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Spears was always destined to be a star! Here she is as a teeny tot, already serving looks in a pink-and-white dress and big loose curls.
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Oh, baby, baby – she’s been adorable since she was a baby! The star could not look any cuter posing between her parents Jamie and Lynn Spears.
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This Mickey Mouse Club Mouseketeer was cast on the hit ’90s show, alongside now-famous castmates Justin Timberlake, Christina Aguilera and Ryan Gosling.
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Fun fact: Spears is the middle child. She has an older brother, Bryan, and little sister, Jamie Lynn.
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This U.S. Open outfit screams ’90s, from the thin-framed glasses and pigtails to her mini skirt and sneakers.
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We would give ANYTHING for a Britney Spears and ‘NSYNC reunion.
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We can’t apologize for the wave of nostalgia that just hit you when you saw the star’s 1999 Got Milk ad.
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Backstreet Boy Nick Carter and the teen sensation snapped this amazing photo back in April 1999 in Tampa, Florida.
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It’s impossible to choose the best thing in this photo: Is it Joey Fatone’s red hair? Chris Kirkpatrick’s braids? J.C. Chasez’s sunglasses? It’s probably Britney’s high pony.
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Here’s Brit living her best life in Paris after the release of her second studio album, Oops I Did It Again.
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This photo of Spears next to Jennifer Lopez proves that true star power is ageless.
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Ah, young love. Spears and her ex-boyfriend Justin Timberlake were all smiles during a charity basketball game.
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Here the former flames are seen on the carpet at the Grammys when Timberlake still wore his hair in tight, bleach-blond curls.
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The queen of pop performed alongside the king, Michael Jackson, in 2001 during his 30th anniversary celebration.
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The star is seen cheesing next to former TRL host Carson Daly.
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Spears must have been feeling the heat, posing with ’90s heartthrobs 98 degrees.
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Of course, no Britney flashback is complete without a shot from her iconic “…Baby, One More Time” music video, which launched her straight to superstardom (and made us consider pigtails a viable hairstyle).
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Everyone talks about the star’s double-denim VMAs look, but we think this glam Grammys ensemble from 2000 should get more love.
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