5. South Park
Directors Trey Parker and Matt Stone arrived to the 2000 Oscar ceremonies dressed in drag to support their film South Park: Bigger, Longer, and Uncut. The song “Blame Canada” had been nominated as Best Original Song, and the two directors were more than eager to take advantage of what they assumed could be their only Oscar invitation ever. Stone arrived dressed in a stunning pink gown; similar to the one Gwyneth Paltrow wore the previous year. Parker wore a green dress with a plunge front similar to the one Jennifer Lopez had worn. The two were fun and good humored, and interviewers loved to talk to the pair.
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