"Oh, my God – fantastic! They're calling from the Museum of the Moving Image. We have couriers on motorcycles on the way!" It's an early evening in late August, and David Letterman is giving a predictably sarcastic postmortem on tonight's taping of Late Show, which ended just a few minutes ago. He's sitting in the sparsely decorated midtown Manhattan office of his business manager, Fred Nigro, and he's exchanged his tailored on-air suit for a logoless navy-blue T-shirt and a baggy pair of khaki shorts. Tanned and relaxed, he looks like he could be renting windsurfers at a beach shack; a few sunburn patches fleck his nose. He recently returned from a vacation in his Montana home, where, among other things, he hosted a doctor and nurse who'd helped perform the emergency quintuple-bypass heart surgery that saved his life in 2000. "These are people who were complete strangers when they opened my chest," he says. "And now, eight years later, they're among my best friends."
Letterman is now in his 26th year in late-night television – the longest run in the arena besides that of Johnny Carson, who walked away when he'd done a tidy 30. Though Letterman began his career as a wiseass talk-show arriviste – mocking the staid form with Monkey Cams and giant suits made out of Alka-Seltzer tablets, he has become, at 61, the standard. His old rival Jay Leno, who famously beat him out for The Tonight Show, dominates him in the ratings, but Letterman's irreverent influence resonates in everything from The Daily Show and The Colbert Report to Conan O'Brien, Jimmy Kimmel and, yes, Leno. A night with Letterman isn't as enterprisingly wacky as it once was, but it's still capable of greatness. Every time the "Dave's lost his relevance" whispers start, there's a moment with an Oprah, a Bill Clinton or a Paris Hilton – or, going back, his nervy performance just one week after 9/11 – that reasserts his rare place as one of TV's last great broadcasters, a Midwest-raised wall between America and showbiz BS.
In a pair of interviews with Rolling Stone – one in person in New York and another on the phone to Montana – it became clear that these are energetic days for Dave. The foremost reason, of course, is Harry, his four-year-old son with his longtime girlfriend, Regina Lasko, whom Letterman occasionally prides over on air. There's still an afterglow from his surgical recovery. Professionally, there's a tantalizing shift in the late-night world – next spring, O'Brien will take over The Tonight Show desk, with Leno prematurely setting off for destinations and networks unknown. It's an unsettled, exciting time, and Letterman's infamous self-laceration streak has been supplanted by…well, maybe not total happiness. He is David Letterman, after all. But it's something close.
The first time this magazine did a Comedy Issue was in 1988, and you were photographed for that cover with Johnny Carson. It's a great photograph. Do you remember much about that shoot?
I was nervous – I felt like Johnny only might have been doing it because he sort of liked me, but it didn't occur to me that maybe he was sort of interested for his own reasons. That picture was literally two exposures – two clicks and we were out of there. They put Johnny on some sort of a box so that he and I would appear to be the same height. As I left Burbank that day, I just felt like, "At least Johnny is a little shorter than I am." That was the only way I could feel good standing next to him.
Carson, of course, was hugely influential on you. But how did it feel to develop a personal relationship with the guy?
You know, there are people in everyone's life who you can't believe you have a relationship with, and you are truly in awe of them, because they are so iconic and so influential that you're just kind of pretending. You know if you behave the way you really behave, they would recognize that you're a complete dope and they would never have anything to do with you ever again. That was kind of the way I felt about Johnny. I was so worried that I would say something idiotic and he would just pull me out of his Rolodex. I remember the first time I was on his show. It's like all of a sudden after seeing Abe Lincoln on the five-dollar bill, you look over and you're sitting next to Abe Lincoln on a bus. He had that effect on comics for many, many years. I never got out from under the feeling that he and I really could be friends, because I idolized him and I knew by any measure I would always fall short.
When Carson died, people didn't know that he had been pitching in on the "Late Show" here and there, writing some jokes for you that you used on-air.
It started a long time ago, when I was still at NBC, and more so after he retired. In the beginning, I thought, "For heaven's sakes, Johnny Carson is going through the trouble of calling in these jokes, you absolutely have to have them!" And so the more we would do them, I think Johnny was pleased by that, and so it sort of took on a bit of a life.
Now you're on the cover of a Rolling Stone Comedy Issue with a pair of comedians – Tina Fey and Chris Rock – who have that kind of respect for you.
There are people in show business who are very successful who may not necessarily be absolutely funny, but these two people are. For me, I feel like the fact that I'm in this picture – it can only make me look good. I'd like to see the list of people that turned down the offer before it got to me. But it was fun, I got a real kick out of it.
Your late-night legacy is secure. But do you ever miss those old days – the seat-of-the-pants stuff, not knowing if you'd keep your job?
A little. But there was also great uncertainty about it because we never knew: Do people want really peculiar things on TV? Or does that make people uncomfortable? The pendulum would swing almost nightly – we were like long-haul truckers driving in the fog.
I'm comfortable knowing that I've been able to do this for a long time. I've done pretty much everything I ever wanted to do, and when it's time – when the network says, "We're not interested in going forward," I'd say that makes perfect sense. I don't feel that I got cheated.
How are you feeling about Late Show right now?
I like it. I like the people I'm working with. It's a completely different show than it used to be, it's more host-friendly than it ever has been.…
What do you mean by "host-friendly"?
I'm not working as hard as I used to [laughs]. All I have to do, really, is pick out a tie and sit down.
Are the best nights when there's that great guest? When it's a Hillary or Bill Clinton, or Howard Stern, and you just feel that energy in the theater.
Early on, I always had some trepidation about Howard. He seemed like he was without the capability of empathy. And then, when I realized he's just kind of a goofball like everyone else, that leveled the court. We have an expression …he can take a punch. And when you realize that neither of you are gonna get hurt too bad, then it's a lot of fun. People like Bill Clinton…intelligence just leaks out of him, it forms a cloud around him. You can't penetrate it. I'm thinking about cartoons and he's talking about how to save the planet, so I always feel in over my head there. I feel like Hillary and I have a little more rapport, and I think maybe that's just because she's been on more times than her husband.
Madonna, of course, is another famous Late Show regular.
I remember being very intimidated by Madonna, because I didn't know anything about popular music, and I didn't know whether we should even worry about her after her first appearance. And then there was that time she came on and she was angry with me because I'd been telling a lot of jokes about her sex life, because she had published a book about her sex life. I'd felt that was kind of fair game – here's not only a book, it's a coffee table, a 300-page book, photo pictorial – "Here I am, naked, bent over. Here I am in a costume, naked, bent over. Here I am, the UPS guy.…" Now we find out that she's outraged, and she comes on and was unpleasant and all of that. I think she kind of realized that she had underestimated the impact of doing that. But now that seems so long ago that we're both like, "Who cares?" It's like ballplayers. You can't get too upset if you lose two or three games in a row because, good Lord, you're playing 162.
Then the other fact is that it's all artificial. We're all pretending. We're putting on a show and trying to be cute and trying to say funny things, and we don't really mean much of it.
Probably the biggest guest in the past few years was Oprah Winfrey, whom you begged and begged to come on. What is the state of Oprah/Dave relations these days?
[Laughs] Well, I would hope it would be good. I saw Oprah when she interviewed Tom Cruise recently at his home in Colorado, and, wow, that was just bizarre. I kinda felt bad for Oprah, because it looked like she went into that with her hands tied, but it was reassuring to me because I thought, "Oh, I'm not the only one who gets myself into things you can't get out of."
Was there really a rift between you and Oprah?
Yes, I think there was. I think that she, like anyone would, got tired of me making jokes about her. Also, years ago, we were doing the old show in Chicago – she came out and somebody in the audience heckled her, and I think she resented the fact that I didn't rise to the occasion and, you know, beat up on the guy. Which I probably should have, but I was completely out of control and didn't know what I was doing. So she had a real reason not to want to come back on.
The show you did with Warren Zevon, when he'd been diagnosed with terminal cancer and only had months to live: He'd been on many times. Was it a difficult show to do?
Oh, it was awful. Warren was so good about it. After the show, it was heartbreaking – he was in his dressing room, and we were talking and this and that. Here's a guy who had months to live and we're making small talk. And as we're talking, he's taking his guitar strap and hooking it, wrapping it around, then he puts the guitar into the case and he flips the snaps on the case and says, "Here, I want you to have this, take good care of it." And I just started sobbing. He was giving me the guitar that he always used on the show. I felt like, "I can't be in this movie, I didn't get my lines." That was very tough.
On a lighter note, it seems that you are also enjoying this new generation of guests, like Paris Hilton, who's made several appearances on your show, and Lauren, Heidi and Spencer from The Hills.
Well, you know, Paris Hilton is kind of an open book, or seemingly so. The Hills show I knew nothing about. When we were going to have them, I started watching the show – I don't know how many of them you've seen, but pretty soon your jaw goes slack, and you realize that something very strange is happening. And when I realized that, I got all excited. I couldn't have been happier to have them on, and I'd like for them to be on again. And talk about being able to take a punch! You can say almost anything you want and they're smart enough not to care. Because you're grandpa and they're, "We're 24 and more popular than you'll ever be, so, yeah, say whatever you want."
Did you have any regret about how you roughed up Paris Hilton? When you asked her on the air about her prison experience, she was clearly not prepared to discuss it.
At the time, I thought we were just goofing around. Later, when somebody told me she was in tears, I got upset with myself. I sent her a letter and apologized. And then she called and she wanted to come back on the show and, you know, to her credit, she said, "Oh, you were so mean to me, I'll come back on, but you can't be mean to me like that." And I said, "OK, I'm sorry." I desperately wanted her to come back. I thought it would be great if she came on and jumped all over me for being inconsiderate. So, you know, I loved all of that. What can I say, she's still kind of cute.
How are you getting along with CBS? There hasn't been much rumbling with your bosses recently – you have to go back a few years to the days when you were mocking CBS chief Les Moonves for visiting Fidel Castro.
[Laughs] Yeah, Les and I had a big showdown. We were like high school kids that were gonna do everything but throw punches, and that went on for a couple of days. He was upset that I was making fun of him, and maybe it was more than making fun, maybe it was just making ugly comments, which for me is great fun. At the end of the day, I realized I needed to grow up and be a little more mature. Through all of this I feel kinda bad for everything I subjected these people to. But to answer your question, from my point of view, things' are very good with CBS.
Sometimes, however, I imagine it's hard to help yourself. Making fun of your bosses has long been part of your show. And sometimes Les Moonves must do things that seem like a big fat strike coming down the middle.
Yeah, you're exactly right, but I've taken enough batting practice.
In the past you've described yourself as suffering from anhedonia, the inability to feel happiness. Where are you on the anhedonia index these days?
Well, I think it has always been a defense. If you mention often enough how disappointed you are in your own behavior and your own performance, then you've pretty much just pulled the rug out from under people who were just about to say, "Jeez, that was really disappointing, we're not pleased with his performance."
Isn't that just false modesty?
Jeez, no. I don't think it's a false modesty. It's just everybody has their own mechanism for getting through the day, and I guess it's easier for me to pretend to be a perfectionist. Or, maybe, I really was a perfectionist and there's no difference there.
Is it fair to say that becoming a father has made you more serious-minded? You talk more these days about big issues, especially the environment.
I resist giving in to that a little because I know that happens to everyone who has children. But you see things and you say to yourself, "What effect will these things have on my four-and-a-half-year-old-son?" and, "Jeez, is there anything I can do besides trying to raise the child the best I know how?" Well, maybe very little other than to talk about the environment, talk about the economy, talk about the war and on and on. So it has been a factor. Again, I'm always uncomfortable trying to influence people in matters of conscience, and I feel so ill-equipped because I'm not as smart as I oughta be for this job.
How are you doing as a father? Years ago you were asked about your own father, and you talked about him being "the battery to which all the cables were hooked to," this tremendous source of energy. How do you compare?
I remember my father's energy because of his job, working six days a week, 10, 12 hours a day, he didn't have the luxury of spending the kind of time that I can with my son. I do try to recreate that energy, because I think in this world to turn my son loose without having him been exposed to a lunatic like myself would be a mistake.
What's domestic life like in the Letterman home?
It's a living hell.
Six Flags? Olive Garden?
The current project is a treehouse. A year ago, my son was out walking around and found a tree, and he said, "That would be perfect for a treehouse," and I didn't know that he knew anything about a treehouse, and I had a treehouse when I was 12 or 13, so I thought, "My God, I'll build one." I've always heard from friends, "You're too old to be a father," and I say, "I don't feel too old, I can do this and that," and I'm here to tell you that at my age, you're too old to build a treehouse. The thing is still under construction, it's coming up on a year.
Did you always want to have a family?
Yes. I thought for sure I would, [but] it looked for a long time like that was not going to happen. Now that it has happened, I have no regrets other than …it's not even a regret, but now that I have one, it would be fun to have two. That's not really a regret, but it's an observation. And there's no chance of that happening – I mean, look at me.
How are you feeling these days?
I was across the road picking up fence posts all morning in the 90-degree heat, so I'm feeling pretty good.
After the major heart surgery in 2000, did you always feel that you were going to come back to the show?
There was never a doubt. It was the chief motivator – just to come back and show myself that I could do it. I loved the nature of the project: Today, you walk four feet. Tomorrow, you walk 20 feet, by the end of the week you're walking a quarter mile, with the ultimate objective of coming back to work.
Did you watch when people like Regis and Bill Cosby were filling in for you?
My doctor said, "You have a brand-new life ahead of you, don't waste a second of it [laughs]." I don't know. I knew it would be troubling one way or the other.
Too good, or…?
I suppose. Or maybe I couldn't stay up that late, I don't know. I never did watch them.
You called your surgery "the most exciting thing" that had happened in your life. But a lot of people go through a depression after a traumatic event like that.
I'd heard that as well. I'd heard because of the barbaric nature of open-heart surgery, that you would almost automatically be depressed by it. In my case, it was this grand excitement, and then I would just burst into tears for no reason- just racking sobs. But even that, I loved. It was such a relief.
Do you look at the surgery as being a major delineation in your life?
Of course. I have always said that there are four things I am just thrilled about in my life. I always put the heart surgery first, because the other three wouldn't have happened without the heart surgery. Then there's the birth of my son, and the third was winning the Indianapolis 500. Maybe there were only three. I can't remember the fourth.. I guess talking to you.
I recently went back and watched the show you did a week after September 11th. That show was highly praised, but it was really unnerving, very raw, and takes you right back to that very difficult time. Did you want to do that show?
No, I didn't want to, and maybe this is human nature, but I wanted other people to do it. I wanted the president to do things, I wanted Mayor Giuliani to take care of everything.… You always look for a leader in every situation. You're stuck in an elevator, you look for the guy with a Swiss army knife. I didn't want to be any of those guys. I just wanted somebody else to make everything right. I didn't want to go back because I didn't know what to say, and I didn't feel like going back and it felt like a mistake. If they had said, "All right, we're not gonna have any more television for another six weeks," I would have thought, "OK, that's about right." Then a few days after the attack, the Mayor said, "You've got to continue living your lives, you've got to go on," and I decided I had to go back. But I was just filled with trepidation and, "Oh, jeez, this is when you need Johnny Carson to come back on the air."
In recent years, you've also been praised by some for confronting people who aren't terribly used to being confronted, like Rush Limbaugh or Bill O'Reilly.
It's been so long since I even thought about Rush Limbaugh. I remember in – the beginning I had the impression that here's a guy who clearly knows better than what he is saying, but knows it's a show-business hook. I sort of feel the same with Bill O'Reilly. I even said so much to him. Maybe he feels that way, maybe he doesn't, but I made the mistake of taking Bill O'Reilly way too seriously, because he's just like any other boob. I hope he's coming back on the show because I would treat the whole thing differently now.
In which way?
Well, I think in the beginning I felt like I had some sort of responsibility to attack everything he said and try to counter it with my own intelligence, but that reservoir is pretty shallow. So now I think, "Well, here's a guy who really is no different than Paris or Regis, so I'll just sit there and make fun of them." It doesn't make any difference what they're saying, I just make fun of them.
As much as you've made fun of the current White House occupants, it's obvious that as the Iraq War progressed, they've also made you angry. Not long ago, you wondered aloud if there was "any humanity" to Bush or Cheney.
Right. Yeah, that is [something] I wonder about. I don't know, you wonder how can they go to bed at night. We're talking about a lot of people who are dead. We all know that's the nature of war, but I don't know. It's very confusing to me, because obviously something needed to be done. I'm very ill-equipped to comment, but I do question the humanity of everyone involved.
You seemed to have supported the war at first, as did a great many people who wanted to feel like they were doing the right thing and supporting the country.
I think I'm no different than everyone else. I'm just a hothead reactionary and I wanted to see something done. The question that I like to ask people is, "What if Al Gore had been president? Who would we have attacked? And when? What mistakes would a Democratic president have made?"
Does it anger you a little more because some of these people have been on the air? Bush has been on the show, and McCain was on in 2001 linking the anthrax to Iraq. Does it feel personal to you?
Yeah, it does feel very personal to me, maybe more so than it should. When you sit down there together more than once or twice, you've created a camaraderie. I'm just waiting for a guy to explain to me how things are going to be OK. This is going to sound nuts, but the guy that I believe is Al Franken. I don't know why – believe me, I've asked myself this question, but when he talks and he says something, I believe him more than I believe anybody who currently holds a seat in the Senate. He may not be elected. Maybe it's because we're peers, we're the same age, we're in the same business, but I believe Al.
You've had fun with McCain on the show, as a guest and a subject. Is Obama harder as a comedic subject?
I've heard that, and maybe so. It's certainly easier to make fun of John McCain in the obvious sense: He's an old guy. Every time we have these jokes about him being old, I always think to myself, "This is not entirely fair." In terms of Barack Obama, I think you're right, I don't think people have a way to get in there. There's nothing automatically that you can go to.
We don't know as much about him at this point.
He's been on our show a couple of times, and he wore a suit the second time he was on, where I thought, "Holy cow, I'd like to have that suit." It was stunningly beautiful. So I'd vote for him on the strength of that suit.
Are you voting for Obama?
I can't tell you who I'm voting for. I don't know who I'm voting for.
The late-night landscape is moving around in a big way in the next year – probably the most since you moved over to CBS. On NBC, you have Conan O'Brien going from his 12:30 slot to take over "The Tonight Show," with Jay Leno stepping aside, and it's not clear what he's gonna do, maybe a new show with another network. How closely are you following this?
Well, it's interesting. It was always hard to imagine what NBC was up to, facilitating Conan to 11:30 – what would become of Jay? I'm not quite sure why they would do that, so much so that one wonders if that's actually what's going to happen. I'm glad that I'm not involved directly, because after a while that can be wearying. It's nice not to have a dog in this fight.
Do you mean that NBC might blink and say, "Hey, we're gonna stick with Jay"?
Well, I think we're getting pretty far down the road for that. But unless I'm misunderstanding something, I don't know why, after the job Jay has done for them, why they would relinquish that. I guess they thought it was a less messy way to handle what happened to me at NBC. I don't know. I like Conan, I think he's a very funny guy, but it seems…
It seems they're stuck in an unenviable position.
I guess it's possible that Jay recognized this opportunity that would give him a blank check anywhere else he wanted to go. But I wouldn't think that, I would think he'd want to stay there, where he's been so successful.
Do you empathize at all with the situation that Jay's in at NBC? He's made no secret of course about loving The Tonight Show job and doesn't seem ready to retire at all. I guess empathy is the right word. It's hard to know what he felt about it. I have to believe he was not happy about it.
Could you ever envision a scenario where you have Jay on your show again? He used to be a guest years ago.
It'd be interesting. I think he'd be a great guest on the show. The first night that he is out of a job, I think that would be a great situation.
How much do you care about the ratings battle with The Tonight Show and Jay anymore? Does it matter to you who comes first in this whole game?
Well, absolutely. I wish that we – and when I say, "we" I mean "me" – I wish I could have prevailed. I think it would have made things easier for us. But the reason is the difference between me and Jay. I think more people are responding to Jay than will ever respond to me, and after a while you have to face that. I'm doing the best I can, I enjoy doing what we do, and we get a certain amount of recognition for it, but the truth is, if there's a difference between the shows, it just comes down to me and Jay. I think he has greater appeal for more people than I do.
That's a contrast to years past when people in your camp explained the ratings gap between Jay and you by saying it was because of the lead in programming or 11 o'clock news and so on. Now you're saying, in your view, that it really does come down to personality.
I think so. As much as I would like to point the finger and say, "Well, here's the real story" – and everything's a factor, really – maybe years ago I was unwilling to recognize the difference in Jay and myself as being more meaningful. But I just think that we've been at this long enough. I have a tremendous staff, I have tremendous writers, tremendous producers, so what really would make the difference? Well, the answer is me. I just think that Jay has a wider appeal than I do and, you know, good for him.
I get the sense that this is not something that agonizes you anymore.
Yeah, and also it seems unlikely that now, after years and years of trying under a wide variety of circumstances and advantages and disadvantages, that suddenly I'm going to prevail. You can't go through life fooling yourself, you have to be honest with the situation. That's fine. I can say it's fine, because I've been lucky enough to do the show and I've had a lot of fun doing it. So if I didn't get this, well, that's too bad, a lot of people suffer far greater than I have.
Do you basically develop a respect for anyone who can go out and do a show every night? Yeah. It's a pretty small group of folks, and only the people who do it know how difficult it can be. I remember when Conan O'Brien was first on our show – and he'd been on maybe about two years, and he said, "It's going great, we've now done 18 shows in a row that are tremendous," and I thought, "Holy Christ, he's either lying or insane." At the time I'd been on the air close to 15 years, and I don't think I've done 18 shows that were tremendous in the whole time. It's not easy. I wish I was one of those guys who made it look easy. I don't have that gene.
It's likely that this time next year, you'll be facing off with Conan. Have you envisioned that competition?
I haven't given it much thought, but I guess it's because I still find it hard to believe that Jay won't be there. It's only until recently that I felt this thing had traction. It just seemed so preposterous to me. It will be weird to see Conan at 11:30, don't you think? Which is not to say he can't succeed, but, no, I don't know what the competition will be like. I hope we're able to do OK.
How do you feel about Craig Ferguson? The sense I get from your folks is that he's been a pleasant surprise.
Well, all credit to [former Tonight Show Starring Johnny Carson producer] Peter Lassally – it was his recommendation, and we went with Craig because of my regard for Peter, and I will guiltily tell you that I didn't pay much attention to him. And then I started finding myself up late – I guess it was during the writers' strike – and I realized that here is a guy who has tremendous energy doing the same thing that everybody else is doing, but he's doing it so differently that it doesn't seem like it's the same thing. He has no budget, has no real resources that everybody else has and, jeez, I think he does a tremendous job. I started calling people and saying, "Have you seen…" and everybody else had the same feeling.
Your contract is up in 2010 – do you have a sense for which way you're leaning, Packers or Jets?
[Laughs] Boy, what's the deal there? Honestly, really is that what [Brett Favre] wanted to happen, the poor guy? A friend of mine said he'll never get off his back – every game flat on the turf.
Well, the way I feel now, I would like to go beyond 2010, not much beyond, but you know, enough to go beyond. You always like to be able to excuse yourself on your own terms. If the network is happy with that, great. If they wanna make a change in 2010, you know, I'm fine with that, too.
So you are motivated to keep doing this.
Yes. The way things are, the way I feel physically, I would love to continue, so we'll just see what happens.
Jon Stewart's name comes up as a possible successor, if and when you decide to step down. If you were running CBS, would he be someone you'd take a look at?
Absolutely. I don't know this for a fact, but I have a feeling that all of that has been taken care of or discussed. I would be surprised if there's anything like what is happening at NBC taking place at CBS. People have had a lot of time to consider this in a cooler environment.
They don't bring you in on that conversation?
No. There may have been a time where I wanted to be involved in that, but I just feel like, "Thank you and goodnight," and everybody parts friends is what I'm looking for.
What will you do when you stop doing this?
Well, I have Regina and I have Harry, and we have a little couch and a little desk in the living room. I can continue to do the show at my house for quite some time, until they absolutely refuse. And I control the money, so they really can't refuse. So I don't see a need to ever actually stop.
Who would be the first guest on the home show?
Of course, it would have to be…I guess it would be Regina. I'm not saying she would be the best guest, but she'd be the first guest.
Hearing you talk like this, about fatherhood, about your job, I get the sense that there is real hope and things that are heartening for you. There are many things to get up out of bed in the morning for.
Yeah. For the first time, two days ago, my son got up on a horse, and now we can't get him off. I don't know if that exactly fills the category you're describing, but for me, that was more than enough to get out of bed the next day, because there was great hope.
This story is from the September 18th, 2008 issue of Rolling Stone.