Britney's classic debut single influenced a generation to confess their loneliness.

Twenty years ago this month, Britney Spears released her epochal debut single “...Baby One More Time.” This week, Billboard celebrates the pivotal pop classic two decades later, ending with a deep dive on what made the song so special upon its release, and why it cast such a large shadow over the generation of pop music to follow.

Being a teenager is a constant state of flux. You’re trapped between childhood and adulthood, not a girl, not yet a woman, never quite enough of either. For the first time, you’re conscious of how others see you: will the opposite sex like me? Will the same sex? Naturally, teenagers are drawn to pop-culture figures who seem to articulate the same struggles they’re going through; who embody how they’d like to see themselves.

Pop songs, like fairy tales or Disney films, are supposed to be universal, but they can feel too perfect for the conflicted adolescent mind -- like an ideal you can’t live up to. Bubblegum-pop standards like “Teenage Dream” or “I Want to Hold Your Hand” present love as right, and easy; that we deserve to get what we want. Then there’s the other kind, the unrequited love song -- “You Belong with Me,” “Bleeding Love” -- where it’s the object of your affections who’s wrong, and if only they could see you for who you really are, everything would fall into place.

“…Baby One More Time” is different. It’s about how love is terrifying and obsessive. It’s about accepting responsibility for your emotions. But it’s ultimately joyous, too, as so many iconic pop songs are. Released as a single on October 23, 1998, its 3 minutes and 31 seconds have reverberated through the last 20 years. The story of its recording has been told many times -- let’s talk about how Britney Spears spoke to a generation.

Imagine it’s October 1998, and you’re hearing “...Baby One More Time” on the radio for the first time. That iconic, aggressive three-note piano riff bursts out of the speakers. The drums are stiff, sharp, precise -- like “Billie Jean” -- with samples of exhalations mixed in. And it’s slow. At 93 beats per minute, it’s paced more like hip-hop than funky, uptempo teen cuts like “Wannabe” or “Everybody (Backstreet’s Back).” You can still dance to “...Baby One More Time,” but the tempo forces you to pay attention. There’s a sense of purpose to every note. You know this record’s unlike anything you’ve heard before.

And then there’s Britney’s voice, which sounds unlike any teen pop singer before her: soulful, yet girlish; dramatic, but conversational -- like Clueless via her 16-year-old Louisiana twang. Her trademark vocal fry is unmistakable, even on those first five syllables: “Oh baby, baby.” Swedish super-producer Max Martin -- previously known for his work with the Backstreet Boys and Robyn -- may have written the words, and even sang on the demo, but Britney brought the song to life. She makes every word believable, even “hit me baby one more time” -- an odd (and potentially problematic) turn of phrase only a non-native English speaker could have written. Though Britney’s going through heartbreak for the first time, she doesn’t sound naive. She admits her mistakes -- “I shouldn’t have let you goooooooo,” drawing eight notes out of the last syllable, in a way that’s somehow not showy. She knows what she’s feeling isn’t normal.

When the drums drop out in the bridge, and Britney sings over piano alone, “Oh pretty baby/ I shouldn’t have let you go,” we get a brief glimpse of how her romantic despair would sound without the danceability. Stripped back to its minor-key melody and chords, this is a gloomy song. Time stops, then the song resumes with more intensity, backed by a choir of Britney vocals, as if they’re her internal monologue. It should feel triumphant, climactic, but the song keeps circling back to the piano riff, the same phrases: “confess,” “loneliness,” “give me a sign.”

Previous Max Martin songs -- “Show Me Love,” “As Long As You Love Me,” “Quit Playing Games (With My Heart)” -- imagined the listener as a lover, imploring them to reciprocate their feelings. “...Baby One More Time” is also directed at an ex, but there’s one crucial difference -- the song isn’t about him. Britney’s love interest appears only once in the video -- played by her own cousin, of all people -- and as iconic as the clip is, it’s unlikely you can even picture his face.

Teenage girls write diaries for themselves, to work through their own emotions. But crucially, Britney extends that to her audience, as if we’re not lovers, but friends: “Show me how you want it to be/ Tell me baby, ‘cause I need to know now.” She implores us to open up, to confess our troubles to her. Said to yourself, a phrase like “my loneliness is killing me” sounds downright suicidal. But when you sing it along with Britney, when it’s the most popular song in the country, it feels like a declaration that we’re all crazy in love. It can’t be that bad if we’re alone together.

Despite its lyrics, “...Baby One More Time” has never been a tragic love song. The video, which was Britney’s own concept, doesn’t literally tell the song’s story. It shows how a song might soundtrack a teenage girl’s life: how they’d dance to it; how they’d glam up a drab school uniform, tying off a shirt at the midriff; or what they’d choose to wear - every piece of clothing was purchased at K-Mart. Britney’s star quality is dazzling, but rooted in her ordinariness. In an alternate version of the video, all she does is dance and lip sync while looking at the camera. Even without an elaborate treatment, the video could’ve been every bit as iconic.

In 1999, Britney felt not like a celebrity, but a girl’s best friend, or an older sister. Maybe she was the kind of girl we'd crush on, unable to imagine her having a vivid emotional life of her own, until we heard a song like “...Baby One More Time.” Perhaps for young queer boys looking for role models, Madonna was a generation past; the Spice Girls were idols, but not exactly down-to-earth. It was the first time generation Y - anyone from 5 to 19 in 1998 - truly heard one of our own articulate our feelings with such emotional maturity and resonance.

“...Baby One More Time” replicates the feeling of locking yourself in your room, headphones on, obsessing over something you can’t control. For older ‘90s teens, that band might have been Nirvana, whose equally iconic “Smells Like Teen Spirit” brought a sense of emotional realism back into popular rock. Grunge’s influence led directly to the rise of female-fronted acts like No Doubt, Fiona Apple, Hole, Garbage, Sheryl Crow, and especially Alanis Morissette -- who was a teen dance-pop act before Jagged Little Pill. Alanis’s music was was radio-friendly, but still rooted in singer-songwriter confessions. By 1998, Natalie Imbruglia’s “Torn” was an enormous pop hit -- a song with the lyrics and melody, but not the grungy sound of the band who wrote it, Ednaswap. Alt-rock’s influence had fully been absorbed into the mainstream.

By 1998, that emphasis on relatability had trickled down to teen pop, too. Past pop groups like New Kids on the Block and the Spice Girls prioritized colorful personalities and catchy songs, like a dance crew crossed with a team of superheroes. Though *NSYNC sang about “Tearin’ Up My Heart,” did they really make you feel it? With Britney, all of that appeal was condensed, magnified, into one girl. Says The Song Machine author John Seabrook, “This was a very significant moment in pop history: The signing of Britney Spears as a sort of girl-next-door teenager, rather than as a Whitney Houston-esque diva.”

She didn’t feel like a marketer’s creation, at least at first -- but her impact was immediate. Britney became the center of pop, with Max Martin and his team of Cheiron Studios songwriters around her. Every other pop girl was marketed in comparison to her: Christina was the rival, a fellow ex-Mouseketeer with a bigger voice; Mandy Moore was younger and more bubblegum. Even Avril Lavigne’s edgier pop-punk presentation was a direct reaction to Britney and her ilk.

“...Baby One More Time” was so iconic a debut single that it couldn’t help but frame the rest of her career, too. “Oops!... I Did It Again” was a near-identical composition, with an inverted power dynamic -- now Britney’s the one breaking hearts. The chorus of “Stronger” went even further: “My loneliness ain’t killing me no more!”

By 2000, seemingly every pop producer wanted to sound Swedish. Subsequent hits like Jessica Simpson’s “Irresistible,” Blue’s “All Rise,” and Samantha Mumba’s “Gotta Tell You” lifted the harmonic-minor, R&B-inflected feel of “...Baby One More Time,” without the romantic conflict that was so crucial to the song’s message. One song that did get it, however, was Justin Timberlake’s “Cry Me a River” -- which responded to his breakup with Britney by taking minor-key pop to operatic heights, shattering both their teen-friendly images at once.

Even 10 years after “...Baby One More Time,” Britney wasn’t out of the woods yet. While tabloids gawked at her public unraveling, fans who’d grown up with her looked on in horror. 20 years after her debut, Britney’s no longer solely defined by her relationship to the celebrity machine. She’s just announced her second Vegas residency, but more importantly, she’s a doting mother of two -- and her Instagram’s a delight. We couldn’t be happier for her.

Part of growing up means reevaluating the art that made us. Many TRL-era pop songs have been forgotten; others are best suited for “I Love the ’90s” playlists. There’s nothing new to say about “Candy” or “Irresistible.” They feel like memories -- it’s impossible to hear them in the present tense.

“...Baby One More Time” may not sound like a 2018 pop production, but in every other way, it feels like it hasn’t aged a day. That piano riff still makes people rush to the dancefloor. The song’s a karaoke classic; the costume’s a Halloween staple. Every few months, another artist’s covering the song, or a celebrity’s dancing or lip syncing to it. We still look up to the 16-year-old Britney -- she’s cooler than we’ll ever be.

This year alone, Anne-Marie’s “2002,” Lauren Alaina’s “Ladies in the ’90s,” and Charli XCX’s “1999” have quoted “hit me baby one more time.” None of them sound like “...Baby One More Time,” which has become too iconic to imitate directly. But modern pop artists and fans alike aspire to its essence: emotional catharsis you can dance to. Britney informs Robyn’s “Dancing on My Own,” Drake’s “Take Care,” every post-2015 single by The Weeknd. And if they hadn’t grown up with Britney, Lorde, Lana Del Rey and Sky Ferreira might well be cult singer-songwriters, not pop stars. Millennial pop is darker, weirder and catchier for Britney’s influence.

No one born since 1998 remembers “...Baby One More Time” in its initial run. That’s a whole new generation waiting to discover it, who won’t see it through the rose-tinted glasses of ’90s nostalgia. As long as there are teenagers, and as long as millennials have loneliness to confess, the message of “...Baby One More Time” will endure. The album’s European cover says it all: there’s Britney, hands clasped in prayer, the eternal teenager.