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Britney Spears’ Iconic ‘Oops I Did It Again’ Turns 23!


It was no mistake: Britney Spears was poised for world domination on the pop charts with her debut single, and she did indeed repeat the streak!


Spears has been a vital piece of our cultural lexicon for over two decades, to the point where it’s difficult to believe there was ever a time in history when she was busy creating the foundation for a career that comes once in a lifetime.

The Kentwood, Louisana native was only 16 when she released her first single, “…Baby One More Time,” in the Fall of 1998. The premise for its music video saw Spears as a bored student fantasizing about escaping the monotony of a school day to create an afternoon to remember.

The legacy Spears would go on to create on the heels of her debut single and the first album would only become stronger with the release of “Oops I Did It Again,” the first single from the album of the same name in April of 2000.

Spears Would Show The World She Was No ‘One Hit Wonder’

If there was any skepticism that Spears was on the edge of a so-called “sophomore slump,” it certainly wasn’t felt by Spears herself.

Spears showed “Oops I Did It Again” was about having confidence and agency; she knew exactly what she was doing when she played with men’s hearts and ‘got lost in the game.’ Navigating a relationship would be Spears’ journey and Spears’ journey only. The man in question thinks Spears is in love? Oops, the joke’s on them, buddy.


Even though Spears memorably sings that she’s “not that innocent,” the song’s relatively innocent premise about the early feelings of having a crush still lingers, no matter how much brash confidence she displays!

When discussing the song upon its release in April 2000, Spears spoke of those sweet and universal feelings; “The song is basically about a girl… all these guys fall in love with her, and she just can’t help it,” she told MTV. “When I meet a guy I’m attracted to; I get butterflies in my stomach. I get a total brain fart and don’t know what to say. That’s what I like about the song… it’s different and fun to perform,” Spears said. (per Stereogum)

Spears Still Has Love For Her Career-Defining Hit

Like her fans, “Oops I Did It Again” is never too far behind in Spears’ mind as one of her most vocally strong performances.

In February, Spears brought the song back from the vault on Instagram when she performed a rare acapella version; The Blast was on hand to share Spears’ thoughts about the stripped-down rendition. 

She captioned the video, “Have you guys heard !!! I’m a star now, mamma !!! LOL, just kidding !!! Most of this sounds pretty flat … but I liked DOING IT AGAIN !!! Wait for OOPS !!! That was so lame, I know !!!”

Unfortunately, Spears turned off the comments on her post which kept fans from participating in the big moment, but that doesn’t mean fans have never been serious about their love for “Oops, I Did It Again!”

Fans Reflect On Their Favorite Memories Of ‘Oops I Did It Again’

Britney Spears PR tour in Paris

The legacy of “Oops I Did It Again” would only grow more vital as the album of the same name was released a month later in May 2000.

Actress Hailee Steinfeld knew from an extremely young age that “Oops I Did It Again” would be a gateway album into an eventual career as a performer.

Steinfeld told Nylon upon the album’s 20th anniversary, “I was four years old when the album came out, and somehow I distinctly remember dancing around the family room to each song for hours. I loved it. I even have this memory of trying to get the album down from the fireplace mantel, as it was most likely placed there in the first place to give the house a break from Britney,” she adds.

Musician FLETCHER noted the importance of Spears’ agency over her image at the time.

“I feel like she embraced her body and her power and her sexuality in a time [where] people were slut-shaming women,” she told the publication. “and she was like, ‘f**k it, this is who I am. I’m proud of the way that I look, and I’m proud to use feminine form.’ And I think that specifically shaped the future of women in pop music. That’s always the stuff that cuts through the noise is when you’re just like, ‘f**k the system, f**k that. I stan pushing boundaries and not listening to the rules.”

“Oops I Did It Again” was initially released on April 11, 2000, with the album following on May 16


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