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.
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.
This Mickey Mouse Club Mouseketeer was cast on the hit ’90s show, alongside now-famous castmates Justin Timberlake, Christina Aguilera and Ryan Gosling.
Fun fact: Spears is the middle child. She has an older brother, Bryan, and little sister, Jamie Lynn.
This U.S. Open outfit screams ’90s, from the thin-framed glasses and pigtails to her mini skirt and sneakers.
We would give ANYTHING for a Britney Spears and ‘NSYNC reunion.
We can’t apologize for the wave of nostalgia that just hit you when you saw the star’s 1999 Got Milk ad.
Backstreet Boy Nick Carter and the teen sensation snapped this amazing photo back in April 1999 in Tampa, Florida.
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.
Here’s Brit living her best life in Paris after the release of her second studio album, Oops I Did It Again.
This photo of Spears next to Jennifer Lopez proves that true star power is ageless.
Ah, young love. Spears and her ex-boyfriend Justin Timberlake were all smiles during a charity basketball game.
Here the former flames are seen on the carpet at the Grammys when Timberlake still wore his hair in tight, bleach-blond curls.
The queen of pop performed alongside the king, Michael Jackson, in 2001 during his 30th anniversary celebration.
The star is seen cheesing next to former TRL host Carson Daly.
Spears must have been feeling the heat, posing with ’90s heartthrobs 98 degrees.
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).
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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