But that was then; this is wow. Today, O'Brien, 33, is one of TV's hottest properties. His show consistently whops Tom Snyder's Late Late Show in the Nielsens and this year earned an Emmy nomination for writing. Details has dubbed O'Brien Late Night's Newest King. And last June, Shales wrote an almost apologetic ode to the conquering Conan.
O'Brien, who describes himself as "genetically incapable of being cocky," claims there's no mystery to his metamorphosis. "If you put a donkey in front of a typewriter, in three years he'd get better," he says. But would the donkey get more relaxed around showbiz guests, as O'Brien obviously has? "I know I'll have fun with him," says Bay-watch's David Hasselhoff. "He genuinely makes me laugh."
Honing the show's warm but irreverent wit is hard work. O'Brien—who grew up in Brookline, Mass., the son of a doctor and a lawyer—puts in long hours perfecting such delicious bits as "In the Year 2000," an askew look at the future, and "What If They Mated?" a computer amalgam of celebrity offspring. Says Late Night producer Jeff Ross: "I have to push him to go home."
Even then, O'Brien takes work home with him in the form of Late Night talent booker Lynn Kaplan, 28. The two met in 1993 and are prone to discussing the show in their SoHo loft apartment. Such dedication has its rewards, though. Recently, NBC raised O'Brien's annual salary from $1.2 to $2 million and renewed his contract through 1997. Yet somehow this has made O'Brien less secure. "You tell me I'm hot," he says, "and I picture a magazine a year from now saying, 'Conan—what happened? We found him wandering the streets of Santa Monica wearing a mop over his head, weeping.' "