Leno's Regrets

As Conan takes over his slot tonight, Jay Leno is realizing his new 10 p.m. show will be far different than what he was promised by NBC and even his team is being reshuffled. Kim Masters reports that the pressure to succeed is even greater than when he took over from Johnny.

05.31.09 10:37 PM ET

After taping his final Tonight Show last Friday afternoon, Jay Leno went to a party at a The Castaway, a seriously un-Hollywood banquet hall in the hills north of Burbank.

“The party was at such a Jay place,” says one of the guests—a longtime Leno associate. It was outside and everybody was freezing. There was food and beverage but—nothing pretentious. Let’s put it that way.” Not one for parties, Leno was glancing at his watch by 7:30 p.m.

This guest came away with the sense that Leno is resigned to moving on from his late-night throne and was fixed in his determination that the transition for the new host, Conan O’Brien, be “classy.” Leno was ushered in to the Tonight Show 17 years ago with a chilly handover from Johnny Carson amid hostilities with Carson’s favorite son, David Letterman. “It was such a horrific, horrific experience,” this associate says. “He wanted no part of that kind of transition—and he remembers it like it was yesterday.”

“Jay thinks of his body as something to carry around his head,” quips a former network executive. “He does not take particularly good care about diet or exercise. It wouldn’t be surprising if at some point, that machine has to break.”

To this observer, Leno seemed calm and fit—looking far better than he did at an extraordinarily uncharacteristic appearance a couple of weeks earlier in front of an important audience of advertising executives in New York. Leno is legendary for never having an off night when he does standup, so it came as a surprise when he turned in a flat performance in a packed New York theater just after the network unveiled its fall schedule.

His material was dated. His jokes were stale. “He was doing Hurricane Katrina jokes. I mean, gimme a break,” admits an insider. One of the most striking aspects of Leno’s appearance was his mane of silver hair, which was strangely long and unkempt. An executive at a rival network says the performance—and the look—were discussed at a staff meeting the following week, where he heard that Leno’s hair looked “like it was done by a weed whacker.” An advertiser who skipped the comedy night got the same report from a colleague.

“Somewhere there was a hugely dropped ball,” says a former high-level NBC executive. “The question is what does it reveal?”

Indeed, there were recriminations within NBC about how this was permitted to happen. And the episode raised a question about Leno’s health. A couple of weeks earlier, the 59-year-old comedian had gone to a hospital, calling in sick for the first time in 17 years, and canceling the taping of two shows. He told People magazine, “I think I just probably got worn out.”

That simple diagnosis doesn’t surprise some who have worked with the tireless comic and who say his health has never been a priority. “Jay thinks of his body as something to carry around his head,” quips a former network executive. “He does not take particularly good care about diet or exercise. It wouldn’t be surprising if at some point, that machine has to break.”

In late-night circles, where some are watching the experiment of putting Leno on the air in prime time with undisguised malice. They say that Leno is angry and upset that he allowed himself to be talked into taking the 10 p.m. slot. He has realized that the new arrangement will alter the kind of show that he has to deliver far more than he anticipated. And he knows that he will be under intense scrutiny as the person who could save NBC—or not. “They’ve put a tremendous, tremendous amount on his back,” says a longtime colleague. “If we think he was under pressure when he replaced Johnny, that’s nothing compared to now.”

“Except for the first year, he’s been king,” this former colleague continues. “He’s never gotten the love and respect from critics. He’s gutted it out and it’s been a phenomenal performance. And the reward was, ‘Thank you very much. We’re going with Conan. We won’t be in a position where we lose Conan but we will be in a position to lose you.’ ”

Leno’s ambition was always simply to be king of late night. Now he’s been forced into change—and by all accounts he despises change. The proof, former associates say, is that he stayed at NBC. “God knows, Jay had choices,” one says. “There were two networks that would have paid very handsomely for him... Without a doubt, he knew he had choices but he chose the comfort of staying at home.”

Which turns out not to be so comfortable. Sources say Leno initially was led to believe he could essentially stick with the old format. Now the network has made it clear that he can’t. Late-night rivals figure Leno will have to limit the number of guests that he interviews or—as one puts it—“Conan’s people are going to have a fucking fit.” NBC is pressing for more sketch material and one source says that’s fine with Leno because he has never been especially fond of interviewing celebrity guests.

But that will only be part of the required change. In late night, the beginning of a program matters most; the last segment can be tossed to a band or a comic. The earlier part of the show counts more in the ratings. But with NBC’s affiliates demanding the strongest possible lead-in to their local news shows at 11, Leno will not have that luxury. A knowledgeable source says NBC feels that Leno can still sandwich softer segments into an earlier part of the show. The key will be to have “a lot of comedy up top and to end strong with a signature comedy bit,” he says. But a former NBC executive says any softer material invites viewers to change channels. “All 40-plus minutes of content and time are going to be critically important,” he notes.

And the changes go beyond what is seen on the air. A former associate says one point of great pride for Leno has always been his image as “a super-nice guy who never fires anybody.” (During the 2007 writers’ strike, Leno famously paid his staff out of his own pocket for part of the time they were out of work. Though it must be noted that many writers think he compromised that super-nice-guy image by going back on the air during the strike despite his public support of the guild, of which he is a member.) But now his team is being re-shaped thanks to cost pressures and the creative demands of the new show. Veterans are being pushed out. The former associate says Leno is a “robot” who isn’t particularly attached to individual staff members. But he worries deeply about potential damage to his image—and he simply hates change.

If Leno can adjust—as many expect that he will—that flat night with the advertisers in New York will quickly be forgotten. Even the advertisers know that they are not the audience that Jay attracts, says a former NBC executive. It will be America—especially the part between the coasts—that counts.

But another ex-colleague thinks that for now, Leno is not happy. “He is a huge professional,” this associate said. “But it’s not going to be easy and Conan’s not going to defer to Jay and lose his chance to be a star. He should have gone to ABC, where he could have kicked Conan’s ass.”

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Kim Masters is the host of The Business, public radio's weekly show about the business of show business. She is also the author of The Keys to the Kingdom: The Rise of Michael Eisner and the Fall of Everybody Else.