"There's A Kiss:" MTV Execs And Insiders On Madonna, Britney, Christina & Making History

“I made it through the wilderness, somehow I made it through,” Britney Spears coos from the summit of a 20 foot wedding cake in Radio City Music Hall on August 28, 2003. Decked out in a custom wedding dress, cinched with a Boy Toy belt, the pop princess du jour is paying homage to the undisputed Queen of Pop, Madonna, who once famously stood atop that very cake herself, in a star-making performance at the inaugural MTV Video Music Awards 20 years prior. The MTV Class of 2003 looks on from the audience, some, like a newly solo Beyoncé, with curiosity, and others, like the typically sullen Avril Lavigne and Kelly Osbourne, with disdain.

A second woman emerges from the cake’s first tier — a bellowing bride with a killer tan who swiftly reveals herself to be Christina Aguilera, another contender for the pop crown, and a known rival to Spears. Though the pair famously began their careers sharing a stage on The All-New Mickey Mouse Club, the ladies are not thought to be on friendly terms in 2003, and the vision of them both writhing around the stage floor singing “Like A Virgin” is a sight to behold.

Suddenly, the music halts and the ladies frantically look toward the top of the cake where their groom is ascending. The audience, led by dutiful husband Guy Ritchie, takes to their feet to pay respect to the Queen of the VMAs, the one and only Madonna. “Everybody comes to Hollywood, they want to make it in the neighborhood,” she declares to her subjects before warning: “How could it hurt you when it looks so good?” What happens next, well, is history. Madonna takes the hand of each of her ladies in waiting, cavorts to the end of the stage’s catwalk to the soundtrack of Stuart Price’s Jacques Lu Cont remix of “Hollywood,” and anoints them both with a gobsmacking French kiss that left the audience, and the world, agog, before being joined by Missy Elliott, as a page boy of sorts, for a rendition of “Work It.”

It’s a moment that’s crystallized in pop culture history, a cornerstone in all three artists’ careers and one of the last occasions the VMAs felt like truly essential viewing. As the kiss turns 20, NYLON spoke to a number of stakeholders involved in its creation to better understand how exactly it came together — and to seek answers to some of the questions that have always swirled around it.

“The idea definitely came from within MTV,” explained Sally Frattini, then Senior Vice President in charge of productions for MTV. “It started with, 'Let's honor Madonna,’ but then we thought we should add on some women. We went to her with the idea, though she definitely embellished it. She was really into the idea of working with Christina and Britney, and she eventually agreed to take over the creative with her team.” The team in question: Madonna’s choreographer Jamie King, set designer Ron Norsworthy, and longtime stylist Arianne Phillips, who created the pop stars’ bridal looks, as well as the dresses worn by the flower girls who opened the show (Madonna’s real life daughter Lourdes Leon, and her then-manager’s daughter Honour Norman).

The choice of who should join Madonna on stage for this seminal moment has caused much speculation in recent months leading up to the 20th anniversary, stemming mostly from an interview Jennifer Lopez gave to E! News in January of this year in which she revealed that she was originally due to participate in the performance, alongside Spears. Lopez stated that scheduling conflicts due to her film commitments meant that she had to drop out, claims that were recently confirmed by former MTV president Van Toffler in an interview with Rolling Stone.

Shortly afterwards, P!nk gave an interview claiming that both she and Gwen Stefani were also invited to participate, sending the internet into a tailspin over how this different iteration would have unfolded. Ron Norsworthy, the designer responsible for the iconic, ginormous wedding cake, tells NYLON that indeed he did recall P!nk and Stefani’s names being mentioned in early discussions. Perhaps most shocking of all, however, he also revealed the name of another starlet who was apparently in contention to be a bride. Your mind may reasonably wander to the likes of Beyoncé, Ashanti, or Shakira, but the woman in consideration was in fact… Kelly Osbourne. In the context of 2003, Osbourne was an MTV darling as a star of The Osbournes, one of the network’s first forays into the world of reality television. She also, in her attempts at pop stardom, had recently covered Madonna’s “Papa Don’t Preach.” “I don't know if she was in the mix for very long but I do know, I did hear her name,” Norsworthy recalls.

Today, it’s hard to imagine the performance with anyone but the final cast. After all, a huge part of what makes it so memorable was the shock of seeing Aguilera and Spears, suspected arch nemeses, join forces before the world. But for those on MTV’s side of the equation, it seems the pair were always at the top of their list. “I mean, from as early as I was involved, the first choices were Britney and Christina,” says Beth McCarthy Miller, who directed the 2003 VMAs. “They had a huge rivalry, and I don't think they were speaking at that time, so that alone was so newsworthy. Maybe it was a thing that they couldn't get both of them to agree to do it, so we had other thoughts as a fallback plan.”

Frattini confirms this hypothesis: “I don't remember P!nk or those conversations, but I'm sure we had a short list of people, we always did,” she explains. “Plus, there was a little bit of a rivalry at the time, so we didn't know whether Christina and Britney would agree to do the same thing.”

“Beth called us from rehearsal and said, ‘You're not going to believe this, but there's a kiss: Madonna kisses Britney’ and we were all like, oh my God.”

Once casting had been finalized, the artists began weeks of rigorous rehearsals, first in Los Angeles and later in New York. McCarthy Miller, under instruction from Toffler, flew to the LA rehearsal space two weeks before the show to get a sneak peek at what the execs could expect from the ladies. In doing so, she became the first person outside of Madonna’s team to learn of the kiss, or rather kisses, that would set the world on fire. “They marked it out for me, step by step, and then they got to the end of the runway and they kissed each other on the cheek. I was like, ‘Yeah, that's not gonna be what that is….’”

“I called [Van] and I was like ‘You're gonna be either really happy or really sad, but I think you're gonna be happy!’” she recalls.

“Beth called us from rehearsal and said, ‘You're not going to believe this, but there's a kiss: Madonna kisses Britney’ and we were all like, oh my God,” Frattini remembers. “Something like that you keep quite confidential, but obviously it needs to be raised to the presidential level and all the executive producers because it's a decision the channel has to make.”

“I remember us all huddling and we were like, ‘This is gonna be amazing but, like, is this okay?’ Because, you know, people didn't do that back then,” Frattini continues. “We did our diligence by discussing it, all the way up to people like [then Chair and CEO of MTV] Tom Freston. He was like, ‘If Madonna wants to do this, let’s do it.’”

Equally as infamous as the kiss itself was the decision to cut to Spears’ recent ex-boyfriend’s pensive, painfully controlled reaction. “All you can do is plan it and script it and block it,” Frattini notes. “We knew Justin [Timberlake] was going to be there, so I think that was intentional.” The domino effect of the call was losing most of Aguilera’s kiss in the process, a move that caused much controversy, with Aguilera’s camp reportedly furious at the network for spoiling her moment. As director, McCarthy Miller was the one who pulled the trigger on the cutaway, a decision she looks back on without regret.

“I feel bad about that but I mean, that cutaway makes the whole performance, his face in that moment is priceless. If I didn't do that, people would have been like, ‘I can't believe we didn't see Justin react to his girlfriend being kissed by Madonna,’” she says. “That reaction is worth every single second of it, and we did go back and you saw Christina. Her people felt like it took away from her moment, but she had come out with “Dirrty” and had already pretty much changed her image, whereas Britney had not. I do think that even if I didn't do the cut away everyone would [still] have been talking about Britney and Madonna kissing.”

Whilst Aguilera’s camp responded with reportedly stern phone calls to MTV the next day, the artist chose to respond in the press, giving a now notorious interview with Blender magazine in which she expressed decidedly negative sentiments about the performance and referred to the decision to cut to Timberlake as “pathetic.”

Aguilera also criticized the VMAs as a whole, commenting: “The VMAs were so vanilla. So predictable, so safe, no edge. Apart from Madonna, Mary J. Blige, and myself, I cannot think of another female performer who had her mic switched on. That is very disappointing to me.” She went on to tell the magazine that she only accepted the “last minute” invitation because Madonna had told her it was mandatory to sing live, and that Spears had in fact sung live during rehearsals but an apparently last minute change of plans unbeknownst to Aguilera saw her mime to a prerecorded track during the actual performance. Recently leaked footage from the dress rehearsal seems to confirm these statements as Madonna and Christina’s vocals are different to the televised performance, whereas Britney’s sound identical to what we heard on the night. The live audio from the performance was later included as a track on Madonna’s Remixed & Revisited album.

“[Christina] was live live. She could sing. Britney's voice always needed a little bit of background vocals underneath it,” Frattini explains. Norsworthy, now a successful visual artist in his own right, recalls the trio practicing the song during rehearsals. “There was actual singing! I remember Madonna, joking of course, when Britney was singing, saying, ‘Oh my god, Britney, even I can sing “Like A Virgin!’”

Norsworthy also recalls the artists rehearsing the famous kisses repeatedly, and suggested one reason why Aguilera may have been disappointed with how things transpired. “Here's some tea: During the rehearsals, the kiss with Christina was much hotter and sexier. She committed to it every time. Britney kind of went, mwah, and walked away. She was like, ‘I'll save it for when the cameras are rolling.’ The camera panned to Britney and Madonna, but Christina and Madonna arguably had a more intense kiss.”

Timberlake may hold the title of most memorable reaction shot, but the audience as a whole were very much the fifth star of this performance. Rewatching it two decades later, the clip is a veritable who’s who of early noughties pop culture, and McCarthy Miller and her team expertly cut to shots of them watching the women on stage to tremendous effect. You’ve got the pop stars’ many opponents in the press, such as the aforementioned Lavigne and Osbourne, as well as Eminem, who had famously taken misogynistic shots at both Aguilera and Spears in his lyrics, and Mary J. Blige looking utterly unimpressed at Aguilera’s entrance. (She would later go on to publicly state her dislike for the singer.)

“We need to be on the cover of every newspaper the next day.”

Also visible are their peers (Beyoncé, Myá), who seem genuinely interested and impressed by the spectacle, as well as those who are just there for a good time, like the dancing Hilton sisters and Lindsay Lohan or, best of all, Carson Kressley and the cast of Queer Eye, seen holding onto each other with jaws dropped, seemingly the only people in the room fully grasping the gravitas of what they were witnessing on stage. “It was an energy of shock that I have never experienced before, not at any sports games or championship,” recalls singer Myá, who presented Best Male Video with Pamela Anderson that night. “The audience was so loud and excited. I was happy to be there in the flesh to experience such an invigorating, shocking moment. We just knew that it was going to be a headline topic.”

Needless to say, a headline topic it was. The following morning the New York Post ran the headline “Madonna’s 2 Kinky Kisses,” referring to the performance as “a red-hot, all-girl smooch-fest,” whilst Entertainment Weekly called it “sexy, vaguely transgressive, and as meaningless as it was entertaining.” CNN aired coverage vox-popping viewers opinions which ranged from “obnoxious” and “nasty” from the female passersby to “sexy” and “very good” from the men. The artists’ peers also weighed in; Beyoncé remarked that she couldn’t do what they did, calling the performance “a real eye-opener,” and Dave Navarro, who later that night performed with Aguilera for a rendition of “Fighter,” commented that Madonna looked younger than both ingenues. Stevie Nicks was less diplomatic, labeling the performance “the most obnoxious moment in television history” and commenting that Madonna was too old to be kissing the younger ladies.

Rewatching the performance two decades later, it’s slightly difficult to see why it caused such a fuss. By today’s standards, the performance is relatively tame, but in 2003, the world was more easily shocked, and most countries were even more uncomfortable with the idea of two women kissing than they are today. In the years that followed, Spears and Madonna would reference the moment on a number of occasions, firstly in Spears’ music video for “Me Against The Music” later that year, and again in a photo taken at Spears’ 2022 wedding in which they recreate their historic smooch. Aguilera, meanwhile, has mostly remained silent on the topic, save for her savage remarks to Blender, though she did touch on the topic in a 2018 interview with Andy Cohen, recalling seeing the newspapers the next day and realizing she had been “left out” of the moment, but that she still walked away pleased thanks to her own solo performance that night.

When Norsworthy recalls being onboarded to the creative team for the performance, he remembered the brief from Madonna being quite simple: “We need to be on the cover of every newspaper the next day.” With that in mind, it’s safe to say she achieved what she set out to do, and then some. This monumental performance has dominated VMAs coverage not just the following day but arguably every year since, being listed by MTV as the number-one opening moment in the award show’s history in 2010.

“Only Madonna knows how to do that,” Norsworthy declares, and it’s true. Who else could pay tribute to one of the most shocking and memorable VMAs performances of all time with an homage that would actually eclipse it in public memory?