The star stepping up for a near-impossible Oscars job

As former talk show host Conan O'Brien takes the helm of the Academy Awards for the first time, Kevin EG Perry examines how he'll walk a precarious Hollywood tightrope

- Kevin EG Perry

What can we expect from Conan O'Brien when he takes the stage as Oscars host for the first time next 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 nervewracking 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 Oscarwinning 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