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David Letterman: Happy at Last

When he stopped being miserable, he knew it was time to go

David LettermanDavid Letterman

Letterman at the Ed Sullivan Theater in New York, before taping of one of his final broadcasts.

Photograph by Mark Seliger

I feel like I’m talking too much. You tell me some stories.”

It’s 10 till seven in a conference room high above West 53rd Street, and David Letterman has just exhausted his capacity for self-reflection. We were scheduled to talk for 45 minutes; we’ve been at it for 44. After nearly 50 years of live broadcasting, he knows instinctively when a segment is about to run long.

Normally, Letterman doesn’t love talking about himself; what he wants to say, he says on his show. But today, he’s sitting for an exit interview of sorts. A few weeks from now, at approximately 5:30 p.m. on Wednesday, May 20th, Letterman will wave good night, the lights at the Ed Sullivan Theater will go dark, and the Late Show With David Letterman will have taped its last episode. There’s a long goodbye scheduled before then, featuring a once-in-a-lifetime lineup of A-list guests — Hanks, Clooney, Seinfeld, Winfrey, Murray, Roberts, at least one Obama — as well as plenteous highlights from his 22 years on CBS. It’s shaping up to be the kind of star-studded send-off television may never see again. And Letterman, of course, is not looking forward to it.

“I’m dreading it,” he says, grimacing. “As Regis used to say, ‘I don’t like going down memory lane’ — and I’m afraid that’s what this is all about. After we get through with it, then I’ll sit back and see what we’ve done. But for now, I just want it to be over with.”

Today is the first day of April, and Letterman has just finished taping his 5,994th show. He’s changed from his suit into his evening wear: long-sleeved brown Carhartt T-shirt, green canvas pants and beat-up hiking boots that aren’t so much unfashionable as they are unacquainted with the concept of fashion in the first place. His nose is slightly sunburned — a souvenir of his spring-break trips to Wyoming (for skiing) and St. Bart’s (where he keeps a home) — and behind his amber-framed glasses, his 67-year-old eyes look tired. “When Johnny Carson left, I remember asking him why, and he said, ‘I just don’t have the energy,’ ” Letterman recalls. “That rings true to me.”

He’s leaving as the champ, of course: Maybe not Sandy Koufax, quitting after a 27-win season, but at the very least Ted Williams, hitting dingers in four different decades. He changed not just late-night TV but the very nature of comedy itself. Self-awareness, Stupid Pet Tricks, sneakers, irony: He taught multiple generations what it means to be funny. “Everything about his show informed not only our writing but our actual human interactions,” says Tina Fey, a Letterman fan since his short-lived morning show in the summer of 1980, when she was 10. Sixteen Emmys and a few thousand Top Ten lists later, even Jay Leno has acknowledged that Letterman’s the better broadcaster. At this point, it’s Copernican: settled science.

Preparations for his farewell have been underway for months, but for now, Letterman is largely steering clear. “It’s funny,” he says. “In the old days, if there were any kind of special show, I’d want to be right in there. And now I just feel like, ‘Let’s do something polite and happy, and get out of here.’ ”

Letterman has had his share of all-time moments over the past few years: the audience-free shows he did during Hurricane Sandy; his immortal encounter with Joaquin Phoenix. But you also get the feeling he’s sometimes mailing it in, occasionally reinforced by him saying, “I’ve been mailing it in.” “If I haven’t gotten it out of my system after 6,000 shows,” he says, “who am I kidding?” And yet, there’s a part of him that clearly doesn’t want to go — like he’s leaving because he thinks he should, not because he’s actually ready. “I do like it,” he told Howard Stern last year. “And if it were up to me, I would not quit. On the other hand, it’s not always up to me. And you can’t go on forever.”

Jerry Foley has been the Late Show’s director for the past 20 years. “Lately, he’s just been wandering the theater, soaking things in,” Foley says. “A couple of weeks ago, we caught him standing behind the drum kit during a commercial break — somewhere the house cat never goes. Or he’ll wander out to 53rd Street, just letting it wash over him. You can tell he’s savoring it and trying to upload as much as he can.” 

“Embracing the ending?” asks his longtime sidekick Paul Shaffer. He laughs. “No, I don’t think so. I think he’s more of the mind of ‘My God — what have I done?’ ” 

Paul Shaffer and David Letterman

Three days a week, Letterman wakes up in his downtown Manhattan loft at 6 a.m., drives to his offices at 53rd and Broadway and immediately goes back to bed. He used to commute at a more normal hour, but at some point he decided he hated traffic so much that he’d rather sleep in segments than spend an extra 15 minutes in rush hour. Now he gets to his 12th-floor suite around 6:30, sleeps for three more hours, then gets up to start his day, “refreshed and ready to go.”

Letterman spends a few hours doing preproduction: talking to producers, making phone calls, reviewing monologue jokes. But he rarely goes to meetings, and he doesn’t do rehearsals. “My input now is less than it’s ever been,” he says. “They’re sick of me saying this, but I tell the producers, ‘I’m not a producer, you’re the producers. You come get me when the show is ready, and it will either go smoothly or it won’t.’ ” A knowing pause. “Which is maybe an indicator that you shouldn’t be hosting your 11:30 comedy show much longer.”

At 2:45, he heads down to his second-floor dressing room for makeup and “to put on my little outfit,” then hits the stage at 4:25 for a brief audience Q&A (originally two and a half minutes, tops; lately seven or eight or even more if he’s feeling chatty), followed by the Late Show With Daaaaaaavid Lettermaaaaaaaan! Then it’s back upstairs for a quick postmortem (which involves less shouting and more laughing than it did in the old days). If a guest has a movie he or she is promoting, he’ll watch it in the office screening room. He’s usually home by 8:30 or 9 to put his son, Harry, 11, to bed. Thursday mornings he takes Harry to school, and that afternoon he tapes two shows — one for the following night. “And then Thursday nights I go home and pick up the dogs” — his two yellow labs, Sully and Dutch — and he drives to his home in Westchester County, an hour or so north of New York. “And then,” he says, “the real fun begins.”

After his quintuple-bypass surgery 15 years ago, the biggest turning point in Letterman’s life came on November 3rd, 2003, when, at 11:53 p.m. — just about the time he’d normally be opening the Top Ten list — Harry Joseph Letterman was born. Letterman named the boy after his own father, an Indianapolis florist who died when Dave was 25. Even casual fans know how much fatherhood has changed him. Says his good friend and frequent guest Tom Brokaw, “You cannot overstate how important Harry is in his life.”

Letterman had talked about having kids for years, but by his mid-fifties it seemed like it might not happen. But then, all of a sudden, there he was, a first-time dad at 56. He jokes that he doesn’t worry about screwing up Harry too much, since “by the time the kid’s out stealing cars, Dad will be dead.” Still, he tries to impart lessons where he can — like how he takes him out every April to pick up beer cans from the road around their house. “I don’t know if it’s the kind of thing that will be meaningful to him, or the kind of thing where he’ll be like, ‘Yeah, when I was a kid, my old man used to make me clean up the goddamn road,’ ” Letterman says. “It could go either way.”

These days, the happiest he is in conversation is when he’s telling stories about taking Harry fishing. At their house upstate, they have a fishing pond stocked with bluegill, carp, largemouth bass and a “nasty, evil snapping turtle that’s the size of this table.” Says Letterman, “We’ve caught everything but the carp. I won’t have any business with it, but Harry is determined. It’s hard to hook them — so far, to our observation, they only eat Brussels sprouts. We decided the best thing to do is net them. So on Sunday, Harry spotted one, and he says, ‘Dad, let’s go get him!’ We leave a trail of Brussels sprouts, and I’m standing in the pond with the net, just hoping to God it doesn’t come around. Because I want no part of it. I mean, they’re three feet long! They’ll kill you. You see them in, like, an armada, just waiting. So that was our weekend.”

“Once Dave retires, there’s nobody left to be scared of,” says Tina Fey. “It’s all friendliness now.”

About six years ago, at the bold age of 62, Letterman decided to take up skiing. He was looking for something he and Harry could do together as he got older. He found a little hill near their house — “a miniature-golf/paintball/laser-tag kind of place” — and signed up for lessons. The first time, he wiped out hard.

“They had one of those ski-pole fences up, and I just went right over it,” he says. “People stopped and gasped: ‘Jesus, what was that? Avalanche?’ But then we progressed, and it just took. And then Regina, bless her heart” — his wife of six years and companion for almost 30 — “she’s not very athletic, but she saw that Harry and I were getting serious, so she started skiing too. And that was huge. Because then it wasn’t just Harry and me out there. Now it’s the three of us. And this is great,” he says. “Because now Harry will ski for the rest of his life. And Regina and her second husband will ski for the rest of their lives.”


hen Late Night With David Letterman premiered on NBC, on February 1st, 1982, the most popular shows in prime time were 60 Minutes, Dallas and Trapper John, M.D. Lawrence Welk still had his own show, and Archie Bunker and the Fonz were still on the air. MTV was six months old. If Jimmy Fallon lasts as many years as Letterman, he will retire in 2042.

“What I’d like,” said Letterman when he started, “is for this show to stay on long enough to become just a pattern of American television. If we’re still on the air in five years, I’ll think of it as a success.” He undershot it by a factor of seven.

In the beginning, Letterman was “hip,” “ironic,” “groundbreaking,” “cool.” Thirty-odd years later, he’s getting labeled a “grandpa” by Justin Bieber. Johnny Carson always promised himself he wouldn’t “stay too long at the fair”; sometimes Letterman worries that he has. “If you look around at the other people doing it and look at me, it’s almost like a pair of shoes you haven’t worn in a hundred years,” he says. “ ’Gee, I think we can probably get rid of these.’ I still enjoy what I’m doing. But I think what I’m doing is not what you want at 11:30 anymore.”

Early on, the rap on Letterman was that he was bad at interviews and mean to guests. “It wasn’t his strong suit,” Shaffer admits. “But every night he studied those interviews, and he got better.” Now he’s one of the best conversationalists on TV, whether talking to a guest or spinning a yarn about a bear invading his home in Montana. He can still be mean, but these days he’s more liable to sit back and let a guest embarrass himself. (As Fey once put it, he’s “a professor emeritus at the Here’s-Some-More-Rope Institute.”) Carson famously observed that late-night shows are “all about the guy behind the desk.” No offense to Letterman’s replacement, Stephen Colbert, or the Jimmys, but when he leaves, the desk will be a little bit smaller.

Letterman speaks warmly of his younger colleagues, calling Jimmy Fallon’s show “bright and colorful” and “a commercial for itself” and Jimmy Kimmel “friendly” and “very sweet.” He says the lack of YouTube-ability is “a weakness of our show. I hear about things going viral, and I think, ‘How do you do that?’ I think I’m the blockage in the plumbing.” At the same time, he must look around at the celebrity Pictionary and the twerking pranks and figure maybe it’s not worth it. He’s like the last T. Rex after the asteroid hit, watching a bunch of chipper mammals scurry around the plains he used to roam. “Once he retires, there’s nobody left to be scared of,” says Fey. “It’s all friendliness now.”

“He’ll probably hate this,” says his old friend Michael Keaton, who’s known Letterman since their days at the Comedy Store in the 1970s. “But I always thought it was kind of cool that he was never, except for a few times, number one. To me, it was perfect. It made his cachet and his legacy that much greater. Maybe he wasn’t quite as popular. But everybody knew, qualitatively, that he was the best.”

Letterman announced his retirement on the air in April 2014, and he did it with a fishing story. He and Harry had been out at a reservoir one afternoon the previous fall when they spotted an eagle. They weren’t sure if it was a bald or a golden eagle, so Letterman came to work the next Monday and spent the whole day trying to figure it out. Photos were Googled; staffers were enlisted; the Audubon Society was called. Finally they had the answer: It was an immature bald eagle. Back home that night, Regina asked him about his day, and he eagerly recounted the whole investigation. “That’s great,” she said. “Who was on the show?” Letterman couldn’t remember. That, he told the audience, is when he knew it was time to go.

In reality, he admits, the story was “a convenience.” The specifics were true, but he and Regina had been having serious conversations about his retirement for at least a year and a half. “I just thought, ‘I don’t want this to be mawkish, I don’t want it to be maudlin,’ ” Letterman says. “ ’Let me see if I can’t just put it all off on the kid.’ ”

Publicly, Letterman had been talking about leaving for decades. “Ten years seems just about right,” he told Carson in 1991. “I’m too old for this,” he told Rolling Stone five years later. He laughs now, remembering how he once said he couldn’t see himself going past 40. “I think I was probably being disingenuous,” he says. “I was trying to get ahead of ‘When is he ever gonna stop?’ But I never really wanted to.” 

David Letterman and Johnny Carson

But then came his heart surgery in January 2000, and then Harry. His contract extensions kept getting shorter and shorter: four years in 2006; two each in 2010 and 2012. Then, in 2013, he passed Carson for longest-running late-night host, and there weren’t that many milestones left. The last extension he signed was for a year. “The next day, I woke up in a bloody panic,” he says. “ ’Holy crap! What if I can’t do this for another year?’ ”

Carson was 66 when he retired from The Tonight Show. When Letterman’s contract ended, he would be 68 — a prospect that horrified him. “I’ve made my peace with 68, I feel OK with 68,” he says. “But a couple of years ago, you just think, ‘Oh, Jesus, God.’ I remember Tom Brokaw coming on the show when he was 68, and thinking, ‘This poor bastard.’ ”

The most decisive moment, though — what Letterman calls “the anchor in the water” — was, in retrospect, the obvious one: when his old sparring partner Jay Leno hung up his gloves. “It caught me off guard,” Letterman says. “I thought Jay would have that job as long as he wanted. His ratings were strong; he showed no sign of slowing down. I know he loved it. I know it must have been hard for him.” When Leno announced he was leaving, Letterman called him up. “I was sort of touched by it,” he says. “I said, ‘Jay, are you actually retiring?’ And he said yeah, you know, so and so. And I said, ‘Well, I hope this is good for you, and I’m sorry you’re leaving.’ He was very nice and earnest about it.”

“For 30, 40 years, I was anxious, hypochondriacal, an alcoholic and many other things.”

When it was time to make his own announcement the following year, the first person Letterman told at the Late Show was Paul Shaffer. “I think it was a Monday, and the two of us were in the wings about to go out for warm-up,” Shaffer says. “And he says, ‘Come here, I gotta tell you something. I’ve realized it’s time.’ ” Shaffer says he wasn’t surprised: “You look around at these other shows that are younger and changing the format, and you can kind of see it’s time to step aside.” A few days later – exactly one year after Leno’s announcement — Letterman summoned the senior staff to his dressing room. At first, executive producer Jude Brennan — who’s worked with Letterman since the 1980 morning show — was worried he might have a disease.

Letterman tried to downplay the occasion. “I wanted to make it as casual and organic as possible,” he says. “I felt self-conscious about it. I didn’t enjoy it.” But to the rest of the staff, it was a surreal, almost slapstick scene. Letterman had just cut himself shaving, so he had a giant blood-soaked Band-Aid on his face. He also had a radio on in the background, which was playing, of all songs, Pharrell Williams’ “Happy.” Recalls head writer Matt Roberts, “Here he is going, ‘This 30-year career, we’re finally bringing it to a close . . . ’ and all I can hear is ‘Clap along, if you feel. . . .‘ ”

“Afterward,” says Letterman, “I kind of expected everybody to go, ‘OK, sure, that makes sense. But I remember Jude Brennan asked, ‘Why now?’ That’s when I thought, ‘Oh, Jesus — maybe I’ve made a huge mistake.’ ” Three hours later, he went onstage and told the eagle story.

In addition to being talk shows, the Late Show and Late Night were dysfunctional workplace comedies, as much as Taxi or The Office. There was a whole cast of characters: Dave and Paul and the band, of course, but also Biff Henderson, and Alan Kalter, and Rupert down in the deli. Much of his staff has been there 25 years or more, and the overwhelming feeling of denial. “Maybe we’re just rats that have been running in a wheel for so long we can only focus on the wheel. But I don’t feel it,” says Rob Burnett, former Late Show head writer and current CEO of Letterman’s production company, Worldwide Pants. Adds Brennan, “In a weird way, I’m not really thinking about it at all.”

Executive producer Barbara Gaines has also been with Letterman since the morning show, where she started as a receptionist on May 21st, 1980. When she reports to work for the last Late Show on May 20th, it will be exactly 35 years since she started in Letterman’s employ. Hanging on the wall in her office is a giant corkboard full of color-coded index cards, mapping out the last six weeks of the show — pink for bits like Top Ten lists and prepackaged remotes, green for musical acts and yellow for guests. She’s putting together a greatest-hits tribute, choosing from classics like the Taco Bell drive-thru and “Dave and Steve’s Gay Vacation.” Short of Andy Kaufman showing up, the biggest surprise would probably be an appearance by Leno; Letterman’s camp has invited him, but he has yet to accept. The staff remains hopeful: “It’d be great to just let them chew on whatever they have to chew on,” Burnett says. “To see Dave turn to Jay and say, ‘What’s your beef?’ ”

If Carson’s Tonight Show is any model — as it has been for most of Letterman’s career — the finale might not include any guests at all. Carson simply sat on a stool in front of an audience of friends and family, and showed highlight reels and talked tearfully about how much the show meant to him. It’s not hard to imagine Letterman doing something similar. “I kind of know what I’m going to do, which to me is, selfishly, all I care about,” Letterman says. “But if I cry,” he adds, maybe not quite convincingly, “then something is going terribly wrong.”

One afternoon, with a month to go, Letterman breezes into the greenroom after a taping, in excellent spirits. A few minutes earlier, he’d made a minor mistake with a musical guest, accidentally calling him by the wrong name — the kind of insignificant slip-up that might once have sent him into a spasm of self-directed rage. Today, he’s smiling. “Yeah, I hashed it all up,” he says, shrugging. “But then I thought, ‘I’ve got eight more shows — what do I care?’ ” (Says Shaffer, “He’s developed a real ‘what the fuck’ attitude in these last couple of shows. He’s having more fun.”)

Letterman just got back from a week in Montana — just him and the dogs. It was snowing when he landed there, and he took his new horse, Woody, out for his first ride. “We saw a dozen bighorn sheep, a bunch of mule deer, that big high mountain sky . . . ,” he says, full of wonder. “Here in New York, your view is dictated by the length or width of a city block, but on the Rocky Mountain Front, you just have this never-ending view. It’s like if your belt’s too tight, and you finally release it and can breathe naturally. I don’t mean to sound ridiculous, but it’s pretty close to that.”

When he first bought Montana property in 1999, Letterman avoided the southwestern part of the state, where celebrities like Brokaw and Ted Turner live, and instead went north, near Glacier National Park. Letterman’s Deep Creek Ranch abuts the Bob Marshall Wilderness, which Brokaw calls “the last great, unfettered wilderness area in America.” Jack Hanna, the director emeritus of the Columbus Zoo and another longtime guest of Letterman’s, owns property on the other side of the Rockies. “Where Dave’s ranch is has some of the most incredible wildlife in America,” Hanna says. “Grizzlies, black bears, mountain lions, elk, moose, wolverines. It’s like going back in time. Those plains have not changed in 500 years.”

“It’s phenomenal,” says Letterman, “just phenomenal. And the more you see of it, the more you want to see.”

The closest municipality to him is Choteau, an old cowboy town, population 1,700, about a hundred miles south of the Canadian border. Letterman has been known to ride a horse-drawn wagon in the Fourth of July parade; during his emotional monologue after 9/11, he paid tribute to the NYPD and the FDNY, but the closest he came to losing it was talking about how the people of Choteau, in the midst of a crippling drought, held a rally in the school gym to raise money for people in New York. “If that doesn’t tell you everything you need to know about the spirit of the United States,” said Letterman, holding back tears, “then I can’t help you.”

Letterman visits Montana year-round, but mainly in the summer, when Harry is out of school, and he can invite friends like Shaffer and Bill Murray along with their families. “It’s more fun to have people there,” he says, somewhat uncharacteristically. “It gets to be just like camp: hiking and fishing and kayaking and horseback riding.” And he loves camping out, but has one rule: “No tents.”

“In the summer, it doesn’t really get dark until 11, maybe midnight,” Letterman says. “So you stay up as late as you can, and then finally, about 11:45, when it’s just crepuscular, you wait for that last line of light to duck down behind the mountains. It’s beautiful — the Milky Way is so bright that it actually washes out stars. I always sleep with my glasses on, so that when I wake up in the middle of the night — which, at my age, is every 18 minutes — I’ll be able to see satellites and planets and constellations and shooting stars. It’s just remarkable.”

“I came very close to having the whole thing explode on me. The only thing that’s important, I had ruined.”

When he first started going out there, Letterman didn’t know anything about snowpack or livestock or Montana ecology. But now, with the help of his ranch manager, Andrew Bardwell, he’s started raising a bona fide bison herd. He’s got more than a hundred; he sends them to market and everything. “David’s a pretty active rancher,” says Brokaw. “This is not boutique stuff.” Hanna says, “In the last four or five years, Dave has become one of the greatest conservationists I’ve ever met. His land, his grasses, his water, how he plants his fields — he knows everything. It’s absolutely amazing. He studies like you wouldn’t believe.”

Hanna says that before Letterman bought the ranch, he asked Hanna what it was like up there. “Dave, where you’re looking at is one of the wildest places on the North American continent,” he recalls telling him. “You’ve got to be a real mountaineer. It’s desolate. There’s high winds. It gets very cold in the winter. It’s one of the most solitary places in America. You don’t see many people.”

Said Letterman, Hanna recalls, “That’s it. That’s where I’m going.”

Letterman’s introversion is, by now, legendary. Regis Philbin says that after all these years, he’s still never been invited to his house. “He’s very shy,” agrees Brokaw. “We’ve tried to get David to see us in Montana, and it’s always, ‘Nah, I don’t think so.’ ” He’s a paradox: a host who dislikes company. But Letterman says he gets the socializing he needs from the show. “You never feel as good as you feel after the show,” he says. “All these things are coursing through your system, and you just feel great. You might have a nice time at somebody’s bridal shower, but you don’t get that. So why go to the bridal shower?” 

David and Regina Letterman

One person who does spend lots of time with him is his (by all accounts) incredibly sweet wife, the former Regina Lasko. They were together for 23 years and had Harry before getting married at the Teton County Courthouse in Choteau in March 2009. (Letterman’s truck got stuck in the mud on the way.) She has tolerated his public flirtations with superstars like Julia Roberts and Drew Barrymore, and has been his island of sanity when he’s feeling anxious — which, to hear him tell it, is a near-constant occurrence. 

“For me, to hysteria is a pretty short drive,” Letterman says. “But she is determined to be a pleasant presence in any circumstance. She’s very smart. She worked in broadcasting, so she knows everything I do here. And in addition to being a practical combination, we just have a lot of fun. Harry and I have a lot of fun making fun of her, and she has a lot of fun pretending to be outraged. And I know she’s sick of all my jokes. But she has been excellent company and has readily played along with the nonsense and bizarre stuff that the family has done.

“And the best part of it all is that we’re still together — when I came very, very, very close to having the whole thing explode on me.”

In the fall of 2009, after finding himself the target of a $2 million blackmail plot by the boyfriend of one of his former assistants, Letterman confessed on the air to having had sex with multiple female staffers. “It was easily the lowest point in my life,” he says. “I don’t know how else to describe it. I felt like I’d dug a bottomless pit, and I was falling into it.” For a while, he thought he would lose the show: “Regina knew more about it than I did, because, unbeknownst to me, she was looking up everything on the Internet. So one night in the kitchen, she came in and said, ‘Well, I guess you’re going to lose your job.’ That hadn’t occurred to me — but I thought, ‘Well, of course.’ How could the network be pleased with that kind of publicity?”

In the end, he kept the show. But far more frightening than losing his job was the fear that he had “blown up my family.” “The biggest panic was on a Friday night, when we heard Regina was on her way to file for divorce,” he says. “It turned out not to be true. But that just turned me inside out. The only thing that’s important to me, I just ruined. I remember when they first handed me my son, thinking, ‘Oh, look — something perfect.’ And now I’ve jeopardized him as a part of my life and me as a part of his life.”

Michael Keaton says he called Letterman in the thick of everything, just to check on him. “I don’t want to sound like we talk all the time, because we don’t,” Keaton says. “But I sensed that he might be feeling down or low, so I got him on the phone and just yakked for a minute. And he was so extremely grateful. I was shocked — according to him, not many people had called. Actually, he told me nobody did. Which I think is probably not correct. But that’s what he said.” (It’s not correct, Letterman’s camp says.)

Harry, who was five at the time, doesn’t know about what happened. “No. No. No, not . . . no,” says Letterman. “I mean, he will one day. We’ll have to have a conversation about it. But not yet.”

In the meantime, Letterman is just grateful Regina stuck around. “I can’t imagine going through this stuff where I only get to see Harry on weekends. It just breaks my heart when I see guys like that. So irrespective of the daily nonsense, that’s ultimately the best satisfaction I have in life. Because I wouldn’t want to be going through this without her.” 

David Letterman and Harry Letterman

Back in October 1981, a bushy-haired 34-year-old Letterman appeared on a short-lived CBS interview program called Signature. His morning show had been canceled a year earlier, and he was still a month away from getting Late Night. At the time, he didn’t know if he’d ever work in TV again. You can almost smell the defeat on him. At one point, the interviewer asks why he’s touching his face so much. “I’m very nervous,” he says softly.

Late in the program, the host asks Letterman what he’s going to do next. “I would like to be on television,” he says. “I think my true identity or personality is someone who just hosts a TV show.” Even back then, this was all he wanted.

So what happens when the show goes away? “I do think about retirement,” Letterman said in 2010. “But I don’t know what I’d do. I’d do a show in my house. Put up a little desk and have people in. Interview the Domino’s guy.” He knows he doesn’t want to act in movies or be in a sitcom. He does admit he was “very irritated” when he saw Jerry Seinfeld’s Web series, Comedians in Cars Getting Coffee, “because I thought, ‘Well, that’s the perfect idea, goddamnit.’ For a moment, he even pondered doing his own version in Montana — Comedians on Horses Getting Coffee. “I thought that would be so much better than riding around in a car, because then you see what the guy is made of,” he says. He floated it to Seinfeld, but the latter was noncommittal. “I’ve still got my nose out of joint about that one.”

(For what it’s worth, Tom Brokaw thinks it’s a good idea. “I’d like to see Louis C.K. on a horse, for example.”)

How about a podcast? “Well, sure,” says Letterman. “But, I mean — does anybody listen to a podcast?” He is assured that they’re quite popular. “And it’s like NPR? Well, OK. That would be good.” One thing he’s likely to do is a few live events — specifically the lecture series he founded at his alma mater, Indiana’s Ball State University, where he hosts in-depth interviews with guests like Rachel Maddow and Oprah Winfrey. “Those are fun,” Letterman says. “That would be an easy place to start. And maybe that’s all there will ever be.”

When Carson retired, Letterman was one of his final guests. “I’m getting a lot of ‘Are you gonna miss Johnny?’ ” he said on the show. “Am I gonna miss Johnny, are your folks gonna miss Johnny, is your clergyman gonna miss Johnny. . . . I think there’s another perspective to consider. You’re not passing away. You’re still funny, you’re vibrant, you’re charming, energetic, entertaining. . . . You’re a very healthy man. You’re not going to prison. You’re still gonna be in show business.” But this was wishful thinking. Carson left the next week, and except for a handful of appearances, he was never seen in public again. By all accounts, he had a lovely retirement, playing tennis and sailing his 130-foot yacht. But it was an exceedingly private one.

Those who know Letterman well agree that he seems unlikely to pull a Carson. “His brain is too active,” says Rob Burnett. He’s constantly peppering people with seemingly random questions — about history, geography, herpetology, string theory, the name of Edith Wharton’s house. “There’s a long history of him being intrigued by a subject and throwing himself into it for months,” Matt Roberts says. “He’ll get into astronomy, and suddenly he’s got a telescope and knows the name of every star cluster and constellation that’s out there. Then, six months later, you ask, ‘How’s the telescope?’ and he says, ‘Oh, I’m into snowboarding now.’ ”

He’ll need some kind of outlet for this restless curiosity. As a wise man once said: There is no off position on the genius switch.

“Weirdly, without the pressure of a network talk show, I actually think Dave could end up doing something more beautiful,” says Burnett. “Something smaller that doesn’t have to please everybody.” Who knows what kind of arcane weirdness he might come up when he’s not beholden to CBS? “The completely unadulterated version of Dave could be breathtaking,” Burnett says.

“Here’s how I would put it,” Letterman says finally. “I would like to do this show maybe three days a week, two weeks out of the month.” He laughs a little. “Do they have shows like that?”

The last time I meet Letterman, he’s in a foul mood. (I can tell, because he says, “I’m in a foul mood.”) An ill-advised joke he made during a pre-show warm-up has become a minor scandal in the gossip press. It’ll evaporate in a day, but for now, it’s agitating him. That said, it’s a little hard to take him seriously, given that he’s dressed in a pair of blue-and-white-pinstriped overalls, fully strapped and buckled like a kindergartner on the first day of school. His press officer, in an attempt to lighten him up, jokes that it looks like Letterman has been working on the railroad. “I wish I was working on the railroad,” he pouts.

Once upon a time, a mood like this might have lingered for days, but today the clouds part in a few minutes. This is a fairly recent development. “For years and years and years — 30, 40 years — I was anxious, and hypochondriacal, and an alcoholic, and many, many other things that made me different from other people,” Letterman says. “The hypochondriacal behavior . . . it sounds stupid, but it was killing me! Doctors kept telling me not to come back. ‘Really, Dave. There’s nothing.’ Finally, I found out it’s all a manifestation of anxiety. Once you realize that, you can self-monitor. Which I’ve found very useful.” 

A few days earlier, Letterman celebrated his 68th birthday. He’s an ongoing self-improvement project. Twenty-five years ago, a doctor suggested he try antidepressants, but he worried they might take the edge off his comedy. Then around 2003, he agreed to start a low dose of an SSRI, the class of serotonin-boosting drugs that includes Paxil and Lexapro. “I was suspicious, and skeptical, and nervous about it,” he says. “But it changed my life. I used to have kind of a hair trigger; I used to put my fist through Sheetrock.” Now he does transcendental meditation and no longer talks about “enduring” life beyond the show. He’s also a regular in therapy – he calls it “an emotional tuneup.” In fact, he’s on his way to his therapist tonight, which in part explains the overalls. “I like them because they’re comfortable and they’re comforting,” he explains.

Letterman once said there were two great motivators in his life: guilt and fear. Lately, he doesn’t seem driven by either of them. He finds it hard to talk about his legacy: The closest he will come is an admission that he feels “wistful.” Maybe it’s because he’s not ready to process it yet, or maybe it’s too vast to reflect on with any perspective. “Ultimately, it’s the body of work that speaks for itself,” says Burnett. “It’s 30 years. It’s an ocean.” 

David Letterman

Regrets? He has a few. “I wish I could have done a better job more consistently,” Letterman says. “I wish I could have been a little more solid in my performance. I wish I wouldn’t have let the wrong things distract me. I wish I could have been impervious.” A big one is that he didn’t capitalize on his production company, Worldwide Pants, in such a way that “it could have an afterlife, whereby some of these people who’ve worked so hard all these years could continue to be employed.” And he wishes he’d started having kids early enough to have a second — preferably a little girl.

“I really can’t remember many times, if any, that he has enjoyed his success,” says Burnett. “It’s just not who he is. It is kind of sad — you wish the guy could enjoy what he does. But I think on some level, maybe in a quiet moment, he has to acknowledge what he’s accomplished. It feels impossible not to.”

Letterman isn’t looking forward to this September, when summer vacation is over, Harry goes back to school, and Colbert comes on the air. “I remember talking to Carson after he retired, and he said it took a while to sink in. So I think in the fall, when Stephen’s show starts up, that’s when my stomach will kind of go, ‘Oh, shit. I’m not really on vacation, am I?’ ”

In the meantime, he says, “what I’ve decided to do — and what I really want to do — is give myself over to my son and my wife. My schedule is no longer a factor, so whatever they want, that’s what we’re going to do.” Recently, he got a big book of hiking trails across the U.S., and he’s excited to visit some national parks, like Arches, in Utah. A friend of his has also planned a fishing trip down Montana’s Big Hole River. “It should be a great summer,” Letterman says.

For his birthday, Harry gave him a brand-new tenkara fly-fishing rod. “It’s a Japanese rod that’s self-contained,” Letterman explains. “It has no reel. It extends out, and you just attach a line to it.” It’s supposed to be good for small streams, he says. He and Harry are excited to get to Montana and try it out.

“I don’t know how to use it,” Letterman says. “But I’m happy to learn.”


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