The War for Late Night (36 page)

 

Conan’s now certain arrival in six months was not quite so easy to ignore. The departure of Jay might mean opportunity for Letterman, it was true, but it also carried risk—huge, momentous risk. Losing to Jay, conceding Jay’s ultimate ratings superiority, had been tough enough to swallow. No one at
Late Show
wanted to ponder what it would mean if Dave now lost again—to Conan.

Rob Burnett, still an executive producer on the show and the executive in charge of Worldwide Pants, whose tenure extended all the way back to Letterman’s days at NBC, never stopped being a true believer. For him NBC’s selection of Leno over Letterman could be linked to the concept of original sin: NBC picked Jay over Dave and had never really overcome plucking the apple from the wrong tree.

Had NBC seized the moment back then and elevated Dave, as this virtually religious tenet posited it, the premier late-night network would likely have preserved the utter dominance of
The Tonight Show
that Johnny Carson and all his predecessors had enjoyed. How? By ensuring that another network did not secure the one star capable of a successful late-night schism: Dave. Surely, this dogma went, Jay Leno, without the built-in loyalty of the
Tonight Show
viewership, could not have set up his tent at CBS and pulled in the same kind of crowds that he did at NBC. And if CBS had tried Jay and he had misfired, then NBC with Letterman would have owned the eleven thirty time period exclusively for who knows how long.

Of course, this doctrinal wisdom did not take into account the part where Dave would have refused to work the affiliates, court the advertisers, massage the press, and give succor to his network whenever it was in need. Letterman would likely have shut all that out at NBC, just as he did at CBS—one big reason why he didn’t win the
Tonight
job in the first place.

Many in the Letterman camp never fully accepted that particular downside of Dave’s persnickety personality. For them, it was all black and white: Dave, a comedy genius; Jay, a machine politician. Dave playing Mozart; Jay playing Salieri.

Or in Rob Burnett’s favored metaphor: Jay equals Coke; Dave equals Pepsi. Burnett’s answer to NBC’s attempted dismissals of Dave’s heroic efforts at CBS was to cite Pepsi’s entering the soft-drink market as rival to Coke. Maybe Coke still outsold Pepsi overall, but there was now a Pepsi where there was none before—which enabled people to let their tastes decide between two more or less equal choices. (It would not be the last time Coca-Cola raised its metaphoric head in the late-night saga.)

But with Jay now bowing out of late night, Letterman’s people were concerned that Conan might well represent an all-new brand of soft drink. Dr. Pepper? Maybe even Mountain Dew? People had grown accustomed to Coke and Pepsi. If Mountain Dew was now going to try to grab some slice of their market, Letterman’s team couldn’t just sit around and let it happen.

The question for the
Late Show
brain trust was this: How could they best prepare to prevent Conan from doing the unthinkable—beating them?

Initially there was some general discomfort with that entire idea. Dave had always been personally fond of Conan and admired his fresh, impressive comedy work. He had more or less blessed Conan as his successor by appearing as a guest on
Late Night
in February 1994, when Conan was barely surviving NBCʹs attempts to smother him in his crib. Later, when Conan was finally starting to break through, Dave turned up again as an unbilled walk-on during Conan’s third-anniversary show with some advice for Conan and Andy: “In nine years you guys can switch networks and start making some real money.”

Even though they shared New York and thus had likely booking conflicts, there had never been friction between the two shows. Quietly Dave had even called Conan personally when he was leaving the
Late Night
show to wish him well, which had meant a lot to Conan. And of course everyone knew the level of Conan’s idolatry regarding Dave.

But leaving aside the issue of not really wanting to go after Conan, the staff had to confront another question: the limitations on exactly what steps Dave might take to elevate his game. He certainly wasn’t going to go back to monkeycams (handheld cameras on the back of chimps), or create some new adventures for “The Strong Guy, The Fat Guy, The Genius,” or take a camera back into the souvenir shop up the street to banter with Sirajul and Mujibur. (For one thing, their Rock America store had long since closed.)

Through the choices he had made in recent years about what he would and would not do on the show, Dave had been sending a clear message: He was no longer the guy breaking new ground in late night. As Burnett put it, “You can’t be on the cutting edge forever or you start to look ridiculous.”

That didn’t mean Dave was any less Dave; it only meant he relied more on the pure essence of wit extracted nightly from his brain. He had taken to building act two largely around a conversation he had with the audience every night from behind his desk. Some nights, when he had a prepared piece of comedy laid out in front of him, he would choose instead to discuss what had happened over the weekend at the house or out on the ranch in Montana. (Most famously, a grizzly bear once made his way into the kitchen for some snacking.) These impromptu asides were often far more hilarious than whatever the writers had come up with.

The most ambitious reinvention Dave and his team did adopt in the months before Conan’s hour-long time shift was much more throwback than leap forward. He started telling more—lots more—monologue jokes.

For most of his run at CBS Dave had averaged about eight jokes a night—more than he had during his
Late Night
days at NBC (three or four, tops), but still nothing like the fusillade (thirtyish) Jay was firing off every night. In trying to keep the show as much Dave as possible, while also not requiring him to run around town on his time off as he used to do during the nineties, the staff looked to the opening monologue as a target of opportunity.

In their no-concessions way, Letterman’s team had for years resisted any notion that Jay was the master monologist and hence the natural heir to Carson in that regard. Dave had just as much talent for standing on that mark and delivering a finely crafted one-liner, they argued. Of course, Jay pounded his point home every night in a gag barrage, and Letterman himself had never hesitated to grant Jay his props as a stand-up; Dave would routinely say Jay had been the best he’d seen at the joke-telling craft. In the meantime, Dave limited his nightly joke total, believing it was better to tell a few polished jokes than spray the room with a joke hose.

In the early days, however, Dave did fill the show with those ambitious cutting-edge comedy concepts. Not only was he disinclined to do them anymore, but it now seemed those innovations that he had introduced had all become staples of everyone else’s late-night shows. Conan went everywhere, from bartending school to Finland. Jimmy Kimmel had a recurring piece at a black barber shop that scored for him every time. Jay sent his “Ross the Intern” character to the same places—award shows, big sporting events—where Dave had sent his stage manager, Biff Henderson, for years. If those ideas were now to be relegated to the scrapbooks, then Letterman needed something else to freshen the show. So the monologue made a comeback.

“It was so hot in New York that when I was driving home last night, the navigation lady says to me, ‘So you want to stop for a beer?’ ”

“It was an especially fine day today, a day like a New York cabdriver: only a slight chance of a shower.”

“Jenna Bush is getting married over the weekend. I thought this was nice. For their wedding night, President Bush is loaning the groom his ‘Mission Accomplished’ banner.”

Only privately did some Letterman acolytes mention one ulterior motive for the new direction: It might be another way to distinguish Dave from Conan, who had never done all that nightclub slogging—basic training in the art of monologue.

In mid-2008 another factor was compelling Dave to add jokes at the top of the show. It was a presidential election year, populated with a host of characters inviting comment every night, from John McCain and Hillary Clinton to side players like John Edwards, Fred Thompson, and, once the summer hit, Sarah Palin—all of them offering rich material for monologues.

“At last night’s debate John McCain brought up Barack Obama’s relationship with sixties radical William Ayers. Then Barack Obama brought up McCain’s relationship with John Brown at Harper’s Ferry.”

Letterman found himself at the center of the news on September 24, during the height of the presidential race, when McCain, who was scheduled to make his thirteenth appearance as a guest, abruptly canceled because he said he was being forced to suspend his campaign to rush to Washington to deal with the collapsing economy.

Dave first made some generous remarks about McCain, citing his war heroism and noting that the senator had called him personally to apologize for this last-minute emergency that was forcing him to cancel. McCain had actually announced his plan to run for president on Letterman’s show in 2007; the two men had a comfortable relationship.

But then Dave learned that McCain, instead of rushing to the airport, had turned up at CBS News headquarters for a quick sit-down with Katie Couric. The interview was taking place at the precise time Dave had begun his taping, and because it was on CBS, he could pick it up on the internal network feed. The audience, brought in on this breaking event, pushed Letterman on with their laughter.

“Hey, John,” Letterman yelled into the monitor, only starting to get revved up. “I’ve got a question! You need a ride to the airport?” Egged on by his fill-in guest, the pro-Democratic MSNBC host Keith Olbermann, Letterman questioned McCain’s motivation for what seemed to Dave like a PR stunt. “You don’t suspend your campaign,” Dave said, mixing comic delivery with righteous anger. “No, because that makes me think, well, you know, maybe there will be other things down the road. If he’s in the White House, he might just suspend being president. I mean, we’ve got a guy like that now!”

The event became part of the news cycle in the race. McCain had stiffed Letterman, and Dave made him pay. He got more licks in on McCain for several nights after, and McCain ultimately had to make a date in his otherwise packed calendar to return to New York (a state he was hardly going to win) on October 16 to formally seek Dave’s pardon.

For the Lettermanites, the McCain episode underscored what they saw as the gravitas Dave now brought to the role of late-night host, another quality they believed set him apart. No one could picture Jay, for example, rising up and chastising a presidential candidate for reneging on a booking.

“He’s bigger now than almost anyone who sits across from him,” Rob Burnett said. “On his home turf, sitting behind that desk, where he’s sat for so many years, you get the feeling that with whoever it is there, sitting across from him, Dave has the upper hand.”

That kind of framing was no accident. What Burnett and other staff members of the show and Worldwide Pants sought to convey was that Letterman had assumed, formally, the mantle held for so long by Carson. Not the “King” thing, but rather the cultural relevance thing. The monologues Dave began performing—Johnny-style ones—played right along with that. Dave not only did more jokes, but more pointed jokes, sharper, tougher material.

The lengthening of the monologue brought with it a reshaping of the first act of the show. For years, the format had been: Dave’s opening routine, followed by a brief piece of music from Paul Shaffer and the band while Dave did his walkover to his desk. From there he would jump into whatever had been planned for the next piece of comedy. The act had gotten so long that the first commercial break came much deeper into the show, a fact that actually hurt Letterman’s ratings, because shows had started to be measured by how many people were watching the commercials, not the programs themselves. On
Tonight
, Jay had always ended his monologue and thrown right to a commercial—so that first ad was invariably on earlier than Dave’s. That had become another ratings advantage Jay’s show enjoyed. With the longer monologue,
Late Show
could switch to a similar commercial rotation, with the first ad following the monologue. It might even help in the ratings.

To feed the new structure,
Late Show
began hiring more writers specifically to work on the monologue. Dave started stretching out the joke quotient, eventually pushing it up to sixteen, then eighteen, then twenty a night. When some in the press noticed, they leapt to the immediate conclusion that Dave was intent on stealing away Jay viewers, who liked to hear a lot of topical material.

The reason for the monologue expansion had more to do with Dave looking for a way to reinvent his television act—again. He had done that with resounding success in 1993 when he jumped to CBS, but more significantly, invaded the eleven thirty time period.

The prevailing challenge for Dave in 1993 was supposed to be—as Conan’s was—broadening out the show, though even then the concept was difficult to define. Should Dave be less edgy, more conventional, less innovative? At the time, one of Letterman’s top producers, Robert Morton, had tried to simplify what the move up an hour was really all about. “The new show has to be about success. It can’t be about failure,” Morton had said. The old show had celebrated failure: If something about the show went wrong, the camera went right for it, zoomed in on it. As in a memorable night when a trick by Kamar the Discount Magician had failed spectacularly (because he forgot to plug in his levitation table).

If the same act was being done on a show playing at 11:35, Morton argued to Letterman, “You want to see the trick work; you want to see the best trick ever.”

Dave had levitated the expectations of the show in just that way when he moved up an hour and over to CBS. But this latest reinvention was not going to be a question of success or failure so much as it would be a question of age. Dave needed to find an age-appropriate way for a sixty-one-year-old guy to keep being funny in late night.