SmartLess - "Graydon Carter"

Episode Date: July 14, 2025

Don’t curse - it’s Graydon Carter. Soft Power, subtitles, and a cat teaching itself to read. Meta much? We’re offending somebody. It’s an all-new SmartLess. Subscribe to SiriusXM Podcasts+ to listen to new episodes of SmartLess ad-free and a whole week early. Start a free trial now on Apple Podcasts or by visiting siriusxm.com/podcastsplus.

Knock knock. No, I guess you can't say. So I'll do okay. I'll play both. Knock knock. Who's there? Smartless. Smartless who?

It's an all new Smartless. Smart. Smart. Smart. Smart. Smart. Smart. Smart.

Smart. Smart. Smart. Smart. Smart. Smart. I realize that I think that I curse too much. You do? Yeah. What are you fucking talking about? There we go. Wait, really? Why do you say that? I don't think you do. Because don't you fucking talking about?

Wait, really? Why do you say that? Don't you think I do? I feel like I do. It just occurred to me that I feel like I curse too much. I think not enough. Did you get that feeling because you were hanging out with your dad and you caught yourself a couple of times? No, truly. Where did this thought come from? You caught yourself a couple of times? No, truly, where did this thought come from?

I think I was talking about hockey with somebody the other day and I realized that especially when I talk about hockey, I'm like, these fucking guys and look at this fucking team. And I saw this review of some gadget that somebody, that they've just released, some AI gadget that documents the words that you say throughout the course of a day or a week or a month, et cetera, and this woman was talking about how much she had heard she was cursing,

and I was like, I wonder how much I curse. Really? Yeah, a little bit. It used to be my, if I got nervous, I used to swear a lot. Like the very first time I met Steven Spielberg in his office. Oh no.

All I did, every other word was fuck. What? I was like, yeah, and his kids were playing video games. I was like, oh, that's fucking cool. When did you fucking get that? That's fucking amazing. I couldn't stop saying it. I remember I once had a,

the guy who wrote and directed, I think he wrote, but he definitely directed Napoleon Dynamite, this guy Jared has, he's a great director. Yeah, amazing, he's great. And I got a meeting with him just after Napoleon Dynamite, I was so excited, and just like, I get lazy with cursing, it's just like,

sort of like a way to bond, you know? Yeah, that's what I'm saying, yeah, right. And so I'm just like every word is this, and that fuck, and that blah, blah, blah. And I'm driving home and I call my agent. I say, oh, the meeting went really, really well. And he goes, you know, I was going to say something. I was wondering if it did,

because I know your family lived in Salt Lake City for a few years, and I was wondering if your family had any Mormonism in their background. Did you guys talk about Mormonism? Because you know, he's a big, big Mormon. Oh, I didn't know that. And I'm like, oh no. Because then I started, like,

then I was flashing back to the meeting, so I'm driving home like, yeah, he didn't say anything that was off color. And of course, I never heard from this guy yet. I'll feel, I was to this day. To this day, have you spoken to him? anything that was off color. And of course I never heard from this guy yet. I'll feel about it. To this day, have you spoken to him? To this day, no.

I probably was just deeply offensive to him. That's so funny. We gotta get him on here and ask him about that. I'm sure he didn't even notice. Well, I don't know. That's funny. I tell you what. This is a segue, Sean.

This is a segue. Incredible, it's so what. This is a segue, Sean. This is a segue. Incredible, it's so smooth. This is a segue. And my guest, my guest is, you know, we all like cool things and we like being, feeling like that we're part of, you know, that we're up on culture, that we're up on what's going on in the world.

This is a guy who's been not only at the forefront, but I think, I would dare to say, been shaping it for many years. He happens to be- Yon Winner? Oh. He happens to be from my home- Is it Yon Winner?

It's Canada? Yon Winner's not Canadian. Are you sure? I'm very sure that Yon Winner's not Canadian. Okay. He, you didn't know him when he was in Canada, but he'd started a magazine in 1973 called the Canadian Review that was very popular.

He then moved to the States and he worked for Time Magazine. He worked for a bunch of other things, Life Magazine. And then in 1986, he co-founded a very, very popular and influential magazine known as Spy Magazine. This is not Graydon Carter? Left that in great shape. It is Graydon Carter. It went on to become over 25 years

the editor of Vanity Fair. He's got a new book coming out called When the Going Was Good Guys, it's Graydon Carter. Nice. Good morning sir. I read the airmail email this morning. Bless you. Yes, you didn't mention airmail, sir. I read the Air Mail email this morning. Bless you. Yes, you didn't mention Air Mail, Willie.

I know, well I was about to get to Air Mail because you kept saying Graydon Carter so I was like trying to get through it. This is an awesome guest. I know. Nice going, Will. Welcome, Graydon, and I mentioned all the various things that you did that you started.

You started as a young writer and you founded, how old were you when you founded the Canadian Review? What was that in 1973? I was 23. That takes a lot of, I was going to say guts, but it takes a lot of chutzpah to start a magazine when you're 23 years old. Wow, how do you even start?

How do you get there? How do you know where to start? I actually didn't start it. I bumped into a bunch of guys who were starting it in college and they needed an art director and I said, well, I can draw and they said, well, one should be the art director. And then little magazines are just festering pits

of bitterness and jealousy and envy. And so one by one, they all left and then I became the editor. And it wasn't as good as Will was pointing out. He was being very kind about it. Nobody knew what they were doing. And that was completely evident to readers and advertisers that we were completely incompetent.

But it did lead to a job at Time Magazine when Time Magazine was like probably one of the most important magazines on the planet. Yeah, and what did you do there at Time? I was a writer, but you know, this was 1978. The city was still teetering after bankruptcy and was dangerous and there were burnt out cars everywhere, but rents were really cheap and And I lived in Greenwich Village.

My first apartment was about a block and a half away from here. And it was $200 a month, and it had high ceilings and a garden. But then when I got to time, they were restocking it with a bunch of young writers. And there was people like Walter Oskarsohn, who became the great biographer.

There was Michiko Kakutani, who became the chief book critic with the New York Times for 35 years, Frank Rich, who became the theater critic with the New York Times, and then the producer of Succession, and Maureen Dowd, who was there, Rick Stengel, who became the editor of Time, my best friend Jim Kelly, who became the editor of Time. Anyway, it was just a remarkable period

and we were all still keeping touch with each other. And it was very intimidating for me because I thought, wait a minute, are all Americans this smart? And thankfully they're not. Well, that's true. You're talking to three of them. There you go.

Exactly. Well, two and a half. You guys are the smartest. Yeah. Yeah. That's amazing. And so you work at Time Magazine with all this great talent,

and then you and Kurt Anderson form Spy Magazine, which, boy, I remember Spy Magazine and a lot of people do. It was so, it's been described as like, as sort of like vicious and cruel, but also like really dead on. And you sort of, somebody quoted something like, you despised all the right people.

Well, you know, there was a, there was the time all of a sudden in the mid 1980s, New York had sort of come alive financially. And, you know, investment banks had been sort of invented and that meant there were investment bankers around and they already had a lot of money and they loved showing it off. And accidentally, I think our timing was wonderful.

And we used to call it a stringent rather than mean. Stringent. But you know, that, it did occupy a space of sort of, I don't know what the term might be, sort of a healthy cynicism and a, you know, like David Spade had, we've talked about it a few times on this show, he had a segment on Saturday Night Live,

I think it was called The Hollywood Minute, where you'd kind of watch through your fingers, you know, sort of like you didn't want to see it or hear it, but it was always so accurate. And- And funny. I don't know what point I'm making, but I guess I want to say that there,

I don't know if it's unique to this country. You feel that it's gone or no? No, I don't. I feel like there is a space somewhere for people having the balls to call out that, which is kind of apparent to all of us, yet only discussed in quiet circles with your closest friends, yet everybody says it. You just don't say it in a big group.

You say it in small groups. You're just calling out accuracies on people's foibles. And it is interesting and maybe healthy. I guess this is the question. What do you guys think? Is it healthy to have mainstream media, to have a place in mainstream media for that type of release?

I mean, look at people like John Oliver and Seth Meyers and their news elements, and they do it better almost than, they do do it better than the evening news in a certain way. You know, not everything is objective. If you're talking about the earth being round, they do it better than the evening news in a certain way. Not everything is objective. If you're talking about the earth being round, you don't need somebody from the Flat Earth Society

to come out and give the counter argument. All right, but Jason's, I think maybe, I don't want to put words in your mouth, but maybe you're talking about insults. Well, yeah, but that cynicism that exists in some corners of mainstream media, like, I don't know if this is fair, because I'm not a student of all this, but I feel like Vulture on the New York Magazine,

they sometimes, they even have a hot radar, they've got a term for it, and they just call out basically what everyone's talking about in sort of, I put in quotes, the cool circles. And I mention it only because it does seem to drive some pop culture successes and create some pop culture failures when it's discussed at sort of that,

again in quotes, that high level, and then it sort of filters out into less cynical parts of our country and our media. It drives like what films get seen. I mean, it's sort of the theory of like having critics. You know, it's like one person says something is good, and then that starts to disseminate, and then it actually forms a wave of either success

or failure for some things. And I wonder if that is a healthy thing that we should have in media. My guess would be yes, but it's hurtful. But at the same time, you know, like everybody, excuse me, on the internet, everybody's a critic. Yeah. It's a sewer by and large.

But if you have people who have proper opinions and they're within the realms of accuracy, it can make a good difference. And the internet, word of mouth, is the most powerful tool in the world. And the internet just lets it grow exponentially rather than arithmetically. Well, the problem is though,

with the internet and with social media, is that often some of these voices all come at the same volume, and volume that they don't deserve. And so things get lost in the shuffle. But Jason, I think you were referring to the approval matrix, right, that they do. And there was something about Spire that did that,

which was, which is it just held things up to a light and sort of brought them into focus a little bit, things that, I remember there was a piece you guys did, you probably don't even remember this, but there was a piece you did, you may have already left, but it was certainly really tonally right in line with the kind of thing that you had set forth at Spy, which was they had a woman holding a pair of roller blades

over her shoulder, and they had her go to different neighborhoods of the city to see what reactions she'd get in different reactions. They put her on the Upper West Side, Upper East Side, flat iron, downtown, and what people would say to her at different street corners. And the Upper East Side goes like, do you like to skate in the park?. On the Upper East Side, I was like, do you like to skate in the park?

And then the Upper West Side, the guy's like, hey, you look great, why don't you put those down, let's go get a drink. And then in flat iron, the guy's like, why won't you talk to me, bitch? And you know. Lower East Side is get the fuck out of my face. And that's the kind of thing that,

I do think that that sort of thing is missing because everybody is so nervous. Yes, that's the kind of thing that I do think that that sort of thing is missing because everybody is so nervous about offending and also everybody is so quick to be offended and this is gonna get, I hope this will be a pull quote about me railing against people being offended. But there was a notion back there of like, I don't give a shit if you're offended, who cares?

As long as I'm not hurting anybody or saying this completely, I'm offended, okay. Yeah, there's a healthy space for that too that I feel has been lacking in the last few years as we needed to make and are still working on this sort of correction for those that are marginalized. But I think the consensus is starting to come out that maybe there was an over-correction

and it's starting to come back to middle a little bit now. And so there's a healthy level of, hey, listen, offending you is part of the joke or part of this thing. And so there's some casualties that are a part of the joke or part of this thing. And so there's some casualties that are a part of that metric. What do you think about that shift that's going on right now, Graydon?

Will and I would know this better because it came from Canada, but the pendulum in America swings in great arcs like this. And in Britain it swings like this, and in Canada it swings like this. So America goes way out, I mean, in the 1960s, you know, the pre-love movement was much further out in America than it was in say in San Francisco

than it was in Toronto. And, but then it swings right back. So in the 1980s, the investment banker ethos was much more pronounced in New York than it was in Vancouver, say. So America is these, it just has larger swings and so the extremes are greater. And I think it is coming, it will come,

it's a correction from the far left and then it's gone, went way too far to the far right and it will settle somewhere in the middle. You just hope that it does sooner rather than later. I think it will. Yeah, and of course, nobody's advocating for the marginalization of people who are different at all, and that's never been,

I think that anybody, certainly all of us, I would assume none of us would ever advocate for that. But I must say, it makes sense for someone who likes to comment on culture and whose writing and whose profession is informed by that. Of course, moving to the States is a natural progression for you, right? Because you've-

And you, yes. And me as well, of course, yeah. Because there is that ceiling in Canada where you can only go so far, unfortunately. It's a great place to be from. It's a great place to live still. I'm not suggesting anything otherwise. I love Canada.

Keep going, Will, yeah, you gotta put out the fire. Yeah. You're offending somebody here, yes. I am definitely offending somebody. How far have I dug now? Can I even see the top of the hole that I'm in? Yeah. You know, I've told that story before,

the difference between the Canadian lobster fisherman and the American lobster fisherman, right? What is it? They're walking on the road after their day of lobster fishing and the American lobster fisherman says to the Canadian, he says, I notice you don't have a top on your pot thereby, aren't you worried about your lobsters getting out?

And the Canadian says, no, these here are Canadian lobsters. If one of them tries to get out, the other ones will pull them back down. That's great, that's great. And there's an element of truth to that. But moving to the States and starting Spy Magazine and then moving to Vanity Fair, which has an even greater audience

and even sort of a broader demographic, if you will, that must have been, you must have been very excited at the prospect of kind of opening up a huge demo to what you wanted to say and what you thought was important to talk about. Yeah, and talk about having a piece of media that anoints week to week, or was it month to month?

I think it was month to month. Who is it? You know, you and Lorne Michaels were basically, had the two levers that existed on putting people. Two Canadians, by the way. Two Canadians here, yeah. Putting people on top of the mountain at your discretion, which was pretty incredible.

I didn't, it's funny, looking back, and I realize some of what you say is, it was evident to others, it never was to me. It was a matter of survival for the most part. I wanted to, I had a lot of children, and I wanted to, I had to feed them, and clothe them, and educate them. And so when I got to Venice,

I was the least popular person to get there because we had spent five years at Spy making fun of the editor, of the house writing style, of many of the contributors. So when I walked in, it was funereal, the whole mood of the place. And I didn't fire anybody for two years, but I eventually, there was, most of the people,

some of the people were left over just to talk about my inadequacies as they went around to dinner parties in New York. And so I, but I let everybody stay for two years, I thought I'd give them a chance to come around my way of thinking. And then I got rid of these three troublemakers in one week after being there for two years.

And all of a sudden it shifted and I could bring my children into the opposite bus and it was poisonous and people started saying thank you and please and working together in a collegial way. And because I don't like office drama, I like people to work together. I think you get something better out of it. And then I sort of built it from there

and I was fortunate to have one of the great owners, Cy Newhouse, who gave me the tools to succeed. He gave me the budget so I could bring in the, I thought, must have been the greatest stable of writers ever. The first writer I brought in was Christopher Hitchens. Wow. Wow, he's great.

Oh, he was heaven. And then also I had photographers like Annie Leibowitz and Helmut Newton and Bruce Weber. So I was blessed by having these incredible colleagues and I was so appreciative of what they did because taking pictures and writing stories is a lot harder work than being an editor. You're just sort of a wage ape,

and kind of like a cross between a chef and an air traffic controller. And a piece of mold just on your ceiling. We don't really have a point, but other than trying to assemble the thing each month, and anyway, it was just, it was a great perch during one of the greatest periods, but by the was just, it was a great perch during one of the greatest periods, but by the same token, it was a golden age of magazines.

But one of the reasons, anytime you have a golden age, it's a golden age because everybody is good. So every other editor was firing in all cylinders. All magazines were good in the 1980s and 90s. It was an extraordinary period. And also the magazine business attracted the best and the brightest then. Right.

Right. And we will be right back. And now back to the show. What was your ethos then when you got there at Vanity Fair, when you sat behind your desk for the first time in those first couple of years and going forward, what was your, did you have an objective, like this is the kind of stuff that I want to do.

Did you have something like that, a plan in mind in a way? Nothing so far, but a sort of an evolving thought that what I wanted to do is every month present the reader with something that is highly, highly compelling that they'll read with and have wonderful stories that could range 15 or 20,000 words, which is the fifth, the size of an average book. And that they would come back the next month.

I used to write thank you notes to all my contributors every month. Thank you notes to our advertisers who paid for the journalism. The advertising would came in at about $100,000 a page and that sort of, you know, paid for the heat and the light and the electricity. And, but then there was, I got other ideas

that really changed the direction of the magazine from, one from David Halberstam to create something called the new establishment, which is the, in the past, the establishments were the head of General Tire and General Motors and a bunch of New York banks. But in the early mid to mid 1990s, America became an entertainment culture and economy. And so what we shipped around the world

weren't cars and tires and things like that. It was intellectual property in terms of like video games and movies and television shows and magazines and technology. And so we did a huge portfolio that Annie shot and it sort of showed the world that there was a new, because there was a new economy, there was a new establishment to that economy.

And then doing the Oscar party, which was started off small and terrified that it'd be a failure and it just sort of grew each year. It kind of rivals the Oscars itself in terms of its prestige. As you're well aware, lots of people go, will often just go to the party and not the Oscars themselves.

And a lot of people who are big film stars, people, names that everybody, all of us know, and of course the three of us have gone many times and enjoyed that. And it has become its own thing, which is quite miraculous really if you think about it. It's kind of in some ways dethrone the Oscars at its own party in a way. Which, you know, you spoke, you mentioned something that's kind of in some ways dethrone the Oscars at its own party in a way.

Which, you know, you spoke some, you mentioned something that's interesting, the idea that America's true expert is its culture and its obsession with celebrity peaked, you know, it reached the peak, a fever pitch, if you will, in the 90s, as my father calls it, celebrity, in a way that I think that he does that

just to demean the term itself. And he will claim that that's the actual way that you should pronounce it. But he also says to Motto, here's my point. It occurs to me, and I've long thought this, if we were really smart about wanting to sort of peddle influence around the world in a way that America seems hell bent on doing,

we would, and this would never go down with the people who, you know, with the military industrial complex, which is, you know, a trillion dollars, I think, as of yesterday, a trillion dollar a year business. What we could do and much more efficiently is, if we wanted to influence a certain country and its people, etc., all we need to do, at the time I used to say drop our DVDs of our TV shows and dumb them down as much as we're dumbed down.

If we could pump in Netflix and Amazon Prime and Macs to all these countries for free, they would immediately lay down their weapons because they'd become just as dumb as we are. Or as smart. Sorry, or as smart, thank you for allowing me. But do you know what I mean? I mean, that would seem to me to be the answer to all of it. Well, it's an element of soft power and we've sort of given up all our soft power

in the last three months. We should be pumping them with TikTok and YouTube and paying for it and star linking it into their country. And believe me, they'll be like, hey, listen, we were gonna go and fight on the front line and like, hang on a second, I just gotta watch this thing about a cat teaching itself to read.

Do you know what I mean? Yeah, I mean, we do do that in a certain way. I mean, America, if you look at the way most kids dress anywhere in the world, they're wearing, you know, American style trainers, blue jeans, T-shirts with something written on them and plaid. Everybody looks like they're in a writing room, no matter what country you're in. You know?

It's so true. And you see rally, you see these people protesting and they have effigies of the president and whatever and they're wearing baseball caps backwards and they're wearing a guest jeans switcher and you're like, wait a second. And the irony is completely lost on everybody. That's our gift to the world.

Well, and sort of expanding on that, Graydon, do you have an opinion about what sort of the current prognosis is for America being able to bear and withstand what some people are saying, kind of the hit that the American brand is taking across the world? Like, do you think after everything settles, at whatever point that is, that America will still hold a respectable place in the world? I think it'll all depend on the next sort of three or four years.

I think it's really tarnished. And I, you know, we're leaving for Europe on next weekend and for a spell. And we have these little pins made up. We made up for our airmail shop over in Hudson Street here. And it just says- It's a great shop, by the way. I was there two weeks ago.

It's fantastic. And the little pins, they just say, I didn't vote for them. And so when you're at a market in France or in a pub in England, people, it's just, because it'll be difficult. It was difficult during the years of George Bush, George W. Bush as well.

And it may take a generation for the so-called American brand to correct. Great, and do you want me to send you over a couple of these Canada patches? Love them. From your back. Love them. They are useful to have.

They are really useful. All of a sudden, everybody who travels is a Canadian. You have Americans practicing their Canadian patois. Because Canadians end every sentence with a question mark. Like an American will say, I'm going to the store. A Canadian will say, I'm going to the store. As if like, can I get you something sort of thing. Right.

Yeah, that's nice. Wait, great, as far as journalism goes and kind of to what Jason was saying about Scott Galloway, you know Scott Galloway? Oh yeah. Yeah, we got to have him on the show. He's brilliant. I know.

Yeah, he's great, very, very smart man. And I saw this clip either again on TikTok or Instagram or something, and he said- We can take over your house in two minutes. Yeah. You wouldn't get off the couch. Yeah, exactly. He said nobody wants to read anymore.

That's not true. Period. And he goes, everybody's getting their information from obviously TikTok or Instagram because nobody wants to sit down and read articles or magazines or books or anything. And so, and that said, people know that people of influence know that. So they'll just speak to these kids or these people

about what it is they should know. And that's how they get their information out. Okay, well, a counter-argument to that would be that the fact is the New York Times has never been more successful. It's never been larger. If you look at a magazine like, say, The Atlantic, The Atlantic is exponentially larger

and more influential than it was say 15 years ago. But that's a certain demographic, I think. It is a certain demographic, but at the same time most people watch TV with the, even with most people watch TV with the, the Chiron, you know, the whatever it is. Yeah, yeah, with the professional show people call that. Subtitles.

Subtitles. And so young people, I think it's harder and harder, and I have a feeling that most of us, if we were growing up with TikTok, and that we would read less than, and but it also, you know, most, I have five kids, and I know that some of them didn't read that much when they were in their teens,

but they're all huge readers now. They're all writers, and so they're all huge readers. You just have to wait a bit and it'll come around. Yeah, yeah, that's true. Yeah, Sean and Jason, what are you guys waiting for? Yeah. I always say to these guys, but anyways, they're unlucky.

I've got a boring story I won't bore you with about why I'm not a great reader, but I will tell you that- Does it have to do with you don't know how to read? Is that the headline? It's top to bottom, left to right. Right? There's now you can...

Every article online is now you can listen to it. Right, that's what I'm saying. And it is something that's helped both of my girls where they have these large reading assignments for school and now all those books are audio books as well. And so one of the teachers suggested, and I thought it was a great idea, get them the audio book so they can listen to it

as they read it. I agree. And that's helpful and you get some momentum going, you get engaged in the story, and now maybe you don't need that crutch for chapters five through 10. You can actually just read the book. And so I do, that's helpful.

That's somewhat of a phenomenon where, like you say, the New York Times grade, I would imagine their online business is larger than their print business. I think it's 9 tenths of it, but still they're reading it online. But they're still reading it. I will say that though,

and I do bang this drum quite often, but there is a certain reading it, for me reading at the end of the day, I find to be such an extreme luxury. And it's very calming because we do live in a digital world. I'm looking at my screen all day, I'm looking at my computer, at my thing, whatever.

And to have that moment for 45 minutes every night to read, I do find that it is so calming in this sort of chaotic world in which we live, if nothing else, apart from the fact that it's interesting and you can beat all the other great things about reading. But in that way, and especially as we get older, I'm not speaking to you, Graydon, I'm speaking to Sean and Jason. Because I am older, yeah. You need to calm down. You need to calm down, both of you. Especially as we get older.

You need to calm down. I still read a lot online and stuff. What do you attribute, Graydon, not the demise, but the way that magazines have not, you say like the New York Times for example, never been more profitable, yet it is now intense online now. Why did the same not translate for the periodicals? I mean, the financial crash of 2008 was an issue because the first thing that people could take off their balance,

off their accounts were advertising because then you don't have to fire anybody. So the advertising started disappearing. The new, and then even in New York City, there used to be a newsstand at every major intersection, sometimes one across the street from each other. There was a newsstand in every office building. Now, when you see a newsstand on the street,

it's often a movie set thing because they're gone. And in office buildings, wherever there was a newsstand, it's usually, they're selling gum and flip-flops and lotto tickets. So just the fact that you used to be able to see magazines everywhere you went. You know, in Los Angeles, those things in Hollywood,

but the long walls of magazines. I love those. Anyway, that's sort of, they're gone. And I think a lot of magazines companies were late to transfer their way, a magazine looks, to an electronic version. And the thing about Air Mail is Air Mail was put together by magazine people and we didn't have to work with a legacy brand and then transfer it to the internet And the thing about Airmail is Airmail was put together

by magazine people and we didn't have to work I can read them all on my iPad. But before you go too far past Airmail, I just love what you, it's so, and this is probably not the right term, but there's nothing like, here's, it's basically like looking at the table of contents page. Are you talking about the subscription to Vanity Fair? Or no, to Air Mail?

No, it's switching to Graydon's new thing, is this thing called Air Mail. So you get this email and here's like five stories that you can click on, that then if you decide to click, then it expands into the story. So there's just like, you don't have to buy a whole magazine or you don't have to go to a magazine's website or anything and like have to like deal with all the advertising

and the big pictures and all that. It's just, here's some ideas, some stories, if it's interesting to you, click on it. If not, go to the next email. Like so it's not in your face, the medicine goes down easy and they happen to be incredible stories. So I don't know, I just think you tacked to a format that speaks to the current reader's appetite,

as far as the attention they have to get. And there's a tonal shift too, right, JB? I mean, there's a tonal shift in it from Vanity Fair to Air Mail that's, you know. Yeah, there's no selling element to it that I think people have grown sort of an allergy to. And you're just, you're very current on that, which is not surprising coming from somebody like you.

Well, we wanted to look beautiful because I think design means everything these days. And look at the amount of work that goes into an iPhone, say. So, you know, as I said, I'd written thank you notes to all my advertisers at Vanity Fair, and so I wanted those advertisers in Air Mail. I didn't want advertising for, I don't know, foot fungus or, you know, Geico insurance ads.

I wanted, you know, much better to have Hermes and Dior around Florida. So, all the advertisers, once I got Hermes, all the other advertisers felt safe coming in, but it's put up by people from Time Magazine, when I worked there, Spy Magazine, and Vanity Fair. That's the core group, and then there's about

eight young people who are in their mid-20s, and they form the core in the future. Yeah. Well, we'd be remiss if we didn't mention our mutual friend, the great Linda Wells, who are in their mid-20s, and they form the core in the future. Well, we'd be remiss if we didn't mention our mutual friend, the great Linda Wells, whom I adore. Me too. Yeah, whom I absolutely adore and have known for many years,

and she's a big part of Air Mail. I'm not telling you, I'm telling our listener, our single listener. But I will say that when you were at Vanity Fair, there was a real balance between covering high society profiles, if you will, celebrity and investigative journalism. I remember there's a great article that I've referenced many times and had people read, which was about

the Salton of Brunei's brother. Love that story. That story is an incredible story, still holds up. It's incredible, it's hilarious, and it's right on point, and it's scathing and yet very fair. So you do that at Vanity Fair. And then now that you're at Air Mail, how would you define, what is your relationship,

well, I was gonna say what's your relationship with celebrity culture. Before I say that, what was, because you were at the forefront of defining celebrity and covering celebrity culture back at Vanity Fair, and you still are at Air Mail in a way, when you were in that position, what kind of incoming calls did you get from people,

from publicists and celebrities themselves who wanted you to either amend something that you wrote about them, and I know you already mentioned this about Mr. Tisch, but what celebrities did you get? Did you ever get a call from that Donald Trump pseudonym? John Barron. John Barron.

No, but I would get calls from Trump, and once they invented Twitter, he went to town on me. He would call me a floppy, I was a loser. The Waverly Inn was a failing restaurant. The Oscar party wasn't hot. The magazine was terrible. But I would take any phone call. But mostly, doing the covers was actually

the least favorite part of the job. But the fact is, movie, you know, show people like you are more attractive than the rest of us. So having a very attractive person on the cover who happened to be talented was a great way of getting the attention of the reader so that they'd pick it up and they wouldn't be embarrassed putting it on their coffee table.

But once you got that, that was sort of like the wrapping and then the magazine itself was sort of the gift in the box. But most of the calls, and we did get a lot of complaints, but they were routed through the office of the person who, of the people who booked the covers. So I got, I would get occasional complaints. Most of the complaints often would come from staff members.

And I remember Christopher Hitchens did a pretty rough story on Mother Teresa. And he accused her of like cozying up to dictators and that sort of thing from money. It came out of the blue and it was wild. And Rinaldo Herrera, who's the husband of Carolina Herrera who was on the staff, and he came, he was sta. And, Rinaldo Herrera, who's the husband of Carolina Herrera, who was on the staff, and he came, he was staunch Catholic, and he came into the office,

stormed into the office, and said, Graden, you've gone too far this time. What do you mean? He said, Mother Tracy, I'm canceling my subscription. I said, you can't cancel your subscription. You get it for free. And so, but at Spy Magazine, once we did a story on the 10 most litigious New Yorkers,

and Gore Vidal was on that list, and we were listening to the phone book, and he called me up and he said, I really object to this, I'd never met him before, I really object to this, and if you don't take my name, if you don't correct that, I'll sue you." And I said, wait a minute, if we don't correct that you're one of the most litigious New Yorkers,

you're going to sue us. He said, yes. And I said, don't you get the irony in his own thing that he just hung up. That's great. That's so good. We'll be right back. And back to the show. Your new book, Graydon, is When the Going Was Good,

which is out now. And talk a little bit about that. First of all, what a great title. You're clearly not talking about yourself. Because things continue to have a nice arc. You're talking about a cultural shift, yeah. Is that the sort of, talk a little bit about the book. No, I think that the, you know, if you look back

and the 80s, the 90s and the aughts, with the, I mean, if you look back in the 80s, the 90s, and the aughts, with the, I mean, the 80s and 90s in particular, it was a great time in America. It was very aspirational. The middle class was doing well. We still had two World Trade Center towers. You could get on an airplane without stripping down. There was no cell phones or social media.

And it was a, it was just a much more natural, organic time. When my wife and I happened to love watching Frasier before we go to bed, because they're like perfectly written plays, and nobody has a cell phone, and there's just something, you know, I mean the same thing with Will and Grace, or Friends, or I'm trying to think what else, Seinfeld say.

And it was just a great time. And so the 80s, 90s and aughts, with the exception of, you know, obviously 9-11 and everything that came after that, were a great time for television, a great time for movies. And I think television has overtaken movies now too, in terms of driving the culture.

Magazines do not drive the culture like they used to. It's obviously the things like Instagram and television in a big way. So do you think we'll ever get back to what you're describing? No. No. Ever, or a version of it?

A version of it, perhaps. I think young people will come to love magazines the way they love vinyl. Yeah, I was gonna say. But there'll be specialty magazines. There won't be a million circulation and they will be largely visual. Like, you know, you go to like Casa magazines

on Eighth Avenue over here. Yeah. And there's a ton of these big, expensive, $20 perfect bound, thick paper magazines. And they get scooped up by young people, not by people over 30. There's one of those great, there are about four every corner

from West Broadway to Sixth Avenue. There are three or four bodegas on every corner. There's that one at the corner of Sullivan and Prince that still has a really robust magazine section. You know that, you know what I'm talking about? I know exactly what I'm talking about? I know exactly what you're talking about. I've been listening, I've been living half a block from it

for the last sort of six months and it's been phenomenal and I've gone in there, I found myself going in there from time to time and perusing magazines again and I feel like I'm stepping back in time. Yeah, I think it'll come back, I think. What do you think is the, you know, we talk often about, and we've referenced it here today, the effect of social media has had on our culture, which to me, in large part,

I think has been quite a negative effect. What do you think the future is for things like social media in going forward? Do you think there will be a whiplash or a backlash rather? I was gonna say, I think I'm hoping that because- I wasn't asking you. I mean- No, no, but I want to say,

no, it's funny because you brought up social media because I think we've so overshared our lives in such a massive way and billions of people, now we know everything about everybody always, that I think if I'm guessing correctly, we will go the opposite way in five, 10, 20 years, whatever it is, I don't know, where people will be like,

wait, we've all overshared, I'm going to get off it. I think it's cooler to hang out without it. I think it was a long way away, but I think that's what's going to happen. Greta, what do you think? 100%. I think, yeah, I totally out without it. I think it was a long way away, but I think that's what's gonna happen. Greta, what do you think? 100%, I think, yeah, I totally agree with Sean that it is, again, it's a correction. And so the correction, now you share everything,

pictures of your children, picture of your children's birthday, them having cake on their nose and all the rest of it. I have five kids, none of them have a social media presence and no tattoos either. So that's a major accomplishment. But I don't have a social media presence and no tattoos either. So that's a major accomplishment. But I don't have any social media presence and I think, and I know this sounds strange

for somebody who's just written a memoir, but I'm a very private person. And I think a private life will have greater currency in maybe three to five years than it does now and it'll be much cooler for young people than having social media presence. A greater currency, and it gives you more cache. Much more cache, there's a mystery.

Well, it's so great, and kind of on this, this sort of this cultural transition period we find ourselves in, hopefully, and you being the head of a major media effort, talk to us about your process with you and your team when you decide what stories it is you're going to go forward with there on Airmail. Is there any agenda such a pejorative? But do you consider the effect and the move

that you guys can make for people, as you try to encourage them towards a better, healthier, you know, cultural position? Or is it just stories of interest to you guys personally? I mean, I put the next issue together on a Sunday morning, and it's my favorite process of the week. personally? I mean I put the the next issue together on a Sunday morning and it's my favorite process of the week but by and large we look for stories that have not appeared in the American papers. It's sort of intended as the

weekend edition of a non-existent international newspaper like the old International Herald Tribune. And the fact is there's so much to celebrate about life. It's not all about Donald Trump that we have. It's hard to avoid Donald Trump. I mean, it's certainly worth the effort to avoid him, but it's almost impossible. And so he winds up in there.

But it was designed as a, we started it during the first Trump administration, and I was living in France, and it was designed as a, sort of not the same, like every single newsletter you get in America is, you know, it's all basically Boston to Washington to sell a corridor news and we have very little of that. There's enough of that to go around.

So ours is very international. Stories have to be just interesting and things that reflect changes in the culture, hopefully for the better, not always. And just sort of spirited writing that could be funny, but informative, and some new fresh voices. And it's just something that you can wake up Saturday morning and read it

without completely hanging your head in despair over the news. I took the New York Times alerts off my phone. Yeah, every 45 seconds is like the end of the world. And it was like, I know. Same here. And I've been doing my best to try to avoid it. Totally, same.

Do you, you've been a, for lack of a better word, a tastemaker for decades. It's just simply true. What cultural trends, are there any that you now that you miss most or, and what do you think, what cultural trends do you think are wildly overrated now? Well, the social media, as I think Sean points out,

that it will have a swing back because the not sharing everything will be a value in both in your life and your personality and your interactions with others. I think kindness would make it be a wonderful addition back in the world, because I think the sort of wanton cruelty you see coming out of Washington is a,

it sort of reflects badly in us, even though most of us are not like that. And I don't think it's gonna get better soon, but I think it will get better. And- I think so too. He's a very strange man. I've known him for 40 years.

He's both loved me and hated me. Yeah. And he reads young, he reads like a young 78, whereas Biden read like an old 81. I know, you gotta give him that credit, it's hard not to. Graydon, at the great risk of offending you, okay? Oh, go ahead.

Uh-oh, oh boy, oh no, this is his favorite. Can you please walk me through the genesis of your incredible and impressive hair? Oh my God, we'll take a good look at it because it's disappearing as we speak. No, no, it's, no, no. What it is is it's one of my favorite things about you, always has been.

To the extent you're comfortable, can you please walk us through how it started and what the process is to make, is there a pick involved? Yeah, because put a baton in your hand and you can conduct the New York Phil. I just fucking love it so much. No, I had this hair, it's the same hair I have

on the cover of my book when I was 30. And it's sort of, you know, in the old days, when I didn't have much money, you'd get it all cut off and you'd wait three months and it would grow back. Now I get it cut every month or so, and it's just, but it's gone gray, and if I come out in Los Angeles and I go and there's a lot of people my age in the room,

I'm the only man with gray hair, which I find really amazing. How's that possible? It's pretty cool, it has something to do with the water out here, I think. The styling of it is just, I just love it, because it's just a perfect juxtaposition between this incredible place of,

oh, influence and success and sophistication that you hold and it's sort of offset, I mean, it's like Einstein, you know, like Einstein was like the greatest brain ever, yet he counterbalanced it with his. Well, Pete Davidson once said, Pete Davidson told a friend of my daughter, he said, your dad, he looks like, and with that hair, he looks like he should be on Money.

Which I'm not gonna compliment anybody. It's sort of, you know, there's a confidence to it, which is intoxicating, I must admit. That's code for what a fool who would do that. No, not at all. No, no, no, no, no. Anybody who says how brave of you to wear that or something like that.

No, the opposite, the opposite. Well, great, now I'll leave you with this, and again, we pointed out all the great things, Spy Magazine, Vanity. Well, great, I'll leave you with this. And again, we pointed out all the great things, Spy Magazine, Vanity Fair, Air Mail, and now your book, When the Going Was Good. After decades. And don't forget the Waverly Inn. And the Waverly Inn.

And the Waverly Inn, which, sorry, the Waverly Inn, which is, I must admit, I haven't been to in a long time, but I love the Waverly Inn. And you can make a reservation through my email. Is that true? Yeah, do all the seating, do the seating every night. We'll treat you well. No, really?

Fantastic, oh my God. Oh my God, what a dream. I'm coming back. I mean, don't put it on your website or anything like that. No, no, no, no, no, no, no, no, no. Oh, believe me, I'm going to guard it with my life. I will tell you, and this probably won't be much of a compliment, because I'm probably one in a long line,

but I just finished doing this show and it's about an incredibly beautiful, hip restaurant on the Lower East Side. Called Black Rabbit. Shots of inside of Waverly End was up on our production designer's board. Oh, sweet. And we basically modeled modeled the aesthetic in there is just so incredibly beautiful.

And built down in Atlanta? No, actually we shot in New York. We built an entire restaurant at Steiner. Oh my God. You know what would be great to do? Let's do something like, now that we have Graded here, let's do a thing where we get Thoreau banned from the Waverly Inn forever. Like you know what I mean?

And don't let him know. You don't see Justin Thoreau anymore. Like he just, you're always busy, you're full, so we can get every other fucking time. Yeah, no, Con Ed has shut us down, yes. Yeah, but when we opened it, we wouldn't take reservations from the 203 area code, because that's Greenwich,

and that's where all the hedge fund guys were. So we didn't want them. Con Ed, that's so good! So they make a reservation, we'd say, oh sorry, shut, you know, Con Ed. Like they're kind of all over the place. Listen Graydon, you're speaking our language. I have said many times, nobody is more responsible

for the destruction of this planet than sort of private equity guys and bankers. They have absolutely rude. Except for Dandies. Except for Dandies, who is one of the all-time great guys. Everybody else. One of the all-time great guys. Double D. But I want to ask you this,

as a sort of parting shot, if you will, what would you like your, because it's a tough one to answer, I'm sure, what would you like your legacy to be, if you've even thought in those terms? As a Canadian, you probably never have. No, I mean, first of all, I'm really proud of being a Canadian, and especially now,

I'm sure you feel the same way. I like Mark Carney. I think that you just want to leave, if you got to a beach and it's filled with candy wrappers, my inclination would be, and I'm sure for you guys as well, to sort of clean up the candy wrappers and try to leave something in better shape than when you got there.

And in a large part, we do that through our children. And it's my kids, I'm very proud of them, and they're truly good humans and funny and well-read. And that's, because that's your legacy, because they're going to go on after your turn to dust and all the rest of it. And leave a modest body of decent work behind you. Yeah, what a great answer.

Yeah, for sure. Well, listen, Graydon, thank you so much for joining us today. Such an honor. I mean, I'm really, I don't know. You're a great man. The honor is ours. Thank you.

Yeah, we've been such fans and we've spoken about you before, the three of us have, and we've been just a fan of everything you've done from Spide suits to Vanity Fair to Air Mail. And now your book, When the Going Was Good, is out now for all our listener. All our listener?

All our listener. Tell him to get there quickly then. Or her, or her, or them, or them. I encourage him or her or them or whoever it is to go out and get it today. Graydon, we wish you nothing but continued success and thank you so much. Thank you, Graydon.

Thank you so much, guys. Yeah, nice to meet you, Graydon, yeah. Okay, pleasure. Thank you, Paul. Cheers, bye. Bye, buddy. Nice guest, Willie. That is sad. Now, you know Nice guest, Willie. That is that.

Now, you know, again, every time we have somebody that is not one of these big fancy A-list celebs whom we love, I just love talking to other folks. It's great. Well, he, I mean, think about it, and it is true. Not only, and Jay, you said it, I said it, John, you said a version of it, that he was a tastemaker, if only because he was on the front lines

of reporting what was happening culturally, whether it was a film or television or art or media, et cetera. But the vanity fair. Because of that position, he ends up, in a lot of ways, steering culture because of what he decides to report on. And what's in, what deserves attention. And Lorne Michaels is still doing it.

Like who's hosting Saturday Night Live and who's a musical guest will tell you who's the top of the zeitgeist. He and Lorne are still doing it. And again, I should be pointing out that these are Canadians. And I think that there's something to that. Fresh eyes.

Well, Canadians, we just inhabit just a slightly higher place in the space. You're breaking up a little bit. Are you going over a canyon? I'm losing you. No, I've got full bars. Shut off this mic. You turn off this mic. Well, you know what?

There is this, and I've spoken about this before. As Canadians, we grew up, we are so culturally close and geographically close. So we are kind of observers of American culture in that way and very close. And so we do- Wait, what do you think that is now though, if it's not Vanity Fair, maybe it still is Vanity Fair

that is the quote tastemaker. Like where do people look? Cause it seems so fragmented now. Yeah, you're right. Well, you know what? It's much more, I think that it's been divided into these different pieces. Vanity Fair was much more of a catch-all back at the time that inhabited a big space.

I don't know if there's anything that inhabits that big. Unless it's this airmail, which I didn't know. I think a lot of podcasts do. Oh yeah, that's true. Maybe Smartless, maybe the Smartless podcast. You know, I haven't heard that, but I did hear about it, and I hear it's not great. That's one of the, it's not great. That's one of the things, it's not great.

It's a little overrated is what I'm hearing. It's very overrated, and these guys, they swear too much, they interrupt people, but you know what they do have really down pat? Bye! Reference our own bye as the bye. Bye all night, bye! You mean how they say goodbye at the end of each episode. Bye!

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