#27: ‘South Park’ Creators, Trey Parker, and Matt Stone in Replica Oscar Dresses
When: 72nd Academy Awards, 2000
When it comes to red-carpet fashion, everyone knows to expect the unexpected. But no one expected to see the creators of South Park, Trey Parker and Matt Stone, dressed in replicas of the dresses J-Lo wore at the 2000 Grammys and Gwyneth Paltrow’s pink number from the Oscars the year before.

Understandably, the screenwriters made this wild decision, but somehow, they ignored the very obvious stunt. When asked about their dresses during interviews, they simply answered, “It’s a magical night tonight.” The pair have since said that they were under the influence of certain substances, which can help explain this rather wild night.