Letterman is probably the most decorated and longest serving late night host in the history of television, a legacy he wears with his signature mix of pride, deflection, and self-loathing. I’ve interviewed a lot of people in my life. But I’m not sure if I’ve ever interviewed anyone quicker — with a joke, with a dodge, with a perfectly off-kilter anecdote — than David Letterman. At 77, he is still, improbably even to himself, working. Today, he launches something called the Letterman TV FAST Channel, on Samsung TV Plus, which is a collection of highlights from, and new commentary on, The Late Show with David Letterman. Letterman also still hosts a regular talk show on Netflix called My Next Guest Needs No Introduction. “I’m surprised that I’m still doing it at my age,” he told me. “On the other hand, I still get a kick out of what we’re doing. So what does that mean? I don’t know.”
In our conversation we talked about, well, nearly everything — the art of interviewing, the cost of showbiz on the soul, the impossibility of retirement, Letterman’s years of late night wars with Jay Leno, his influence and total aversion to nostalgia, his skepticism of fame (“If fame has crushed you personally, I prefer that kind of person than somebody who wears it well”), and much more.
This is our third GQ Video Cover Story (the first two were with André 3000 and Dwayne Johnson), a new format that delivers all the access and depth of a classic GQ print profile, but does it via longform digital video. Watch it above, or on our YouTube channel.
Check out some of the best moments from GQ’s conversation with David Letterman below.
GQ: If you read pieces about you, piece of press, profiles, stuff like that from the eighties and nineties, even a little bit in the two thousands, you were often portrayed as miserable.
David Letterman: Yeah, that’s great. I love that.
So: fair characterization?
Yeah I think so. There’s a couple of things going on there. I was drinking heavily in those days — that may have provided some fuel for misery. And I guess not achieving what I imagined to be, like — you take Johnny Carson, there’s never going to be anybody as good at that kind of show as Johnny. Nobody better. Maybe there are people now who are excellent broadcasters and as good as Johnny, but nobody better. So here I am thinking: Oh crap, I am not going to be as good as Johnny. What am I doing here? I like the idea that I was characterized as miserable. That’s delightful.
Early in your career, you were criticized, fairly or not, for not being a great interviewer, right?
Probably. Yeah, I think that’s true. Any criticism that has befallen me? I’m sure I had it coming. Here’s the issue with me. When I got to California, and I don’t know if this contradicts everything I’ve said here before, but when I got to California, it was like: Okay, I’m here. Let’s get ready to go. I thought, I’m the guy we’ve all been waiting for, and operated like that for a little bit. And the first time I realized it was a mistake, I had a morning show on NBC. It was on for a day and a half, and then it blew up the network. And that’s when I realized, well, you know that thing about me being the guy? Maybe that needs to be, like, take another look at that.
And you think that somehow affected the conversations you were having?
I dunno about conversations so much, but just my presence on television. I realized that maybe I need to have a broader lens of this pursuit.
Do you feel like you improved over time? Got better?
I don’t know. I mean, one hopes. God, 30 years plus one hopes you get a little better. I do say that, for the last handful of years, my favorite part of the show was just talking to people. Because doing comedy each and every night, each and every night, each and every night, that’s meaningful and not just laughable, that’s tough. That’s really tough. And I was always lucky to have men and women who were really smart and really good writers. I just, I’d be in the next room. But the thing that I enjoyed mostly was actually just talking to people.
The interesting thing about some of the interviews from earlier in the run is they could get confrontational.
Yeah, I guess so. I will say that I also, in those days, it was probably under some real or imagined mandate that that would provide energy, that would help the show succeed. But no, that’s right.
When you look back on those now, how do you feel?
I wince. Because having the notion that I was the guy American television was waiting on skews your perspective. And so if I think that that’s who I was, then I have to question almost everything I did.
At the time, would you walk away and say, “Oh, that was the guest,” or would you walk away and say, “Oh, that was me”?
Always me. I mean, even if somebody would come out and go to sleep, I would feel like there should have been a way. I’m where that all stops. I don’t care what happened in the life of the guest or the pre-interview of the guest, but if the guest is sitting there, then the guest in that relationship, and that impression becomes my responsibility. So you own a restaurant and somebody gets food poisoning. It’s your fault. And by the way, I’ll say this, in all the years we were on, not one guest had food poisoning. And you can Google that.
Do you feel like you these days approach conversations differently than you would then?
Well, these days I just, whatever causes curiosity, I just hop right on it. I don’t have to worry about, Oh, we’re going to hear from their publicist. The audience is going to walk. It’s civilian stuff. And so that’s much easier for me. And probably I see people do it now on tv, I think, well, God, this is so much easier. Why did I think it was so hard?
Easier — in what way?
It just seems to come effortlessly. And occasionally people have been nice enough to have me on their shows, and they are just so comfortable and gracious that it makes me feel like, why did I think this was a fist fight? I don’t know.
Why did you think it was a fist fight?
I can’t help you there.
But it doesn’t feel like that anymore?
I think it was in my head, the struggle of: Everything’s got to be perfect. And if there’s even a dent in this, I’m going to be embarrassed and made to look foolish. Right? Because, you remember, I was the guy American television was waiting on.
I heard you say, and please clean this up if I have this wrong. I heard you say that you felt like you were glad that you were mostly out of showbiz because showbiz had been making you kind of a worse person.
Yeah.
Do I have that, right?
Yes. You’re exactly right. And I don’t know, maybe it’s only because I went through show business. I got that out of my system eventually that I can concentrate on being a better person and probably couldn’t have reached this point if I had not gone through the exercise of trying to succeed at show business.
I kind of wondered what you meant by that, making you a worse person.
I just feel like personally, I have greater humanity than I did when I was in show business. It was all single-minded and great pressure, real unimagined, and I felt like it’s all on me and it’s all on me, and that it was all nonsense.
Your reputation in your show years, I don’t know, accurate or not, was: not social.
I felt like whenever I would go out, there would be an expectation to which I could not live up.
What was the expectation?
Oh, here he comes. He’s going to do a show. He is going to be funny. We’re going to be entertained. And I kind of felt like that expectation takes quite a lot of energy, so I didn’t want to bleed it off before or after the actual show, which was always in desperate need of entertainment.
Do you feel like that was your entire measure of energy for the day? It went into the show?
Oh, without question. Yeah.
And then so the rest of the day: skeleton Dave. Barely there.
That’s right. You would either then spend time preparing, time ruminating about what may have gone wrong or trying to enjoy what may have gone right. And anything else didn’t matter. And that’s the mistake of having a career where it’s the same thing each and every night. Now, I still advise people not to retire, but it was so single focused. If we can make these three, 400 people laugh every night, that’s our responsibility. So the idea that it actually transported beyond that would always come as kind of a glaring surprise.
Do you feel like a happier person now than you used to be?
Yep, yep, yep. I do. I am sorry. I’m a dumb ass show business moron talking about himself, and that’s stupid.
But that is the point of this exercise.
The one of your old magazine, ain’t it? So all I cared about was television, one hour of television that I was responsible for for 30 years. That’s all I cared about. Everything fell apart, went away. I didn’t even know if it was falling apart or not. And now I have the energy and the broader focus to recognize humanity has other fulfilling pursuits,
Such as?
Oh, for love of God. Well, helping people need help, big or small. And just to be a nicer person, because I don’t feel like I’m always in the electric chair.
It must’ve been a crazy feeling to feel like you’re in an electric chair.
Well, it was one of the stage hands goofing around and the goddamn thing was electrified once. That’s a true story.
What do you chalk being happy up to? I’ve heard you say meditation in the past.
Yeah, I do a little meditating. Sometimes I just meditate hoping I fall asleep.
Does that work?
Yeah, sometimes it does. Yeah, it’s pretty good. But I did, when I was working, I would meditate because when you’re doing five nights a week, you got to go out tired, sick, lonely, happy, scared. You got to go out. And the meditation sometime would give you a boost of energy. But what I found when I did it religiously, it just gave me more energy to be angry. So I thought, well, this may not be what they’re talking about.
And then you’ve said medication too, right?
Yeah, yeah, medication. My doctor, the guy who saved my life, begged me to go on an SSRI, because I used to get so upset and we had an office, an adjunct office, an office in the office, I’m sorry, a closet in the office full of telephones because if things went wrong, I would pick up my telephone, yank it out of the wall, and heave it across the room. And so we had a deal with Westinghouse, the people who used to make the phones and they’d have a regular delivery stop resupplying us with phones. So that was a cue – that maybe I needed help.
And you don’t have that feeling anymore, that urge to hurl a phone?
How have I been today?
I haven’t seen you throw one phone.
I think I’ve put up with quite a lot.
Would you call yourself semi-retired? Not retired at all? Retired?
Retirement is a myth. Retirement is nonsense. You won’t retire. The human mechanism will not allow you to retire.
For the record, people do retire.
But what do they do? Sit there and wait for, give me the name of a show, Judge Judy to come on?
Late Night with David Letterman.
Oh ha ha ha. But you know what I’m saying. As long as you are healthy, you still want to produce. And you will find ways to, once I stopped doing the show, it took me a couple of years to figure out that, oh, this is a completely different rhythm. And without the rhythm that you’re accustomed to, largely unsatisfying. So you got to find something that’s important to you
You talked to a lot of, well-known people in the show and did so for years on the show before that, do you feel like you’ve learned anything profound about fame or celebrity having been around that machine for so long?
Some people wear it pretty well, and those are the people I’m always impressed by that because to me, if the fame has crushed you personally, I prefer that kind of person than somebody who wears it well.
You like to see someone kind of trembling under the wheel.
A little bit. Yeah, because you’ve achieved exactly what you would hope to achieve and beyond, but yet it has left you a little if not broken, dented. So that to me is fascinating.
Do you think much about the show in general these days?
It’s awful. It’s just god awful. From the day I stopped doing it to last night two or three times a week, I have an anxiety dream related to the TV show. And it’s maddening. It’s just maddening. The dream is I show up and here I am. I’m ready to do the show. I’m on the old show schedule. I’ve been to rehearsal, I’ve been to hair, I’ve been to makeup. I come down and it’s people I don’t know, looking around me saying “okay, we’ll get to it.” “But what about the audience?” “I guess they’re here.” So it’s me in the same mode. Everything else is incomplete, and it’s that anxiety that usually wakes me up in a start.
What do you think it means?
I think it’s akin to the college dream of, oh, I forgot where the English building is. I think, I don’t know. Or it could be some sort of psychosis.
Let’s hope it’s not psychosis.
Yeah.
This question will sound more morbid than I mean into the sound, but yeah, your age, you mentioned earlier, is 77. How much longer will you work for?
I don’t know. Like I said, I’m surprised at the number that I’m still doing it at now. I think if I start in the middle of talking to a world famous guest – I fall asleep. I was doing some show for Netflix a couple of years ago, and the schedule was ridiculous. We were doing three shows a night, twice and then three shows another night twice. And it was just insane. And the stage manager came up to me between one of these production shows and she said, You’re going to have to sit up straight. Look, I know you’re exhausted, but can you just sit up straight? And I just thought, well, maybe that’s a sign. Maybe that’s a sign.
PRODUCTION CREDITS:
Director: Cole Evelev; Zach Baron
Director of Photography: Carter Ross
Editor: Brady Jackson
Talent: David Letterman; Zach Baron
Coordinating Producer: Camille Ramos
Line Producer: Glenn Pratt; Jen Santos
Production Manager: James Pipitone
Production Coordinator: Elizabeth Hymes
Talent Booker: Dana Mathews
Assistant Director: Glenn Pratt
Camera Operator: Matt Spear; Addem Oppenheim
Assistant Camera Time Jacks: Taylor Eisele; Sam Caravana
Gaffer: Mike Tambasco
Grip: Adam Rockhill; Dominic Espinoza
Spark: Andy Mesin
DIT: Tyler Carrell
Sound Mixer: Zach Thorpe
Production Assistant: Jake Huber; Alexis Doan
Stylist: Karolyn Pho
Groomer: Jennifer Sotolongo
Tailor: Jaime Bushong
Post Production Supervisor: Jarrod Bruner
Post Production Coordinator: Ian Bryant
Supervising Editor: Rob Lombardi
Assistant Editor: Justin Symonds
Colorist: Oliver Eid
Filmed on Location at Indianapolis Motor Speedway
