One of the joys of seeing Conan O’Brien infiltrate the highest echelons of Hollywood society is that he’s a man with a very pointed sense of the absurd, being exposed to some very absurd spaces and rituals. He is, for instance, a guy who will be struck by the profound strangeness of being invited to host the Academy Awards, and then being told that he can’t do a promo sketch in which the Oscar statuette is depicted wearing an apron. “No clothing on Oscar,” O’Brien was told by some extremely serious Academy officials. “Oscar is always naked.”
O’Brien discussed these surprising restrictions on a recent episode of his Conan O’Brien Needs A Friend podcast, where he was chatting with his long-time writer Mike Sweeney, who served as head writer for O’Brien’s Oscars material. “The Academy of Motion Pictures, they are very serious about certain things,” O’Brien noted, being careful to acknowledge that the group’s members were also gracious and kind during the whole process. Describing the promo in question, which depicted himself and an Oscar in a failing marriage, O’Brien said, “At one point, I thought wouldn’t it be great if it’s just on the couch? Let’s lay it on a really big couch and I’ll be vacuuming and say, ‘Could you at least lift your feet? Or could you at least get up and help? Load the dishwasher?’ We wanted to do it and they just said, ‘No, no no, that can’t happen.’” After some deliberation from the members of the Academy present, one came forward and clarified: “Oscar can never be horizontal.”
The whole podcast is a genuinely fascinating look at how a show like this gets made, with O’Brien revealing that he actually worked out material in front of much smaller audiences before trying it out at the Dolby Theater. (He asked them not to record or rebroadcast any of the jokes, and they were happy enough to oblige). Also: He and his writers had to check all the other award shows leading up to the show to make sure they weren’t repeating any bits. He and Sweeney also gave a post-mortem on at least one very ambitious opening bit that ended up getting cut, which would have depicted O’Brien inserting himself into multiple movies, Billy Crystal-style—only to get called out for doing Wicked first, and being unable to purge himself of the green dye staining his skin as he ran through parodies of Conclave, Gladiator 2, and Dune.
Anyway: If you’ve ever wondered why nobody ever puts pants on “Oscar”: Now you know.
