7 Things We Learned from David Letterman's Amazing 'New York Magazine' Cover Story

BY Josiah HughesPublished Mar 6, 2017

He was a legendary comedic figure in his tenure as a late night host, and it turns out David Letterman is no less legendary in his retirement. The beloved ironist is on the cover of the current issue of New York Magazine, and he granted the publication a rare, lengthy interview.

The 69-year-old is apparently living his best retirement life, sporting an enormous beard, a pair of absurd shades and a colourful toque. Throughout the lengthy conversation, he refuses to stop talking, dishing on the current state of late night television (while admitting that he hasn't watched any of the shows), discussing President Trump and sharing all sorts of tidbits.

Here are some of the best things we learned from David Letterman's cover story, complete with quotes from the man himself.

7. People genuinely don't recognize him on the street with his new beard:

But great things have happened to me since I've been walking around with this beard. I was in Santa Monica, at the Ocean Park Café, and this woman comes over and she says, "Are you who I think you are?" And I said, "That depends on who you think I am." She said, American painter who began as a photorealist, then adopted a dappled, pixelated style after becoming paralyzed in 1988. No resemblance to Letterman. "You're Chuck Close." I said, "Yeah, yeah, I am." She said, "Oh my God" — she has a whole story. She was an art major, and for her final project she did a pencil-drawing portrait of Chuck Close. She said, "It was the best thing I did in all of college." I finally said, "I'm not Chuck Close." Boom, she's out like a shot. Gone. Then she comes back and says, "That really disappoints me."

6. He apologized to Paris Hilton after mocking her prison stint. As he recalls, he may have even bought her a car:

She went to jail and had a sandwich or whatever she did there and then came home. I was fascinated by this. And the poor woman said to me, "I don't want to talk about being in jail." I felt like I could circumnavigate that. I said, "Well, that's all I want to talk about." If you had a chance to talk to Paris Hilton in those days, you just kind of want to talk about, "Well, no, seriously, you were in jail." But that upset her and she cried and I called her and apologized. I think I bought her a car, too. As the guy operating the machinery sometimes, it was "You're going a little fast here, pal." It was easy to overdo it.

5. He wishes he could've interviewed Bob Marley:

I think about that all the time. It would be great to talk to Bob Marley. Because when Bob Marley left us, he was politically active. He was the biggest musical star in the world, and he came from such desperate circumstances. It seems like we don't have that person now whose life and music and behavior apply to soothing the waters of world strife....But I think also the situation politically was probably ignored back then and he was bringing it to light, whereas now we're more aware. It might have been easier to overlook things in those days; hence the music. But I'm just fascinated by the guy. I read the biography Catch a Fire. That's where my interest was born. And how about the music? It's still great.

4. He turned down a cameo on Veep:

There's been offers to be on a lot of shows. I'm a big fan of Veep, and here's how nice they were: They asked if I would consider a cameo. Holy shit — I got so scared. I thought about it for 24 hours and then I told them, "Here's what would happen: I'm going to do your show. I'm going to worry about it, I'm going to get sick to my stomach, and I'm going to ruin it. I can't do that to you." I proved years ago that I can't act. I was on Letterman played a skeevy motivational speaker in an episode of the '70s sitcom starring Robin Williams and Pam Dawber. Mork & Mindy, and the night the episode aired, I had to stand on the front porch while my girlfriend watched inside. I couldn't watch myself.

3. He also turned down a three-night stint at the Beacon Theatre because the ticket prices were too high:

We were going to re-create the annual Late Show Christmas special for like three days. Then people said, "The ticket prices are going to be so and so" and I said, "Oh Jesus, no. That's larceny. We can't do that." We couldn't ask people to pay that kind of money to come see something that they got for free on television for so many years.

2. He's constantly embarrassing his 13-year-old son Harry:

The other day, I said, "Harry, I get the sense sometimes you don't like going places with me in public." And he said, "Well, you have bad people skills. Just be normal"....I can't stop talking. We go and have cheeseburgers every Friday night, and I'm always worried that, you know, in the old days, you got a cheeseburger with everything. Not a problem. Now, you may not get everything. So I have to grill the counter kid: "Am I going to get everything on the burger?" And Harry's just, "Oh my God. Stop it, please." So I want him to be proud of me, but I don't know that having a television show is what makes a kid proud of you.  

1. He's baffled by Donald Trump, who he refers to as "Trumpy":

The man has such thin skin that if you keep pressure on him — I remember there was a Actually, it was the other way around. In a 2007 playoff game, a swarm of midges from Lake Erie caused Yankees reliever Joba Chamberlain to blow the game with a few wild pitches. baseball game in Cleveland, and a swarm of flies came on the field and the batters were doing this [mimes swatting at flies] while the pitcher was throwing 100 miles an hour. Well, that's Alec Baldwin and Saturday Night Live. It's distracting the batter. Eventually Trump's going to take a fastball off the sternum and have to leave the game.... On the other hand, Donald Trump can be Donald Trump, but if he doesn't help the people that need help, then he's just a jerk. That press conference that he held berating the news media? I mean, how do you build a dictatorship? First, you undermine the press: "The only truth you're going to hear is from me." And he hires the Hunchback of Notre Dame, Steve Bannon, to be his little buddy. Bannon looks like a guy who goes to lunch, gets drunk, and comes back to the office: "Steve, could you have just one drink?" "Fuck you." How is a white supremacist the chief adviser to our president? Did anybody look that up? I don't know.

Enjoy David Letterman's full interview with New York Magazine here.

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