I Hated Britney Spears Until I Saw Myself In Her

The first, last, and only time I kissed a girl, she was dressed as Britney Spears.

If you had asked me how I felt about Britney during the fall of 1999, the year I turned 14, I probably would have told you that I hated her. I didn’t know it at the time, but I hated Britney for the same reason that many teenagers hate many things: because, on some deep, intuitive, lizard-brain level, hatred is a useful way to define and clarify your position in the world. In that way, hatred is as valuable as love — or at least it can feel that way, especially during the long, slow, sweaty pressure cooker of adolescence, when the self seems most in danger of explosion or evaporation.

Both of these outcomes seemed possible (probable, even) on the night I kissed a girl. It happened at a Halloween party thrown by my twin sister’s friend Jamie, down in the thick-carpeted basement of her parents’ McMansion. I don’t remember wearing a costume. Certainly I was sporting my late-’90s bowl cut, and my palms were sweating, clamped around whatever red plastic cup of Coke or Sprite I had been handed but was now too scared and too excited to drink. It was my first high school party (although, blessedly, not one cool enough to involve alcohol).

I do, however, remember Jamie’s outfit: She was dressed like Britney in the “…Baby One More Time” video. Jamie and my sister Katie both went to an all-girls Catholic school where white blouses and knee-length plaid kilts were the standard uniform, so the costume was an obvious choice. All Jamie had to do was pull her thick, chestnut brown hair back into pigtails and sweep her eyelids with some shadow.

The costume was also — and I knew this with the delicate sensors that my own, all-boys Catholic high school was calibrating to an often painful acuity — a tiny bit passé. “…Baby One More Time” had first topped the Billboard Hot 100 back in February, and its famous video had been retired from MTV’s Total Request Live months ago, to be replaced by other visions of Britney: Britney in a tight, white top dancing on the beach; Britney in sparkling green, palling around (and dancing — always dancing) with a post-Clarissa Melissa Joan Hart and a pre-Entourage Adrian Grenier.

But the image of Britney-as-schoolgirl stayed with me for a very specific reason: Only a couple of months before the party, People magazine ran a story about a young man in LA who “beat out 30 real girls” to win a Britney lookalike contest with a “jailbait vixen Catholic schoolgirl costume.” The story’s easy celebration of cross-dressing thrilled me in ways I couldn’t yet explain; it hinted at the existence of a world very different from the one I lived in, as alluring and forbidden as Britney herself.

My sister and Jamie quickly disappeared into the eager sea of girls in the basement, but I hovered at the party’s edges, queasy and uncertain. Jamie must have noticed, because before long she sent over two boys from my high school — thinking, probably, that I would be able to talk to them. All three of us were freshmen, but the similarities ended there. They were taller than me, more athletic, and I was half admiring and half afraid of the easy way they stood together, sipping from their plastic cups, checking out the girls.

After I said “hey” and confirmed that we all went to Saint Francis, my words clotted in my throat. Soon there came a pause I was beginning to recognize with my new sense of the social: that particular moment when someone you’ve just met decides that you aren’t worth their time. After a few minutes of uncomfortable silence, the other boys simply walked away.

This failed interaction confirmed a suspicion that had been festering in my mind since before high school began. I was convinced that an impassable gulf separated me from what I was coming to think of as “real boys”: boys who played sports, who talked like men, who spat and swaggered and swore. Boys who liked girls.

And yet, later that night, I was the boy Jamie picked, the one she targeted with her perfectly focused pink laser beam of teenage girl attention. Who knows what we talked about? It didn’t really matter; she had decided to like me, probably even before the party began. Like the costume, I was an obvious choice: the shy and unthreatening twin brother of her new friend. I was flattered by her attention and embarrassed by it, intrigued and afraid. But this was what was supposed to happen. It was the thing that Britney had been singing about all summer from the radios of our parents’ cars and the CD players in our rooms: the boy and the girl and the kiss. It was the thing that she would sing about again and again until we would want something else from her, something not that innocent.

So when Jamie stepped closer and announced that we should kiss, I obediently leaned in. It was a chaste peck, no tongue and no teeth and no want. Still, as I pulled away, I felt a little crackle of pleasure that surprised me — awed me, even. In the post-kiss glow, my mind didn’t hold thoughts, exactly, or even words; instead, what took shape was a radiant burst of possibility. Could it be this simple? Could I feel for girls what all boys seemed to? And would that, then, make me a real boy?

I’m not sure if I ever saw Jamie again after that night. My sister stopped bringing me along to her friends’ parties, and after her freshman year, she transferred to a different high school. But if my time with Jamie — my first and only girl kiss — was over almost as soon as it began, then my time with Britney was only just beginning.

Over the years to come, I would watch Britney transform from sex symbol to imploding star to somewhat resurgent pop princess. Each incarnation of Britney would teach me something new about desire: about the yearnings of the boys I grew up with, and about my own wants, my own stubborn needs. But most of all, Britney would make me think about what it means — and what it costs — to survive in a world that can’t quite stop hating you.

It’s hard, now, to remember a time before Britney was famous, before her face was on everything from T-shirts to prayer candles to a $26 “couture” lollipop with a pale pink rhinestone-studded stem. But you can still uncover glimpses of the days when she was just beginning to command national attention. The New York Times’ first in-depth article on Britney is an odd one, a disgruntled review of a concert that she headlined in July of 1999 at Woodstock, of all places. (Neither Britney nor any of her opening acts, music journalist Neil Strauss sniffs, “said a word in praise or recognition of Woodstock’s legacy.”)

The article also includes many of the themes that still dominate pieces written about Britney today. Strauss complains that Britney doesn’t really sing, she only lip-synchs — and briefly, at that. Then, of course, there is the problem of her sexuality. Britney was only 17 at the time, and her look, he writes, is “simultaneously sexual and presexual.”

Her songs only compounded this ambiguity. There’s the teasing suggestion that maybe Britney wants you to slap her in “…Baby” (the ellipsis in the song title concealing the “hit me” in the hook), and the hint in her second single “Sometimes” that, although she’s scared of you, she really just wants you to keep chasing her. Strauss dismisses this line of thought by concluding that the darker implications in those lyrics “are not so much intentional as they are evidence of careless songwriting, glitches in the pop machine.” I didn’t read this article at 14, but even then I would have called bullshit. Because Britney’s appeal was always rooted in sex — but sex that could be disavowed. In her videos she would smile knowingly, eyes locked on the camera; and yet in interviews she seemed sweetly down-to-earth, even artless (a “down-home Southern girl,” as one interview from this period puts it).

Of course, that ambiguity didn’t matter much to the boys in my high school: Britney entranced them, shimmered through their brains like a collective fever dream. During my junior year, the only guaranteed moments of silence in the entire day came during the 120 seconds of Britney’s “Joy of Pepsi” commercial, which aired every morning during breaks in the teen-oriented news show Channel One. "Ride, just enjoy the ride," Britney sighed, gyrating in her flared jeans, her abs taut and tanned and perfect, and the 20-odd boys in my homeroom — in every homeroom — stared at the dingy little TV mounted in the corner, her image burning through the fine layer of dust that coated the screen.

All of this only stoked the jealousy that bubbled in my heart. Because by my junior year, I was able to admit something to myself that I couldn’t quite acknowledge at the start of high school: that I would never want to kiss another girl. That the right look or grin from the right boy could kindle a light inside me that would glow for hours. But there was no way I could find to act on these feelings. Instead, I watched the boys around me the way they watched Britney: armpits damp and throat tight, yearning for the impossible.

My teenage hatred of Britney was a largely private experience. I rolled my eyes at her dewy-eyed magazine covers; I quietly coveted the “Spear Britney” T-shirts sold at the local Hot Topic; I mentally rewrote the lyrics to “Lucky” so it was instead titled (in a sad attempt at wit) “Sucky.”

Hating Britney was easy. It was a way of announcing — to the world, in theory, but in practice only really to myself — that I was different from the other boys in my high school. Better, more refined. Their desire was common, sloppy, relentless; mine was rare, secret, forbidden.

But after I graduated from high school and came out as gay, my feelings toward Britney started to become more complicated. Freed from some of the fear that Saint Francis had brought, I wanted to do more than look at the boys that I liked; I wanted them to look back. I wanted to make them look back. And Britney had always been an expert in that.

So, for Halloween during my first year of college, I borrowed a friend’s schoolgirl kilt and a white blouse, tugged on black tights and leather boots with a formidable heel. I pulled my hair back into (what else?) spiky little pigtails. I smoothed raspberry-flavored gloss over my lips, concealer over any zits, and a smudgy, smoky cloud of shadow over my eyelids.

Watching myself transform in the bathroom mirror at a friend’s house, I felt a wild excitement ripple through me, not so different from what I’d felt after kissing Jamie. It was a feeling that was all about becoming — a sense that a thousand possible selves waited before me, a thousand possible lives. Britney understood. In “I'm Not a Girl, Not Yet a Woman,” she sang, All I need is time, a moment that is mine, while I’m in between…

That Halloween night, my friends and I went party hopping, wandering through suburban kitchens sticky with spilled beer and down into finished basements where girls dressed like sexy angels and sexy devils and sexy cats were giggling into their red plastic cups. I knew my costume was a success on my way into the first house, when a girl I’d just met heard me speak for the first time and snatched at my arm, exclaiming, “Holy crap — you’re a guy?”

Everywhere I went that night, boys watched me. They looked at me in a way I had never experienced before: slowly and unabashedly, as though it was their right to look for as long as they pleased. At my high school, no boy looked at another for more than a few seconds; any longer would have been an insult, a provocation. In the wider world, too, men’s eyes met only for the space of a brisk handshake. But the usual rules dissolved when I pulled on the schoolgirl kilt. Even boys who already knew me let their eyes travel over my body — over my slim waist and sock-padded bra — before arriving at my face and blinking hard, their surprise giving way to rueful smiles.

On one level, it was thrilling to command attention that way. There was a power and a fierce pleasure in it. But beneath my excitement ran a chilly trickle of fear. Some cautious part of my brain couldn’t help asking, What if someone doesn’t like being fooled? And, as it turned out, more than one boy didn’t. When they learned the truth about me, some guys clenched their jaws and held tight to their cups, mouths setting into hard, thin lines; one barked out, “That’s gay!” — as though the others needed to be warned.

That night, if I learned what it felt like to be wanted, then I learned, too, how quickly desire could curdle into something ugly. Something destructive. It was a lesson I’d be reminded of again and again in the years to come, as the real Britney transformed from glittering teen queen to walking punchline.

There’s a Britney meme you can find in less than a second on Google Images (type in “if br…” and autocorrect will do the rest). It’s a photo of Britney in a gray hoodie, her head clean-shaven and her teeth bared with fury. IF BRITNEY CAN MAKE IT THROUGH 2007, the white block text around her face reads, THEN I CAN MAKE IT THROUGH THIS DAY.

The photo, of course, was taken during what tabloids like the New York Daily News called her “meltdown,” and magazines like People called (with puzzled decorum) “a period of strange behavior.” We all know the details. In February 2007, Britney checked herself into and out of rehab, shaved off all her famous blonde hair, and — in photos that will never, ever leave the internet — attacked a paparazzo’s car with an umbrella.

This last event, in particular, seemed to serve as the high-water mark of her crazy. In YouTube videos of the attack, you can hear the single dull thud of what must be the umbrella hitting the car, and her livid “Fuck you!” — but you can’t actually see it happen. What you can see clearly is Britney in the moments before: She’s sitting in the passenger seat of her car, the paparazzi’s cameras flashing relentlessly around her. There’s no mistaking how angry she looks, or how trapped.

Watching what was supposed to be Britney’s comeback performance at that year’s MTV Video Music Awards is hard for different reasons: Britney seems dazed and disoriented, shuffling through the choreography a half beat behind her dancers. The song she’s lip-synching to, “Gimme More,” only adds to the ironic pathos: The lyrics promise a Britney who savors the spotlight, who is supremely confident in her appeal. They want more? she asks during the bridge — voice drowsily pleased, like a dictator’s wife who wakes to find crowds chanting her name beneath her palace window. Well, I’ll give them more!

Critics trashed the performance. The New York Times bluntly announced that “she was awful” and quoted Sarah Silverman’s post-performance joke that Britney “is amazing! I mean, she is twenty-five years old and she’s already accomplished ... everything she’s going to accomplish in life.” For a time, you couldn’t find footage of the actual performance on YouTube. The top result instead was a parody video of a fat man with a yellow mop of a wig askew on his head, miming Britney’s confused movements in women’s underwear. Once, I’d been the only person I knew who hated Britney. Now it seemed to be a national pastime.

Maybe that’s why I found my feelings for Britney changing yet again. Not long after her failed comeback, I started teaching English in the south of Spain. On paper, it sounded like the ideal post-college job: only 12 hours of teaching a week, and the rest could be spent as I pleased. In the weeks leading up to departure, I imagined my expatriate life in Seville in a series of giddy diary entries: There would be medieval castles, café con leche, European men.

But once there, I found myself dazed and adrift. I wasn’t teaching in Seville, but in a tiny town about 45 minutes outside the city, where my blonde hair made me conspicuous. Strangers watched me as I walked down the narrow, sun-bleached streets, and I gritted my teeth, always waiting for someone to mutter the Spanish word for “faggot”: maricón. It was a word I heard said often in Spain, even once by my favorite teacher at the school where I worked. It was a word used to mark the line between a real man and a failed one.

During those first few months abroad, I retreated back to the person I had been in high school: a silent boy, his throat closed with fear. At the orientation for new English teachers in Granada, I sat next to another American I’d met on the train over. He was handsome and outgoing, with a smile that lit up his whole face. Immediately, I wanted to charm him, and not only because he was good-looking. What I wanted most, I think, was to show myself that I could still pull people to me the way I’d learned to do in college: make them laugh, make them start to like me. But my brain buzzed with anxiety, and I couldn’t find the right words. Our conversation faltered. A few moments later he simply walked away — exactly as the boys had that night at Jamie’s party. Ashamed, overwhelmed, I held my body as stiff as a stone, but I was evaporating anyway. I could feel it.

It was around this time that I first heard Blackout, the album that Britney had been trying to promote at the VMAs. I found it at a listening station at a music store in Seville, and soon it became a weekend ritual to clamp the station’s cushioned headphones around my ears and sink into the dark and gleaming world of the album. If I was in danger of evaporation, then the Britney of Blackout was already gone, a ghost winding through an underworld of pounding, synthetic beats. Most of the songs on her previous albums had promised access to the “real” Britney, to her secret interior life, but Blackout seemed designed to thwart such intimacy at every turn. On track after track, Britney’s voice is buried under filters, distorted with Auto-Tune, or melded with those of her backing vocalists. Her voice isn’t really hers: It’s one more futuristic sound effect on an album full of them.

And yet, in spite of this erasure of self — or perhaps because of it — Blackout is good, truly good. No less an authority than Pitchfork praised what it called the album’s “creepiness, its black hole heart.” The Spanish press agreed. That fall, in the teachers’ lounge of the school where I taught, I found a magazine with a glowing review of the album. The article was titled something like “La resurrección de Britney,” and it featured an illustration of her in the glittering black bikini she had worn at the VMAs — only this version of Britney was beaming with triumph, blonde hair swirling around her head like manic tongues of flame.

I didn’t exactly resurrect myself in Spain, but I did make a friend: F., the only other American boy in my town. Like me, F. was there to teach English, but our similarities (I thought) ended there. F. was much braver than I was, more confident in the language. He ambled through the town loose-limbed and nonchalant, striking up long conversations with strangers on the street — people I would pass by with a bland smile, lips sealed.

Still, we were united by our mutual status as town curiosities, and at least one evening a week, F. would ring the doorbell to my dusty apartment with a one-euro box of red wine in his sun-browned hand. We would sit in my living room and drink, talking about our schools and our students, about the weirdness of life abroad, while outside in the courtyard children played soccer, their shouts rising into the dusk.

More than once — frequently, actually — I steered our tipsy conversations toward girls, or celebrities he found attractive.

“What about Britney?” I asked once. “You think she’s hot?” F. gave a rueful smile, a little shrug. “Used to,” he admitted, “till she shaved her head. Now it’s kinda ruined her for me.”

In some odd way, hearing that made me feel closer to Britney. I remembered the Halloween I’d spent as a schoolgirl, remembered how it felt to inspire both desire and disgust. Other times, I made F. tell me about his hookups in college. “She was in a skirt, but man, when she bent over, I could see she wasn’t wearing any panties…”

I watched his jaw clench, his eyes half-lidded from the wine and the memory, and there was an answering pang in my gut, a tightness in my throat. This is what it’s like, I thought, to be a real boy. This is what they think about; this is what they want.

Still, I couldn’t admit the most obvious thing to myself: that F. and I weren’t so different. He told me about the girls he wanted — about the desire that twisted in him — and I sat apart, as though my own relentless wanting was something more noble, or more refined, because it wasn’t aimed at women. It was a story that I had been telling myself since Britney first strutted onto TRL, and I wasn’t ready to let it go, not yet. Instead, I sat and listened as he told me about another girl, and then another, my head buzzing and my lips dark with wine, a real boy in spite of myself.

It’s been nearly 20 years since the Halloween party where I kissed a girl, but I still feel the need to check in on Britney from time to time. She’s doing much better these days — that’s the official story, anyway. Last year she appeared on the cover of People with her two beaming young sons; the profile inside proclaimed that she’s the “happiest [she’s] ever been.” As the star of a Planet Hollywood residency that earns her millions of dollars a year, she has plenty of reasons to celebrate: She can perform at a lavish Vegas venue for thousands of screaming fans, then fly back home to California by private jet in less than an hour.

But there are reasons to wonder about this new, seemingly blissful Britney. For one, there’s the fact that, since 2008, she’s been under a court-approved conservatorship that limits the kinds of decisions she can make independently. Britney can’t marry, for example, or buy a home without the approval of her two legal guardians: her father, Jamie, and a lawyer named Andrew Wallet. Even her spending habits are carefully monitored. As the Times explained in an article published last May, Britney’s “most mundane purchases, from a drink at Starbucks to a song on iTunes, are tracked in court documents as part of the plan to safeguard the great fortune she has earned but does not ultimately control.”

There’s a certain uncomfortable irony in the fact that Britney, a sex symbol before she was legally an adult, is now, at 34, still a child in the eyes of the law. At the same time, there’s an unsettling sort of logic to her situation: Long the object of male fantasy, Britney’s life is now legally subject to the will of two men. Maybe that’s what makes me question her purported happiness. Maybe that’s why I find myself looking so closely at that People cover, why I think there’s still a lingering hint of uncertainty — of sadness, even — in her dark brown eyes.

But maybe the conservatorship rankles because it suggests certain parallels to my own life that I’d rather ignore. I left high school behind years ago, and yet I still can’t totally shake its influence — can’t free myself from the old worry that I’ll never quite be a real boy. Sometimes, as I tie a brightly colored scarf around my neck or tug on a new T-shirt, I’ll catch myself thinking, Does this look too gay? I struggle, too, to act on the desires that I worked so hard to repress at Saint Francis: I use the usual dating apps and websites, but I don’t often move beyond looking.

Britney is also single, and — according to a recent appearance on “Carpool Karaoke” — has no plans for that to change. “I’m done with men,” she cheerfully told host James Corden. She was there to promote her new album, Glory, which critics have hailed as her best work in years.

One of my favorite songs on it is “Coupure Électrique,” a track she sings entirely in French. It’s the final song on the deluxe cut of the album, and it’s a strange one, echoing and spacey, Britney’s familiar purr made alien by the language barrier. Literally translated, the title means “Power Outage,” but it’s also a nod to Blackout. It’s an allusion, in other words, to a complex moment in her life: to music that, in spite of the chaos and pain of that year for her, was a triumph.

Technically, “Coupure Électrique” is a love song. Desire has always been Britney’s favorite theme, and — by serving as a lighting rod for our culture’s sexual fears and fantasies — she certainly taught me about mine.

But when I listen to this song, I think I can hear something else. I hear what it sounds like to look back on the person you used to be with sympathy rather than contempt. I hear what it sounds like to no longer need the heady rush of hatred to solidify your own sense of self; I hear, too, what it sounds like to be shaped by the fears you carry with you, but not destroyed by them. In the end, what I hear in Britney now is what I’ve always heard in her: the story I most need to tell about myself.