Britney Spears’s ‘…Baby One More Time’ music video debuted on MTV’s ‘TRL’ on this day in 1998

On this day: Nov. 26, 1998

The Happening

As Thanksgiving Day approached in 1998, the world had no idea they were about to witness the metamorphosis of a former Mouseketeer into a global sensation.

Britney Spears’s debut single “…Baby One More Time,” which was initially turned down by both TLC and the Backstreet Boys, had already dropped on Oct. 23. The buzz was building across the music industry about the premiere of its accompanying music video set to drop on MTV’s TRL. Directed by Nigel Dick, the video featured a provocative Spears in a sexy Catholic school uniform bought at K-Mart with pink poms poms and pigtails.

This wasn’t just any video debut — it was a moment that would be etched into pop culture history.

Her journey started years earlier. After waving goodbye to the Mickey Mouse Clubhouse in 1994, Spears returned to Louisiana to resume a normal teenage life while trying to pursue a solo career. In a twist of fate, a demo tape caught the attention of Jive Records. Her voice, imbued with a unique mix of innocence and allure, seemed to come at the right place at the right time.

“…Baby One More Time,” written by legendary songwriter Max Martin, disrupted the dominant R&B and rock genres, allowing poppy bobs to enter the zeitgeist in a fresh way. It was the perfect vehicle for Spears to transition. Her public image, largely shaped by the video’s themes of youthful innocence and desire, would stay with the singer for the rest of her career.

Randy Connor, the video’s choreographer, remembers getting the call from Jive Records about a “fresh face” they were wanting to develop into a pop princess.

“It was an amazing time,” he tells Yahoo Entertainment. “Britney was 17, and a ball of energy. It was really a dynamic situation between me and her. Britney was a hard worker, she was very confident. She really, really wanted it — and she worked for it.”

Chris Sawyer, one of the principal dancers hired by Connor to be featured in the music video, says Spears’s timing couldn’t have been more perfect.

“When she came out, we were just getting off the Michael Jackson, Prince, Madonna stage,” Sawyer tells Yahoo Entertainment. “Her and Christina Aguilera, there was a new crop of ladies that were coming up as pop stars — a new crop of ‘Madonnas.’ I know Jive Records was patting themselves on the back because it was exactly the perfect time.”

The “soulful” choreography, mixed with jazz modern movement, was an intentional choice on Connor’s part. “The song was really poppy and mainstream, so I wanted to create something with soul, particularly in moments like [when she sings] ‘Hit me baby one more time…’, with the hand movements and gestures.”

“We didn’t do any of our breakdance moves or any of our urban hip-hop moves,” Sawyer recalls. “We were doing all the things you saw in the ’80s with Janet Jackson. We brought that back.” And despite the lack of experience, Spears was keeping up with the best of them.

“She was still a new artist and kind of feeling her way around professional dancers,” he continues. “She was like a freshman in college, learning and very observant, very quiet. She didn’t talk too much. She was just listening to Randy and listening to us, and working so professionally with all of us.”

Connor recalls Spears being “nervous” before the video dropped.

“I think she was a little scared, but I think we all knew [it would be successful]. My dancers would say, ‘She’s gonna be this huge star,’” he remembers. “At the end of the day, it’s because she made it so beautiful and elegant. Everything I gave, she embraced and took hold of it. She felt the energy and vibe I was going for and was completely open to receiving it. And that’s why it worked.”

Oddly enough, as Spears writes in her memoir The Woman in Me, the original setting of the video was going to be in space — until she canned it.

“The mock-up I saw had me looking like a Power Ranger,” she writes. “That image didn’t resonate with me, and I had a feeling my audience wouldn’t relate to it, either. I told the executives at the label that I thought people would want to see my friends and me sitting at school, bored, and then, as soon as the bell rang, boom — we’d start dancing.”

“I thought we should wear school uniforms to make it seem more exciting when we started dancing outside in our casual clothes,” she continued.

What Happened Next

“…Baby One More Time” became the fastest-selling album by a teenage solo artist, debuting at No. 1 on the Billboard charts. It also earned Spears her first Grammy nominations for Best New Artist and Best Female Pop Vocal Performance. She’d later win Best Dance Recording for “Toxic,” among eight career nominations. As a single, “…Baby One More Time” is still the fifth best-selling by a female artist in the U.S., behind Cher’s “Believe” and Whitney Houston’s “I Will Always Love You.”

Virtually overnight, Spears became the queen of teen pop and set the tone for what the early 2000s would look and sound like. Her charisma struck a chord with fans and catapulted her into a stratosphere of fame that few artists ever reach. The next two albums — Oops!… I Did It Again (2000) and Britney (2001) — also debuted at No. 1, making her the first female artist to have her first three albums achieve this feat.

“She hit so quickly and so substantially,” says Sawyer.

For better or worse, it also turned Spears into a sex symbol. And contrary to popular belief, much of the video’s aesthetic was led by women. When addressing the provocative schoolgirl outfit worn by the singer in a 2018 Billboard interview, Dick stressed that the producer and executive producer, both of whom were women, praised the look as a “really good idea.”

“Music magazines said this artist was conceived by a bunch of dirty old men in a conference room wearing raincoats,” he said, “which, in my experience, was not how it occurred at all.”

Where We Are Now

A quarter century later, it’s evident that Spears’s sound has influenced generations of young performers in her wake. Contemporaries like Christina Aguilera, as well as later superstars such as Lady Gaga, Miley Cyrus, Katy Perry, Dua Lipa and Billie Eilish have all pointed to Spears as influences.

Spears experienced an immense amount of unfair scrutiny in the following years, as she publicly wrestled with mental health issues and a conservatorship that she characterized as abusive in her memoir. Still, the singer always credits the music video as one of the best times of her life.

“Making that video was the most fun part of doing that first album,” she writes.

As for Connor, he’s now a successful music producer. He continued to work with Spears for the promotional tour of the album, before leaving to help Diddy choreograph dances for a Nelson Mandela tribute concert in Africa. By the time he came back to the U.S., he says Spears was already a “huge star” and went on to work with choreographers like Wade Robinson and Brian Friedman.

“I just continued on my busy path. I was touring all over the place, and was really happy for her,” he says now. “I ran into Britney a couple times here and there, but we never had the opportunity to celebrate the immense success of the video in real time. I still get calls from fans all over the world.”