The War for Late Night (37 page)

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 miserable 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—either 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.

“And do what?” Dave asked.

 

Dave was never less than eloquent when speaking
about
Johnny Carson, if not to him. He openly admitted to being “in awe” of Carson and how he felt that he literally owed his career to Johnny.

Carson’s had been the vote that sent Dave off to CBS when NBC was still dangling the fever dream of
The Tonight Show
in front of him in 1993. It was Johnny who had told him that the eighteen-month hold in the deal made it sound bogus, and that he certainly would not have accepted it for himself. That was enough for Dave.

Nobody, not even Jay, really doubted who Carson believed deserved to succeed him, but Johnny himself didn’t have a vote in that. He kept his opinion on the matter private, at least until it was revealed after his death that Carson had regularly submitted monologue jokes to Dave.

That was the handiwork of Peter Lassally, the longtime executive producer for Carson, who took on the same role for Letterman after Johnny retired—first while Dave was still at NBC, and then for a time at CBS. Lassally, whose expertise in broadcasting stretched back to Arthur Godfrey’s days in radio, became Letterman’s chief counselor, advocate, and father figure during the turbulent days after NBC threw Dave over in favor of Jay. Throughout the late nineties and into the next decade, their relationship, like most others involving Dave, cooled and warmed, warmed and cooled. At the same time Lassally, to his delight, was growing much closer to the retired, and now more relaxed, Johnny.

The separation from the show that had been his life and utter preoccupation for thirty years had proved jarring for Carson. Friends reported that it had taken at least six months after he stepped down before Johnny could have a normal day—one in which he didn’t feel the withdrawal pangs. Even after he settled in to his postshow life, however, Carson could not turn off the trenchant comic instincts honed over a lifetime. He would read the paper in the morning, watch the news, hear about some zany event taking place somewhere, and the joke would simply come to him, like music. And what good is a perfectly crafted joke if you can’t tell it to someone?