June 3, 2000. Sony Pictures Studios in Culver City. If you weren't there, or if you weren't glued to a CRT television screen a few days later when the tape delay finally aired, it is hard to explain the specific brand of lightning MTV caught in a bottle. The MTV Movie Awards 2000 wasn't just another awards show. It was a cultural collision. It was the exact moment where the 90s hadn't quite died and the digital age was still a terrifying, shiny mystery.
Sarah Michelle Gellar and Sean Patrick Flanery won Best Kiss for Cruel Intentions. Think about that. A movie about wealthy, manipulative teens winning over massive blockbusters because the fans—not some room of aging academy voters—decided that was what mattered. That was the magic of this specific year.
The Night Sarah Jessica Parker Wore Everything
You can't talk about the MTV Movie Awards 2000 without talking about the hosting. Sarah Jessica Parker was at the absolute summit of her Sex and the City fame. She didn't just host; she performed a marathon of costume changes that felt like a fever dream. Fifteen outfits. Or was it fourteen? Honestly, by the time she walked out in a massive pink tutu and later a "John Travolta" inspired suit, nobody was counting. They were just watching.
It was ridiculous. It was high fashion mixed with total absurdity.
One minute she’s doing a parody of The Blair Witch Project—which, let’s be real, everyone was parodying back then—and the next she’s introducing Metallica. This wasn't the polished, sterilized PR-managed hosting we see today. It felt frantic. It felt like anything could go wrong, which is why we all watched MTV in the first place.
Tom Cruise and the Mission Impossible Era
The year 2000 was a massive year for Tom Cruise. Mission: Impossible 2 was the behemoth of the summer. He actually showed up. That’s something people forget about the MTV Movie Awards 2000—the A-listers actually respected the Golden Popcorn.
Cruise didn't just sit in the front row. He participated in one of the most famous sketches in the show's history: "Mission: Improbable." This was the introduction of Ben Stiller as Tom Crooze, Cruise's intense, squinting stunt double. It was self-deprecating in a way that Cruise rarely is anymore. Seeing the world’s biggest movie star laugh at his own intensity alongside Stiller was a peak "pre-couch-jump" moment. It showed that the show had enough gravity to pull in the biggest names in Hollywood but enough irreverence to make them look silly.
The Matrix vs. The World
If you want to understand the cinematic landscape of the turn of the millennium, look at the winners. The Matrix didn't just win Best Movie; it swept the floor. It took home the gold for Best Male Performance (Keanu Reeves) and Best Fight.
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The fight scene? Keanu Reeves vs. Laurence Fishburne.
It beat out the lightsaber duel from Star Wars: Episode I – The Phantom Menace. That was a huge deal. It signaled a shift in what the youth culture valued—moving away from the nostalgia of Lucasfilm and toward the high-concept, leather-trench-coat cyberpunk aesthetic of the Wachowskis. The MTV Movie Awards 2000 acted as the official coronation for The Matrix as the definitive film of a generation.
Interestingly, The Sixth Sense was also all over the ballot. Haley Joel Osment won Best Breakthrough Male. He was this tiny kid standing on a stage that usually smelled like cigarettes and expensive perfume, thanking the fans for liking a movie about dead people. The diversity of the nominees was wild. You had American Pie competing against The Green Mile. It was a chaotic era for cinema where "prestige" and "gross-out comedy" lived in the same house.
Musical Performances that Defined the Y2K Sound
MTV was still Music Television in 2000. Sorta.
The performances at the MTV Movie Awards 2000 were a snapshot of a transition. On one hand, you had D'Angelo performing "Untitled (How Does It Feel)." It was minimal. It was soulful. It was incredibly bold for a room full of screaming teenagers.
Then you had N'Sync.
They performed "It's Gonna Be Me." This was the peak of the boy band era. The choreography was tight, the hair was frosted, and the screaming in the audience was loud enough to blow out the speakers. But then, just to keep the "rock is not dead" crowd happy, Metallica showed up to play "I Disappear" from the M-I:2 soundtrack. This was the era where Lars Ulrich was starting the whole Napster war, and seeing them on an MTV stage felt like the last gasp of the traditional music industry before everything went digital and fell apart.
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Why 2000 Was Different from the Modern Era
Nowadays, awards shows feel like a chore. Everyone is afraid of being canceled. Every joke is run through five lawyers. But back in 2000?
Jim Carrey won Best Villain for The Grinch... wait, no, that was a different year. In 2000, Mike Myers won Best Villain for playing Dr. Evil in The Spy Who Shagged Me. Think about that. A comedic character won Best Villain over actual scary antagonists. Why? Because the MTV Movie Awards 2000 was about what was fun.
The "Best Musical Sequence" category was still a thing. South Park: Bigger, Longer & Uncut won for "Uncle F**ka." Can you imagine that happening now? A profane, animated musical number winning a major award on a televised broadcast? The censors were working overtime, but the energy was undeniable.
The Fashion Disasters We Miss
We have to talk about the red carpet. It was a sea of low-rise jeans, tinted sunglasses, and leather blazers.
- Aaliyah showed up looking like a literal goddess in Roberto Cavalli.
- The Spice Girls (well, some of them) were there.
- Fred Durst was everywhere.
The fashion wasn't curated by stylists trying to get a "Best Dressed" nod in Vogue. It was celebrities dressing like they were going to a very expensive club in the year 2025 as imagined by someone in 1985. It was tacky. It was brilliant. It was honest.
The Best Kiss Legacy
The Best Kiss award is the "Big One" for MTV. In 2000, it went to Selma Blair and Sarah Michelle Gellar. This wasn't just a win for a popular movie; it was a massive moment for LGBTQ+ visibility in mainstream media, even if it was presented through the lens of a teen thriller. When they went up to accept the award, they didn't just say "thanks." They leaned into the moment.
It highlighted what the MTV Movie Awards 2000 did best: it focused on the visceral moments of movies. The Academy cares about "cinematography" and "sound mixing." MTV cared about the kiss that made you gasp in the theater and the fight scene that made you want to take karate lessons.
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The Forgotten Winners and Oddities
Not everything has aged perfectly. Austin Powers: The Spy Who Shagged Me took home a lot of hardware. Does it hold up? Parts of it do. But in 2000, Mike Myers was the king of the world.
Adam Sandler won Best Comedic Performance for Big Daddy. It’s easy to forget how much the "Sandler Era" dominated the early 2000s. He was the voice of the everyman, and MTV was his pulpit.
Then there were the nominations that feel weird now. Star Wars: Episode I was nominated for Best Movie. History hasn't been kind to that film, but at the time, the hype was still a physical force. The fact that it lost to The Matrix tells you everything you need to know about where the culture was heading. We were tired of the old myths. We wanted the red pill.
How to Revisit the Magic
If you’re feeling nostalgic for this era of pop culture, you can’t exactly go buy a DVD of the broadcast. MTV famously doesn't release these shows because of music licensing nightmares. Trying to clear the rights for Metallica, N'Sync, and D'Angelo on the same disc is a lawyer's worst nightmare.
However, you can still find the highlights.
- Search for the "Mission: Improbable" sketch on YouTube. It’s still one of the best parodies ever made.
- Look up the 2000 fashion galleries. Specifically, look at what Beyoncé and Destiny’s Child wore. It’s a time capsule of "Survival" era aesthetic.
- Watch the Cruel Intentions acceptance speech. It’s a reminder of a time when the Movie Awards felt genuinely edgy.
The MTV Movie Awards 2000 was the end of an era. Shortly after, reality TV began to swallow the network. Jersey Shore and Teen Mom were on the horizon. The focus shifted from movie stars to "people famous for being famous." But for one night in June, the biggest stars in the world gathered in a room to hand out gold-plated popcorn and celebrate the fact that movies were still the coolest thing on the planet.
To truly understand the impact, go back and watch The Matrix or Cruel Intentions. Look at them not as old movies, but as the films that defined the year 2000. That energy—that weird, leather-clad, Y2K-bug-fearing energy—is preserved forever in the footage of that night in Culver City. It was the last time the "Youth Vote" felt like it could actually change the direction of Hollywood. And maybe, in some small way, it did.