Conan O’Brien might be the funniest man alive. Can he navigate hosting the Oscars?

The former talk show host and all-time great ‘The Simpsons’ writer is taking the helm of the Academy Awards for the first time. Kevin E G Perry looks back at his storied career and examines how he’ll handle Hollywood’s biggest night in a city still reeling from devastating fires.

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.

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.

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.”.

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.”.

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.