At the twenty-seventh annual New Yorker Festival, the flame-haired former late-night host Conan O’Brien swapped sides of the proverbial desk with the magazine’s editor, David Remnick. O’Brien, who is apparently a hundred-per-cent Irish, is much less than a hundred-per-cent lucky: he has been nominated for an Emmy Award thirty-six times, and won six. His most recent win was for his work as the host and executive producer of “Conan O’Brien Must Go,” on HBO Max, where he capped off one of the longest tenures in late-night-talk-show history, with a total of twenty-eight years as a host; he was the 2025 recipient of the Mark Twain Prize for American Humor. In addition to producing a podcast series, “Conan O’Brien Needs a Friend,” he has kindly agreed to host the Academy Awards once again, next year.