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Britney Spears Pictures From 1999

20 Years Later, Look Back at Britney Spears's First Year as a Pop Icon

May 1999
Image Source: Getty / James Devaney

You never forget where you were during a truly historic moment, so yes, of course I remember what I was doing the first time I heard ". . . Baby One More Time." At age 11, my hair likely pulled back with butterfly clips, I was in a hotel room with my mom listening to Radio Disney as we got ready for dinner. The song played, I flipped out, and I insisted we change our plans and order room service so we could stay in the room, keep listening to the radio, and hear it again.

". . . Baby One More Time" came out in late 1998, and the following January, Britney released her album of the same name. That's right, ladies and gentlemen, it's been 20 years since Britney Jean Spears dropped the . . . Baby One More Time album and seemingly became a pop icon overnight. That year, she was everywhere: award shows, Disney concerts, TV specials, you name it. We belted her songs, learned her choreography, and obsessed over the rumor that she might be dating *NSYNC's Justin Timberlake, which — #neverforget — was confirmed the following year.

In 1999, Britney's first album hit No. 1 on the Billboard 200. It's the year she kicked off her first tour, and the year of that Rolling Stone cover. It's the year the "Sometimes" video made turtleneck crop tops happen and the year "(You Drive Me) Crazy" blessed us with an iconic music video to go along with a teen movie starring Melissa Joan Hart. In other words, 1999 was a BIG year for Britney, so two decades later, let's relive some of the highlights with a whole bunch of nostalgic photos that will take you right back to Britney's beginnings.

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