The War for Late Night (26 page)

As the 2008 calendar rolled through spring, May becoming June, Conan O’Brien could not help but think of the date looming one year in the future. His first night on
The Tonight Show
was set for June 1, 2009.

The prospect filled him with a real thrill because O’Brien, despite his long-held Letterman worship, also had a deep personal connection to Johnny Carson’s
Tonight Show.
He associated Carson directly with his dad and the fondly remembered experience of watching
The Tonight Show
as a twelve-year-old in 1975, in his den, next to his father, and recalling how his father laughed and enjoyed Carson’s matchless delivery and timing.

That reverence only deepened when Conan had occasion later—just a few times—to interact with Johnny. The first came before he even went on the air with
Late Night
in 1993. As a thirty-year-old kid, just named out of nowhere to replace Letterman, Conan met Carson at a celebrity-strewn lunch that the Center for Communication in New York held in Johnny’s honor—an event at which Johnny performed his final topical stand-up in public (though no one knew that at the time). Johnny’s best line of the afternoon: “I’m optimistic about television. Of course, you know, in the entertainment business, an optimist is an accordion player with a beeper.”

After the lunch, Carson greeted Conan amiably and offered a snippet of advice: “Just be yourself—it’s the only way it can work.” The comment seemed nothing but generous to O’Brien, though he later had a rueful second thought: And even
then
it might not work.

Later OʹBrien contacted Carson—and all the other giants of late night, including Steve Allen, Jack Paar, and, yes, Letterman—when he was hosting an NBC special about fifty years of late night on the network. Conan asked for Johnny’s input on the clips chosen for the special. He said they looked fine.

Most memorably for Conan, Carson had checked in with a call after NBC had named Conan as Leno’s successor (officially, that is). That brief conversation, which took place only a few months before Carson died in 2005, mainly consisted of congratulations. Conan joked that getting the show was a great honor, “if I live to see it.” Johnny agreed that “it does seem like a long engagement before the marriage.”

The exchanges with Carson may have been fleeting, but they were enough to validate for Conan the emotion he felt for Johnny and the show that had made him famous. O’Brien took to calling
The Tonight Show
“sacred ground.”

In many of his private moments, Conan felt the surge of adrenalin—he was getting
The Tonight Show, Johnny’s
show. How exciting was this? And eager as he was to get it, he continued to have flashes of doubt:
This is about me? And I’m that kid from that elementary school whose pants don’t fit? And do they know that I had acne as a teenager? Do they know that I don’t always know exactly what I’m doing?

Those moments, which had come in abundance in his early days of
Late Night
, were much more sporadic now. Still, he recognized that ever proximate condition: the imposter syndrome—the thought that, no matter how successful you became, “they’re about to catch up to you.” Conan encountered it with some frequency, but was comforted by knowing the syndrome affected everyone in show business, as he became aware one night when the comic Chris Rock visited
Late Night
as a guest. At the time Rock mania had gripped the land, and Chris was being celebrated everywhere as the comic genius of a generation.

On the show Rock sat down next to Conan and within seconds had the crowd by the throat, wringing gales of laughter out of them with just the slightest effort. Conan felt blown back by the power Rock commanded over the audience, shooting out one explosive line after another. It seemed to Conan that everything around Rock had turned liquid, the air around him was so blazing hot.

Then the commercial break arrived, and Conan leaned over to tell Rock, “Man, that was fantastic!” And Rock stretched close to Conan’s ear and said, “I just hope they don’t catch on.”

To outsiders Conan mostly kept his guard up in revealing any cracks in his confidence about the coming change in his professional life. But sometimes the lingering insecurity seeped out unexpectedly, as in a moment after he performed for advertisers at NBC’s infront presentation in the spring of 2008. While chatting with a small group that included Lorne Michaels and Tina Fey, celebrating the renewal of their
30 Rock
sitcom, OʹBrien got a sudden faraway look in his eye. He pulled aside one of the group, someone Conan had known since his first year at NBC.

“Can I ask you something?” Conan leaned in to whisper. “Will you root for me?”

Those shaky moments hardly dominated Conan’s days and nights, though, for he had far too much to do and think about. Beyond daily preparation for the
Late Night
show, Conan and his staff, led by head writer Mike Sweeney, had begun noodling, even a year in advance, with ideas for the coming
Tonight Show.
They sorted out what bits they might retain (definitely “Conando,” the wildly exaggerated takeoff on a Spanish-language
telenovela,
with Conan in pencil mustache) and what they might have to abandon (“the Masturbating Bear,” “Vomiting Kermit”).

Already Sweeney had beefed up the writing staff with a few additional monologue specialists. They knew
The Tonight Show
would demand a longer monologue than Conan had ever performed on
Late Night.
There he had mostly followed Letterman’s precedent from his days on that show and tossed out just four or five gags before moving on to the more creative comedy.

But over the course of this last year, the monologue began to creep up to eight to ten jokes a night. That did not begin to approach Jay, who often hit the thirty-five mark, but Conan was stretching, a concession to the need for a substantial top-of-the-show joke barrage at 11:35. The additional jokes tested the limit of Conan’s stand-up technique, which he had never really needed to perfect before, since it wasn’t his signature thing. Now he had to work on the necessary moves—while dropping some of the unnecessary tics.

For years Conan had told his few opening jokes in the same almost throwaway manner. He would stand at center stage and read the setup off his cue cards in a kind of singsong delivery.

“Despite protests from conservatives, President Bush today appointed an openly gay man as his assistant secretary of commerce. . . .”

Stop, pause, head nod, and throw each hand out to the side, as if to signal in a kind of stand-up semaphore:
OK, folks, the punch line is on the way. . . .

“Yeah, Bush claimed a gay man is perfect for the commerce department because ‘those people love to shop.’ ” Outthrust hands brought together with an audible clap.

Conan executed this exercise so routinely that few on the show were even aware he told most jokes this way. With the longer monologue, however, varying the delivery became imperative, and Conan set to work on it.

Rick Ludwin still sent notes, of course, and Conan and staff dutifully read and considered them. Mostly, the suggestions—still always along the lines of more interaction with the audience—did not result in any changes. Not that Conan didn’t appreciate Ludwin’s efforts. He knew how important Rick had been in steering
The Tonight Show
into his hands. But comedy writers and performers are rarely disposed to believe that “civilians” know what’s best in comedy.

The NBC suggestions all had a whiff of mothballs to them: Be broader, be more traditional, more eleven thirty than twelve thirty. “I think people are overthinking the twelve-thirty-to-eleven-thirty shift,” O’Brien said. “Because television is so different now.” The younger people who favored Conan were more and more watching the show in new ways: on DVR playback, where they sped through to the favored moments, or catching up to it online rather than watching every night. As Conan analyzed it, he needed to kick-start
The Tonight Show
into a new century with new media and new audiences. He had to put his own stamp on the show, no matter how much tradition was draped all over it.

He didn’t accept that the show had to be stodgy or hidebound. In several published accounts he compared the show to a classic but sleek, fast, and sexy sports car. “They’re handing me the keys to this beautiful Ferrari of
The Tonight Show
,” Conan told the Cleveland
Plain Dealer
. “I’ve been driving around in a Jeep Wrangler called the
Late Night
show. A fine Jeep Wrangler with a busted radio, but now they’re handing me the keys to a Ferrari called
The Tonight Show
. And I don’t want to just gently put it into gear and drive it at fifty-five miles an hour down the highway so I don’t burn out the clutch.”

No, he had other plans. “I want to see what this baby can do. I want to get this thing up over a hundred miles an hour. I want to clip some fire hydrants. I want to get it up on two wheels, on its side, like James Bond in that alley.”

 

As the days of 2008 dwindled down, the ever nearing prospect of losing Jay Leno cast a threatening shadow over every other decision on Jeff Zucker’s plate. After all his masterful maneuvering—the coup of keeping Jay and Conan together for five more years as the network’s late-night profit juggernaut—Zucker and NBC were back where they had started. They still found themselves on the verge of playing the sad-sack victims in an old familiar horror movie, menaced by the same intractable bogey-man, apparently every bit as unkillable as Michael Myers in a
Halloween
movie: the chair that two men wanted, but only one could sit in.

Where the hell did Zucker go from here? That last option, the one he’d kept in reserve, had not quite burned a hole through Zucker’s pocket, but it had been in there smoldering for a long time. Before he gave in, pulled it out, and threw it on the table, he needed backup, and so he commissioned some special studies from NBC’s research department.

Out in Burbank, Jay was still telling his pointed jokes. He did a bit about car navigation systems and the programmed voices they used. The conceit was that the voice, rather than some disembodied robot character, was someone you know, in this case a nagging mother: “When are you going to get a new job?” (Pause.) “ABC would be nice!”

Meanwhile, Rick Ludwin was still doing his job. Whenever he chatted with Jay, as he routinely did, he had a message: The cash might be greener elsewhere, but that didn’t mean the grass was. Just look at the other examples of stars jumping from their home networks, Ludwin urged him, citing the one Jay would be most viscerally familiar with: Dave. Look what happened when Letterman went to CBS, Ludwin pointed out. Sure, he beat Jay’s brains out for a couple of years, but once NBC retook the late-night title, Dave was a loser for the next fifteen years. And the examples extended beyond late night. How about news stars, like Katie Couric? She was America’s sweetheart in the mornings on the
Today
show. Now look at her—last place on the
CBS Evening News
.

How much impact these arguments had on Jay, Ludwin could not be sure, but he felt he had at least planted some seeds of doubt about a happy switch to ABC.

Those seeds might have fallen on stony ground, but others had already dug some deep roots in Jay’s consciousness. More than anything else, what gnawed at Leno about his contract situation was NBC’s ability—and now intention—to beach him for at least six months. Conan would start June 1; Jay couldn’t get back on the air until after January 1.

When NBC agreed to Jay’s five-year extension back in 2004, it had carefully included, along with the obligation to pay him in full for the life of the deal, the right to shelve the comic at any time the network desired. In other words, NBC had Jay Leno for five years, and if at any point during that time it decided to replace him, it was completely within its rights to put him on a (symbolic) beach for as long as it wanted for the duration of that five-year period. Jay could work Vegas, Reno, and every Native American casino from Temecula, California, to Ledyard, Connecticut—but nowhere else on television until after January 1, 2010. Now, it was true that NBC had basically agreed up front that it would not exercise the right to shelve Jay until June 2009, when Conan was slated to start. But that was more handshake than handwritten.

Nobody was more aware of this situation—and obsessed by it—than Jay Leno. As he looked forward and considered his options, he could not help but look backward and chafe under his limitations. ABCʹs desirability as a destination was undercut by a sobering realization: Before he could reach it, he would have to endure the test—torture test, really—of an enforced absence of six months or more from television.

One top Hollywood agent, a strong Jay supporter, found himself befogged when Jay told him of this dilemma. With the clear leverage Jay had had back when NBC came to him with this cockamamie five-year plan, the agent knew Jay could have protected himself against getting boxed in like this. “The guy always went in by himself to make his deals,” the agent said. “He was the big dog. Somebody representing him would have said, ‘OK, five-year deal, you’re making Jay leave. But the
minute
you take him off the air, he’s free to go anywhere he likes.’ ”

Jay usually couched his concern about being off the air for so long in terms of what it would mean for his staff. If NBC really did send him into enforced exile starting in June, that meant months of no pay for his writers and other staff members. He conjured a worst-case scenario in which he got stuck in neutral all the way until April. That would be the case, he estimated, if he couldn’t hook up with anyone at ABC or Fox until January and couldn’t even talk to anyone before that. He couldn’t be expected to launch a new show overnight.

But the circumstances were actually quite different. From his conversations with Kimmel, it was clear Jay had a reasonably good idea that ABC had an 11:35 spot laid out for his arrival. As for the staff worries, could he not push his suitors for some assurance that nobody would lose income for that interregnum? A raise or advance in salary for key staff could have covered that issue.