Conan O’Brien Shares Bizarre Oscars Rules That Left Him Stunned
Conan O’Brien, known for his sharp wit and outlandish humor, recently dished on some of the bizarre rules he encountered while hosting the 2025 Academy Awards. During his Conan Needs a Friend podcast with head writer Mike Sweeney, O’Brien revealed that the Academy had some surprisingly strict guidelines on how Oscar could be portrayed that weren’t up for negotiation.
One rule that baffled O’Brien was when The Academy strictly forbade the 9-foot-tall Oscar in his promo from lying down.
“One of the people from the Academy came forward and said, ‘Oscar can never be horizontal.’ And that blew my mind. Like, wow, this is like the thigh bone of St. Peter. This is a religious icon,” O’Brien jokingly recalled.
No Clothes for Oscar—Ever
O’Brien also wanted to dress Oscar as a housewife in an apron for a skit about domestic life with the famed statue. But apparently, even the idea of a clothed Oscar was too much for the Academy to handle.
“No clothing on Oscar. Oscar is always naked,” officials told him. So while the promo still got made, it was significantly toned down from his original vision.
A Scrapped Oscars Opening That Almost Happened
O’Brien also shared details about his original Oscars opening. While the final show kicked off with his now-famous spoof of The Substance (where he literally emerged from the back of Demi Moore), his initial plan was a much bigger and more chaotic.
The concept was a running gag where O’Brien was digitally inserted into multiple Best Picture nominees—but with one glaring problem: his green makeup from Wicked wouldn’t wash off.
“It starts with me and I’m in Wicked and I’m all green, finishing ‘Defying Gravity’ or one of those songs. And I finish it and then you cut to the next thing, which is Gladiator II and ‘clang, clang, clang’ with swords and you see that I’m a gladiator but then you notice that I’m still green,” he explained.
The joke would’ve escalated as O’Brien popped up in Conclave and Dune: Part Two, with Javier Bardem breaking character by calling him out for ruining every scene with his lingering green tint.
“We loved it,” Sweeney said of the scrapped skit. “It was hammered out before the fires happened, and even after that we kind of honed it.”
A Last-Minute Change of Plans
Unfortunately, after the devastating Los Angeles fires, the Academy decided to take a different approach. Instead of Conan’s parody-packed opening, the show began with a montage of famous movies set in LA, leading into a Wicked-themed performance by Ariana Grande and Cynthia Erivo before O’Brien’s monologue.
Still, the behind-the-scenes chaos and the Academy’s bizarre rulebook provided plenty of laughs for O’Brien and his team. One thing’s for sure—next time Conan takes the Oscars stage, he’ll know not to mess with the Academy’s golden boy.
