What can we expect from Conan O’Brien when he takes the stage as Oscars host for the first time this weekend? His track record suggests he should be good for a few laughs at least: there’s a pretty convincing argument to be made that he’s among the funniest people alive. For a start, consider his contributions to the funniest TV show of all time. Back in 1991, shortly after quitting a writing gig at Saturday Night Live, a then-28-year-old O’Brien joined the staff of The Simpsons and found himself heading to a “story retreat” at a hotel to pitch episodes for the hit animated sitcom’s fourth season. He was, he recalled later, “petrified”.
Presided over by legendary director and producer James L Brooks, who would literally bang a gong to decree he approved of a pitch, Simpsons story retreats were notoriously nerve-wracking affairs for new contributors. It was rare for a writer to get more than one story idea accepted. O’Brien sold his first two. Then he pitched a third: a monorail comes to Springfield. “It was like being in Vegas,” O’Brien remembered. “You’re hot, you just go for it.” Showrunner Al Jean told him: “You’re still the only guy who has cleared three in one day.”
Marge vs the Monorail, O’Brien’s madcap melding of Oscar-winning musical The Music Man and the disaster films of the Towering Inferno producer Irwin Allen, is now widely considered among the greatest episodes from arguably the greatest season of a sitcom ever made. Not bad for a writer who previously had only ever written sketch comedy.
O’Brien spent just two years at The Simpsons before he was handpicked by SNL producer Lorne Michaels to take over from David Letterman in the coveted role of host of the US talk show institution Late Night. Despite some disparaging early reviews, O’Brien would continue hosting various wildly inventive, Emmy-winning and consistently hilarious late-night shows for almost 30 years up to his retirement from the format in 2021. In that time he also hosted the Emmys twice, in 2002 and 2006, and in 2014 memorably rounded up 50 celebrities, including Taylor Swift and Andy Samberg, to help him introduce his gig at the MTV Movie Awards. The biggest surprise when he was announced as host of this year’s Oscars is that he’s never done it before.
What makes O’Brien such a good awards show host is the same thing that cemented his popularity as a talk show host. He’s sharp-witted and breezily self-deprecating, with an ability to flit easily between high and low brow. Some of the most memorable moments from his talk show years saw him embrace anarchy, whether it be the 2000 episode where he was attacked by a kangaroo, or the even more famous 1997 episode where he egged Norm Macdonald on to savage comedian Carrot Top’s ill-fated shot at movie stardom, Chairman of the Board (“I bet board is spelled B-O-R-E-D.”)
While his style of comedy is certainly edgier than the talk show hosts he followed onto the air – among them Letterman or Johnny Carson – he has a knack for putting celebrity guests at ease in a way that mercifully avoids coming off as cloying. He’s happy to follow guests down whichever rabbit holes they lead him into: witness his long-running bit with Paul Rudd where every time the actor appeared on one of O’Brien’s shows, he’d play the exact same bizarre clip of an alien in a wheelchair going over a cliff from 1988’s Mac and Me instead of whatever Rudd was supposed to be promoting. Since 2018, O’Brien’s Conan O’Brien Needs a Friend podcast has showcased a more relaxed and vulnerable interview style compared to the tightly choreographed highwire act of late-night TV.
Perhaps the only reason O’Brien hasn’t taken charge of the Academy Awards before is that the job is so often seen as something of a poisoned chalice. Jimmy Kimmel has done it four times since 2017 but reportedly turned down the chance to return this year citing a preference to focus on his own late-night show. Stand-up comedian John Mulaney is thought to have passed up the opportunity too. Asked why he agreed to the gig, O’Brien was as usual ready with a wisecrack. “I’m saying yes to things that I wouldn’t have done before,” he told Good Morning America. “I’m a black belt in karate now. I’m a licenced neurosurgeon. There’s all these things I’m doing now that I didn’t think I would ever do before.”
Unlike Nikki Glaser, who made her name at celebrity roasts and won plenty of plaudits for her finely calibrated needling of the stars at January’s Golden Globes, O’Brien isn’t the sort of host likely to try and score points by mocking his star-studded audience. He’ll prefer to be the butt of the joke himself. “I can let someone have it if I think, in the moment, they really need it,” he’s noted. “But I’m also very comfortable, as a comedian, putting the joke on me.”
He is, however, likely to embrace spontaneity and lean into any mishaps. When he split his pants on his talk show, he immediately turned it into a bit. Expect any fluffs or slip-ups at the Oscars to be similarly mined for comedy gold. O’Brien said recently that it’s a misconception to think hosts want everything to go perfectly. “I’m someone who hopes that things go a little off the rails, because that’s where the real memorable moments happen in late-night television and at the Oscars,” he told iHollywoodTV. “So I’m going to plan for some terrible, terrible mistakes.”
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And don’t rule out a big song-and-dance number. In 2014, O’Brien took to the stage at the Hollywood Bowl to perform “The Monorail Song” from that celebrated Simpsons episode, so he’s not above putting on the ritz when required. He joked to GMA that after spending “a lot of my own money polling Americans” he found a shocking response to whether the country hopes he’ll sing: “People don’t want it, which means I’ll probably try and do it.”
In truth, how broad and exuberant a performance O’Brien is able to deliver will have to be finely calibrated to the prevailing mood in Hollywood, a town still reeling from the devastating fires that so badly affected multiple neighborhoods across Los Angeles. O’Brien himself was one of the thousands forced to evacuate from the Pacific Palisades, although his home was ultimately spared from the flames. He’s described the atmosphere in the city as “fragile,” noting: “This [was] something that touched everybody, regardless of income.”
There are many who have questioned whether the Oscars should even be going ahead. Hacks star Jean Smart argued the ceremony shouldn’t be televised, while author Stephen King said he wouldn’t take part in voting and thought the show should be cancelled. “To me,” he wrote on social media, “it feels like Nero fiddling while Rome burns.” The Academy subsequently announced that the ceremony would do without Best Original Song performances and will instead use that time in the show to “honor Los Angeles as the city of dreams, showcasing its beauty and resilience.”
The weight of that responsibility makes the Oscars hosting gig an even more precarious tightrope than it already was. Speaking at the Sundance Film Festival last month, O’Brien told The Hollywood Reporter that he and his writers have “a million ideas” for the Oscars but that they won’t know until much closer to the day what they’ll actually use. “What’s going to be appropriate? What’s the right tone?” he asked rhetorically. “The tone might shift somewhat one way or the other. It’s a moving target, so I want to make sure that we do the show that meets the moment on March 2, and that we put a light on a lot of the people in LA that have been affected.”
He went on to say that he hopes the show will land somewhere between sensitive, understanding, uplifting and fun. “It’s a crazy combination,” he acknowledged. “This is a massive moment, this is a terrible thing that’s happened in Los Angeles. I know that people are politicizing it and yelling about it, [but] it’s just a human tragedy.
“We see these all the time, all around the world on our television sets and then we go back and, you know, eat our turkey burger that just got delivered. Now, I happen to live in the city where something like this has happened, and I think we’re taking a moment to try and absorb it. As an entertainer I need to try and figure out: What’s the best way to respond to this? We will figure that out over the next five weeks, and it’ll probably come together 45 minutes before the show.”
It’s a near-impossible gig, so the Academy are surely thanking their lucky stars they’d already booked the ideal person to take it on. Over three decades on television Conan O’Brien has proved time and again his ability to read the room, understand the moment and, somehow, find the laugh.
