Spears's debut single "...Baby One More Time", released in the end of 1998 became an instant international success. It peaked at number one on the Billboard's Hot 100 and has earned nine million sales worldwide and was ranked 25th on Rolling Stone and MTV's "100 Greatest Pop Songs of all time". The music video accompanying the song featured Spears dressed in a schoolgirl uniform. The album of the same title was released in January 1999, reaching number one on the Billboard 200. ...Baby One More Time was certified Diamond, with 25 million copies sold worldwide.
The album received mixed reviews. All Music Guide gave it 4 out of 5 stars, stating that the album "has the same blend of infectious, rap-inflected dance-pop and smooth balladry that propelled the New Kids and Debbie Gibson." While Rolling Stone gave it 2 out of 5, noting that, "While several Cherion-crafted kiddie-funk jams serve up beefy hooks, shameless schlock slowies, like 'E-Mail My Heart', are pure spam."
The success of Spears's music coupled with her controversial image made her one of the year's biggest stars. 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. At the 2000 Grammy Awards, Spears received two nominations in the categories of Best New Artist and Best Female Pop Vocal Performance for ...Baby One More Time, but lost to Christina Aguilera and Sarah McLachlan respectively.
Following the success of her previous album, Spears released the album Oops!... I Did It Again, which debuted at number one in the U.S., selling 1,319,193 units during its first week of sales, breaking the SoundScan record for the highest sales in its debut week by any solo artist. The RIAA awarded the album with a Diamond certification with 10 million copies sold in the U.S. and 20 million copies sold worldwide. Concerning both musical content and sales, the album was very similar to Spears's debut, although it fared better with critics. All Music Guide once again gave it 4 out of 5 stars, saying that the album "has the same combination of sweetly sentimental ballads and endearingly gaudy dance-pop that made One More Time." 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." 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.
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. She finished the year with two more Billboard Music Awards, and two Grammy nominations for Oops!... I Did It Again in the categories of Best Pop Vocal Album and Best Female Pop Vocal Performance.
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