The War for Late Night (19 page)

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. He stripped away almost any other interest—other than his vehicles, which he worked on avidly, filling just about every waking hour when he wasn’t writing or telling jokes. He certainly didn’t chase women. His marriage to Mavis did not strike colleagues as gooily romantic (they didn’t seem to spend much time together), but it was, by every indication, solid and comfortable to both. Jay, in establishing his mainstream bona fides, would always point out, “I’m still on my first wife.”

He and Mavis had never had children. They rarely vacationed together, mainly because Jay abhorred the very idea of vacation. During weeks off he booked himself into Vegas or some high-paying corporate retreat, while Mavis often traveled the world. Jay loved to tell a story of an ill-advised decision to take a booking in Hawaii, with an extra day scheduled afterward to relax on the beach. A morning on the beach led him to wonder if his watch had become filled with sand, because it indicated that only an hour had gone by when surely he had been out there all day. He was on a plane back to LA before noon. Jay also famously asked NBC to consider hiring a separate staff of writers and producers for the six-to-eight-week period that the show was scheduled to be dark so he could work all fifty-two weeks of the year while the rest of the regular staff got a break. (NBC politely declined.)

His aversion to going anywhere except places where he could tell jokes led to his making pronouncements that even his closest associates acknowledged sounded bizarre. “You start taking vacations and you go, ‘Uh-oh, what if I like this?’ Then you’re screwed.” The whole notion of going somewhere and doing something simply because it was pleasurable or interesting was a concept Jay simply didn’t get. “I understand how people spend money to buy things they need or they like,” Jay said, summarizing his philosophy. “But spending money on an experience? That seems like an extravagance to me.”

Of course, even though he always avowed that he never spent a dime of his NBC salary and lived only off the money from his stand-up dates, it didn’t seem to dawn on Jay that most of the people coming to see him tell jokes were on vacation and were paying for that experience.

Critics—as well as occasionally the network and his own producers—often cited Jay’s apparent lack of interest in the stories guests on the show told. Certainly most of the staff knew that Jay devoted little time preparing to speak to guests. Worse, at least for some, was a habit Jay adopted later in his
Tonight Show
run. As described by one A-level movie star guest, an appearance with Jay could be thoroughly disconcerting.

“I’m sitting there telling him a story about some damn thing that happened and I realize he’s not looking at me at all,” the star said. “His eyes are going straight past me. The audience can’t see this because he’s still looking vaguely in my direction, but his eyes are not on me at all. When he went to commercial I took a look over my shoulder. There was a guy with cue cards standing off to the side behind him. Jay was just reading the questions off the cards. Not paying attention to me at all. The whole thing was so artificial; I was totally put off by it.”

Jay’s day was so consumed with reading and deciding on jokes that he usually had to be clued in that it was time to stop. “By the afternoon he would have been reading jokes for about five hours,” one longtime staff member said. “He would have culled them down to about a hundred fifty by that point from at least five hundred. Then about four p.m. someone would go to him and say, ‘You can’t read any more jokes.’ He would go down to rehearsal, but while rehearsing whatever the comedy bit was in act two, Jay would still be reading more jokes right through the rehearsal.” Throughout the process, Jay would rarely, if ever, laugh.

But for Jay his method worked. Forget the Emmy Awards, the critics, the comparisons to Dave or anybody else. Others might watch him and shake their heads in wonder. Some might call him a robot, with no apparent inner life at all. Jay didn’t care, nor did he even seem to disagree all that much. He had boiled it all down to the most basic level, in a way that made others in the field of comedy sometimes wince and moan. No matter; Jay stuck steadfastly to his approach. After all, it was the secret to his success:

“Write joke; tell joke; get check.”

F
or six months or so Jay Leno would be fine.

Throughout the fall of 2004 and early 2005 his routine would be as it always had been. Around first light he would climb into his chosen vehicle for the day (1937 Bugatti, 1955 Buick Roadmaster, 1915 Hispano-Suiza, 1987 Lamborghini Countach, 1934 Rolls, 1996 Dodge Viper, 1926 Bentley, 1932 Duesenberg, 1909 Stanley Steamer—whatever choice from his ever expanding collection he and his garagemates had most recently restored to full driving condition) and make his way over the hill to Burbank from his home in Beverly Hills. Upon arriving on the NBC lot he would park in his designated spot adjacent to the entry ramp, pull out his battered leather saddlebag of a briefcase stuffed with jokes and the research the staff had provided on news stories and guests, and roll on in to work.

Many mornings the first one in, he’d settle down at his desk and pore over the jokes he and his head writer Joe Medeiros had committed to index cards late the night before in Jay’s home office. At the same time he would be culling printouts of the e-mailed jokes that had been submitted by the group still known as the faxers (a holdover from a bygone technological day), the pay-by-the-joke freelance contributors who got seventy-five or a hundred dollars apiece for every gag Jay used on the air.

When Debbie Vickers arrived hours later, she would take a reading of Jay’s demeanor. Most days she could discern the familiar attributes: steady, purposeful, joke obsessed. It didn’t mean Jay was no longer feeling the disappointment, resentment, and regret that NBC’s long-range termination notice had planted inside him. It meant only that, for the moment anyway, he was living by what he called “the first rule of show business: Don’t create anything bigger than your act.” Jay interpreted the rule to mean that, if you found yourself consumed by something bigger than what you are known for, your downfall was assured. If something distracting or dispiriting was going on in his life, his duty was to shrug it off, get back in the game of telling jokes, and be funny, day in, day out.

But after those initial six months passed, Vickers knew that every day would no longer be conventional. There came a morning, and then several mornings, when Jay’s demeanor was clearly different: sullen, chagrined, joke obsessed. On those days Leno would unburden himself to Vickers, spilling out his undissipated confusion over NBCʹs decision. His unhappiness was only exacerbated if he played a gig somewhere and faced bewildered fans asking, “Why are you retiring, Jay?” He would try to laugh it off, tell them of course he wasn’t really retiring, he would still tour and be around plenty. But the exercise was excruciating. So was having to deal with the guests who brought up the subject on the air, with cracks about being put out to pasture or some other dopey expression.

“I’m just sick of lying,” Leno told Vickers.

On the bad days he would openly kick around his options. At worst, he would announce, he would end up a really rich person. Or he just might decide to defect; maybe he would go down the road to ABC. They might be interested in him over there.

That was the scenario that eventually filtered back to Rick Ludwin from his contacts on the show. In his capacity as supervisor of late night for NBC, Ludwin always spent a great deal of time around the
Tonight
studio, but Jay wasn’t sending a message to NBC about his litany of unhappiness through Rick—maybe because Jay had begun to suspect that Ludwin had been one of the architects of the Conan elevation.

Inside the confines of the
Tonight Show
world, Ludwin heard Jay had been telling staff members things like: “Instead of getting off the freeway off-ramp for Bob Hope Drive and turning left, we’ll just turn right and go up to the Disney lot on Buena Vista. We’ll take the whole staff and just move on up to Disney and ABC.”

Ludwin would dutifully report back to his management about Jay’s prospective driving directions. The news didn’t really surprise anyone; Ludwin and the others at NBC hardly expected Jay was going to pack it in and take up gardening.

Jay’s message could also come through at times in his monologue. More jokes began to appear about NBCʹs expertise in coming in fourth in the network rankings. A failure by a politician or sports team in the news somehow led to comparisons to NBC. When he returned from a dark week and NBC had done some redecorating on his stage, including installing a new desk, Jay feigned surprise, saying, “It’s not like NBC to get rid of something that’s worked perfectly well for fifteen years.”

When Brett Favre of the Green Bay Packers was let go by his team after long years of exceptional play, Jay remarked, with an obvious edge, “His bosses don’t want him anymore—even though he was doing a really good job.” Later, during the 2008 presidential primaries, Jay went through the news of the day, which included a story about Hillary Clinton’s camp making a secret offer to Barack Obama to run with her as vice presidential nominee. Jay’s joke: “Obama is wondering why he’s being offered the second position when he’s still in first place.” Pause. “I’ve been wondering the same thing myself.”

And occasionally Conan would get a pointed reference, as in one holiday-period show when Jay turned to his bandleader, Kevin Eubanks, and asked, “Kev, you ever regift?” (Pause.) “I do. I regifted; I gave Conan something I got fifteen years ago.”

At least Jay could derive a little cathartic satisfaction from nailing NBC with a good shot every once in a while. It was fun for him—in a small way. But it wasn’t as though it was going to make any difference. Leno had resigned himself to the fact that nobody was going to reverse the decision. The NBC executives were hardly going to change their minds.

 

In meetings of his entertainment group, Jeff Zucker enjoyed putting people on the spot, usually in jest, though for the most part the executives under him never really believed he was kidding. When late night was being considered, Zucker truly was only needling his executives through 2005 and 2006, raising questions about how things were shaping up. He was feeling no regrets. Profits were still pouring in from both of his hour-long shows, profits he had protected by locking in both stars; ABC and Fox still weren’t in the entertainment game in late night. All seemed right in that world.

But as the years rolled by, with all the players back on their isolated islands, the endgame, once a blip on the horizon, began to come into focus, gather shape—and the shape looked dark and smoky, like a distant storm.

Zucker, whose prime-time headaches had gone from annoying to chronic to blindingly intense, now had to endure a faint but growing buzzing in his ear: the sound of Jay Leno humming, “Na, na, na, na. Na, na, na, na. Hey, hey, hey, good-bye.”

So as 2006 rolled into 2007, Zucker began calculating what losing Jay Leno might really mean—especially if he landed in the late-night arms of a competitor. Zucker, an eye on the long-range calendar, began foraging for kernels of ideas that might grow into a feasible possibility to keep Jay attached to NBC in some capacity.

So Zucker, whenever he dropped in on his entertainment staff in Burbank, running the meetings as always, had sharpened his late-night focus. He would turn to Rick Ludwin, employing his usual half-puckish, half-pointed tone.

“So, Rick, how’re you sleeping at night?” Zucker would ask, and then scan the table, letting the group know how playfully pregnant the question really was. Ludwin, looking bookish as usual, was flanked almost always by his late-night deputy Nick Bernstein, so boyish next to the much taller Ludwin that they were affectionately known as Batman and Robin. Ludwin had a ready answer: “Like a baby.”

The cause for Zucker’s concern about the degree of Ludwin’s restful-ness was no mystery to anyone at the meetings. Jay was still winning handily; Conan was . . . well, doing fine. Rick—backed by Nick—never backed down, never wavered in supporting Conan’s ascension to
The Tonight Show
. The two NBC late-night executives had complete faith in OʹBrien and were willing to defend that faith against any doubters.

In these meetings doubters had begun to speak up with questions about Conan, and they always sprang from the same concern: Should we worry that he’s a little too narrow, a little too hip, a little too New York, a little too young male college guy and not enough middle America, middle age, middle brow?

Ludwin always went to the same place to answer the doubters. The Conan you will see on
The Tonight Show
is that guy who stood up on that stage at the Emmy Awards and charmed people with broad, easily accessible humor. Conan went into the Emmys with the intention to entertain not only the audience in the Shrine Auditorium but the millions more watching at home. He killed doing bits that were all Conan, bits that pleased his hard-core fans and yet didn’t require newcomers to know any of the backstory to get the comedy. He would do the same at eleven thirty, Ludwin promised.

His stout defense may not have swayed everyone at the meeting, but it certainly did persuade them all that Rick Ludwin had strength in his convictions—and he was unalterably convinced that Conan O’Brien was the right guy at the right time for NBC.