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For Jay, the job always seemed to be as much about the self-abnegation involved in the effort as the effort itself: “It just seems like common sense. If you go to a party, or go out drinking, I win. It doesn’t seem that hard to understand. I’m amazed at people who can’t get that.” (Jay swore that he had never consumed an alcoholic beverage in his life. Of course he never took drugs, either, and, he said, he steered clear of caffeine as well.) How much of this attitude was a function of his relationship with his mother was always difficult to guess for those close to Jay, because Leno rarely exposed his emotions. But Jay brought his mom up often, on stage and off, and usually in the context of how repressed she was.

Like in his story about Carnegie Hall. As his career was taking off, thanks to his many breakthrough appearances on Letterman (sixty, he estimated at this point), Jay was booked in the hallowed New York concert venue. At first, he said, his mother found this simply astonishing. “Why are you going to be in Carnegie Hall?” he quoted her. “She thought it was a mistake.”

But of course he wanted his parents at such a prestigious show, and he got them excellent tickets in the third row back, right in the center. Behind them was a row of seven or eight college-age guys. “These guys knew all the bits from watching Letterman,” Jay said. “So whenever I started something they recognized, these guys would go woo, woo and start to laugh and applaud.” Jay threw himself as usual into the bit but could not help noticing from the stage that his mother was turning around in her seat.

“She starts to go, ‘Shush! Shush!’ She’s trying to shush them.”

Appalled, Jay stopped his act to speak out to his mother. “Mom! You don’t shush people.” He realized it was another example of his mother being somehow humiliated and embarrassed by the attention he was getting. It made her completely uncomfortable.

Her discomfort seemed amplified when the contrast between her sons grew wider. Patrick’s life took unexpected turns, all unhappy in various ways—his marriage, his career. Jay, meanwhile, thrived. He started making solid money as a comic at a remarkably young age and was able to buy a house before all the other young comics in the LA scene at the time. He got on television. He was, of all things, booked into Carnegie Hall.

And then, The Tonight Show beckoned. It should have been a glorious accomplishment to share with his family, but it didn’t quite go that way. Jay sensed that Patrick had issues accepting his kid brother’s success. And his mother seemed to resist expressing a lot of joy about it as well. Jay, making millions, could afford to give his parents anything, but that became a sensitive area. Sometimes Jay would return home to Andover with an expensive gift for his mother—a piece of costly jewelry, for example. Jay would present it to his mother, who would quickly get fluttery and say, “Don’t tell your brother you bought this,” and then would run and hide the gift away.

Jay would explain all this and say he understood it; his brother had to feel cheated in certain ways. Patrick was stuck with the Scottish traits in the family; Jay inherited the Italian. (That’s where the good teeth and fantastic head of hair came from.) Patrick became a worrier, stressed over everything in his life. It only swelled the cloud of sadness that hung over his mother.

Jay’s confidants—and they were few—could only draw inferences from the snippets of his background that he dropped here and there. Jay never spoke of his mother without evident deep affection. Still, if some suspected that Jay had missed out on a full, externally expressed measure of motherly love, leaving him with a hole in his heart that he could never fill, and even refused to address, he was certainly no candidate for therapy. Jay disdained any kind of psychological mumbo jumbo, and not just because as a comic he was supposed to make fun of people’s foibles. Leno was not inner directed because he was primarily joke directed.