A few years ago my friend Paul posted on Twitter: “when you finally ‘get’ the britney spears song HIT ME BABY ONE MORE TIME like 15 years after hearing it for the first time.” This had been on my mind, too: how “...Baby One More Time” had started to strike me as very deep and very sad. Spears’s first single is comfortably one of the most important pop songs of all time. The song and its iconic music video, featuring sixteen-year-old Spears in a Catholic school uniform dancing provocatively through a high school’s hallways, rang in the teen pop craze of the late nineties and early aughts, when a generation of Spears’s fellow former Disney Channel stars busted out of Orlando and went (a little) wild.

I think most people grant that "...Baby One More Time” is a good song. Its production is visceral: the opening piano chords that summon pop spirits, the wah-wah guitars, the cymbal crashes, and the use of background vocals are all distinctive. And this was the first showcase for Spears’s singing voice, which is sexy, abrasive, and strange. “...Baby One More Time” has all the features of an incredible late-era pop single: simple hooks over tightly layered production, designed to move your mood, not your mind.

Why is it anything more than that? Spears has had two dozen major hits since “...Baby One More Time” was released in 1998, and her singles “Stronger,” “Oops! . . . I Did It Again,” and “(You Drive Me) Crazy” are all remarkably similar to “...Baby One More Time” in their composition. Still, her first song remains her greatest hit. “...Baby One More Time” doesn’t just tower over her other singles because it was the first, or because she tied up her school uniform shirt in the music video. Paul tweeted:

She sings this over and over: So why had I never heard it?

“...Baby One More Time” is a product of the music industry’s bubblegum factory if there ever was one. Shortly after Spears signed with Jive Records, she flew to Stockholm to work with Swedish producers. Joyful, creative, insidiously catchy pop music has long been one of Sweden’s top exports, and its stars like ABBA, Ace of Base, and Robyn along with its super producers like Dr. Luke and Stargate all bow to Swedish pop god Max Martin.

Producer and songwriter Martin wrote or cowrote seventeen number one hits in fifteen years, including the Backstreet Boys’ “I Want It That Way,” NSYNC’s “It’s Gonna Be Me,” Kelly Clarkson’s “Since U Been Gone,” Taylor Swift’s “We Are Never Ever Getting Back Together,” and Katy Perry’s “Roar.” Martin first met Spears in 1998 when he played her the demo for “Hit Me Baby One More Time.” TLC passed on the song, but Spears and her team instantly saw that the track was, as a Jive A&R executive put it, “a fucking smash.”

“...Baby One More Time” is so entwined with Spears’s persona that it seems bizarre that it wasn’t written for her. How could any other artist have sung it? But then again, of course they could have. Pop songwriters are necessarily mercenary, offering their services to the artist who will take them. And the song’s connection to TLC is an interesting one. Spears’s emergence signaled a sea change in popular music, away from the funky R&B of the mid-1990s, exemplified by TLC and Janet Jackson, toward a sound that was younger, whiter, and on the surface, more sexually innocent. Spears’s record label tried to tone down “...Baby One More Time” by removing the “hit me” from the title, but the song is still knowing in a way that’s closer to CrazySexyCool than “As Long As You Love Me.” Like any good opportunist, Martin found a way to turn the old thing into the next big thing.

I was an actual Catholic schoolgirl at the age of sixteen, and it was so dismally far from the music video fantasy. The Catholic high school I went to for a semester in Nebraska was underfunded and strange. At the end of the school year we had to hot-glue our textbooks back together. From what I could tell, the school’s prime objective was to instruct students not to have abortions or vote for John Kerry.

I jumped ship the first week of my senior year. I decided to get my GED, which if you’ve been to a majority of high school is, as my GED counselor told me, “a mute point.” But because I was under eighteen, regulations put forth by the state of Nebraska to dissuade people from dropping out of high school dictated that I had to take ten hours of GED training at the local community college. I finished all of the preparatory materials before my ten hours were up, so the teacher running the training sessions let me put my head down on my desk.

In the same obstructive spirit as the required training hours, I was told I could not actually receive my GED certificate until I was eighteen. However, they did give me a letter that served as notice that I had passed the exam. At sixteen, I sent the University of Nebraska my GED letter and an essay I wrote about a book I hadn’t read, and they let me into the honors program.

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?” RollingStone 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.

A little while later, Paul texted me, “do you ever feel that your level of intelligence dooms you to be alone.” My reply began, “My answer is I think sort of obviously yes.” My intelligence setting me apart is a lie that has driven my life in ways I’m only beginning to interrogate. When I tell people I went to college at sixteen, they get a vision of a super-special whiz kid that I’m happy to indulge. When I think about my college experience, what I see is not overachiever syndrome but an almost sociopathic delight in being ahead, in tricking the system. This shows a kind of intelligence, but not necessarily that of the wunderkind I’ve pretended to be.

I did not really pay attention or learn anything in college. Many weeks I skipped more classes than I went to. I spent four years alone in the dark of my parents’ house eating canned ravioli and watching MTV. I manipulated and bullshitted my way to a bachelor’s degree at the age of nineteen, and I knew exactly what I was doing. But when I think about my classmates who went to class and read the books, whom I felt so much distance from, it’s obvious the joke was on me.

That’s why sixteen-year-old Britney Spears has started to fill me with such pathos — she knew exactly what she was doing, too, though I’m not saying it was the same thing I did. I was very lonely in college. I knew I was different from the people surrounding me, but it wasn’t because I was smarter than they were. It goes back to the reason I wanted to go to college at sixteen at all, a decision that from the beginning guaranteed only that I would never have a dorm-rooms-and-keg-parties college experience. I got too good at isolating myself, which was not intelligence but more likely the clichéd coexistence of self-hatred and self-obsession.

Is pop music smart?

It is easy to attribute the brilliance of “...Baby One More Time” to the familiar accident where a whole is greater than the sum of its parts. We can draw up a diagram of the contributing factors for its success: Max Martin, Jive Records, trends in Top 40 radio, Debbie Gibson, Monica Lewinsky, the Disney Channel, and, very last, Spears herself. It goes back to capitalism’s odd vision of “the market,” which knows everything but is not intelligent by the same standard we would judge life on other planets.

But to my mind, “...Baby One More Time” speaks as keenly about the loneliness of love as any other artifact of our culture: it’s not about losing someone but the impossibility of ever really having them. “When I’m not with you, I lose my mind,” Spears sings. Romantic love doesn’t lessen the opacity of other people’s thoughts and motivations. It heightens it, because the desire to know and inhabit the beloved’s mind is so great. That’s what makes us sick in love, crazy in love. Short experiences of union reinforce that each of us is, once and for all, a single person, alone in a body, known only to the self.

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.

“I guess I can’t see the harm in working and being a mama,” Spears sang in 2007, just after her series of personal crises, with her signature false naïveté. Britney Spears’s music is about desire; from the beginning, Britney Spears herself has been about a prodigious contradiction, a prodigious loneliness. Watch the end of the “...Baby One More Time” video, as Spears holds her face with boredom and smirks at the camera, her pigtail braids secured with feather scrunchies, and witness the spark: it’s not the dumb hand of the market patting her head with approval, nor sex and its dumb compulsions, nor even the dumb intelligence that is satire or critique. It’s that other thing. Art.