Once the dust had cleared on the Y2K transition, the popular press went back to fussing over Britney Spears, the Louisiana-born Mickey Mouse Club alumna who’d been the leader of teen pop’s female infantry when it stormed the gates two years prior. Her first album, …Baby One More Time, had spawned multiple MTV-ruling singles since its titular single’s late-1998 release. Keenly aware that time and pop were often at odds with one another, she wasted little time gearing up for its follow-up album, given the winking title Oops!… I Did It Again and set for release in May of 2000.

The album’s title track, released as a single 20 years ago today, gave listeners their first hint at what direction Spears might be going in for her second record. Sonically, it wasn’t too different from the directions taken by album-one stompers like “…Baby One More Time” and “(You Drive Me) Crazy” — the banging chords at the opener, the slightly more languid tone taken by the pre-chorus, the choir beamed in from above backing her pouty vocals at just the right time. Max Martin — who had helmed “…Baby” with his fellow Cheiron Studios pop scientist Rami and who was ruling the airwaves so thoroughly that heavyweights like Bon Jovi and Céline Dion brought him in to work his magic on their own music — was nothing if not savvy.

But where “…Baby” and “Crazy” were about a woman who was willing to do anything for even the most doomed romance — loneliness killing her, because she was so excited, and in too deep, et cetera — “Oops!” had Britney singing from a place of strength. She was the woman who kissed the boys and made them die, but not too bothered about it in the grand scheme of things.

“The song is basically about a girl… all these guys fall in love with her, and she just can’t help it,” Spears said in the “Oops!” episode of MTV’s Making the Video. “When I meet a guy that I’m seriously attracted to, I get butterflies in my stomach. I get a total brainfart, and I don’t know what to say. That’s what I like about this song… it’s really different, and it’s fun to perform.”

Given the way Spears had been treated by the media in the wake of “…Baby One More Time” crash-landing into the pop consciousness, a treatment given to so many young women during America’s turn-of-the-century teen pop boom, you’d think she was a femme fatale in waiting. Rolling Stone invited its readers into Spears’ “heart, mind, and bedroom” for its 1999 cover story about the singer, which opened with a description of her “honeyed thigh” and was accompanied by a horndoggy David LaChapelle photo shoot; Neil Strauss, who would later go on to write the pickup-artist bible The Game, described her as “simultaneously sexual and presexual” in a New York Times concert review that summer.

“Oops!,” however, was an early on-record signal that Spears, for all the projections placed on her by the world’s gazing males, could be way more interested in camping it up than getting on down to business. Yes, a lot of attention was given to her claiming that she’s “not! that! inn-o-cennnt,” but that’s because she’s resisting the sort of deification that results in puppy love; she’s a player who does, in fact, crush a lot. The music video was set on Mars; an astronaut who’d discovered a copy of Oops! in the planet’s red sands summoned Spears, who wore a red catsuit and, either because they were more aerodynamic or easier to dance in, black sneakers; and the astronaut became so enamored with Spears that he somehow found… well, let’s just go to the dialogue from the song’s breakdown:

(“All aboard!”)
GUY: “Britney, before you go, there’s something I want you to have”
SPEARS: “Oh, it’s beautiful! But wait a minute, isn’t this… ?”
GUY: “Yeah, yes, it is.”
SPEARS: “But I thought the old lady dropped it into the ocean in the end!”
GUY: “Well, baby, I went down and got it for you.”
SPEARS “Aw, you shouldn’t have!”

And then, instead of a sappy love scene, the song crashes back into another chorus, Spears oops-ing her way through her last laugh at the latest poor sap, who went to all the trouble of getting her a necklace — and not just any necklace, but the super-expensive Heart of the Ocean, also known as “the hurled into the Atlantic at the end of Titanic.” There’s a spiritual link to Madonna here; in the video for her 1984 consumerist smash “Material Girl,” Madonna was similarly blasé about receiving a trinket that might have been made from real diamonds. “Oops!” raised those stakes to absurdist levels, leaving potential love interests hanging and giggling at them all the way to Mars.