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"...Baby One More Time" (1998)
Oh, baby, baby. This was the single, music video, and album that started it all, folks. Back in '98, Britney broke onto the scene as an unknown singer with a killer voice — and a shockingly sexy image for a 16-year-old. The "Baby" video is now the pinnacle of the naughty Catholic school girl in our pop culture lexicon.
Britney + *NSYNC = Magic (1999)
At the 1999 MTV VMAs, the boy band sensation joined forces with the hottest new thing in pop with an epic mashup of "...Baby One More Time" and "Tearin' Up My Heart." A musical match made in heaven. And it became apparent that it was a romantic match, too. This was the year that pop's first It couple, Spears and Justin Timberlake, started dating.