The War for Late Night

by Carter, Bill

  Palin seized the moment. While she and her husband, Todd, took turns volleying fire at Letterman, accusing him of being “sexually perverted” for telling a joke “about raping” their young daughter, the backlash against Letterman, especially in the conservative media world of Fox News and talk radio, threatened to blow up into a wildfire. Two days later Letterman spent more than seven minutes during his at-the-desk segment in act two defending himself and explaining the mistake that had made the Rodriguez joke go wrong. In a tone of self-mockery that the audience took for humor—because they laughed all through it—Letterman acknowledged that the jokes were ugly.

  “These are actually ugly. These are borderline,” he acknowledged, laying the reason down to “an act of desperation to get cheap laughs, which is what I’ve been doing for the last thirty years.” He also apologized—after a fashion—for the mix-up about the two daughters. But he adamantly defended himself against the charge that he had suggested that Willow might have sex with a grown baseball player.

  “These are not jokes made about her fourteen-year-old daughter. I would never, never make jokes about raping or having sex of any description with a fourteen-year-old girl.”

  Letterman summed up: “Am I guilty of poor taste? Yes. Did I suggest that it was OK for her fourteen-year-old daughter to be having promiscuous sex? No.”

  And then, signaling he was not going to prostrate himself before a woman he seemed to believe was a grandstanding politician, Letterman also mentioned a line—one Palin had labeled in an interview as “pretty pathetic”—that he had used the same night as the Rodriguez joke in a top ten “Highlights of Sarah Palin’s Visit to New York”: “Bought makeup at Bloomingdale’s to update her slutty flight attendant look.”

  No apology for that one. “I kind of like that joke,” Letterman said.

  Palin supporters bombarded CBS and Letterman’s office with calls of complaint and demands that he be fired. FireDavidLetterman.com, a Web site launched by Palin supporters, tried to gin up a rally to take place the following week outside the Letterman theater on Broadway.

  The concern was real inside the Letterman camp. They took the protest seriously enough for Dave to take the unusual step of offering a second apology on the air the next Monday, made directly to Palin, admitting that his own intent was meaningless compared to how the joke had been perceived. That was good enough for Palin, who, having gotten as much as she could have possibly hoped to squeeze out of this episode, accepted the apology. The planned protest fizzled; only about fifteen people showed up carrying signs. They were vastly outnumbered by the media assembled to cover the event.

  But if that protest was flaming out, another was still in full blaze.

  As soon as the first news of the Palin-Letterman contretemps began breaking, Jeff Zucker sent a message to his Conan team: The perfect move in this circumstance was to book Sarah Palin as quickly as possible.

  There was only one problem with this plan: O’Brien didn’t want to do it.

  Conan explained it as best he could to some of his West Coast colleagues: He didn’t want to appear to be taking advantage of a situation Dave had gotten himself into; he didn’t want to come across as a pawn in some machination of Palin’s. If the show booked her at that moment, Conan told one associate, it would be obvious she was on only because of the news in the David Letterman world, and Conan would be vulnerable to the perception that he had been suckered into doing it. Not only would the press accuse him of pandering for ratings, but his fans would likely judge the move unseemly.

  As both a producer and a boss, this reaction drove Zucker nuts. As a producer, he knew how to manipulate audiences—that was simply what you did as part of the job. He looked at Palin as the first of-the-moment guest who could change the game for Conan. As a boss, he couldn’t believe Conan would stand in the way of what was obviously the smart business move—for him and his network.

  Zucker pressed the issue with Jeff Ross: Letterman wants to kill you. He wants to bash your brains in. And you’re bringing a knife to a gun-fight. This guy wants to kill you, and you guys aren’t doing all that well.

  The Today show, still under Zucker’s direct aegis, did book Palin in the middle of the Letterman fracas. In her interview, Palin told Matt Lauer, the show’s biggest star, that he would have to be “extremely naive” to believe Letterman’s “convenient excuse” that he was not referring to Willow but Bristol Palin in the joke. She also backed a statement by her spokesperson that it would be wise to keep Willow away from David Letterman. And when pressed by Lauer about what that statement was meant to imply about Letterman, she added, “You can interpret that however you want to interpret it.”

  At NBC it was taken for granted that Jay would have booked Palin without a moment’s hesitation. That was certainly what Ebersol thought O’Brien should do. His argument: “This is your fucking competition. This is a business. You’re making eight figures.”

  The Palin issue came up in meetings between the Conan staff, Ludwin and Bernstein, and other NBC executives. As Jeff Ross heard it later, there was not one person in these discussions who did not comprehend why Conan balked at booking Palin at that moment. The move had the potential to blow up in his face. No one questioned how seriously Conan took this situation—he had clearly thought it through, as he did everything involving his career. He was making a judgment based on what he believed was best for his show.

  When Conan laid out his reasoning, Rick Ludwin, for one, could not find a reason to challenge it. In general, Ludwin believed it was wrong to try to force hosts to do something they were clearly opposed to doing. That could lead only to bad moments on the air. The network’s job was to make the host look good.

  One Conan supporter did acknowledge that the show was forsaking the “ratings pop” that would have come with a Palin appearance. “Conan didn’t want to dictate what his Tonight Show would be based on someone else’s late-night show. The challenge for late-night shows, forever and always, is: At what price is the pop?”

  For Jeff Zucker there was a much simpler—and less justifiable—explanation for Conan’s decision to bypass a Palin guest shot: He didn’t want to piss off David Letterman.

  CHAPTER EIGHT

  STILL DAVE, AFTER ALL THESE YEARS

  On the morning of December 9, 2008—six months earlier to the day of its host’s controversial Palin joke—excitement coursed through the usually sedate offices of Late Show with David Letterman , and it had nothing to do with Christmas season in New York.

  Among the staff who actually interacted with the star on a daily basis—and that was a limited number, it was true—Dave’s arrival that day was much more than usually anticipated. The burning question passed around over coffee: What is Dave going to say about this?

  “This” was NBC’s announcement that it had reached its agreement with Jay Leno to keep him on, transferring him to prime time, of all places, ten p.m. each weeknight. That move seemed to resolve, once and for all, the head-to-head rivalry between Jay and Dave, which reached back sixteen years to the decision over the Carson succession—and even further than that, to nights as stand-ups on stages like the Comedy Store on Sunset Boulevard in LA in the seventies.

  Letterman had said little on the subject since NBC had installed its five-year layaway plan for The Tonight Show, with Conan O’Brien the designated heir to Jay. But then, he said little on how he felt about most topics, especially in public. On this matter, he had deigned to speak for the record only once, in a Rolling Stone interview the previous September.

  At that time he had made the remarkable statement—remarkable at least to those still guessing how Dave might feel about Jay—that he no longer harbored any hope of ever topping Leno in the ratings. His acceptance of that fact was remarkable mainly for the reason Letterman cited, an explanation for his ratings shortcomings that defied all previous efforts by his own entourage to blame uncontrollable factors like CBS’s lead-in shows and NBC’s stronger local stations (as well as the we
ll-known limited artistic tastes of the American public).

  “The answer is me,” Dave said. “I just think that Jay has wider appeal than I do.”

  His admission likely stunned those at NBC who had been hammering away at that same argument for years in the face of the litany of excuses being thrown up by Letterman’s defenders. With Dave himself conceding, “I think more people are responding to Jay than will ever respond to me,” the excuse well had officially run dry.

  Given Jay’s now acknowledged victory in what, by that point, seemed like the Hundred Years War of Late Night, NBC’s decision to relieve Leno of his Tonight chair in favor of Conan left Letterman nonplussed. While he recognized that the network may have been attempting to find a “less messy way to handle what happened to me at NBC,” he still seemed thrown by the whole concept. Maybe because he knew his counterpart so well—perhaps as well as anyone who had interacted with the near impenetrable Leno in his long career—Letterman suspected (correctly, of course) that Jay would have preferred to stay exactly where he was.

  So even then, ten months before the switchover was due to take place, Letterman found himself wondering whether it was really going to happen. The few times he would talk about it around the office with his producers and writers, Dave tended to agree with those who speculated that NBC would find some way not to go through with the handover to Conan. The pattern seemed far too similar to how the network had tried to handle Dave’s departure for CBS. NBC had offered him The Tonight Show at the last minute, but only if he waited eighteen months to get it. All his advisers at the time had warned him that NBC would have stiffed him in the end if Jay’s numbers looked good.

  Here they were, fifteen years later, and with the numbers still looking good for Jay, a stiffing seemed in the offing—this time for Conan. Either that or NBC would be inviting Jay to pull a Dave and launch another separate franchise, probably at ABC this time.

  In either case, Dave knew for certain that the balance in late night might shift for the first time since the early nineties. For his staff, it felt like a potential reversal in the earth’s rotation—back toward Dave.

  When Dave arrived that December day, summoning a few of his key people together in his office for a regular morning meeting, anticipation hung in the air like swirling smoke from a lit fuse. Then Dave walked in, sat down, and said not a word about any of it. His number one nemesis was not only leaving the field but was going to prime time, and Dave was shrugging it off, as if . . . whatever. All he said to the group was “So what are we doing on the show today?”

  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.”