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Oops!... I Did It Again At 20: How A Seminal Classic Shaped Pop's New Generation

Eight pop musicians — from Hailee Steinfeld to Ava Max — reflect on 20 years of Oops!...

Twenty years ago, on May 16, 2000, an 18-year-old Britney Spears unleashed her sophomore album, Oops!... I Did It Again, into the world. She'd teased the new era a few months prior with the title track, its music video blasting across screens around the world, forming the now-iconic image of Britney in a red latex catsuit conquering space. She was at a new height in her still young career, the first peak of what feels like many — her face on lunchboxes, Barbie dolls, toys, and apparel. So, of course, its arrival made history. Oops!... sold over 1.3 million copies in its first week, breaking the record for most first-week sales by a female artist (Adele's 25 claimed that title 15 years later). Her future was wide open and limitless. "My ultimate goal is to be around for a really long time and be someone like Madonna or Janet Jackson," Spears told MTV at that time. “It all boils down to the music. That's what causes longevity.”

Two decades later, one would be hard-pressed to name a Britney record that hasn’t solidified itself as a time-tested masterpiece. Oops!.. I Did It Again remains as fresh, relevant, and wholly idiosyncratic as the day it was released, arguably gaining cachet as time goes on. With help from now legendary pop producers Max Martin, Darkchild (aka Rodney Jerkins), and more, Spears delivered unrelenting bop after unrelenting bop. Of course, there's the title track, but there was also the empowering anthem “Stronger” that followed, the dreamy, unexpectedly vulnerable narrative of “Lucky,” and the R&B yearn of “Don’t Let Me Be the Last to Know,” just to name a few. Together, they formed a multifaceted, simultaneously relatable and aspirational pop star while also sketching out the blueprint of a sound that would rule pop music for the better half of a decade. Not yet fully weighed down by the paparazzi, tabloids, gossip, and vulturous media eye, Oops!... I Did It Again Britney was a star blooming into herself.

As for me, I was 5 years old when the album came out. The most potent memory I have was lugging its hard plastic CD case with me everywhere I went — from day care to home, to the grocery, to home again. Its cover — Britney peering through a beaded curtain, her midriff exposed — I could probably sketch from memory. I imagine I share this impression with millions of people around the world, young people who have grown up alongside Britney, including those talented few who are venturing into pop music themselves at the current moment.

Hannah Diamond, an English singer-songwriter who’s signed to left-field pop label PC Music, reflecting on the impact Britney left on pop music, told me by phone recently: “You know that phrase like, ‘She walked so we could run,’ or something? I think it's actually more, [Britney] ran so we could walk." The young tendrils of radical change that Britney would later use to shape an entire industry — unabashed sexuality, raw and honest storytelling, unmitigated confidence — can all be found embedded in the songs on Oops!

Below, eight musicians from pop’s new generation — Hailee Steinfeld to Slayyyter to Dorian Electra — reflect on how Britney’s impacted them, and celebrate 20 years of an iconic American pop classic.


“What an iconic year for Britney's Oops!... I Did It Again to turn 20 in 2020. In 2000, I was in kindergarten. So honestly, Britney Spears is probably the first female pop artist that I was obsessed with. Oh, my god, I'm having the craziest flashback to having — do you remember HitClips? HitClips is like this little baby boombox that's the size of your hand, and you could get all of these tiny little chips that you insert like a CD. The more you had, the cooler you were. And my goal was to get as many Britney Spears HitClips as possible. I had 'Oops!... I Did It Again.' I had Stronger.' I had 'Lucky.' And every recess, I busted it out. I would walk around and I would make up dances in the courtyard to Britney Spears and pretend I was part of her music videos. That's the earliest memory that I have of envisioning, being an artist performing on a stage.

"‘Lucky’ is one that has always—I don't know, I just remember being a little kid and seeing it and being like, 'Ugh, she's so lucky, she's a star, but she cries, cries, cries with a lonely heart,' but it's disguised under this dreamy, synthesizer pop feeling. The way that the story and the lyrics and the melody matches the production. On 'Lucky' for example, when she says, 'And tell me, what happens when it stops' and all the production cuts out and there's a drop out. Listening to that album takes you on a whole journey, emotionally, sexually, and you can feel it in your body because of what Max [Martin] did, and Britney as well.

"I think my music is an embracing of sexuality and exploration and loving who I am, and she was saying that on 'What U See (Is What U Get).' Also, just sonically, her bass lines were always the fattest thing that could just shake any club. Being from Jersey and having many fist-pumping nights, I feel like having that bass line is always the driving force of the song.

"I feel like she totally embraced her body and her power and her sexuality in a time [where] people were slut-shaming women, and she was like, 'F*ck it, this is who I am. I'm proud of the way that I look and I'm proud to use feminine form.' And I think that specifically went off to shape the future of women in pop music. That's always the stuff that cuts through the noise is when you're just like, F*ck the system, f*ck that. I stan pushing boundaries and not listening to the rules."

Hailee Steinfeld

"I was 4 years old when this album came out and somehow I distinctly remember dancing around the family room to each song for hours at a time. I loved it. I even have this memory of trying to get the album down from the fireplace mantel, as it was most likely placed there in the first place to give the house a break from Britney.

"As far as a favorite song off the album it remains a constant battle between 'Oop’s!… I Did It Again' and 'Stronger.' [Britney] laid the groundwork for pop music and pop culture. Not only were the songs incredible, every music video, every live performance, and every red carpet look were simply iconic. She pushed all the boundaries."


“I grew up in a very Catholic religious household, and my mom was not totally cool with Britney Spears. She was always like, Oh, she shows her stomach. You guys aren't allowed to listen to her. But she was [me and my sister’s] secret obsession. I remember I would sing into my hairbrush in my room and I'd be like, 'I am Britney Spears. You can't tell me that I'm not. I want to be Britney Spears when I grow up.' Not a pop star, but I wanted to be Britney Spears when I grew up, specifically.

"I remember that album [thinking], 'Wow, this Max Martin top symphony is so good.' I feel like it was so influential of other music at the time, too; everybody wanted to sound like that really. I feel like [Britney] pioneered a very specific sound in pop music at the time. And a lot of times after that, too. Even with her later albums, Blackout, stuff like that, she's always been ahead of the game. She's the blueprint.

"‘Lucky’ is such a classic. I have memories of me and my sister driving around listening to 'Lucky,' and I always thought that that song was kind of sad because, looking back, I feel like it says a lot about celebrity culture and being sad and depressed. She was America's darling; she was the biggest star of the universe. People would faint when she would get out of her car. And I feel everyone probably was like, 'Oh, what a great life. I want to be Britney Spears.' But every artist [has] struggled with hardships and heartache and emotional distress, and she really could be raw on very sugary pop songs.

"One of the biggest things is listening to her records, I feel like that's why my voice sounds the way it does. I don't try to do a Britney impersonation per se, but I feel I have just a bit of that influence and it's because listening to her music is what taught me how to sing.

"She's just one of the living legends of music. I feel like she still is just as iconic as she always has been. She's going to go down in history as one of the biggest artists of all times and she seems so humble and nice, too. Undying respect for the legend and #FreeBritney is pretty much it.”

Ava Max

Oops!... I Did It Again I definitely heard for the first time when I was... I think I was 8 or 9? I remember hearing it and I fell in love with it. I remember watching the video and her in all red. She was just, she was a breath of fresh air as a kid. I was like, 'Oh, my god, that was the most fun song I've ever heard.' It was just incredible how Britney came in and it was over: she was the queen pop.

"My favorite song on the record was 'Oops... I Did It Again' and then it was 'Stronger.' 'Stronger' is so good; it was very empowering, and I think for me as a little girl, I heard it and I just felt so motivated. She made me more confident through her music. Listening to her music, I felt a fire in me. I wanted to dance, I wanted to sing, I wanted to do it all, not just be a singer. I wanted to perform. I think Britney, her music was energetic, and my music is definitely very energetic and pop. Definitely very unapologetically pop.

"I think [Britney] made it OK for people to embrace their sexuality, because she was very sexual. But in a modest way; it wasn't nasty. It was very like owning her body and that's what I loved. To this day, I still listen to this album, and it gets me going and motivated. I don't think there's... this is like one of the top, one of the top albums in our generation. Probably top 10 albums in our generation.”

That Kid

“So, the first time I listened to the Oops!... I Did It Again album, I want to say I was probably 12 because my introduction to Britney was a bit later than most people. I found a lot of her deeper cuts later on in life and I remember hearing that album and my instant fave from that album was probably 'Can't Make You Love Me.'

"I want to say it actually came in when I started doing music. I feel like over time she's influenced my sound a bit more and more. For example, like 'Break the Ice' or 'Hold it Against Me' or '3,' those really big pop songs and those intense spins, rhyming hooks, really shaped the way I like to write my own songs. I like them to be very dynamic, and Britney's always had these really dynamic hooks in her music. Her writing or her writing style and her songs are always so just huge. They never feel small. They feel like huge moments.

"Songs like 'Lucky,' for example, I look back on and I'm like, 'What was she going through in that moment?' Songs with such an intimate bond. Production wise, it’s so happy and bubbly, but when you really look at the lyrics, it's really a very sad song.

"To me, [Britney’s] the embodiment of a perfect pop star and that's a level of polished and glamour [I aspire to be]. I think she represents that to a lot of other artists as well, where we're kind of like, Britney is almost like a blueprint for a lot of us. [You gotta] have the stage presence, unique vocals, able to really deliver an amazing performance, and also have a sense of realism, because at the end of the day, it's important to be able to be see your face and see that there's something real about that. Yeah, we see the super polished image of Britney a lot of the time, but we all know she's a really human person, and I think that's really nice.”

Dorian Electra

“I think subconsciously, even as a kid, I always loved the song 'Oops!... I Did It Again.' I loved the music video, the red pleather jumpsuit, outfits, and the choreo. When I first started doing music and stuff, I always tried to direct my backup dancers and I always dressed them in silver, and in my mind, it just felt like the most iconic popstar backup dancer color. But I think a lot of it probably had to do, honestly, with that music video. This record coming out in 2000 was such a thing of the future, this space-age vibe and Y2K and all that.

"Listening to the music of that era, in general, it's like listening to harpsichord, which is something I actually use in my music. All that kind of medievally type melodies. Listening back to that music, it's musically rich, and complex, and interesting, and just so catchy and good formulaically genius pop music structure. There's so much stuff. Little things that'll be like ... some little breathy, 'Yes,' or even Britney's vocal fry, I like all that fun stuff.

"I've just always thought of [Britney] as synonymous with pop star. I remember always seeing costumes for Halloween that were a leopard print outfit with the little headset and it'd be a generic off-brand thing, [but] it was an obvious Britney Spears thing.

"When something is that big, your image becomes so iconic that it transcends even you and your name and your actual work. It's just an idea, the idea of this female pop star that's an amazing dancer and is super sexual. I think the narrative, too, of being from Louisiana and having this very American girl-next-door-gone-sexy-bad-girl transformation narrative is really impactful.

"She was pushing so many boundaries. Like when she did the kiss with Madonna, that was a huge moment, too. I feel like for her getting so much criticism for embracing her sexuality and being a sexual object, but then also kind of being criticized for being controlled by the industry and pushed to be this sexual person, and especially at such a young age.

"When we were kids, we were being told those narratives by the media, and I think now people have more of an awareness of things. I think a lot of people are gaining more awareness about mental health and people's privacy and just the idea of celebrity in general, and also feminism. Then we're able to look back at her, and culturally and individually those narratives change about sexuality and mental health. We can learn from her story, which is really cool.”

Hannah Diamond

“I don't remember where I was, but I think I would have been about 8, so middle school. I remember I bought [the album] in ASDA (it's just a supermarket). I used to be obsessed with watching that music channel The Hits, and I remember I watched [the 'Oops!... I Did It Again'] video so many times on that, but I was already a Britney fan because of the album that came out the year before.

"More so for me, I think the way that her pop persona was shaped across her whole career, that's the thing that is most inspiring for me. I feel like every pop girl who's come after her has learned from her, or knows about things to be careful about, or worry about, or think about in your career because with seeing her and hearing her go through it all. You know that phrase like, 'She walked so we could run,' or something? I think it's actually more, [Britney] ran so we could walk.

"One other thing I think is ... a lot of people have really underestimated her and her intelligence and the role she plays in what she does. I think they got her so wrong, just how much of the vision of everything is hers and how much she was... What do you call it? I can't think of the word, but a manufactured pop artist type of thing. I actually think she's a genius. She's fully aware of everything. I feel like older music and older lyrics and even the way that every album has tracked the point in her life where she's at, no one else could be in control of that and it be so coherent and concise about what point in her life everything was happening. And I feel like she's been severely discredited or under-credited throughout her career.”


“So this was 2000, I was 6 years old. Because I'm guessing the title track came out maybe a month or two before... I guess I heard it then because I was always watching MTV, so I'm pretty sure I saw the video and heard the song at the same time. I loved it, just like every other 6-year-old girl in the whole wide world. I mean, it's a great track, [though] 'Lucky' is my favorite song of hers. It's so real and I remember being super young like 6, 7, 8, and listening to that track and knowing everything you knew about Britney, then all of those things made sense, and you were like, "Oh, wow, she's this perfect pop star, but she still has issues like the rest of us."

"I feel like this album was the start of everything for real. This is when she blew and was at the beginning of Britney. Just her as a whole, the whole package: the way she looked, dressed, sounded, everything was just perfect and not perfect. Of course, it was polished but with tracks like 'Lucky' you could see the true Britney that also existed. I think I'm really inspired by just creating a whole universe with everything in it.

"Her whole career, we've seen Britney go through a lot from the start and then 2007 and when she came out of that; I feel she represents life. You're not always going to be the polished whatever person that people see on Instagram. We're all the same, we have issues, we have happy moments and we have sad moments, and unfortunately for her, her really bad and sad moments were in the spotlight. The rest of us can shy away and do our thing until we're happy again. But I think she represents just, like, life. It sounds weird to say just life but, you know what I mean?

"I think whenever they do the next, I don't remember — Voyager is the thing they sent out into space with music? They need to send 'Oops!... I Did It Again.' That should be the anthem of our planet.”