Oops! . . . I Did It Again: twenty-five years later, still haunted
by what’s been done.
Oops! . . . I Did It Again, by Britney Spears,
Legacy Recordings
• • •
“What Child Is This” is the first song Britney Spears performed live, as a kid growing up in rural Louisiana. She was born into a working-class family with an alcoholic father and a disgruntled mother who would scream at him fruitlessly when he came home drunk. Britney would urge her mother to stop shouting, arguing that her father was incapacitated. Rage wouldn’t alleviate anything. She was often nervous on car rides with her father, because he would mutter full conversations between himself and the demons he was likely staving off with liquor by night. Her paternal grandmother, Emma Jean Spears, killed herself at her infant son’s grave when she was just thirty-one. What child is this, who, laid to rest, / on Mary’s lap is sleeping, / whom angels greet with anthems sweet / while shepherds watch are keeping?. . . / why lies he in such mean estate, / where ox and ass are feeding?
The child star is an archetype marked early in life as an elegiac and angelic presence both vindicating the bloodline and implicating it. She possesses ideal ratios of charisma to discipline and study, people-pleasing to individuality and rebellion, and it helps if she comes from a broken home, which imbues her with a repressed subconscious responsibility to assume authority and sovereignty, to mend the people and forces around her instead of wandering carefree through the world playing with dolls and schoolmates. She expects very little support in her ambitions and is fine being the only heroic energy in the cast. Britney fits the description, a natural American idol whose lighthearted down-home trauma would inform her escapism on and to the stage. She felt safer there. Her memoir, The Woman in Me, does not elucidate any prodding from her parents to pursue a career in entertainment while still a minor navigating their dysfunctional household, but headshots and auditions don’t book themselves. Suddenly, she’s an understudy for an off-Broadway musical, and then on Star Search, where Ed McMahon suggests himself as her potential boyfriend. He was sixty-nine; she was ten. Finally, she’s on the Disney Channel’s Mickey Mouse Club, an incubator for ascending megastars. She dances alongside future boyfriend and heartbreak Justin Timberlake; next, she’s signed to Jive Records, then It’s Britney, bitch. A star is born.
Oops! . . . I did it again, Britney’s sophomore album, turns twenty-five this year, and, to commemorate the milestone, an anniversary edition with a remaster and remixes of the title track was issued last week. It’s fitting that both versions are Geminis, doubles, twin incisions into the already festering, by the time of its initial release, wound of Spears’s fame, as the album sounds like a dupe for her debut from two years earlier, or an effort to repeat the breakthrough using the same formula. It applies many of the same, very effective at the time, tropes—forced neoteny and codependent attachment to the eroticized-schoolgirl apologia—introduced by single “Baby One More Time” on her first album. If we listen closely, Britney’s masochism is what deepens her keen and savvy lyrics. She tacitly confesses to feeling like she deserves to be punished, yearns to be scolded, reprimanded, held accountable or deemed unworthy of her status for pathologies that might not be her own but that compromise her innocence nonetheless. It’s consummate Y2K pop music, this sound that graced the radio in relentless rotation when I was a teenager, and I find it now as I found it then, mostly unlistenable, even aggressively so, with rhythms and lyrics so symmetrical and predictable it’s borderline egregious. But fanatics want something to sing along to, perverted men want forbidden fruit to lust after, record companies need a scapegoat they can indoctrinate in the rituals of the industry and kill off if too hard to break in or maintain as an asset. So, what should have been investigated as the makings of a scandal was just a hit record. Notable, besides the opening track and the candy-raver amphetamine remixes of it that take on the vaudevillian air of impending doom perfect for crypto bro / cartel parties in Ibiza, there is her version of “(I Can’t Get No) Satisfaction,” which just looms there, cloying seduction with undertones of begging that seem to come from a hostage playing it cool, being her handler’s alibi before she realizes she’s being coerced or groomed.
In the years following the release of Oops! . . ., Britney would be broken up with by text message. Justin would go on to exploit her to enhance his image, writing phony ballads about their fallout that cast him as a victim of infidelity and her as the heartless villain. She went catatonic around that particular slander, rushed into marriages, had two children, was abandoned by her starfucker husband and again villainized for her bouts of postpartum depression. Her vengeance came in songs, 2003’s “Toxic,” which retroactively implicates all the men in her life, and “Gimme More,” on her 2007 album Blackout, which finds her standing up like a prizefighter who has been knocked out and faked unconsciousness so she could deliver a final blow. It’s harrowing, and maybe her refusal to surrender to a contrived image is why she was ultimately tricked into a rehab facility, given obscene amounts of lithium, and then placed under an involuntary conservatorship from 2008 to 2021. Her father, with the help of Tri Star Sports & Entertainment, seized control of her identity, taunting her, I’m Britney now. In 2017, he and his coconspirator Lou Taylor, the founder of Tri Star, were baptized together in Israel’s Jordan River, sanctifying their mission and missionary impulses.
Reissuing this album is a brazen act. It’s not nostalgia that reacquaintance with this music conjures, it’s suspicion that this woman with a child’s mind is still in trouble and under the same spells by new names. Oops, the handlers will cry if incriminated again. But the documents are sealed, as is the singer’s sordid fate. And I know it’s taboo to harbor empathy for the rich and famous, but consider the possibility that we have erred, that Britney is neither rich nor famous as herself, just expensive public property kept in a virtual Hollywood museum twirling in lingerie to alleviate her PTSD, announcing to fans she’s just turned five (on her forty-third birthday) and lighting up a cigarette on a private jet a few months later, as she did on a flight from Cabo to LA the week this album was rereleased. She was met by authorities upon deplaning and issued a warning. A smoke signal. Pop music from this era always sounded to me like a pulp horror movie, gratuitously oppressive and dark, way too high-pitched and overproduced, and it’s likely because much of it was made and performed by children pretending to have agency over their own bodies and souls, most of them with what the internet now refers to as Sanpaku eyes, with the sclera visible above or below the iris, indicating abuse or susceptibility to it. Their music is haunted, haunts listeners until they’re hooked. I think when we watch and adore American pop stars under twenty-five, we are watching sophisticated child trafficking, in no uncertain terms, and as comforting as it was to see a judge rule in her favor publicly, I don’t believe that Britney is free. Relisten to these now-retro recordings not as camp, or the soundtrack of your adolescent glory, but in the spirit of forensics or real faith in revival, in case she gets out someday.
Harmony Holiday is the author of several collections of poetry and numerous essays on music and culture. Her collection Maafa came out in April 2022, and the extended UK edition was released April 2025.