood, she also attended gymnastics and voice lessons, and won many state-level competitions and children's talent shows. Spears made her local stage debut at age five, singing "What Child Is This?" at her kindergarten graduation. She said about her ambition as a child, "I was in my own world, [...] I found out what I'm supposed to do at an early age". At age eight, Spears and her mother Lynne traveled to Atlanta for an audition in the 1990s revival of The Mickey Mouse Club. Casting director Matt Cassella rejected her for being too young to join the series at the time, but introduced her to Nancy Carson, a New York City talent agent. Carson was impressed with Spears's vocals and suggested enrolling her at the Professional Performing Arts School; shortly after, Lynne and her daughters moved to a sublet apartment in New York. Spears was hired for her first professional role as the understudy for the lead role of Tina Denmark in the Off-Broadway musical Ruthless!. She also appeared as a contestant on the popular television show Star Search, as well as being cast in a number of commercials. In December 1992, she was finally cast in The Mickey Mouse Club, but returned to Kentwood after the show was canceled. She enrolled at Parklane Academy in nearby McComb, Mississippi. Although she made friends with most of her classmates, she compared the school to "the opening scene in Clueless with all the cliques. [...] I was so bored. I was the point guard on the basketball team. I had my boyfriend, and I went to homecoming and Christmas formal. But I wanted more."

In June 1997, Spears was in talks with manager Lou Pearlman to join female pop group Innosense. Lynne asked family friend and entertainment lawyer Larry Rudolph for his opinion and submitted a tape of Spears singing over a Whitney Houston karaoke song along with some pictures. Rudolph decided he wanted to pitch her to record labels, therefore she needed a professional demo. He sent Spears an unused song from Toni Braxton; she rehearsed for a week and recorded her vocals in a studio with a sound engineer. Spears traveled to New York with the demo and met with executives from four labels, returning to Kentwood the same day. Three of the labels rejected her, arguing audiences wanted pop bands such as the Backstreet Boys and the Spice Girls, and "there wasn't going to be another Madonna, another Debbie Gibson, or another Tiffany." Two weeks later, executives from Jive Records returned calls to Rudolph. Senior vice president of A&R Jeff Fenster stated about Spears's audition that "It's very rare to hear someone that age who can deliver emotional content and commercial appeal. [...] For any artist, the motivation—the 'eye of the tiger'— is extremely important. And Britney had that." They appointed her to work with producer Eric Foster White for a month, who reportedly shaped her voice from "lower and less poppy" delivery to "distinctively, unmistakably Britney." After hearing the recorded material, president Clive Calder ordered a full album. Spears had originally envisioned "Sheryl Crow music, but younger more adult contemporary" but felt all right with her label's appointment of producers, since "It made more sense to go pop, because I can dance to it—it's more me." She flew to Cheiron Studios in Stockholm, Sweden, where half of the album was recorded from March to April 1998, with producers Max Martin, Denniz Pop and Rami Yacoub, among others.

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After Spears returned to the United States, she embarked on a shopping mall promotional tour to promote her forthcoming album. Her show was a four song set and she was accompanied by two back up dancers. Her first concert tour followed, as an opening act for 'N Sync. Her debut album, ...Baby One More Time, was released on January 1999. It debuted at number one on the U.S. Billboard 200 and was certified two-times platinum by the Recording Industry Association of America after a month. Worldwide, the album topped the charts in fifteen countries and sold over ten million copies in a year. It became the biggest selling album ever by a teenage artist. The title track was released as the lead single from the album. Originally, Jive Records wanted its music video to be animated; however, Spears rejected it, and suggested the final idea of a Catholic schoolgirl. The single sold 500,000 copies on its first day, and peaked at number one on the Billboard Hot 100, topping the chart for two consecutive weeks. "...Baby One More Time" later received a Grammy nomination for Best Female Pop Vocal Performance. The title track also topped the singles chart for two weeks in the United Kingdom, and became the fastest-selling single ever by a female artist, shipping over 460,000 copies. It would later become the 25th most successful song of all time in British chart history. Spears is also the youngest female artist to have a million seller in the country. "(You Drive Me) Crazy" was released as the third single from the album. It became a top-ten hit worldwide and propelled ...Baby One More Time to sell 26 million copies.

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The April 1999 cover of Rolling Stone featured Spears lying on her bed, clad with a bra, shorts and an open top. The American Family Association (AFA) referred to the shoot as "a disturbing mix of childhood innocence and adult sexuality" and called to "God-loving Americans to boycott stores selling Britney's albums." Spears responded to the outcry commenting, "What's the big deal? I have strong morals. [...] I'd do it again. I thought the pictures were fine. And I was tired of being compared to Debbie Gibson and all of this bubblegum pop all the time." Shortly before, Spears had announced publicly she would remain a virgin until marriage. On June 28, 1999, Spears began her first headlining ...Baby One More Time Tour in North America, which was positively received by critics, but generated some controversy due to her racy outfits. An extension of the tour, titled Crazy 2k, followed in March 2000. Spears premiered songs from her upcoming second album during the show. Oops!... I Did It Again, her second studio album, was released in May 2000. It debuted at number one in the US, selling 1,3 million copies, breaking the SoundScan record for the highest debut sales by any solo artist. The album sold over 20 million copies worldwide. Rob Sheffield of Rolling Stone said that "the great thing about Oops! – under the cheese surface, Britney's demand for satisfaction is complex, fierce and downright scary, making her a true child of rock & roll tradition." The album's lead single, "Oops!... I Did It Again", peaked at the top of the charts in Australia, New Zealand, the United Kingdom and many other European nations. The album as well as the title track received Grammy nominations for Best Pop Vocal Album and Best Female Pop Vocal Performance, respectively.
The same year, Spears embarked on the Oops!... I Did It Again World Tour, which grossed $40.5 million; she also released her first book, Britney Spears' Heart-to-Heart, co-written with her mother. On September 7, 2000, Spears performed at the 2000 MTV Video Music Awards. Halfway through the performance, she ripped off her black suit to reveal a sequined flesh-colored bodysuit, followed by heavy dance routine. It is noted by critics as the moment that Spears showed signs of becoming a more provocative performer. Amidst media speculation, Spears confirmed she was dating 'N Sync member Justin Timberlake.

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In February 2001, Spears signed a $7–8 million promotional deal with Pepsi, and released another book co-written with her mother, entitled A Mother's Gift. Her third studio album, Britney, was released in November 2001. While on tour, she felt inspired by hip hop artists such as Jay-Z and The Neptunes and wanted to create a record with a funkier sound. The album debuted at number one in the Billboard 200 and reached top five positions in Australia, the United Kingdom and mainland Europe and sold over 12 million copies worldwide. Stephen Thomas Erlewine of Allmusic called Britney "the record where she strives to deepen her persona, making it more adult while still recognizably Britney. [...] It does sound like the work of a star who has now found and refined her voice, resulting in her best record yet." The album was honored with two Grammy nominations—Best Pop Vocal Album and Best Female Pop Vocal Performance for "Overprotected"— and was listed in 2008 as one of Entertainment Weekly's "100 Best Albums from the Past 25 Years". The album's first single, "I'm a Slave 4 U", became a top-ten hit worldwide. Spears's performance of the single at the 2001 MTV Video Music Awards featured a caged tiger and a large albino python draped over her shoulders. It was harshly received by animal rights organization PETA, who claimed the animals were mistreated and scrapped plans for an anti-fur billboard that was to feature Spears. To support the album, Spears embarked on the Dream Within a Dream Tour. The show was critically praised for its technical innovations, the pièce de résistance being a water screen that pumped two tons of water into the stage. The tour grossed $43.7 million, becoming the second highest grossing tour of 2002 by a female artist, behind Cher's Farewell Tour. Her career success was highlighted by Forbes in 2002, as Spears was ranked the world's most powerful celebrity. Spears also landed her first starring role in Crossroads, released in February 2002. Although the film was largely panned, most critics actually praised Spears's acting. Crossroads, which had a $11 million budget, went on to gross over $57 million worldwide. In June 2002, Spears opened her first restaurant, Nyla, in New York City, but terminated her relationship in November, citing mismanagement and "management's failure to keep her fully apprised". In July 2002, Spears announced she would take a six month break from her career; however, she went back into the studio in October to record her new album. Spears's relationship with Justin Timberlake ended after three years. In December 2002, Timberlake released the song "Cry Me a River" as the second single from his solo debut album. The music video featured a Spears look-alike and fueled the rumors that she had been unfaithful to him. As a response, Spears wrote the ballad "Everytime" with her backing vocalist and friend Annet Artani. The same year, Limp Bizkit frontman Fred Durst confirmed that he was in a relationship with Spears, only to deny it later. In a 2009 interview, he explained that "I just guess at the time it was taboo for a guy like me to be associated with a gal like her." Spears opened the 2003 MTV Video Music Awards with Christina Aguilera, performing "Like a Virgin". Halfway through they were joined by Madonna, with whom they both kissed. The incident was highly publicized.