Exclusive Excerpt: A New Biography of David Letterman
Two months after Jay Leno left The Tonight Show, David Letterman said that he was retiring from the Late Show. “Once Jay left, I knew I had to get out,” he said. “I was already the old guy.”
He made the announcement from his desk, in a discursive monologue that suggested the question of retirement had hung over him for several years. Letterman explained that his answer had long been, “When this show stops being fun, I’ll retire 10 years later.”
He then told a story about going fishing with his son, a pastime he had shared with his late father. On a recent excursion, Letterman had spotted a bird and taken a photo of it, leading him to speculate about what kind of bird it was. When he returned to work on Monday, he had remained focused on the question and put his staff to work figuring it out. One employee called a “bird place” in Washington, D.C.; another checked with the Audubon Society. Letterman taped his show that night and went home, and when his wife asked him about his day at work, he told her about the pursuit of information about the bird—which, it turned out, was “an immature bald eagle,” a detail that seems almost too perfectly apt. His wife had responded, “Great, but who was on the show?” Letterman told the audience that he told her he could not remember, then he smiled. An epiphany.
Letterman started his talk show career adopting an attitude that telegraphed he was beyond caring that much. (“It’s just television,” he would tell people.) In explaining why he was retiring, Letterman said it was when he realized he didn’t care enough. It was an unusually direct admission of what anyone who watched the show already knew: His detachment during all those years had, at least in part, been an act.
His story about the bird was also a bluntly candid confession of what had happened in his final years: the show had begun to serve him as much as he served it. With an almost apologetic look on his face, Letterman asked his audience that night a rhetorical question: “If you spend all day trying to identify birds, should you really be running a network television program?”
In the months before Letterman retired, he received a send-off befitting a secular saint. Conan O’Brien called him “the North Star” for comedians of his generation, and Jon Stewart, who would stop hosting The Daily Show the same year, to less fanfare, described him as an “epiphany.” No talk show host was more effusive than Jimmy Kimmel, who took the night off on the final episode of the Late Show. He said Letterman was more important to him than sleep, and referred to Dave as “my Jesus.”
The outpouring of affection for Letterman spoke to his singular stature as not just the late-night talk show host who had been around longer than any other, but the one who commanded respect throughout the culture. Several months before his final show, Letterman spoke at a tribute to Don Rickles, at the Apollo Theater, in which Jerry Seinfeld, Robert De Niro, Tina Fey, Amy Poehler, Chris Rock, Johnny Depp, and Martin Scorsese all gave speeches about the comic. Letterman appeared last and was the only one to get a standing ovation.
In his final month, his show returned to the center of the cultural conversation, and every night was an event. Letterman hosted his final Stupid Pet Trick and returned for a rare man-on-the-street bit with Billy Eichner. In Seinfeld’s final stand-up set on the show, he told the exact same jokes he had the first time he was on Late Night with David Letterman, in 1982. Muffling tears, Adam Sandler said goodbye in a moving song that called the host the “king of comedy” and “our best friend on TV.” Steve Martin, who was as close to him as any, steered clear of sentiment and poked fun at him. Julia Roberts kissed Letterman on the air and confessed that she had been terrified when she first met him, because she had seen him “absolutely dismember” so many young actresses. “Stupid people annoy you,” she said, to which he responded, “This answers my problem of self-loathing.”
Norm Macdonald, the deadpan comic who had once parodied Letterman on Saturday Night Live, delivered perhaps the most memorable of many emotional tributes. After a funny stand-up set, he declared Letterman the best talk show host of all time, before saying, “Mr. Letterman is not for the mawkish, and he has no truck for the sentimental. If something is true, it is not sentimental. And I say in truth, I love you.” Bob Dylan appeared as the final musical guest, and when he finished singing the haunting “The Night We Called It a Day,” Letterman shook his hand and thanked him. Dylan responded, “It’s an honor.”
To celebrate his 33 years on the air, some coworkers from the show threw a party for more than 300 current and former staff members at the Friars Club. At the event, he talked to former Late Night producer Robert Morton for the first time since he’d fired him and told him that it had been a mistake. Morton also had a conversation with his successor, Rob Burnett. “Rob came up to me and said, ‘I had nothing to do with your firing,’” Morton explained. “I said, ‘Rob, I don’t believe you, but I forgive you. What you did to me, I did to my predecessor.’”
Many of the original writers attended, but Letterman’s longtime creative companion Merrill Markoe stayed home. Eric and Justin Stangel, who had left the show the year before, also said they had no interest in attending or seeing Letterman. His final episode opened with cameo appearances by four U.S. presidents saying, “Our long national nightmare is over.” This set the unsentimental tone. “I’m going to be honest with you,” he said in his monologue. “It’s beginning to look like I’m not going to get The Tonight Show.”
The emotional peak of the show was a beautiful series of photos from the entire run, assembled with sensitivity and an eye for detail, that told the story of a beloved entertainer who had grown old in front of millions. In his final speech, Letterman did not cry or get emotional, but responded to the adulation he had received. “We have done over 6,000 shows, and I can tell you, a pretty high percentage of those absolutely sucked,” he said.
He thanked Paul Shaffer and the audience, but he singled out his family. He had never liked having them in the audience for his shows, which he thought would be a distraction, but for the first time, his wife, Regina, and son, Harry, were there. “Just seriously: thank you for being my family,” he said. “I love you both, and really nothing else matters, does it?”
In the year after he retired, Letterman made only a few public appearances, moderating a panel, accepting an award. But he rarely performed comedy for a live audience. One exception was when he flew down to San Antonio to appear in a long-running show put on by Martin Short and Steve Martin that included music, characters, and comedy bits.
Sitting backstage with Short, his old self-critical streak returned. He kept telling Short that he was going to bomb, that he didn’t belong there. Short assured him he would do great, that the audience would be thrilled to see him. Then the show started, and during one of Short’s costume changes, he came offstage and saw Letterman, in a suit, waiting with a question: “How many other people have done what I’m going to do?” he asked. Short said none. “That’s because they shouldn’t.” Short responded: “Dave, if you go out there and kill, which you will, will you drop this shit?” Letterman said: “For an hour.” Then he went out and read a Top Ten List about Donald Trump. It killed.
The late-night talk show has always been an ephemeral art form. It’s no accident that Steve Allen called one of his memoirs Mark It and Strike It—industry jargon for taking down the set—to indicate how fleeting his work could be. When Jack Paar arrived at Rockefeller Center, where he had once hosted The Tonight Show, to be a guest on Late Night, he complained that the security guards who met him downstairs didn’t recognize him. Even Johnny Carson faded from memory, surviving in the public imagination primarily as an influential gatekeeper.
Unlike the finest work of other signal comedies of his era, like The Simpsons and Seinfeld, Late Night is not constantly running in syndication. His early innovative work has faded from memories and to large parts of his younger audience, is little known. For some, Letterman will always be the hip alternative to The Tonight Show, but for others, he represents a stodgier, older generation. His longevity is one of his greatest accomplishments, but it also may have obscured some of his artistic legacy. Meanwhile, the late-night landscape has entirely transformed. Letterman’s cynicism about celebrity and his hostility toward show business are almost entirely absent. Hosts not only are sunnier, but they have none of his skepticism of technology or delight in language. And because of DVRs and the internet, you no longer need to stay up to watch these shows. Late-night television isn’t even for late night anymore.
Yet, look hard enough and you can see the influence of Letterman everywhere. The internet has become the home of stupid pet tricks and prankish stunts, and the baffling absurdist comedy of Late Night is now mainstream. When James Corden shoots an entire show in a stranger’s house or when Jimmy Fallon conducts an interview on helium or when Conan O’Brien puts together a deftly edited video of himself interacting with strangers on the street, they are walking in Letterman’s footsteps. The remote pieces that Merrill Markoe pioneered have become common on almost all the late-night shows, and while his biting, ironic voice has moved away from late-night talk, it has become pervasive in popular culture.
But the real importance of Letterman is not only to be found in the way his shows have been copied or whom they have inspired. Some of his best work was funny and exciting precisely because it was too odd to imitate. At his best, Letterman had the integrity and ambition to reach for something more eccentric and personal—a national televised talk show that had the feel of downtown performance art. His comedy always seemed to be commenting on itself, eluding easy readings, and raising questions about its own veracity. While his persistent self-awareness appeared designed to avoid directness, Letterman became one of the most fully realized characters on television, a beloved cranky figure, idiosyncratic, even off-putting, and entirely his own.
Letterman gave all of himself to television—but he needed help. The first two great eras of Late Night were the products of collaboration. In the third one, which bled into the CBS show, the writers were marginalized and an entirely new show emerged that in some ways was the most daring, integrated, and honest one yet. Its strength was not in the writing but in its hilarious portrayal of this difficult, fascinating, and self-lacerating character who hated revealing himself in his work but couldn’t help doing so. The greatest legacy of Letterman was that he proved that hosting a late-night talk show could be an inspired and highly personal art.
Letterman, of course, downplays the importance. And in retirement, he says he pays no attention to late night and goes to sleep too early to watch any of the new hosts. But he does care about how he’s remembered. “Only because of my son,” he said, toward the end of an interview, his glasses pushed up to his forehead so he looked barely recognizable. “My wife will remarry a dentist. But you want your kids to know what you did.”
Letterman says he’s not looking to emulate Johnny Carson in his post-show career. After Carson retired, Letterman spent some time with him, and the portrait he painted was of an unhappy man who refused to engage with his history at all. Letterman’s takeaway, he suggested, was that you have to take responsibility for your own happiness, a sign that he has matured.
Letterman can seem like a man who has moved on with life. Other times, he’s still in the middle of the late-night war.
Toward the end of one interview, I asked Letterman what the most underrated quality in a talk show host is, adding as an aside that Jay Leno had answered the same question in one word: “kindness.”
Letterman’s face remained still upon hearing this. Then he launched into a monologue about handling guests who aren’t performing well, before making one of those pivots he made so deftly every night on his show. “And,” he said, holding the silence for several moments, “kindness.”
Letterman paused again, still deadpan, no smiles, waiting for the perfect split second, eyes widening: “Did I not mention kindness? Let me mention … kindness.”
Letterman: The Last Giant of Late Night is available online and at bookstores throughout the city.