In 1997, Britney Jean Spears was a high school freshman aching to get out of the quiet stretch of Louisiana that bumps up against Mississippi. The most notable thing about her at the time was one off-Broadway credit and her status as a former Mouseketeer. A year later she would become one of the biggest pop stars in the world, thanks to the strength of her debut single, “…Baby One More Time.” Produced by Max Martin — a failed Swedish glam-metal rocker who was making coffee runs while his mentor, Denniz Pop, was producing “The Sign” and “All That She Wants” for Ace of Base — the song would go on to define early ‘00s pop music.

Twenty years after its release (on Oct. 23, 1998), we take a deep dive into one of the most groundbreaking hits in history.

******

Jive Records had just started branching out from its stable of R&B acts (they’d recently signed those Backstreet Boys) when a photo of 15-year-old Britney landed at their office.

Barry Weiss, president of Jive Records: Jeff Fenster^ had come into an A&R meeting and shown us a picture of this really pretty young woman on a red and white picnic blanket, almost like a tablecloth from one of those small, local Italian restaurants. It was kind of funny. I think she might have had a dog in the picture as well. Almost like Dorothy from Kansas.

Larry Rudolph, an entertainment lawyer and family friend of the Spearses, brought her into Jive for an audition.

Barry Weiss: She was wearing a black cocktail dress and high heels. She sang live for us: Whitney Houston ballads, Mariah Carey, Toni Braxton. She really was a good singer. She looked amazing. She was like, 15 years old. And we kind of thought, Wow, this is really left of center. There’s no female pop artist out there right now.

John Seabrook, author of The Song Machine: Inside the Hit Factory: Clive Calder, who was the head of Jive, signed her to a provisional contract. 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. One of the calculations there was, Clive Calder was notoriously cheap, and Whitney Houston was notoriously expensive. So Britney Spears seemed like she would be cheap too, because she was just a teenager from Louisiana, and wasn’t demanding in any way.

Star secured, the Jive team needed, well, music. They turned to Swedish producer-songwriter Max Martin, of Cheiron Studios, who had worked with Ace of Base and co-produced some songs on the Backstreet Boys’ self-titled debut album.

Barry Weiss: There weren’t many U.S. mainstream pop producers that could do young artists. The pop at the time was very right down the middle. But we were looking for edgier, younger-sounding records. We had an A&R office at Jive in Hilversum, outside Amsterdam. Martin Dodd was our A&R guy, and the Max Martin and Cheiron connection.

Max Martin*: I was in Florida and Jeff [Fenster] asked me to stop by the office in New York to meet this girl while I was in America. She was all dressed up. She was 16. She thought I was a 50-year-old producer from the old school. I had really long hair at the time — I looked like Ozzy Osbourne. It was pretty obvious that she had something, even though she was very quiet and very shy.

Image zoom Britney Spears Vevo

Martin went home to Sweden and cranked out a song. But it wasn’t Britney’s… yet.

Max Martin*: I write on the Dictaphone. I came up with the melody first. I wrote the chorus; you just hum it in. Thanks to [my co-producer, Rami Yacoub], that song sounds the way it does. He is much more urban and R&B than me. I’m more of a melody man. So he’s a big reason that the song turned out the way that it did.

NaNa Hedin, backup vocalist: I remember that I thought the song was for teenagers but the production was filled with a grown-up attitude and with sounds that I really liked. I was so impressed by how a guy like Max and the other writers could write lyrics that got into the hearts and spoke to teenage thinking. It really represented [that] whole generation, not them.

Barry Weiss: Martin Dodd had this demo, which was then called “Hit Me Baby One More Time,” and he sent it into us and said, “This is a song Max had written for TLC, but they didn’t really want to cut the record.” I think Arista wanted Deborah Cox — she was the heir apparent to Whitney, and Clive Davis was really into her. But Max was not down with that… When the song came into us, we thought, let’s cut this with Britney. Let’s send her to Stockholm. The magic that worked with the Backstreet Boys, why wouldn’t it work again for Britney Spears?

Jive sent Britney to Sweden to record her debut album.

Britney Spears*: I didn’t know what to expect. It was my first time overseas. They had six songs, [and] I had a week.

Max Martin*: She was very well prepared. Since “…Baby One More Time” was the first song, we really didn’t know where to take it. We just kept on recording. We tried a couple of different styles. After a while, I could hear her stomach growl in the microphone. I asked if she was hungry. We’d been going for eight hours. She said, “No, I’m fine.” I said, “Let’s take a break,” and she had three burgers.

John Seabrook: In those days, and maybe this is still true, Max made all the demos himself. He would sing the different harmony parts himself, too. Max has an amazing voice, and very few people have ever actually heard that demo. I did hear it, and Max sounds exactly like Britney, including all the little sounds that sound improvised; the mow-woww sounds. So Britney ended up sounding exactly like Max.

Chris Molanphy, chart analyst and pop critic: The reason why it remains one of the most iconic songs of the 1990s teen pop boomlet is it’s kind of a perfect marriage of song and artist and songwriter. If Max Martin is John Hughes, he found his Molly Ringwald. His muse-vehicle for his particular brand of writing. You can’t picture it being sung by anybody else.

Barry Weiss: I remember when we got it back with Britney on it, she had that “oh BAY-BAY BAY-BAY,” these ad libs. We thought it was really weird at first. It was strange. It was not the way Max wrote it. But it worked! We thought it could be a really good opening salvo for her.

NaNa Hedin: The magic is the attitude. Deep underneath the pop sound it has a sexy rock rebel attitude, from a young schoolgirl and her voice.

Image zoom Britney Spears Vevo

There was just one problem: the chorus. Specifically: the “hit me.”

John Seabrook: Before the song came out, nobody in America liked the hook, “hit me baby one more time.” Everybody thought it was some sort of weird allusion to domestic violence or something. But what it really was was the Swedes using English not exactly correctly. What they really wanted to say was, “hit me up on the phone one more time” or something. But at that point, Max’s English wasn’t that great. So it came out sounding a little bit weird in English. But when they tried to get him to change it, he said, “No, it can’t be changed. That’s it.”

Barry Weiss: I actually changed the lyric. I was concerned about going to U.S. radio with a song called “Hit Me Baby One More Time.” I don’t know if I’m proud of this or not: I came up with the “…Baby One More Time.”

With a lead single locked in, it was time to shoot a video.

Barry Weiss: I went immediately to Nigel Dick, the video director. He had done the Backstreet Boys videos “Backstreet’s Back,” [and would later do] “I Want it That Way.”

Nigel Dick, director, “…Baby One More Time” video: Interestingly, a lot of people I worked with at the time told me I should walk away from the project. “She’s an unknown girl. She’s 16 years old. It’s candy-floss pop.” I’d done quite a lot of stuff which was a bit more meaty: Oasis, Guns and Roses, blah, blah, blah. I just thought the song was really, really good.

Barry Weiss: Nigel came up with an idea, like, Britney is in outer space. She comes and lands on Mars on a spaceship, and then she breaks into this dance routine. [Editor’s note: You may recognize this as the video treatment for “Oops! …I Did It Again,” which Dick also directed.] I was like, “Wow, this is great!” And Britney looked at this and said, “This is horrible. No way am I doing this. This is really cheesy. Let me get on the phone with Nigel Dick.”

Nigel Dick: She said, “I want to be in a school with a bunch of cute boys and do some dancing.”

Barry Weiss: Her idea was the whole Grease thing, dancing in the hallway. She gave the kernel of the idea to Nigel, and he came up with the rest.

Nigel Dick: Your initial reaction to this is, I’m being told by a 16-year-old-girl what I should do… [But] this girl is 16 and I’m a grown man; perhaps she has a better perspective on her audience than I do. So I swallowed my pride.

John Seabrook: Britney knew better than the adults what people wanted and I think that’s also significant, because I think the adults began to realize that they didn’t necessarily know what the kids wanted anymore.

Nigel Dick: [Shooting] was very easy. There was no real drama. What I did not know at the time was that, of course, you have this experience with the Mickey Mouse Club. As far as I knew, she was just a schoolgirl from the South. [But] she was very relaxed in front of the camera. She was very, very drilled with her dance routine. I’ve worked with her four times, and I’ve yet to work with somebody who puts in as much preparation, and was as eager to rehearse, as she was.

Image zoom Courtesy of Nigel Dick

Every article of clothing in the video was purchased at K-Mart and cost less than $17. An inauspicious beginning for what would become a famous (or infamous, depending on your point of view) outfit for the underage performer.

Nigel Dick: I don’t have kids, so my understanding of what teenagers wore was limited to driving home from the office and seeing kids standing by a bus stop. So I suggested they would be wearing jeans and t-shirts and sneakers and would have backpacks, and Britney said, “Well, shouldn’t I be wearing a schoolgirl outfit?” And I was very dubious about this idea. But I was overruled.

Chris Molanphy: I can’t prove this, but, the fact that all female teen pop stars for the next roughly three years had to shoot a video with their belly button bared — Britney made that look iconic.

Vanessa Grigoriadis, reporter, “The Tragedy of Britney Spears”: She said to Rolling Stone, “All I did was tie up my shirt. I didn’t do anything.” And this has always been the question with Britney: Does she know what she’s doing? It was very much on the edge of what was acceptable then.

Nigel Dick: Certainly, my initial reaction was, “Are you sure we should be going down this route with this young lady?” And the people who were in control, the record label and whatnot, said yes, this is the route we want to take.

Britney Spears**: There are so many other teenagers out there that dress more provocatively than I do and no one says anything about them. How can I explain this? I don’t see myself — hand on the Bible — I know I’m not ugly, but I don’t see myself as a sex symbol or this goddess-attractive-beautiful person at all. When I’m on stage, that’s my time to do my thing and go there and be that — and it’s fun. It’s exhilarating just to be something that you’re not. And people tend to believe it.

Nigel Dick: I was kind of aware that some people might feel that that was exploitative. And as it turned out, I got a huge amount of grief about it once the video came out.

John Ivey, President of CHR Programming for iHeartMedia: I was programming Kiss 108 in Boston, so Jack Fader [head of record promotions at Jive] brought her into the station. Here she comes in, little kid, no makeup. You can tell how young she is. But very wise, already. They had just gotten the final edit of the video [on] VHS. We went into this office and I’m sitting there watching it with her, and I’m looking at her, and looking at the video, like, hey, what’s going on here? It showed what was going to happen very quickly. When you see it you’re like, omigosh, this whole schoolgirl thing, it’s a little sexy. But then I’m sitting here and she’s really little, she’s got no makeup on, she’s just a little kid.

Vanessa Grigoriadis: When I was reporting this article, a lot of people said Britney wanted to be sexy. And the people who are managing her, all the guys who were so involved in her image, they were trying to make her look less slutty, basically, was the word somebody used to me. And she wanted to push the boundaries. I think that it’s impossible to know if it’s actually true.

Britney Spears**: I guess it’s because I do have a younger audience that, you know, parents worry about the role model thing…. But when I was younger, I looked up to people, but I never wanted to be them. I always had my own identity. I’m an entertainer when I’m on stage…and they need to explain that to their kids. That’s not my job to do that.

“…Baby One More Time” was released on October 23, 1998. It debuted on the Billboard Hot 100 less than a month later and spent 32 weeks on the charts.

Barry Weiss: We had her a on a mall tour, handing out cassette singles, in the summer and the fall. The video came out pretty simultaneous with the song. It was just an absolute explosion… By November it was just a worldwide phenomenon.

John Ivey: We felt like it was a hit. There’s sometimes you get records, [and you think], I want to play it as soon as I can. I know I wasn’t the only person that felt like that. Most of the time, for a record like that, I said, I’ll start it out at night, see what the kids think, and see what happens before we spread it out to the day. And obviously it became a big monster hit.

The video came out just as MTV combined two existing programs (“MTV Live” and “Total Request”) into the new, Carson Daly-hosted, soon-to-be-pop-phenomenon “Total Request Live.”

Chris Molanphy: I’m sure if you were 40 and wanted to call TRL, you could. But no one over 20 was calling TRL. So it was this mainline, hooked to your veins, of what teenagers were most obsessed with. And it was either the stuff that made them feel like a hard badass or the stuff that made them swoon. And Britney arrived just as this is beginning. The way she was presented as this schoolgirl gone bad, it had a combination of Swedish pure pop crossed with a little frisson of edge. It could not have been more perfect for the era of TRL.

John Seabrook: MTV had, up to that point, tried to resist mainstream pop, because they wanted to be perceived as cool… But I think with Britney, and the video in particular, and the fact that TRL had launched at around the same time, it really changed MTV.

John Ivey: Britney had the second level. People saw this video and thought, what is this girl? Because everybody latched onto this immediately. It wasn’t very long after that, she was on Rolling Stone.

Image zoom Britney Spears Baby One More Time video screen grab Credit: Britney Spears Vevo Britney Spears Vevo

“…Baby One More Time” didn’t just launch Britney’s career: It kicked off the teen pop boom of the late ‘90s, clearing the way for a fleet of Britney also-rans and boy bands to dominate TRL and the airwaves pretty much until teenagers stopped watching TRL and listening to the radio. It also was the breakout moment for Max Martin, who went on to become one of the most successful, influential pop producers in modern history, and all the Swedish producers who followed.

Barry Weiss: What it was like was worldwide domination. And the differential with “…Baby One More Time” and why it was such a cataclysmic event, it was the reemergence of pop music.

John Ivey: It would be in the top percentile of singles in the past 25 years. Because it broke her as an artist and what she became. It’s like Madonna’s “Like a Virgin,” or Prince’s “Let’s Go Crazy.” It’s the song that made her Britney Spears.

John Seabrook: It was instrumental in putting Cheiron and Max and Sweden on the map. Other Swedish songmakers got the idea that they didn’t just have to write for Swedes or maybe Brits; they could write for Americans and really tap into that huge market.

Barry Weiss: I mean look, was she involved with writing those songs? Max Martin is a genius, okay? He’s brilliant. He tailor-made those records for her. But she would never have had the career without her vision. She has this innate ability to move the media.

Joe Levy, Rolling Stone editor: The public perception is that this is all created, that the record company created this — the artist, the music, the image. I have to tell you, if the record company could have created more than one Britney Spears, they would have done it, and they tried! And people, Mandy Moore is an actress.

John Ivey: There were a thousand Britney Spears wannabes.

Joe Levy: Britney Spears is someone who, from the time she was a child, wanted to be a star. The drive, the determination, the ambition — you have to give this woman the same sort of respect that Justin Timberlake gets. Otherwise, I’m sorry, but you’re engaging in a double standard.

Twenty years later, “…Baby One More Time” sounds as sharp as it ever did: Sultry, catchy as hell, both totally of its time and like something that could have been released this morning.

John Seabrook: I think the melody is eternal, or at least, transcends its late ‘90s period. And I think the words, the first time you hear it, it’s always going to be something that makes you go, what? Can I say that? Can I sing along with that?

Barry Weiss: It sounds as good now as it did then. It hasn’t weathered or dated.

Chris Molanphy: The way the song is structured, how the chorus goes to this chorus of voices — the song is structured to deliver maximum pleasure.