My loneliness. Is killing me.

The most prominent part of Spears’s personal brand has always been that she is like a virgin, vacillating absolutely inconsistently between performing as an adolescent girl and as a sexually mature woman. Part of her “little girl” act is pretending not to understand the sexual attention she elicits. “All I did was tie up my shirt!” she told Rolling Stone in 1999 about the “… Baby One More Time” video. “I’m wearing a sports bra under it. Sure, I’m wearing thigh-highs, but kids wear those—it’s the style. Have you seen MTV—all those in thongs?” 

And yet Spears has been remarkably self-aware—even calculating—about the conflicts in her persona. Her hit “I’m Not a Girl, Not Yet a Woman,” from her coming-of-age movie Crossroads, is the most blatant expression of this trope, or maybe it’s the “Oops! … I Did It Again” video, where eighteen-year-old Spears dances in a skintight red vinyl bodysuit and sings, “I’m not that innocent.”

There is no doubt that her personal contradictions are heightened by the brilliant, dissonant images in her music videos. People have credited the “… Baby One More Time” video with all of the song’s success, a sixteen-year-old brashly seizing on a naughty schoolgirl porno fantasy and immediately positioning herself at the center of the national imagination. “Is Spears bubblegum jailbait, jaded crossover diva or malleable Stepford teen?” Rolling Stone asked in 1999. “Who knows? Whether by design or not, the queen of America’s new Teen Age is a distinctly modern anomaly: the anonymous superstar.”

In “Overprotected,” released ten days after Spears’s twentieth birthday, she makes several startling complaints. “I tell them what I like, what I want, what I don’t,” she sings. “But every time I do, I stand corrected.” She’s singing not as a post-adolescent coming into her own, but as a woman who has been guarded and controlled by handlers since she was fifteen. She is self-aware in performing not only the naughty schoolgirl but also the anonymous superstar, her body a projection screen that all of the world’s desires can flicker across. 

Her early hit “Lucky” is an unsubtle allegory about a starlet named Lucky who dreams of escaping fame. How perverse that Martin would write this song for Spears, and her managers would agree that she should record it, then release it as a single and profit off it. “She’s so lucky,” Spears sings, “she’s a star / But she cry, cry, cries in her lonely heart.” When we confront it, this sadness is so much more dissonant than the sex in her videos. My loneliness. Is killing me. My loneliness. Is killing me.

(…)

I’m not reading too much into the song. Pop music can speak deep truths because it is simple, because the truest truths are simple. What isn’t simple is a sixteen-year-old in her expected setting—a high school—singing about grown-up desperation. Or an artist whose greatest creative preoccupation seems to be a smiling sadomasochism—“hit me baby” and vinyl bodysuits, the giant snake on her shoulders as she sang “I’m a Slave 4 U”—being labeled as “America’s Sweetheart.” Or a woman hunted by paparazzi who photographed her working out, going to Starbucks, driving recklessly with her son on her lap, shaving her head; who photographed her genitals as she got out of her limo for an audience that loved her almost to death.

Alice Bolin, Dead Girls: Essays on Surviving an American Obsession, 2018.

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