It was one of those nights when live television was electric, unpredictable and completely unforgettable. Britney Spears made pop history with her performance of "Oops!… I Did It Again." Fred Durst jumped onstage with Christina Aguilera and fueled tabloid rumors in real time. The evening's wildest surprise came when Rage Against the Machine's Tim Commerford scaled a massive set piece and refused to come down after Limp Bizkit snagged Best Rock Video, sending producers panicking. Add in J.Lo and Diddy's red carpet arrival (and the chaos that followed), and it's no wonder the 2000 MTV Video Music Awards are still considered perhaps the most memorable in the network's awards show history. Salli Frattini, one of the show's executive producers, was the nerve center for all the mayhem, wrangling stars, crafting surprises and keeping the event from going off the rails. "When I went back and scrolled through the show again [before our conversation], I was like, 'Holy shit, all this happened at the same time,'" she says with a laugh to Yahoo. Here's the untold story of a night that lives in pop culture infamy. Before the broadcast even started on Sept. 7, 2000, the energy outside Radio City Music Hall in New York City was intoxicating. This was the height of theTotal Request Liveera, when pop stars and boy bands ruled MTV's airwaves. Frattini says it was no surprise that Spears and NSync garnered the most screams from onlookers who swarmed outside the venue to get a glimpse of their favorite artists. But that year,no entrance turned heads quite like Jennifer Lopez and Sean "Diddy" Combs. "As we're booking talent to come to the show, we very much deliberately would try to go after some of the trending couples. Obviously, J.Lo and Diddy dating at the time was a big one," she says. "They just both loved the press." Their red carpet appearance was orchestrated for maximum buzz. "We tried to really time their arrival so the majority of the press was there," Frattini says, recalling "a lot of discussion with their PR people" prior to the show about what they would and wouldn't do on the red carpet. When they stepped out of the car together, J.Lo and Diddystopped and turnedto a crowd of fans who were screaming from bleachers across the street. The couple posed for photographers and walked hand in hand into the venue. Of course, the most impressive entrances didn't end on the carpet. Eminem made sure of that when he performed "The Real Slim Shady," parading 125 look-alikes from the street to inside the theater. While it looked effortless on TV, it was also a logistical miracle. "A lot of what I had to deal with was shutting down Sixth Avenue, the busiest avenue in Manhattan. We were [airing] live, so it had to be very specific and coordinated — shutting down at this time, then reopening, trying to get the fans outside," Frattini says. "And technically, 20 years ago, we weren't where we are now with technology." Eminem, for his part, was all business. "He was always really professional. He would show up, do his job. He's no nonsense. He wasn't a chitchatter, like some other people. Just, 'Tell me what you need me to do,'" she says. This was also when Eminem was feuding with Spears and Christina Aguilera, both of whom were performing that night. When asked if she had to stagger rehearsals so they wouldn't run into each other, Frattini says it was never that deep. "You know what? We didn't," she says. "There definitely were some requests that would come in for management about 'personality sensitivities.' So we were trying to be conscious of that. I don't think we deliberately set up a sabotage moment. They [all] knew everybody would be there." Producers made sure to get a reaction shot of both Carson Daly and Fred Durst when Eminem rapped the song's verse about their supposed love triangle with Aguilera. That, she says, is just show business. "We strategically had to seat people so we could show [their faces] when [Eminem] would walk by," Frattini says. "It was great." Aguilera had more than just a cameo in Eminem's lyrics — she was about to make headlines herself, teaming up with Durst for a moment that was as unplanned as it was captivating. When Aguilera finished her performance of "Come On Over Baby (All I Want Is You)," all of a sudden, Durst rose from his seat in the audience and swaggered onstage, rapping Limp Bizkit's "Livin' It Up" whileshe sauntered around him. The two had already sparked hookup rumors in real life, and their collaboration came together at the eleventh hour, at Aguilera's suggestion. "That was [Christina's] idea, actually," Frattini recalls. "She said, 'Why don't we have him come up?'" Frattini says it was "barely rehearsed." "Fred's like, 'Yeah, sure, I'll do it,'" she continues. "The crowd went wild." In an era before everything leaked on social media, this kind of genuine shock was rare and priceless. "We were trying to make it a surprise — back then, thingsreallywere surprises," Frattini says. It was the kind of pandemonium Frattini and her team secretly loved: a little risky and the sort of live TV magic that turned the VMAs into appointment viewing, as Aguilera and Durst's onstage chemistry fed gossip columns for months to come. Aguilera wasn't the only pop princess who gave viewers something to talk about. With the world watching, Spears kicked off her performance with a medley of "(I Can't Get No) Satisfaction" into "Oops!.. I Did It Again" as she shed her black tuxedo to reveal a sparkly nude bikini top and tight pants with her abs on full display. Frattini says the stunt was carefully planned from the start. "We knew that was happening. That was intentional," she says. "We knew that was going to get a lot of eyeballs." Frattini says they ran the performance and Spears's wardrobe-shedding past legal and got the proper clearances. "She didn't expose any body parts," she says. Spears knew how to keep the audience's attention that night. She also teamed up with Aguilera to introduce Whitney Houston to the stage, a move that seemed impossible given their very public rivalry. For fans, it was a fever dream: the two reigning pop princesses, side by side under the spotlight, putting feud rumors aside, at least for the cameras. Pulling off that moment took some finessing behind the scenes, though Frattini insists it was never about orchestrating drama. "When we asked Christina and Britney to present together, that was a big idea," she says. The producers thought it was a long shot, but both stars were into it. "No one thought it could happen because there really was a little bit of a rivalry, but they did it, and it was fantastic," Frattini says. The reaction from the crowd was deafening, a moment that sticks with her today. The best VMAs moments are the ones you can't script. The biggest "did that really just happen?" highlight of the evening came courtesy of Rage Against the Machine's Tim Commerford. After Limp Bizkit won for Best Rock Video, the band's bassist scaled the 15-foot scaffolding on the stage in protest, where he dangled for several minutes. "That set was not designed for anyone to climb on. There was such a panic that the whole wall was going to come crashing down," Frattini remembers. "We were getting security in front of the stage to make sure nobody was under it, and we couldn't get him down. It messed up the next award." Frattini called an audible and had someone scramble and find Daly, who wasTRL's host at the time. "I was like, 'GET CARSON!'" she says. "He was always our contingency person." They put a camera on Daly to give viewers at home an update about what was going on. Commerfordwas later arrested. "When people watch all this on TV, they go, 'Oh, that looked easy,'" she says. "No. I know better." For Frattini, the show's enduring power comes down to authenticity and unpredictability, qualities she believes are increasingly rare now in live television. "Everything we did was live, live, live. Because of that, we made mistakes, and because of that, moments happened," she says. But for anyone who watched at the time, the 2000 show remains a master class in how thrilling an awards show can be. "Some of these performances, when you put them up, people are always blown away," Frattini says. It was a time when "everything felt so much more genuine to me and authentic." Over her career, Frattini would go on to executive produce several more VMAs — including the shows in 2002, 2004, 2005 and 2006. But nothing ever quite matched the fun chaos of that singular night in 2000. Now, 25 years later, as the MTV VMAs return on Sept. 7, 2025, Frattini still finds herself nostalgic for the era when anything could — and absolutely did — happen.