How Madonna Kept a Three-Way Kiss a Secret and Made VMA History 

How Madonna Kept a Three-Way Kiss a Secret and Made VMA History 
Video britney spears and madonna

Former MTV president Van Toffler had the history books on his mind when he asked Madonna to open the 2003 Video Music Awards. Toffler wanted to honor the VMAs’ nearly two-decade legacy with a callback to its inaugural 1984 edition. A lot had happened since Madonna rolled around in a wedding dress during “Like a Virgin” at that first awards show, but she remained the video era’s flagship star. Toffler hoped a plum spot on the program would motivate the Queen of Pop to outdo herself.

“I don’t have to encourage Madonna to go over-the-top,” he tells Rolling Stone 20 years later. “That’s in her DNA. We were just saying, ‘We’re gonna give you a lot of real estate. It’s a big moment.’ We talked about guest performers.”

Toffler got what he craved and then some when Madonna, beamed into 11 million homes from Radio City Music Hall, branzely kissed her foremost heirs, Britney Spears and Christina Aguilera, and set off a firestorm.

Today, the kisses seem fairly chaste. In 2003, they were scandalous. The morning after, the New York Post described the performance as a “raunchy, bump-and-grind dance routine that ended in explicit, open-mouth kisses.” (Never mind that it actually continued with Missy Elliott performing “Work It.”) When Madonna appeared on Oprah three weeks later, the kisses were the first topic she was asked about. “I had no idea that it was going to cause the ruckus that it caused,” she said.

In reality, she probably knew. There’s a reason the whole thing had been shrouded in secrecy. MTV didn’t advertise the performance, well aware that two semi-rivalrous pop darlings sharing the stage with Madonna and hip-hop’s reigning empress would play better if no one knew what to expect. Plus, enough had unfolded behind the scenes to leave MTV’s top brass wondering what would actually go down on the night of August 28, 2003.

According to Tom Calderone, former executive vice president of music and talent at the network, the VMAs were looking for a cheerier tone after Bruce Springsteen opened 2002’s show with the anthemic 9/11 memorial “The Rising.” So Toffler put in a call to Madonna’s manager, Guy Oseary, and let the singer decide how she’d fulfill the assignment. Producers might fine-tune a different artist’s act, but not Madonna’s, says Summer Strauch, who worked on the VMAs and other starry MTV programming.

“When you turn to Madonna, they were always very understanding that this is her creative moment,” Strauch says of the network’s chiefs. “They value whatever she chooses.”

Before long, Toffler and his staff learned that Madonna had recruited three peers: Spears, Elliott, and Jennifer Lopez, who was riding the success of “Jenny from the Block” and the No. 1 hit “All I Have.” That roster alone was worth celebrating, until MTV briefly worried everything might fall apart. During a pre-VMAs beach vacation Toffler took, he received a phone call reporting that Lopez had to drop out because she’d already agreed to shoot the movie Shall We Dance? that summer. Madonna’s stage requests were designed for four people. What would happen without one of them? “I was fearful that the performance was in jeopardy,” Toffler recalls.

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Madonna apparently chose Spears and Lopez because they were the best young dancers around, but Aguilera added another layer of excitement. The hot-and-cold dynamic between her and Spears, who co-starred on The All-New Mickey Mouse Club in 1993 and were perceived as pop-culture adversaries, made their dual participation almost as shocking as the ensuing kisses at the time. (Pink has said she and Gwen Stefani were also invited to participate at some point. No one I spoke to for this story recalls that, but producer Alex Coletti recently told PopSugar that he remembers Stefani’s name being floated.)

Once Aguilera replaced Lopez, Madonna’s private rehearsals began as MTV pieced together the rest of the show, which included a Metallica medley, Coldplay’s VMAs debut, and Beyoncé and Jay-Z singing “Crazy in Love.” Eventually, the network learned that Madonna planned to start the performance with “Like a Virgin,” with Spears and Aguilera atop a hydraulic wedding cake from which she would emerge. Then she’d transition into the single she’d just released, “Hollywood,” before tossing to Elliott (“Yo, yo, yo, who that be?!”). All of them would come back together at the end for a sort of tango set to a final reprise of “Hollywood.”

Madonna wanted as few people as possible to know the details, so rehearsals were locked down, Strauch says. The most MTV’s executives saw of the prep process was select videotape footage, and none of it showed any headline-worthy PDA. They watched Spears and Aguilera eat up Madonna’s every word as she tweaked their dance moves and acted as an elder stateswoman. “Madonna kept making them do things over, and they were totally listening to her,” Strauch says. But sources say it wasn’t until about two weeks before the broadcast when a full picture presented itself.

The VMAs’ veteran director, Beth McCarthy-Miller, whose credits include Saturday Night Live and many noted sitcoms, flew to Los Angeles to watch the women rehearse. One day, Toffler’s phone rang. McCarthy-Miller was on the line, whispering from the corner of a studio. “’You’re not going to be able to tell anyone, but I think this is going to make you happy,’” Toffler recalls her saying. “‘Madonna kisses Britney and Christina.’”

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Here came the “fuck-yeah” flash point Toffler and his team had hoped for, the bait that would reel in the kind of controversy MTV courted. “You knew it was going to be a moment,” Strauch says. “I remember everyone smiling and high-fiving.”

After that, secrecy became even more vital. During the official Radio City run-throughs the week of the show, Madonna’s team requested the building be cleared when it was her turn. Even without widespread social media, no one wanted to risk a Page Six leak. “Radio stations around the country were coming to do live broadcasts from there, so we had to get literally everybody out,” Calderone says. “And then you’ve got the gift room — that had to be evacuated. Even security. At the end, there were only a handful of us in that room, and a few people in the truck outside [where McCarthy-Miller and her team dictated the camera shots].”

On August 28, everyone was nervous — and fortunately, everything went off without a hitch. In fact, it was better than anyone could have predicted. Madonna’s six-year-old daughter Lourdes was the flower girl who crossed the stage and kicked the whole performance off. Spears and Aguilera appeared one by one, their faces covered in white veils that they each pulled back for dramatic reveals. After singing the first few lines of “Like a Virgin,” they rolled around the floor in wedding dresses. Then, Madonna ascended out of the giant cake wearing shiny black coattails and a Marlene Dietrich-inspired top hat — the groom for both brides.

Because the number opened the telecast, McCarthy-Miller and the producers treated reaction shots like a roll call announcing the VMAs’ attendees. Today, it plays like the ultimate mid-2000s who’s who: Beyoncé smiling and clapping; Avril Lavigne and Kelly Osbourne (who had recently covered “Papa Don’t Preach”) looking disinterested; a stone-faced Mary J. Blige; the original Queer Eye Fab Five having the time of their lives; Guy Ritchie (aka Mr. Madonna) cheering on his wife; an appropriately amused Snoop Doog; short-lived couple 50 Cent and Vivica A. Fox laughing along; Lindsay Lohan and the Hilton sisters dancing; and a surprisingly game Eminem.

The preeminent reaction shots, of course, belonged to Justin Timberlake: first, a raised eyebrow as Madonna, Spears, and Aguilera danced centerstage. Then, about 30 seconds later, as Madonna removed the garter on Aguilera’s thigh and swapped spit with Spears, associate director Stefani Cohen made the call to cut away from most of Aguilera’s kiss to show Timberlake looking irate. The decision, sources agree, was not premeditated. Cohen was monitoring the camera stationed on Timberlake, who had famously dated Spears and cast a lookalike in his barbed “Cry Me a River” video one year earlier. When the folks in the directors’ truck saw his expression, the choice was a no-brainer. It’s part of what makes the performance so unforgettable — a megastar’s stodgy response to his ex-girlfriend’s harmless frolic.

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Behind the scenes, the cutaway upset Aguilera’s management, even though she had her own separate performance scheduled. “That caused a little bit of grief coming my way,” Toffler says. “It didn’t make life easier that night, but you have to make choices in a live show. Sometimes you’re wrong and sometimes you’re right, but I think the beauty of the VMAs was the combustibility. You wanted to make it fun and semi-chaotic. That’s what we did.” Her team asked MTV to re-edit the performance for subsequent broadcasts, according to Calderone. The network didn’t comply. (Aguilera declined to comment for this story. “It was a cheap shot,” she told Andy Cohen in 2018. “I definitely saw the newspaper the next day and was like, ‘Oh, well, I guess I got left out of that one.’” You can see what the performance would have looked like without reaction shots in this rehearsal footage.)

Others were offended by the display as a whole — and not always the people you’d expect. “First of all, Madonna is too old to be kissing someone who is 22,” Stevie Nicks told an Australian newspaper a few weeks later. “And Britney should be smarter than that. Hopefully she will figure a way out of this hole she has dug for herself. I thought it was the most obnoxious moment in television history.”

MTV, meanwhile, got hate mail, according to Toffler. “It’s just par for the course,” he says. “The older demographic wasn’t ready for it.”

To Aguilera’s point, most people remember the Madonna-Britney kiss more vividly than they do the Madonna-Christina one — and sadly, even fewer remember that Missy Elliott was there at all. But the performance remains a relic of the VMAs’ glory days, when the show was still a watercooler staple worthy of that much star power. When Madonna attended Spears’ wedding last year, a quick smooch between the two prompted many news outlets to claim they were recreating 2003.

“It’s just quintessential Madonna,” Toffler says. “You give Madonna the germ of an idea or just the real estate, and she’s going to take it. She had a history of pushing us and pushing culture, and that’s what was great about her and what was great about MTV. We pushed culture in provocative ways.”