by Carter, Bill
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.
That didn’t mean the staff dismissed what Conan was up to. The booking department kept one eye on the guest list Conan’s staff had lined up for week one. As expected, it contained big names every night. With the odds pointing to a blowout for Conan (especially now that Jay wasn’t going to be available as a guest for Dave on the first night of Conan’s Tonight Show), the Letterman squad decided to borrow a little strategy from Muhammad Ali for their own guests that week. They would go for the rope-a-dope.
That was Ali’s scheme in the famous “Rumble in the Jungle” against George Foreman in Zaire in 1974. Ali essentially laid back against the ropes in the early rounds, allowing Foreman to whale away with his heaviest blows. Then, with Foreman’s best shots exhausted, Ali came back with a vengeance—and knocked big George out.
Citing that precedent, the Late Show strategists decided to stay away from Conan during his premiere week. They had the show’s booking staff, in effect, lay back on the ropes while Conan went for the big swings early. It almost might make it worse for Conan, they guessed, to have a monster first week and then have to start listening to everyone talk about how the numbers were dropping.
“Let’s go after the second week,” Rob Burnett told the show’s bookers.
The show—and Dave—would be loaded for bear.
In his early days at CBS, David Letterman was doing so well, surpassing The Tonight Show in the ratings and winning nonstop accolades, that Dick Ebersol, one of the NBC executives who had supported the last-minute effort to dump Jay Leno and keep Dave, decided to call a friend who worked on the show and ask if everyone there was over the moon about their success.
“Not everyone,” the friend reported. “The first week and a half Dave was happy. Now he’s gone right back to being the most misera
ble person in the world.”
The classic adage applied as much or more to the compelling, complicated, challenging David Letterman as it did to anyone else on the planet: You don’t get older, you just get more so.
By the end of 2008 Letterman’s fifteen-year run at CBS had encompassed a dizzying collection of highs and lows. He had won six Emmy Awards for outstanding comedy or variety series; he had led a driving team that won his dream race, the Indy 500, in 2004; he had experienced the unexpected joy of having a son born into his life at age fifty-six; he had won the admiration of his city and the nation for his sensitive leadership in bringing true comic relief after the horror of the terrorist attacks of 9/11; and he had shepherded countless memorable moments—foulmouthed Madonna, topless Drew Barrymore, post-slammer Paris Hilton—onto television. Oh, and CBS had paid him several hundred million dollars for his labors.
But the toll of lows was also long. Letterman had taken a battering over his one venture outside the cocoon of his show, when he hosted the Academy Awards in 1995; he had been forced to deal with a kidnap threat against his son; he had lost his idol Johnny Carson to death in 2005; whatever hope he had to prove NBC wrong for choosing Jay Leno over him had disappeared under the pile of weekly wins Jay continued to post; and a severely constricted artery had almost cost him his life in 2000, when emergency quintuple heart bypass surgery forced him off the show for seven weeks.
By 2008 Dave had been at it in late night for twenty-six years, closing in on Carson’s record three-decade run. Nothing suggested Dave was about to stop, maybe because he realized, having observed Johnny, that shutting down a late-night show would pretty much entail shutting down life as he’d come to know it.
“Once you give up that chair, it’s over,” said one longtime Letterman associate. “It’s hard to imagine him without a show and it’s hard for him to imagine himself without a show.”
Had Dave mellowed at all? Maybe in some ways, his colleagues suggested; not so much in others. After the heart scare, he modified some behaviors (no more cigars), but if not quite the “maniacal asshole” about the show that he once called himself, he still often made it tough on people to work for him. People got cut off; Dave stopped speaking to them for months on end. That could include anybody, from the top down. One executive producer, Maria Pope, lost favor and contact with Dave (but not her job) for a long stretch of time. Even Rob Burnett found himself ostracized on occasion. The list of advisers Dave would actually listen to grew short, almost to the nub.
Letterman still pushed himself—and others—with an irascible style that took getting used to, especially up close. “This is a guy whose anger feeds everything,” said a veteran Letterman intimate. “Just in everything he did there was an underlying level of anger. He’s the kind of guy who’s having a cup of coffee and instead of just putting it down on the table, he’ll go, slam! He’d open a package and go ‘Raarrr!,’ tearing it apart instead of just opening it.”
As he had from early in his career, Letterman directed most of his anger and disgust at himself. In the old days the staff would often hear him in his office battering his stereo equipment with a baseball bat, all of them wondering, Is he mad at me? Did he not like my joke, or my segment? But when one of the producers would work up the nerve to walk in and ask him if everything was all right, Dave would say, “I hate myself. I’m the biggest asshole in the world. Look how I messed this up.”
For many of the staff, who stood in awe of him, these moments were almost heartbreaking. They would rather have had Dave turn to one of them and say, “You fucked up tonight, and I’m really pissed off.”
The top staff tried to shield the angry Dave from the rest of the employees, but they usually got the message. “It’s like always walking on eggshells,” one writer recalled.
One time Dave came into the office, stepped into the elevator, and saw one of the show’s interns. “Oh, hello,” Dave said perfunctorily.
The intern froze and stared at the floor. She had been told by one superior never to address Dave—never to look at Dave. Letterman went to his producers and instructed them to tell the interns to at least speak to him. They had to assure the terrified young woman that she would be doing them all a favor if she would just say hello to the guy.
Most days, Dave remained intently focused on that one hour a day when his nerve endings would tingle with the anticipation of being fully realized. In the early days he would juice himself up just before going on the air with a ritual of high-test metabolic enhancement. After drinking enough cups of strong coffee to stimulate the economy and before going downstairs to perform, Letterman would sit at his desk surrounded by a pile of Hershey bars. Carefully unwrapping each one, Dave would break four or five of them into their separate little squares and then pile them on top of one another into a little chocolate tower. He would proceed to eat all the squares as he went over the upcoming show with the producers. By the time the sugar rush kicked into his system, he would be backstage and ready to go on the air.
Every night the show, for good or for bad, defined who he was. The act of stepping out nearly daily onto a stage and standing in front of people, millions of people, and soliciting laughs almost defined the term narcissism. Every performer would have needed an outsize ego to get through that crucible every night. Clearly the two giants of this late-night era had that in common, but they reacted to it in totally opposite ways. Jay Leno told friends and colleagues he had the easiest job in the world. One friend remembered hearing Jay say that and replying, “Jay, I know you’re at ease with what you do. But you really think you have the easiest job in the world? Every night getting a report card? Nobody else’s job gives them a grade every time they finish up their work. No, Jay, really this is the opposite of the easiest job.”
The same friend also knew Dave well. The significant difference between them, the friend said, was that “with Jay nothing is ever wrong and with Dave nothing is ever right.”
Jay’s narcissism took the form of an overarching single-mindedness about his career and the material that fed it. To some close observers of Jay over the years, the Tonight Show star didn’t seem to be living life so much as he seemed to be living comedy material.
Dave’s narcissism, however, seemed more officially diagnosable. Some of Dave’s associates who had interacted with him over long periods of time began to look for ways to try to help him cope better with his demons, and dug through psychological tracts looking to match the symptoms of Dave’s apparent neurosis. They settled on a variant of narcissism, because the straight clinical condition—the one defined by grandiosity and egotism—didn’t seem a match. Dave seemed at times the direct opposite of that. His condition was more defined by a swing between huge confidence and feelings of worthlessness.
No one who spent a lot of time with Letterman ever doubted that he had true demons. The guesses about the reasons for that were varied, although, as might be expected, some pointed to his relationship with his mother. His mom’s public persona, from her numerous appearances on the show, was that of a lovely older woman from Indianapolis who baked pies every Thanksgiving. But in countless interviews Dave described her in variations of the same theme: “The least demonstrative woman God ever breathed life into.” It was another thing Dave had in common with his old rival: Jay’s mother seemed to have issues with showing emotion, as well.
Many of those closest to Dave urged him to seek some help, get counseling of some kind, maybe visit a psychiatrist. But that idea always unsettled him. One member of his inner circle said, “Every time I brought up over the years that he ought to see a shrink he always had the same reaction: ‘I wouldn’t be as funny.ʹ There was probably no question that he was right.” For the same reason Dave resisted recommendations that some kind of medication might help.
As committed as he was to staying funny, Letterman didn’t completely disregard his psychological state. Many of his colleagues believed he had occasionally sought some kind of psychological assistance—eithe
r formal or through his own research—because he dropped observations like his conclusion that he suffered from anhedonia, the inability to experience pleasurable emotions. And on the air he would tell guests that he couldn’t come to their play, or party, or dinner because he suffered from a social-anxiety disorder. Invariably the audience would laugh. The Letterman they knew was supremely sell-confident, the master of his domain, in charge of every interaction with his guests. This guy was socially awkward?
Dave did turn up at a private party NBC held for Tom Brokaw at the Museum of Modern Art in 2004, when Tom was leaving the anchor position. Though it was well known that Letterman and Brokaw had developed a solid personal relationship, heads turned all around the room when Dave walked in, accompanied by Regina Lasko, for fifteen years the woman in his life. Regina had an even lower profile in New York social circles, but at the Brokaw event she appeared smiling at Dave’s side, happily accepting congratulations on the birth of their son, Harry, less than a year before. Dave stood back stiffly from the center of the party. When someone who knew Dave well noted to Regina that a lot of people in the room were surprised to see them there, Regina replied, “So am I. It’s the first social occasion we’ve attended in five years.”
It was another case of Dave only getting more so. Years earlier, when Dave was better about talking to people, he still avoided dinners with large groups from the show. And if he was out and ran into someone he knew—a frequent guest from his show, say—he would often be thrown and not know what to do, how to go over to the other table and say a simple hello.
Even with his idol, Johnny, the awkwardness could sometimes seep out. Soon after Carson bought his estate in Malibu, which was not far from where Dave had purchased a much more modest home, Dave appeared on The Tonight Show. After the taping, Johnny pointed out that they were neighbors now. “Maybe we should get together,” Johnny said.
