1998–2000: ...Baby One More Time and Oops!... I Did It Again

"...Baby One More Time" (1999)
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Britney Spears' first major hit single worldwide.
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Spears released in October 1998 her debut single, "...Baby One More Time", which peaked at number one on the Billboard Hot 100 in January 1999 and topped the chart for two weeks.[12][13] 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".[14] Spears's debut album ...Baby One More Time peaked at number one on the Billboard 200 in January 1999.[15] Rolling Stone magazine, in a review of the album, wrote: "While several Cherion-crafted kiddie-funk jams serve up beefy hooks, shameless schlock slowies, like [']E-Mail My Heart,['] are pure spam".[16] 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".[17] 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".[18] ...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.[19]
Britney Spears featured on the cover of Rolling Stone magazine

Spears posed for the cover of Rolling Stone magazine in April 1999, shot by photographer David LaChapelle.[20] Geoff Boucher of The Los Angeles Times reported, "there was no mistaking the titillation factor in the recent Spears cover story and accompanying photos in the April 15 issue of Rolling Stone, which sent eyebrows arching throughout the music industry, where several executives half-jokingly called it "child pornography".[21] Gillian G. Gaar reported, "The American Family Association charged that the pictures, which showed Spears in push-up bras and a minuscule pair of shorts with 'Baby' in rhinestones on the bottom, presented a 'disturbing mix of childhood innocence and adult sexuality' and asked that all 'God-loving Americans' boycott stores carrying her albums".[14] More controversy arose when Spears declared that she would "remain a virgin until marriage".[22] This pledge has been questioned due to her apparently sexual relationship with fellow pop singer Justin Timberlake.[23][24]

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.[25] In December 1999, she won four Billboard Music Awards, including Female Artist of the Year. A month later, she received the Favorite Pop/Rock New Artist award at the American Music Awards.[26]

Following the success of her previous album, Spears released the album Oops!... I Did It Again in May 2000. It debuted at number one in the U.S. by selling 1,319,193 units during its first week of sales, breaking the SoundScan record for the highest album sales in its debut week by any solo artist.[27] The RIAA awarded the album with a diamond certification with over 10 million copies sold in the U.S.[28][29][30] Allmusic gave it awarded the album 4 out of 5 stars, saying that the album "has the same combination of sweetly sentimental ballads and endearingly gaudy dance-pop that made "...Baby One More Time."[31] Rolling Stone gave the album 3.5 stars out of 5 by noting the album as "fantastic pop cheese" and "Britney's demand for satisfaction is complex, fierce and downright scary."[32] The album's lead single "Oops!... I Did It Again" 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.[33] The same 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.[34] Spears earned two Billboard Music Awards for Oops!... I Did