March 26, 2000. The 72nd Academy Awards. While most of the A-list crowd was busy obsessing over their tailoring and diamond loans, two guys from Colorado were sitting in a limousine outside the Shrine Auditorium, absoluteley losing their minds.
Matt Stone and Trey Parker dresses weren't just a random prank. They were a carefully planned act of "malicious compliance" that nearly fell apart at the last second because the duo was peaking on LSD.
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Trey Parker had just been nominated for Best Original Song for "Blame Canada" from the South Park movie. Most creators would see this as their big arrival. A seat at the table. But Matt and Trey? They felt like they didn't belong. They wanted to go, but they wanted to "not go" at the same time. Basically, they wanted to be there while simultaneously making fun of the fact that they were there.
The Plan to Subvert the Red Carpet
The original idea was to show up in something totally ridiculous, like Duck Hunter outfits or medieval armor. But they realized the Academy had a strict dress code. If they looked like they were mocking the event with "costumes," security would probably just bar the door.
Then came the lightbulb moment.
If they wore dresses that had already been worn to major awards shows, how could the Academy say no? It was a genius loophole. They weren't wearing "costumes"—they were wearing high fashion. Sorta.
- Trey Parker chose a replica of the green, navel-grazing Versace gown Jennifer Lopez had worn to the Grammys just a few weeks prior.
- Matt Stone went for the pink Ralph Lauren gown Gwyneth Paltrow wore when she won her Oscar in 1999.
They had the dresses custom-made to fit their... less-than-feminine frames. They even got the accessories right, down to the satin shawls and the jewelry.
Sugar Cubes and Panic Attacks
The dresses were only half the story. To really commit to the "magical" vibe of the evening, a friend gave them sugar cubes spiked with LSD right before they got into the limo.
Bad idea? Probably.
Trey has since admitted in interviews—most notably in the 6 Days to Air documentary—that the moment the limo door opened and they saw the sea of cameras, they realized they had made a huge mistake. The "trip" was hitting its peak. The flashbulbs were blinding. The crowd was a roar of noise.
They had a pact: no matter what happened, they would not acknowledge the dresses. If a reporter asked, "Why are you wearing that?" they had a scripted response.
"It’s just such a magical night. It’s a night of magic. Everyone looks so spectacular."
They said it over and over. Like a mantra. If you watch the old red carpet footage, you can see it in their eyes—they are on another planet. Trey looks like he’s trying to hold onto the Earth’s crust so he doesn't float away.
The Celebrity Reaction: Stares and Shoves
The Hollywood elite wasn't exactly thrilled. This was 2000. People took the Oscars way more seriously than they do now.
- Gloria Estefan: Reportedly gave them a look of pure, unadulterated disgust.
- Phil Collins: He was notably annoyed. This mattered because he was also nominated in the same category for his song from Tarzan.
- Gwyneth Paltrow: Matt Stone remembers her giving him an "icy stare" that could have frozen the Pacific.
However, not everyone was a buzzkill. Michael Caine reportedly thought the whole thing was hilarious. He saw the joke. He knew it was punk rock.
Years later, Trey ran into Jennifer Lopez at a party. He says she gave him a little "shove" as she walked by. Not a mean one, but a "hey, I saw what you did" kind of shove. Honestly, that’s probably the best outcome you could hope for after mocking one of the most iconic fashion moments in history.
The Brutal Come-Down
The worst part of the night wasn't the red carpet. It was the ceremony itself.
Think about it. You’re coming down from an acid trip. You’re sitting in a cramped theater chair. You’re wearing a dress that’s tight in all the wrong places. And you have to sit there for four hours while people give long speeches about "the craft."
They were miserable. Cold, tired, and sober-adjacent, they had to watch Phil Collins win the Oscar. To this day, Trey jokes that losing to Phil Collins was the real tragedy of the night.
Why the Matt Stone and Trey Parker Dresses Still Matter
This moment changed how we view the Oscars. Before this, the red carpet was a sacred space for PR-managed glamour. Matt and Trey proved that you could walk right through the front door and flip the bird to the entire establishment while wearing sequins.
It wasn't just "edgelord" behavior. It was a statement on the absurdity of celebrity worship. By wearing those specific dresses, they were pointing out how much weight we put on what people wear to these things.
Actionable Takeaways for Modern Stunts
If you’re looking to pull off a viral moment or a brand stunt in the vein of Matt and Trey, here is what actually worked:
- Use Malicious Compliance: Don't break the rules; use the rules to make the rules look stupid. They stayed within the "formal wear" guidelines but pushed the boundaries of intent.
- Commit to the Bit: Their refusal to explain the joke made it funnier. If they had spent the whole night saying "Look at us! We're in dresses!" it would have been a cheap gag. By acting like it was totally normal, they made everyone else feel like the crazy ones.
- Know Your Audience: They knew their South Park fans would love it, and they didn't care about the people who didn't.
Ultimately, the 2000 Oscars belong to Matt and Trey. Nobody remembers who won Best Supporting Actress that year without a Google search, but everyone remembers the green Versace and the pink Ralph Lauren.
To dig deeper into the actual logistics of that night, you can watch the 6 Days to Air documentary, which features a breakdown of the event. You should also check out the original red carpet interviews to see the "magical night" mantra in action.
Next Steps for You: Research the "Blame Canada" performance from that same night. Robin Williams performed the song on stage because the Academy was worried Matt and Trey would do something even more "out there" during the live telecast. It’s a perfect companion piece to the dress saga.