At the 27th Annual New Yorker Festival, flaming-haired former late-night host Conan O’Brien switched sides of the table with magazine editor David Remnick. O’Brien is clearly 100% Irish, but he’s far from 100% lucky: He has been nominated for an Emmy Award thirty-six times and won six times. His latest triumph is as host and executive producer of “Conan O’Brien Must Go” on HBO Max, where he concludes one of the longest tenures in late-night talk show history with a total of 28 years as host; he is the 2025 Mark Twain Award for American Humor. In addition to producing the podcast series “Conan O’Brien Needs a Friend,” he has kindly agreed to host the Oscars again next year.