"I think there's a bundle of emotional manifestations with the beard that I have not yet been able to fully examine," he says. "It's almost a signal that I don't do what I used to do. Don't even ask me to do what I used to do. Whenever I happen to see a picture of myself, I think, 'Oh yeah, that's the guy you want to be.' Because I got so sick and tired of seeing myself with a coat and tie: Mr. Jackass on TV."
Letterman, who turned 70 in April, takes a deep sigh."I don't know," he says. "I may have some developmental issues."
The sigh, the confession, the wearily sardonic self-laceration—all are instantly familiar to anybody who followed Letterman through a 33-year career that changed television. Interviewing him, one gets the feeling, is a similar experience to being one of the thousands interviewed by him: He simultaneously projects the sense that he would rather be anyplace else in the world and being so good at what he does—the art of conversation—that he simply can't help himself.
GQ: What's funny today?
David Letterman: The Oh, Hello boys—Nick Kroll and John Mulaney—they, to me, are the funniest thing I've seen in years. I think Norm Macdonald is without peer. Amy Schumer… I don't want to say she's like Richard Pryor, because that doesn't make any sense, but I think she's a real breakthrough.
Why did Pryor come to mind?
Well, I remember being at The Comedy Store when he would come in to work on new material. His frank candor regarding his sexual activity was, to me at least, pretty pioneering. You didn't see that stuff on The Tonight Show. I kind of see Amy Schumer as having done the same thing for women. Both of them seem to be the ones who were just, "I'm confident in this. This is who I am. And I can make it funny."
Don Rickles died recently. Do you see his influence today?
There really was nobody after him who was like him. He ended up, in the truest sense of the word, being unique. If you look at the old Tonight Show, that is officially all gone. That kind of show business: working the lounge in Las Vegas, making fun of Frank… It's all gone. The people we're left with I think are pretty good, but I don't automatically see an evolutionary connection.
There's been a shift from telling jokes to telling stories, right?
When I started in comedy, all my buddies were writing jokes, and you lived and died by the jokes. But if you're telling stories, you have a better chance of survival because of the personal connection. You're exposing yourself. I can remember Louis C.K. saying…and everybody felt this way…that the best at doing that was Bill Cosby. He would come out and spend 90 minutes just telling you stories.
How are we supposed to think of that material now?
Jeez, I don't know. I've known Bill Cosby since before I had my own show. He's a part of American culture. And yet I hesitated before telling that story about Louis C.K. So there's a taint there. If he's guilty of everything he's accused of, that's a ruined, broken individual.
What's the best joke you ever heard?
The best joke I ever heard I can't tell you.
Well, now you have to!
No, no. Here's one: There's a guy in Las Vegas standing outside of a casino, and he says to a tourist walking by, "Can you lend me $100?" The tourist says, "You're crazy. You want me to lend you $100?" The guy says, "Yeah, I gotta get something to eat. I gotta find a place to stay tonight." The tourist says to him, "Now, this is insanity. If I lend you $100, how do I know you won't walk right into that casino and gamble it away?" And the guy says, "Oh, I've got gambling money." That's all I can do. Sorry.❖
❖ "It is not all he can do. Three days later, Letterman calls back with a different joke: "Guy goes into a bar, tells the bartender, 'I want 15 shots of your best Scotch whisky.' The bartender pulls out a single shot glass. Guy says, 'No, no, no. I want 15 shots. Pour 'em all up, right here in front of me.' Fifteen shot glasses full of whisky.' The bartender says okay, fills up the shot glasses, and the customer starts drinking them like crazy—one, two, three, four—and the bartender says, 'Whoa! Geez, hold it! Settle down! Man alive! Why are you drinking like that?' The guy says, 'You'd be drinking like that, too, if you had what I have.' The bartender says, 'Oh, I'm sorry, buddy. What do you have?' And the customer says, 'A dollar.'"
Donald Trump was a frequent guest on your show. Have you had reason to regret that?
No, no reason to regret it. I'm disappointed that this man is representing me and my country. It makes me sick. But we always looked forward to having him on. He was a great guest. He was just a big, wealthy dope who'd come on and we would make fun of his hair. I would refer to him as a slumlord. But now, this goon... I don't know. He's demonstrated himself to be a man without a core, a man without a soul. Is there a guy in there?
Do you have a theory about what might have changed?
I don't know. That's why I would love to have 90 minutes with him in a TV studio, just to talk to the guy. I would just like to say,
"All right, Don: What the fuck happened?"
This story originally appeared in the June 2017 issue with the title “Gods Of Comedy David Letterman.”