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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.
"Oops!...I Did It Again" (2000)
Had the world even seen a red, skintight latex bodysuit before the "Oops" video kicked off the new millennium with this sensual space jam? It features an ethereal Britney, moments of humor, and the sexiest astronaut, ever.
The world didn't know what a dynamic pop force it was reckoning with until it saw Britney slay the choreography in the sleek video for this empowering anthem — with little more than a chair. And the game-changing minimalist concept was all her. “She said, 'I would like to dance in a chair and drive in a car and break up with [my] boyfriend,'" said director Joseph Kahn.