The War for Late Night (42 page)

“I can’t wait for you guys to come on,” Ross told her.

 

The Jay Leno Show
opened on September 14, 2009, with a flourish, proving, if nothing else, that America would still respond to a frequently repeated message: Something big is happening on television tonight.

With good pal Jerry Seinfeld as a comfortable first guest (Jerry tweaked Jay, “You know, in the nineties, when we quit a show, we actually left”) and a fortuitous appearance by Kanye West, just days after the singer’s rant against Taylor Swift at the MTV awards (Jay asked him—not in a funny way—what his mother would have thought of his behavior), the premiere hit an extraordinary number. Ranking as the biggest show in all of television for the night, Leno attracted 18.4 million viewers, with a huge 5.3 rating among the young demos. By contrast, Conan’s spectacular debut on
The Tonight Show
in June had reached 9.2 million people and got a 3.8 rating in the all-important demo.

NBC resisted the urge to call Jay the “New King of Prime Time,” and critics were largely unimpressed, dismissing the show as mostly a remake of the old
Tonight
formula, a rehash, and “a bore.” But critics had never left bouquets on Jay’s doorstep, so he was hardly surprised.

The show also introduced its first correspondent, Dan Finnerty and his Dan Band, singing their way through a car wash. The segment did not find many enthusiasts. But it soared compared to bits from others in the group of largely unknown comics and improv artists who began filling up act two of the show.

Debbie Vickers quickly realized that NBC, in its desire to appease the concerned stations with a strong end to the show, had effectively built in failure as a regular—and early—element. The contributors were mostly tepid young performers executing uninspired ideas. And they were on in prime time—at about 10:12 p.m. (when defectors could still pick up the thread of the cop shows on the other channels). All her instincts about how to retain viewers after the monologue went on alert: This material threatened to devalue the entire show.

But she couldn’t cut the segment from the show. A “comedy hour” ate up material like a ravenous beast. It seemed that every time Vickers looked up, more material they had put on the schedule had already been used. As much as she wanted to bail on some of these weak contributor spots, dropping them would start a chain reaction—and by the next day three acts would be missing. Jay couldn’t physically fill up the whole hour on his own. As it was, the demands on him had escalated. Any bit Jay did outside the studio had to be shot during the few spare minutes of his life. He had committed to performing just as many gigs around the country—160 or so—as he ever had, making no concessions to his increased workload on the prime-time show. Bits inside the studio that involved Jay also demanded rehearsal time—further diversion from his primary mission: putting together twelve to fourteen minutes of monologue daily.

The contributors had to contribute—lame performances or not. Vickers soon realized she was approving material to go in act two of the prime-time show that she would never have allowed to air in late night. How did that make sense? And all because the better act two material—“Headlines” and the rest—had to be saved for the last segment to lead into local news. The bad agreements Debbie believed the show had made to win the stations over looked worse every day. Jay, usually a rock onstage, showed signs of losing his rhythm. He knew well that the key to performing successfully on a daily show was flow—flow of jokes, flow of segments. Splitting the best comedy bits off from the monologue was diverting the flow into a sad little pond.

 

On the morning of October 1, 2009, David Letterman, looking less like a TV icon than a visiting rancher from Montana, stood up in front of a grand jury in Manhattan, sheepish and ashamed, and revealed the details of what the district attorney’s office was branding as a case of extortion. For Letterman, haggard and deadly serious, the essence of his message to the jurors was that he had been threatened and he feared for himself, his family, and his job. He quietly admitted to things that made him sound boorish but explained that he was doing so willingly in an effort to help the DA’s office, which he praised and thanked, along with the grand jury. The jurors were sworn to secrecy, of course, but Letterman knew the incident would break as soon as an indictment was handed down. As he had throughout his incident-dense career (and life), Letterman decided to take the matter straight to his audience.

One of the unique properties of the late-night television show in America is that daily events in the private lives of its hosts become an inescapable part of the presentation, because the presentation is, in almost every case, the host himself. Letterman, more than any of his peers, had raised that act of public self-examination to a level of comedic—and sometimes dramatic—soliloquy. He simply didn’t talk about himself in any other context, which made his desk commentary in act two take on more and more of the aspect of a personal confessional. Most recently he had twice contorted himself, with apparent reluctance, into a regretful posture to apologize to Sarah Palin. But in his years on the show Dave had discussed everything from his encounters with his famous stalker, to the deaths of important people on the show and in his life, to 9/11, his bypass surgery, the birth of his son, and his marriage—all sitting behind his desk communicating directly into the camera.

In this case he might as well have been kneeling like a penitent.

Letterman told the audience assembled for that night’s entertainment that he was glad they were there and apparently in “a pleasant mood” because he had a story he wanted to lay out for them. The story traced his grand jury appearance and the charge of blackmail it involved. Letterman filled in many details: the mysterious package left in his car at six a.m. three weeks earlier containing material that claimed proof of “terrible, terrible things” Dave had done—Dave conceded, “Sure enough, there was some stuff in the pages that proved I did those terrible things”—and the threat that this evidence would come out in the form of a screenplay if Letterman didn’t pay up.

Dave related the steps he took, contacting his lawyer, the two of them meeting with the man behind the plot, the decision to go to the DAʹs office, the sting, which included Dave’s lawyer, Jim Jackoway, wearing a wire and handing over a bogus check for $2 million, and the resulting arrest of the blackmailer, whom Letterman described as menacing.

Throughout the account Letterman maintained a mesmerizing tone that mixed seriousness with a kind of “Can you believe this?” incredulity. The studio audience, not having a clue if what they were hearing was the truth, some tall tale, or maybe the intro to some comedy bit, was obviously thoroughly entertained, releasing regular bursts of laughter, sometimes at inappropriate moments.

“I had to tell them all the creepy things I had done,” Letterman said of his grand jury testimony, which ignited a huge laugh. “Now why is that funny?” Dave asked. But he continued, because it was time to discuss precisely what he had been accused of.

“I have had sex with women who work with me on this show,” he said, this time to silence. He recounted how the grand jury had asked whether this was true. “Yes, I have,” he said.

“Would it be embarrassing if it were made public? Perhaps it would,” he said, adding his only real joke: “Especially for the women.” But to go public and talk about it would be a decision for them, Letterman said.

He got to the essence of the issue: his need to protect his family, himself, and his job. When the smoke cleared, he brought out Woody Harrelson.

For those who had known and worked with Letterman throughout his career, the revelation was at once stunning and yet not unexpected. One longtime Letterman associate said, “I was surprised at how he confronted it. That was a shock to me. In my wildest dreams, I would never imagine David Letterman going on TV saying those things.”

Not because his admissions seemed incredible, the associate said. Everyone who worked around Dave, starting early in his career, was aware that he certainly took a healthy interest in women. They also knew he tended to meet and converse with only women he worked with, because his awkwardness in social settings made it unlikely he would meet them anywhere else. It began with the early love of his professional life, Merrill Markoe, the extraordinarily talented writer who inspired many of his breakthrough ideas and shared his personal life (to her eventual regret) for about a decade. It continued with Regina Lasko, whom Letterman also met at 30 Rock, and who had been his life partner for more than twenty years before they married in 2009.

But as one woman who interacted with Dave in his
Late Night
days put it, “Everybody was after him; he was so cute and sexy.”

The longtime associate who’d been so surprised by how Dave went so public said, “Isn’t that why some people go into show business? Isn’t that why half these guys become comics? So they can fuck around? Isn’t that why rock stars become rock stars? Yes, Dave had his flings over the years, but never once did anyone hear him say he wanted so-and-so to get a raise. He was never like that.”

What was most extraordinary about his confession that October was the fact that Letterman spoke so directly about the situation—on television. One friend from his early TV days said, “This is a guy who used to not like to say the word ‘sex.’ He was skittish about it. It was shocking to me to hear him talk like that. Shocking.”

A big part of the reason for that shock was that Letterman had an almost physical revulsion against anything that he perceived as personally humiliating. One colleague from the show remembered Letterman’s distress over things like a bad haircut. “He would come in on Monday and people would ask how his weekend was. He would say, ʹI had to hide under the house the whole weekend. This fucking haircut. I couldn’t let people see me with this haircut. I look like Howdy Doody.”

Among Letterman’s colleagues, friends, staff members, rivals, old enemies, fans, and nonfans alike, the reaction fell along similar lines: Dave took a situation suffused in negative, even career-threatening, connotations and somehow revealed it, dissected it, and neutralized it in one remarkable performance. It was like a scene out of
The Hurt Locker
: Letterman carefully, systematically defused a time bomb sitting in his own lap. “He went right into it, cut the wires, and left,” said a veteran staff member.

“Not only did he defuse the bomb,” said Jimmy Kimmel, “he then threw the bomb into enemy barracks and fucking blew everybody else up by making himself front and center again.”

The question of course, remained: While it might result in Dave’s getting a little more immediate attention, what would his confession mean for the show long term? Inside the offices at Worldwide Pants—and at CBS—nobody was really certain. What if a parade of former girlfriends marched forth to condemn Dave as a serial womanizer? Worse, what if some women came forward to say Dave either hit on them obnoxiously or took advantage of his position as the boss to get them into bed? No one really knew precisely what Dave meant when he said he had had affairs with women—plural—on the staff.

Some people knew about Stephanie, of course. For years Dave’s evident infatuation with one of his assistants, Stephanie Birkitt, had been the subject of gossip around the office—and even among some viewers. Stephanie, who at thirty-four was about half Dave’s age (sixty-two), had appeared on the show more than 250 times. Dave, who had pet names for her like Monty, Smitty, and Dutch, had her dress in cute costumes or dance goofily for him, or even serve as a comedy correspondent. She interviewed
Survivor
losers, always asking, “Did you see or touch any monkeys?” And she got to take trips to places like Turin, Italy, where she served as the show’s feature reporter for the Winter Olympics in 2006.

When it was revealed that the man accused of blackmailing Letterman, Robert (Joe) Halderman—a CBS News producer—had shared a house in Connecticut with Birkitt, the connection to Stephanie as one of the in-house paramours was easy to make. Much of Halderman’s information on Dave had come from Birkitt’s diary, which he later admitted to reading.

Letterman, stated in his chat on that night of Thursday, October 1, that he would have nothing more to say on the subject. But between the boss-employee relationship and the age difference, the scandal sent out some potent tentacles. So he had to return to it on his next taping, the following Monday. (Friday’s show had been in the can for a week, as usual.)

Letterman didn’t flinch in the monologue, putting the incident stage center.

Referring to the sex scandal involving Mark Sanford, the governor of South Carolina, Letterman said, “Right now I would give anything to be hiking on the Appalachian Trail.”

And: “It’s fall in New York. I spent the weekend raking my hate mail.”

Then he took his place at the desk and again announced that he had some serious business to attend to. His almost offhand reference to multiple affairs with staff members, he explained, had caused many of the women he employed to be chased by the press, looking for confessions of office passion.

“I’m terribly sorry that I put the staff in that position,” Letterman said. “The staff here has been wonderfully supportive to me, not just through this furor, but through all the years that we’ve been on television and especially all the years here at CBS, so, again, my thanks to the staff for, once again, putting up with something stupid I’ve gotten myself involved in.”

And then there was Regina. As his monologue implied, the revelation of the affair with Birkitt had put his recent marriage at serious risk. Letterman, who still felt overwhelming guilt about the breakup of his first marriage, twenty-five years earlier, to his college sweetheart, Michelle Cook, had obviously wrestled for years with his reluctance to marry again. The decision to go through with his marriage to Regina related directly to his commitment to Harry, now five, and the prospect of this family breaking up—and his losing daily contact with Harry—over “something stupid” he’d gotten himself into was clearly wrenching for him.