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At the prime-time Emmy Awards ceremony in Los Angeles on September 19, 2004, Conan O’Brien sat with his group in the audience, close by Lorne Michaels, who, since he still retained an executive producer credit on Late Night, would take home a prize if Conan’s show won for best comedy or variety show. Michaels was also present because his meal ticket, Saturday Night Live, had been nominated in the same category.

Almost every season both shows would share the nominations with Letterman, perhaps Bill Maher’s HBO series, and inevitably with The Daily Show. Inside Conan’s camp the frustration mounted: starting in 2003 Jon Stewart’s show racked up wins every year in that category as well as the best-writing award, a streak that would continue right through 2009. As much as Conan and his group tried to shrug off Stewart’s success—topical and political humor always impressed awards types, they reasoned—it quietly drove them all nuts. They had all worked so hard, come up with so much distinctively original material, but they never got a shot to be recognized—because Jon Stewart was always there.

Michaels, who was losing every year as well with SNL, was more philosophical about Stewart’s winning streak. With his insight into Conan’s darker side, he knew this level of frustration with Stewart’s Emmy dominance could not be productive for the melancholic Irish comic. So, just as the telecast began, Lorne thought he should offer a helpful observation.

“Look around this room,” he said to Conan. “Do you see anyone who looks like you in this room? You know, there are a lot of very small Jews in the room.”

Lorne himself fit that description, though perhaps not as precisely as Stewart. But the joke was meant to let Conan know both that he shouldn’t take the Emmy voting too seriously and that Jon Stewart was no fluke. He was going to be around as a formidable player in late night.

Leno had a similar impression, which was why he feared a double-pronged assault from OʹBrien and Stewart. Leno refused to acknowledge any Emmy envy, however. He was never nominated anymore, which he put down to a typically perverse Hollywood dismissal of the merely popular. Jay would take numbers over trophies anytime. He had made that bargain with himself long before.

When Jay Leno was the most frequent—and popular—guest on David Letterman’s Late Night show in the 1980s, he eagerly embraced the role he had then carved out for himself: Mr. Cutting-Edge Comic. Letterman fans loved him for his ferociously funny harangues on the absurdities of life. Dave would simply set him up with “So what’s bothering you this time, Jay?” and Leno would be off, ranting about this idiocy (airline flights, bad movies) or that (corporate greed).

It gave him a profile in the business, which is what he wanted. But it wasn’t all he wanted. That level of success might make him money and attract favorable critical notices, but Jay was after the ultimate comedy career, and the models there were not Letterman or Richard Pryor or Sam Kinison. Jay consciously set out to have the career that a Bill Cosby or a Johnny Carson or—even more aptly—a Bob Hope had had. He wanted to be a comic for every audience.

That meant jettisoning Mr. Cutting Edge and slipping into Mr. Regular Guy. That persona was a snugger fit for Leno, anyway. He often joked about being “a great believer in low self-esteem,” but he came by the quality honestly.

One constant figure played a central role in Jay’s act, and in most of his stories about the formation of his character and views on life: his mom. Mainly Jay made merry references to his mother’s habitual embarrassment and emotional stringency, qualities he summoned up when discussing why he never wanted the title of his show to be the “Tonight Show Starring Jay Leno” as it had been with Carson, but instead insisted on the “Tonight Show with Jay Leno.” “Why would you want to call attention to yourself like that?” Jay would say, imitating his mother’s pinched Scottish accent. Of course, while the