All the Major Moments Britney Spears’ Oops!… I Did It Again Album Gave Us 20 Years Ago

Oops, it’s been two decades since Britney Spears did it again.

On May 16, the Holy Spearit celebrates a special anniversary, as it marks 20 years since the release of Oops!… I Did It Again, the uniquely punctuated second studio album of her career.

The LP had big footsteps to follow in, as 1999’s (similarly punctuated) …Baby One More Time catapulted the young starlet to pop music superstardom practically overnight with hits like the iconic title track, “Sometimes” and “(You Drive Me) Crazy.” But Oops! did the impossible, proving that, once in a while, lightning could strike twice.

With smash hit singles like the equally iconic title track, “Lucky” and “Stronger,” Oops! managed to outsell …Baby in its first week (though not in its lifetime)—setting a long-standing record in the process—while delivering moments in Brit’s career so major that they still stand out all these years later. From a VMAs performance that left everybody talking to the public debut of an unforgettable romance, the year 2000 was a big one for Britney.

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