Just That Innocent: ‘Oops! I Did It Again’ Turns 20

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Photo: RCA

Originally written and published by me for Spectrum Culture.

The year was 2000. Bill Clinton was still president, Survivor was just about to usher in the age of reality TV, and the iPod had yet to exist. Billboard charts were being dominated by the likes of ‘NSYNC, the Backstreet Boys, Destiny’s Child, Eminem, Enrique Iglesias and Ricky Martin. The ‘90s were over, but the decade’s style and influence still ruled, creating the need for a new culture to emerge in this thing called the millennium. Forget Timberlake or Beyoncé—a new queen was just beginning her own fateful reign. Her name was Britney Jean Spears, and she was about to release her second studio album, Oops!… I Did It Again.

The album’s title track, released in March 2000, was simultaneously a goodbye to the teen-pop days of yore and a continuation of the teen-pop revival of which Britney was the leader. It solidified Spears as the princess of pop and helped usher in a new age of pop girls, each more incomparable than the last (Christina, Jessica, Mandy, even P!nk—take your pick). Mp3s were just a few years away from gaining momentum, followed swiftly by social media and fandom wars. But before Britney would become third-wave feminism’s whipping girl and driven insane by fame and media terrorism, we were blessed with the gift of her sophomore album: an irreplaceable pop record that not only proved that the sequel can indeed live up to the original, but allowed us to imagine—if only for a moment—that we were all, in fact, just that innocent.

Barely two years before “Oops!” came the juggernaut of Britney’s debut single, “…Baby One More Time,” which wasn’t just a commercial success: it was a full-fledged cultural phenomenon. More than a song, it was an awakening. Before anyone even had time to blink, the singer became the face of cultural anxieties surrounding the behavior of young girls—since what Britney Spears represented, in popular culture and beyond, was a lot more than singing and dancing.

The Spice Girls had built off this idea of female artists hypersexualizing themselves, suggesting empowerment coming from within, but Britney was the one who perfected it. Twenty years ago (and still today), many had a hard time believing that she was in the driver’s seat in any kind of way, but a lot of the ideas were hers and, most importantly, she had the talent to back them up. She was a star. “When we signed her, we didn’t even know that she could dance. It was an epiphany when we saw the rough cut for the ‘…Hit Me Baby One More Time’ video. We were all floored,” said the former president of Jive Records, Barry Weiss. “That’s when the light bulb went off. It dawned on us that there was a little bit of Marilyn Monroe, thrown in with a dash of common-touch, Elvis Presley, middle-America appeal. That was what led to this explosion.”

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Spears on the cover of Rolling Stone in April 1999, which the American Family Association slammed as a “disturbing mix of childhood innocence and adult sexuality” (Photo: Dave LaChapelle)

Barely legal, Britney seemed to have an appeal for almost every age group. Her hit songs, knack for choreography and ability to make an impact quickly generated comparisons to the stars who had come before her: Madonna, Janet, Mariah, Whitney and even Paula—at the same time generating interest for older millennials who had grown up under the influence of the MTV era. For younger millennials and Gen Z, Britney was everything you could have asked for in a superstar—a perfect illusion of the cool, youthful “It” girl. But what set Spears apart from her predecessors was just that: she was marketed largely to kids and teenagers, and her risqué image of toying the line between unsexual child and hypersexualized adult was cause for near-immediate backlash. By the time “Oops!” would arrive, Britney had already been exploited as jailbait by male-dominated media, but was safe enough to appease network sponsors and Viacom ad buyers. However, in the wake of her now-legendary home bedroom shoot with Dave LaChapelle for a Rolling Stone cover story in April 1999—you know, the one with the velvet sheets and Teletubby—the American Family Association criticized her “disturbing mix of childhood innocence and adult sexuality” and demanded “God-loving Americans to boycott stores selling Britney’s albums.” But all it did was suggest that Spears had the same kind of star quality as someone like Madonna: not afraid to drum up controversy and anger a few sponsors.

Whereas most of the Baby album felt fabricated and forgettable, Oops! was sassier, bolder and more grown up in a way that couldn’t be faked. While Spears only received one song writing credit, for “Dear Diary,” the lyrical content felt less insecure and more empowering—in a way that was also still marketable to kids. Her loneliness wasn’t killing her no more on “Stronger” and she told us to take her as she was on “What U See (Is What U Get).” She might have been an inexperienced songwriter at this point, but her knack for artistic direction was unmatched. “She wasn’t just some puppet who showed up and sang,” said Jason Blume, who co-wrote “Dear Diary” with her. “I actually said to her, ‘Wow, you can really sing,’ and she laughed and said, ‘Everyone says that.’ What was so clear to me, and what separates someone and makes them a star, is that totally identifiable thing that you know in two seconds who you’re listening to. She wasn’t putting it on. She wasn’t manufacturing that unique sound. That’s just who she was.” But she was still a child, and while any former child star can tell you the consequences of growing up too fast, the lyrics of “Lucky” would come true for Britney in a way that no public figure should ever have to face.

Oops!… I Did It Again came at a time when we were all much more innocent. Music didn’t yet rely heavily on streaming algorithms and we didn’t carry powerful portable computers around in our pockets. That’s the thing about the passage of time; everything always feels like it was so much simpler before. But more importantly, musical mythmaking was a lot easier without naysayers picking apart every word on social media. As Britney sang “I’m not that innocent,” she was letting us know that we were all on the precipice of losing our innocence—the new millennium had a much more complicated world waiting in the wings for us, especially for her. But regardless of any mythmaking in her story, her star power always shines through, no matter what. “There’s a lot of people who still believe it was engineered, like we were some scientists rubbing our hands together in a laboratory saying, ‘We have the formula,’” said Britney’s longtime manager, Larry Rudolph. “Britney was always the one directing the creatives. She did what came naturally to her and had an innate intelligence to figure out what and where everything needed to be.” The mark of a true game-changer: an icon at her finest.