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The Devil in David Letterman

How the late-night talk-show host handled his extortion crisis says a lot about the peculiar mix of function and dysfunction that got him in, and (for now) out, of the mess.

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Illustration by Dan Goldman  

I have a little story that I would like to tell you … Do you feel like a story?

Anyone who works at the Ed Sullivan Theater knows that a personal audience with David Letterman is a rare thing, especially just before showtime. But on Thursday, October 1, minutes before the start of the day’s 4:30 p.m. taping, Letterman had summoned about fifteen of the Late Show’s senior producers, writers, and crew members to his dressing room. One producer wondered who had died.

With the small room packed to capacity, Letterman announced in somber tones that he was being blackmailed: A man had threatened to go public with information about affairs he’d had with female staffers of the show unless he paid him $2 million. The assembled group, one source realized later, were only those who would need to know that Dave was going off-script after his monologue. As he spoke, he seemed almost to be rehearsing what he was about to say on the air. “He explained it much as he did on the show,” says another source, “what happened, and what had been threatened.”

The staffers were stunned. They had lived through unusual events in Dave’s personal life: his stalker, the attempted kidnapping of his son, his quintuple bypass. But what seemed different about this moment was the sense of shame emanating from Dave himself. He ended, one source says, with a typically self-conscious, self-lacerating gesture, telling everyone that if they wanted to resign because of what he had just revealed, there would be no hard feelings. No one took him up on it. “I’m sure there were people who were surprised,” says one staffer. “But I think the prevailing feeling was, ‘How can we help?’ ”

What Letterman said on-air that night was not scripted, at least not by anyone at the Late Show. “Maybe some lawyers had a glance at stuff,” says a Late Show staffer, “but even there, there was no real input.” “Do you feel like a story?” Dave said. Delighted applause. “This started three weeks ago yesterday. And I get up early, and I come to work early, and I go out and I get into my car, and in the back seat of my car is a package I don’t recognize … I don’t usually receive packages at six in the morning in the back of my car.” Laughter. “I guess you can. I guess some people do.” Then he suggested that he was the victim of something sinister. “There’s a letter in the package,” he said, “and it says that ‘I know that you do some terrible, terrible things.’ ” More laughs, some of them uncomfortable now. “There seems to be quite a lot of terrible stuff he knows about,” Dave said about the letter writer. “And he’s going to put it into a movie unless I give him some money. Yeah, I’m like you. I think, Really? That’s a little, and this is the word I actually used, that’s a little hinky.” The biggest laugh yet.

For the next several minutes, Dave turned the spotlight on the alleged extortionist, telling the story of how he, Dave, wouldn’t give in to the man’s demands, how he called his attorney and brought in the D.A. and testified before a grand jury. “And a little bit after noon today, the guy was arrested,” Dave said. The audience cheered.

Only then, almost eight minutes into the speech, did Dave reveal what it was that he had done. “Now, of course, we get to, What was it? What was all the creepy stuff that he was gonna put into the screenplay and the movie? And the creepy stuff was that I have had sex with women who work for me on this show ... ” Then later: “Now, I know what you’re saying. ‘I’ll be darned, Dave’s had sex!’ ” Another round of laughter. “We’ll be right back … ”

After the taping, Letterman’s publicist, Rubenstein Communications, sent out word that Thursday night’s show would contain a disclosure of blackmail. This was a double-taping night, and so after the show, Dave turned around and taped Friday’s show. Only then, in a postmortem that night with a half-dozen producers, did Dave finally talk about the situation again with the staff. The people around him were respectful. Letterman wasn’t exactly emotional, but he seemed more vulnerable than usual. He came around again, a source says, to the idea that he’d done the right thing by not giving in.

When it premiered in 1982, Late Night With David Letterman featured a host whose entire appeal, it seemed, was wrapped up in his sincerity as a performer. “I think of myself as being in broadcasting and not show business,” he told the profile writer Bill Zehme in an interview that year. “I can’t see myself singing in Vegas.” In time, Dave displayed almost everything the younger Johnny Carson had—the irreverence, the inventiveness, the midwestern outsider’s skepticism, even the charm. Among those Dave personally charmed was his show’s head writer, Merrill Markoe—the inventor of Stupid Pet Tricks, and any number of other conventions that are still a part of Dave’s onscreen identity—whom he once called “one of the smartest people I’ve ever known in my life.” They had begun dating in 1978, before they worked together; Markoe left the show in 1986, and they broke up two years later. But there was always something missing from Dave’s persona, something uncomfortable that brought him down to earth: He never had Carson’s studied smoothness, and rather than try, he ran hard in the other direction. In interview after interview, Letterman was a self-confessed basket case, irritable and unconfident and self-defeating. Not getting the job that even Johnny himself thought he should get seemed to confirm Dave’s outsider status. Letterman never overtly campaigned for the Tonight Show job, but once he lost it in 1991, he made it clear he always expected it. He said at the time he didn’t want to disrespect Johnny by asking NBC to succeed him—but it’s also true that having to ask for it would have meant saying he deserved it, and that was something he could never bring himself to do. “I’m too big. I’m too dumb. I’m too clumsy,” he said, comparing himself to Johnny in 1993 as he was starting his new show on CBS.


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