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Graydon Carter, the editor whose two decades at the helm of Vanity Fair transformed the publication, sure knows how to curate. He made the magazine into the cultural touchstone it is today (think: the much-photographed Vanity Fair Oscars Party, the viral celebrity lie-detector tests), though not without trial, error, and lots of nerves. He and I talk about his long tenure, the pitfalls of a project not having a “point,” and what he gets out of being at the head of a completely new enterprise, the digital magazine Air Mail. It’s a creative conversation I didn’t know I needed, and one I’m very glad I had.

Graydon’s memoir, When the Going Was Good, is available now wherever books are sold.

Follow me on Instagram at @davidduchovny. Stay up to date with Lemonada on Twitter, Facebook and Instagram at @LemonadaMedia.

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Transcript

SPEAKERS

David Duchovny, Graydon Carter

David Duchovny  00:07

I’m David Duchovny, and this has Fail Better, a show where failure, not success, shapes who we are. Graydon Carter is the former editor in chief of Vanity Fair, where he spent 25 years overseeing countless stories and photo shoots that became cultural touchstones. Graydon’s influence was instrumental in popularizing the magazine’s unique style, from candid portraits of Hollywood icons to bold investigative pieces. Vanity Fair’s content became a must read under his direction, I was lucky enough to grace the cover in June 1998 photographed by the great Annie Leibovitz, who proceeded to glue dead flies all over my face I never looked better. He was also behind what’s considered one of the most exclusive soirees in the entertainment world, the Vanity Fair Oscar party. In his new memoir, when the going was good, Graydon pulls back the curtain on the glory days of magazines. It traces his journey from starting outsider magazine spy in the late 80s up through his time at Vanity Fair and beyond. Graydon and I chat about weathering the storm of failure, building new platforms like air mail, shaping the media landscape we know today. We talk a lot about resilience and authenticity, going with your gut and learning from mistakes, his ability to capture the pulse of the moment has solidified his legacy as one of the most influential figures in modern journalism. I hope you enjoy this conversation.

 

Graydon Carter  01:41

Hey, you know we, should we have a school connection? I was gonna say three of my sons went to co llegiate.

 

David Duchovny  01:47

Yes.

 

Graydon Carter  01:47

Your old school, and two of my daughters went to Grace Church, where your mom worked. Did she,

 

David Duchovny  01:52

Did she teach her sister.

 

Graydon Carter  01:53

[…] David Duchovny.

 

David Duchovny  01:54

Yeah, did she teach her daughters?

 

Graydon Carter  01:56

No, I don’t think she did. Yeah, that.

 

David Duchovny  01:58

My mom was a legendary teacher over over there at Grace Church. And when I, when I walk around downtown, people will stop me, and they won’t want to talk about any work I’ve done. They want to talk about my mother. It’s true.

 

Graydon Carter  02:09

Isn’t Duchovny, yes.

 

David Duchovny  02:11

Are you? I once visited her classroom. Uh, never forget this. And this little girl, second grade, little girl, came up to me and said, I just love children’s logic. She says, she asked me, Do you know your sister, Lori? I just love the way those minds work. Well, yes, yeah, I’ve seen her around the hallway. So that out of the way, you know, I was trying to think about, you know, how to begin speaking to and one of the things I want to ask you is why write a memoir? What is, what is the impetus for you at this point of writing a memoir?  Is it to set the record straight? Is it to relive the glory days? Is it to say I was in the room and this is how it happened? What compels someone like you to to want to write a memoir?

 

Graydon Carter  02:58

Well, in large part, is for, for my children, I have five of them, and I think, like most fathers, if I ever start talking about the old days, they sort of get bored with all that. But I I’ve never thought of it. And I have the having lunch with James Fox. He’s a dear friend of mine, and he had written the Keith Richards memoir, life, yeah. And he said, he said, If you ever want to do a memoir, I’ll guide you through it. So I thought, yeah, I can probably do this. And I had re retired from Vanity Fair, and I had a bit of time on my hands. This is like 2017-2018 and I really realized how fortunate I was to live through this golden period of New York, golden period of magazines. And I thought, you know, it’s good to I think it’s inspiring for other people, because I was not some exceptional child who is automatically going to rise to the top, but I thought it’d be somewhat inspirational for everybody out there who thinks they’re somewhat average when they’re a teenager or in their early 20s, but has some sort of dreams of being on average, if they can.

 

David Duchovny  04:07

That’s very interesting to me, that you that is the impetus, because I find it moving that you say this is in the sense of failure, not in the sense that average is failure, but you’re saying you don’t have to be exceptional from the get go, to become an exceptional person, or to have an exceptional success.

 

Graydon Carter  04:26

I don’t think so. I don’t think most people, most teenagers I grew up with, they didn’t have a definite career in mind or even a definite profession. It just sort of usually, often happenstance, and you fall into something and it agrees with you, and you work hard and they do well, but I’m I’m always slightly suspicious of a teenager who knows exactly what they want from life. That sounds calculated.

 

David Duchovny  04:51

Yeah, and but when you were a kid in Canada, did you have an image of where you wanted to end up, or an. Ambition. And was the ambition in the arts? Was the ambition just to make enough money to live? Was there something for you that you were aiming at from a young age? Or when did you veer towards the world that you ended up being in?

 

Graydon Carter  05:12

My parents subscribed to time and Life magazine, Esquire, and they sort of, you know, to a young kid growing up in Ottawa, they sort of brought the outside world to me. My life was all about hockey and skiing and and canoeing, but then, but magazines told me about this world outside, specifically the world outside here in New York and and I basically, I wanted to move to New York, but I had no idea what I would do. I needed to make a living. And when I was in college, I stumbled upon a magazine that was being started, created and being launched, and I sort of joined on. And they needed an art director, and I told them I could draw a bit. So they said, you okay.

 

David Duchovny  06:01

Is that true?

 

Graydon Carter  06:02

100% so I sort of fell into the magazine business, and I was a great student of magazines, so I, so I then there were the little magazines were always like, people are fighting constantly. And so the main editor left, and I became the editor, and I found something that agreed with me. The magazine wasn’t very good, but the job was a dream for me.

 

David Duchovny  06:28

Well, how would you describe the an editor’s job at a magazine? You set the tone. You’re like the director of a film, I’d imagine.

 

Graydon Carter  06:37

Llike the director of a film, and a bit like a chef. And that you you, you go, you try to find the most interesting stories, you try to couple them with the the best writers and photographers you can get your hands on, and you try to put it all together in a package that’ll appeal to the reader. Then that the mix and whatever that issue is, you know, has enough different notes that it creates a a good chorus and and that you hope that that reader will like it and come back the next month. So it’s, it’s, it’s basically, you’re, you’re like a cheerleader, you’re a psychiatrist, you’re a plumber. I mean, it’s just it’s, there’s no school for editing, you know, there’s no university that teaches people how to edit. So it’s just it’s trial and error.

 

David Duchovny  07:23

And I’m wondering if you were surprised to learn, if you self describe as an average student or an average person or whatever, but were you surprised to learn that you had a extraordinary gift for taste, for signaling out good writing or good photography, or being able to find people of great talent.

 

Graydon Carter  07:49

Well, I read all the even though, as an average kid, that was an on average reader. I read everything when I was growing up and and I can appreciate good writing. And then most of the stories in Vanity Fair are big. We’re a lot of them were big, epic narratives, some of which I’m incapable of, but I can recognize that talent in others. And, you know, I became better at understanding how photograph, photography can work in conjunction with words. Spending time. I spent two years, two years of Life magazine, which was built around for the great photographers in the era and and I appreciate how hard it is to take a great photograph. I mean, you and I can go out and we can sit on Malibu, on the coast of Malibu, and take a picture of the sunset, and it’s gonna be nice, but Andy leibot has to go out and under difficult circumstances, every single time come back with something fabulous.

 

David Duchovny  08:42

I’m also a big fan of Annie Leibovitz, although when I did my Vanity Fair cover, I put dead she put dead flies.

 

Graydon Carter  08:49

All I remember that I was catastrophic. I know I didn’t quite understand that one, but yeah.

 

David Duchovny  08:54

It was a pun. It was flies and files. If you were dyslexic, maybe you’d get it.

 

Graydon Carter  09:00

I didn’t see. I didn’t even get that.

 

David Duchovny  09:02

Yeah, well, I’m glad to give you the punchline, 25 – 30 years later.

 

Graydon Carter  09:07

Thank you for that, yes.

 

David Duchovny  09:08

Yeah. It was like, you know, here’s my dream, a dream Annie Levis is going to shoot me, and here’s, here’s the under, here’s the failure part she’s going to put and this is before Photoshop. So these are real dead flies. Didn’t even know, being a fix to my face and some airplane hanger up at point, Magoo. But still, you know.

 

Graydon Carter  09:27

I’m sure Mrs. De COVID did not like that.

 

David Duchovny  09:29

I don’t know that Mrs. Duchovny, you know, she, she was not a magazine reader. She was a reader. She once told me that she found it disorienting when she would, you know, check out at the grocery store, which is where they would have not Vanity Fair so much as tabloids back in those days. And she would see me on a tabloid, and she think, well, that’s my son, you know? What does this all mean? It doesn’t make any sense, but, but I want to when you started to write, you know, you having the insight into what makes great writing. You’ve worked with HalBer. Damn Michael Lewis, who’s actually a classmate of mine as well. I didn’t know that, from Princeton 82 Michael hare, of course. So Vanity Fair was this very interesting combination, to me, of the celebrity bait, the kind of celebrity, the bait of satire. And then there was these long form articles that were Pulitzer worthy, and often movie worthy, documentary worthy, as you know, as as you have taken those into other forms as well. So it reminded me very much of when my dad would, you know, tell me that Playboy paid the most for, for for fiction. You know.

 

Graydon Carter  10:40

That’s true.

 

David Duchovny  10:40

And so people would always have the excuse of saying, Well, I buy Playboy for the for the fiction, actually. So well, I want to ask you two things. One about when you sat down to write, were you cowed by, you know, having edited and worked with these great writers? Did it? Did it freeze you up at the keyboard a little bit when you started to write? And was that kind of packaging of glitz and substance? Was Was that the mission statement at the beginning, or was that something that kind of organically arose over time?

 

Graydon Carter  11:10

Well, going opposite. Second one. First, I always thought of the the cover as sort of the the gift wrapping you want to get somebody to go to a newsstand back when we still had newsstands, see something that appealed to them, but we have maybe a half dozen cover lines on it, which told you what was inside the magazine, an appealing cover image, generally not somebody covered in flies. They would take that off and that they would read it, and they’d be happy on the coffee table. But once you got past the cover. It was, it was all substance inside. And on the second part, I wasn’t intimidated because I knew I couldn’t write like Albert Stanford, Michael hare or Michael Lewis or David or Hitchens or anything. I have my own voice, and it it is what it is, and it rise and fall on the strength or weakness of it.

 

David Duchovny  12:01

Did you have a sense of sometimes reaching to write a certain way or to be lyrical or descriptive?

 

Graydon Carter  12:09

I’m not a poetic waxer, really, and and so I, no, I just sort of told it as I thought I’d try to tell it in an interesting way. And I think that it’s the failures that are more interesting and the hiccups that that are more engaging for the reader. So that’s a lot, large part of what I what I included.

 

David Duchovny  12:30

Well, so not not just more engaging for the reader, but more important for one’s own soul and one’s own spirit, in a way, and that’s kind of what we talk about a lot on this is that, and I think you say at one point in the book, you know, you’ve never learned anything from success. Nobody ever learns anything from success.

 

Graydon Carter  12:49

I don’t think so.

 

David Duchovny  12:51

I mean, I think success will inhibit you, because you try to, you try to repeat it, you know. So you you do, you start to do by program what you did instinctually at first. And that’s a that’s a recipe for disaster, and all of a sudden, you’re inauthentic, and you’re you’re doing an imitation of yourself in a way.

 

Graydon Carter  13:12

One of the things when we, when we would do issues, if I put out an incredibly great issue, it would actually make me more anxious because, because I would think, sure, oh my god, we’ll never be able to do that well again. And if I put out a sort of substandard issue, I thought, okay, that’s it. I’ve lost it. We’re never going to get it back. So almost, when you’re when you’re in the world of arts, almost nothing makes you authentically happy, if you really thinking about everything.

 

David Duchovny  13:40

No, it’s really, I mean, as a writer, it’s when I get the galleys, and I don’t know if you had that experience too, it’s like, oh, here, here’s this book. It exists. It’s not out there yet. You know, it’s not.

 

Graydon Carter  13:51

That helps, yes.

 

David Duchovny  13:52

That moment, to me, was one of the richest moments that I’ve had. It’s just when you feel the physicality of the book in your

 

Graydon Carter  13:59

Yeah, you feel it’s real, yeah? The person, yeah. I’ll just type it in pages.

 

David Duchovny  14:04

Yeah, but it’s really only real when it goes out there and gets, you know, destroyed and savaged and loud it, or whatever it is, you know, for other people, what I found fascinating in reading the book, and it really took me back, because you say, and I’m gonna, like, just take, like, a macro view of the late 80s and 90s. And I believe this, that if you look at the tone of those years, I see, like the three, three major figureheads of that are, well, first there’s Letterman, I think, who brings, for lack of a better word, irony to television. And then there’s Lorne Michaels and in with Saturday Night Live. And then there’s you in publishing, two Canadians, oddly.

 

Graydon Carter  14:51

Two Canadians from the same town, really, and about about a half a mile born a half a mile apart.

 

David Duchovny  14:59

Well, what? What’s in that water? What?

 

Graydon Carter  15:01

Go figure, yeah.

 

David Duchovny  15:02

They didn’t add fluoride to that water. They added irony to that.

 

Graydon Carter  15:06

We had this cold water because it was Canada.

 

David Duchovny  15:10

I find that fascinating because, you know, it’s a DNA that I think we still have. You know, I don’t think that that tone that was created by, say, Letterman, Michaels and yourself. And I’m not even saying it was a tone that was deliberately employed. Go beyond before a Vanity Fair and go to spy really. It’s really an outsider tone.

 

Graydon Carter  15:36

100% and Dave’s from, like, I don’t know, Ohio or Indiana.

 

David Duchovny  15:39

Yeah, exactly. So it’s not, it’s not hip. Yet it becomes hip, but at first it’s an outsider tone, and I wonder. And again, this is a kind of a question. It is about failure and success, because it’s when you go into it at first. And what I found fascinating was you talked about Mad Magazine, which was something that was big when I was a kid, and I thought, oh, my God, that is, that’s like rosebud, you know, it’s like, he’s, it is, he’s talking about Mad Magazine, which nobody is going to say is a great magazine, but you’re saying it’s fundamental to your consciousness and your sense of publishing. And I’m wondering if you could talk to me a little about the creation of your publishing mind, your notion of a an outsider, humorous, satirical view of the hip people.

 

Graydon Carter  16:31

Well, you know, man magazine, one thing it did least for a kid growing up in in cold, cold Ottawa, was it explained things to you and explain how adult life worked when you if you’re like a 13 year old, say, when i for i started reading when I was about 10, sure and it was instructive and mad and Looney Tunes, cartoons were very much a big part of migrant my youth and my all my friends when I was growing up, whereas the, you know, the Disney cartoons were all sort of wholesome and sort of wonderful and uplifting Looney Tunes, where were more slightly underground and bugs was like the the epitome of the cool character who’s never is unflappable and and in any situation. And so I think you’d find that anybody my age, Mad Magazine was an influence. And then, and then the National Lampoon as it got bigger. And I think it’s you’re fortunate if you come from outside the geographical area where you eventually work. Because I probably I came to New York when I was 28 you grew up in New York, so I saw New York in a completely different way than you did. You took everything for granted, yes, as as did my kids and but for me, everything was new. And I think you outsiders, like me and Lauren, or like you, most editors that did well in New York, they came from like Denver or Missouri and so. And also, we see things the way the native doesn’t. Also, if you grew up in Canada, and I’m sure Lauren would say the same thing, half of your your culture over, you know, TV and everything like that came from the United States, and half came from Britain. So you have a, you’re a sort of a good bridge of those two sensibilities.

 

David Duchovny  18:56

To me, that’s always the double edged sword of editing, or being a powerful magazine editor, is, you know, the embedded nature of it, like you’re reporting, in a way, on the hip people, and you’re kind of skewering them in the in the beginning, but then you, you’re the failure of your success is that you, you’re becoming one as well.

 

Graydon Carter  19:18

That’s intro. That’s a good question. I mean, I mean, the New York when I came in 78 and the city had just come out of bankruptcy, and it would gone into a bit of recession. So by the time we started spy, and it was completely accidental, when we did start it, which was 1986 all of a sudden, this new sort of, you know, life form of investment bankers had been invented, and the city was awash in money in certain areas, not all areas. And so that was a great time to have a magazine that poked fun at the the people who were sort of the the parade floats of that era. And, and there were people like, you know, Leona Helmsley and Donald Trump and all those ladies who lunched at Le Cirque and, and, yeah, it was a really good time to do all that. And they provided ample copy.

 

David Duchovny  20:12

Yeah, what were you skewering exactly? Were you skewering the pretension that money can buy class or taste or substance, or that there was a sense of, there was a real New York underneath this new hedge fund, New York that was, you know, rat infested, but more bohemian and artistic. What? Or is it just like we’ve got, we’ve got a month to put out this magazine, we’ve got to, we’ve got to figure out what to do, you know, find a bit.

 

Graydon Carter  20:40

More of the last part, but also a bit of the the early parts of your question. And no, it was that New York was filthy, rat infested, still. But most important, if you were in your 20s, rents were cheap. They were and that allowed, you know, all these creative people, to be able to afford to come to New York. I mean, the apartment I had, which is about I live in the village. My first apartment is about 300 feet from where I live now, and I paid $200 a month for it.

 

David Duchovny  21:09

Are you comforted by the fact that you have stayed in the same place and live your life at present amongst the ghosts of the past? Because I find that very difficult in New York for me when I go back, because there’s just so much history. For me, I get a kind of a vertigo.

 

Graydon Carter  21:29

Well, it’s funny, because I have, I sort of, I’m giving away most of my suits that I had made at Anderson shepherd in England when I was at Vanity Fair, and I’ve given them to friends of mine and to my sons, and I only kept two suits, both of them basically for weddings, funerals and memorials. At this point, there’s no other reason to wear a suit in New York and these days. And yes, I mean, I, you know, I’m constantly surrounded by the the memories of people who I worked with, or friends and or I worked with and were friends and anyway passed. I mean, this other building I’m in, you know, Maurice Sendak used to live here, Paul Whiteman Max earns, the building that was very much a center of successful Bohemia back in the day.

 

David Duchovny  22:23

And does that? How does that feel, personally to you? To me, there’s a certain stuckness to it, or a certain staying in the past to it that I find I cannot get out of my own head in that way in New York, in a way that you seem to be able to is there to me, being in New York, there is the past is so heavy that there’s a sense of failure about it, because it’s no longer with me. I haven’t been able to continue. Somehow it’s very human. You know, we all have to age and die, and yet, if you’re like me, you feel like you were supposed to not do that?

 

Graydon Carter  23:02

Yeah, no, no, I think that I happen to I don’t live in the past, but I adore the past, and the bigger is big in the books I read, in the movies I watch, especially the last half of the last century.

 

David Duchovny  23:18

I want to go back to you know, you were saying you only have two suits. There’s no reason to wear a suit. But there was always something about you personally that was a style, you know, you had a certain sartorial style. And I also want to make the connection between the outsider, system basher or pretension. Basher editor is somewhat punkish. You know, punk, the not not being a punk, but like rock. And I wonder if it’s possible to think of your creation of spy and then metamorphosizing into Vanity Fair as kind of a punk, kind of a punk movement. And yet the the role of tastemaker is not punk is pre punk is harkens back to a.

 

Graydon Carter  24:06

Pre empire. I mean, yeah, you know, the thing is, even at spy we dressed, I think most of us came to work in jackets and ties, because that was the thing in those days for journalists. And I always felt that you would be taken more seriously if you were a sort of quasi revolutionary dress in a nice suit than you would if you’re wearing a hoodie.

 

David Duchovny  24:32

So you were a quasi revolutionary. You did think you were a quasi people thought of that.

 

Graydon Carter  24:36

Yeah, we were at spy and then, but I happen to love clothes. I’m not interested in fashion, but I love clothing. I mean, I love clothes, yeah.

 

David Duchovny  24:45

And which clothes do you love?

 

Graydon Carter  24:47

Well, I love all my old suits. And as I say, I’m slowly giving them all away to people roughly my my height and.

 

David Duchovny  24:58

How tall are you? I want to ask now, because maybe. And get a suit.

 

Graydon Carter  25:00

Little over six feet. I like that. Keep me an ego. Okay, I’ve got a nice tweed that might look very good.

 

David Duchovny  25:08

See I’m, I have trouble with style. I’ve always had trouble with style. You know, clothes are always some kind of a signal. And I’m wondering if you were aware. Well, you just said you were. You wanted to give the signal of, I’m a serious person. I’m a professional.

 

Graydon Carter  25:26

No, that we were revolutionaries to be taken seriously. We weren’t necessarily that serious. But, yes.

 

David Duchovny  25:33

But I think you were serious. I think, yeah,I think you were serious. And I think you, you know, you instinctually had a target. You had a kind of a, I see a kind of a punk ethos, and that you were saying the system, whether that system is magazines as they’re configured, or magazines as they’re totally configured at the moment, is, is not for me. You know, I’m going to break it up, and I’m going to, you know, if I’m on the outside, I’ve got to crack some things to get on the inside. So there’s going to be.

 

Graydon Carter  26:07

This goes to your notion of failure. I’d had a magazine, this magazine I had in when I was in school in Canada, and it cost me. I was thrown out of a university because I didn’t attend classes enough, because I spent all my time working on this magazine, the magazine at the end of the day after, after it folded, I realized that it it folded because it didn’t really have a point. It wasn’t far left wing, it wasn’t far right wing, it wasn’t, you know, highly intellectual. It wasn’t all that popular. It was, it was just a magazine, and then put up by a lot of people who had never worked on a magazine before, only when spy seemed to do catch on and do really well, then I realized why. It was because it had a point to it, and my first magazine did not have a point. And so everything to be if you want to be noticed, it has to have a point. And I learned that in the magazine, in the restaurant business we had, we opened the Waverly Inn in the West Village about 20 years ago. I mean, it’s 100 100 and some odd years old now, but we’ve had it for the last 20 years. And we also did a restaurant right nearby, like about two blocks away, called the Beatrice Inn. And the ray Berlin has Red Bank cats and white tablecloths and American comfort food and a wonderful mural around it and fireplaces. And the Beatrice inn had green bag cats and white tablecloths and fireplaces, and was very cozy, but it didn’t do as well in the way as the Waverly end, because if people wanted the Waverly and experience, they came to the Waverly Inn. And so the Beatriz, other than being another restaurant, it didn’t have a point. But the Waverly did have a point. The Waverly, and when we took it over, there were very few American food restaurants, comfort food restaurants in the village, most were Italian or Japanese, and very few restaurants with banquets and with white tablecloths. And so the wayward Ian, right from the beginning, had a point to it, and it’s done incredibly well, right? But the other one didn’t well.

 

David Duchovny  28:23

The other one was a replication of the success in a way.

 

Graydon Carter  28:26

And that’s not a good thing.

 

David Duchovny  28:27

No.

 

Graydon Carter  28:28

But that’s like Jaws four.

 

David Duchovny  28:30

But it’s so easy to fall into yes and yeah, and it feels great because, you know, it’s the same amount of money for less work, you know. So, you know, in reading your book, I think you know one of the obvious one, door opens, another door closes. Or the reverse of that is when you were either up or thinking that you might be up for getting editor of New Yorker, becoming editor of the New Yorker, and instead, you ended up becoming the editor of Vanity Fair. So you could have looked at that as a failure, and maybe you did at the time look at that as a failure, that you that maybe you had your No, you didn’t.

 

Graydon Carter  29:10

No, not a failure at all. It was just, it was a it was just a shock to the system, for the simple reason that at spy, we had spent five years making fun of Vanity Fair, its editor, its writers, its host, style of writing so winding it up there was a lot more awkward for me.

 

David Duchovny  29:29

Sure, I get that personally. But what was, what was it about Vanity Fair that you were making fun of? And then what did you change when you got there to get rid of what you had made fun of, or did you become?

 

Graydon Carter  29:42

There was a baroqueness to the writing and that I that didn’t sit well with me. And one reason we wrote it up Vanity Fair was because it become one of the more successful magazine in the country. And so when I got there, the first thing was to change the baroqueness of the writing. And. Right? And some editors pit people against each other, and hopefully that they the strongest, will survive and the week will fall away. I’m not like that. I’m very much a collegial person. I like people to work together, to respect each other’s talents, to respect each other. And so it took about two years, and I got rid of three troublemakers in one week that had been left over from the previous regime, and that sort of changed everything. And because then all of a sudden, people started working together and saying thank you at the end of notes or and respecting each other. And that’s where it was for the next 23 years.

 

David Duchovny  30:43

Very interesting. What you’re talking about, really, is what a lot of people talk about in sports organizations as a culture. You went in to create a culture that was, you know, paradoxically to me, because I often think of, I’m stuck on like this kind of some waspy in the sense of sting, tone that the that the magazine could have, but behind the scenes, what you’re saying is very collegial and very Thank you, oriented. And I’m interested to dig into the fact that an editor is actually because we asked, what does an editor do? I guess an editor creates a culture.

 

Graydon Carter  31:22

That’s an important thing. It’s funny because people used to think spy must have been put up by a group of like misfits. They weren’t misfits at all. They were all very civilized, very collegial. They’ve all done well since spy. I mean, the big biography of Lorne Michaels is written by Susan Morrison, who was our deputy editor at that at spine, is now an editor at the New Yorker. I’ve been blessed, because every single office I’ve worked at has been like that.

 

David Duchovny  31:52

Well, do you well, would you say? I would say you’re the common denominator, though, right?

 

Graydon Carter  31:55

No, but I inherit. I mean, I just walked into time, but it was very collegial.

 

David Duchovny  32:00

So it’s not the Team of Rivals culture, it’s the opposite.

 

Graydon Carter  32:04

It was, in a way, but it was collegial, and I would hire people who I thought would get along with everybody else, and add to the mix in terms of, you know, stories and talents.

 

David Duchovny  32:16

I also know from directing that actors have different things that they respond to. Some respond to a pat on the back and gentle whispering, and some respond to challenge and panic. You know, some like to work in chaos, and some like to work in structure. So I imagine that it wasn’t just as monolithic as what you’re describing, the culture of it, but that you as an editor, knew how to handle your horses.

 

Graydon Carter  32:46

I did, I mean, I was very appreciative of what writers and photographers do. It’s a lot easier being an editor than a writer, and the writer has to at Vanity Fair. They’d go off for sometimes for months at a time, away from their families, try to get the story, try to build the story and tell it in a great narrative arc. And all I had to do was assign it and edit it and tidy it up a bit at the end and sort of merge it with great photography. But writing is really tough, and so I was I came at it. I treated every writer differently, and some needed more hand holding than others, and but it was I, but I loved dealing with them.

 

David Duchovny  33:32

Do you feel like you ever failed with a certain writer or on a certain assignment?

 

Graydon Carter  33:37

All the time, first, I woke up every morning terrified, because during that golden period of magazines, you were at the coalface of competition. And so it just made everybody, you know, better. And like, anytime you assigned a story, you were terrified that another editor would sign the same story to their writer and they’d get it in better and first. So that was it just, it was just constant anxiety in a good way, in a very healthy way.

 

David Duchovny  34:05

Well, I there, you do say at some point in the book that every day you’d go to work, you’d look up on the board and see if you were still listed as the editor of the magazine.

 

Graydon Carter  34:15

But that was the first, those were the first two years, first.

 

David Duchovny  34:18

Okay.

 

Graydon Carter  34:19

One thing, it’s only two years. It was only two years. Only two years. No, the first two years were brutal. But after that I had, I sort of, you know, then I knew I was okay and I could play a long ball. I mean long game. I mean, a number of our stories took two years to come together and so, but no, the first two years were brutal, and that’s when I would check that little notice board outside the in the lobby of the building, just to make sure my name was still on it.

 

David Duchovny  35:14

You saying in the book at the in the Poor Richard’s part at the end levels for life. One is carry a hanky. I don’t have I don’t have a pocket on my shirt, so I can’t do that. There’s your hanky.

 

Graydon Carter  35:30

I’ve never left the house without one. In fact, I feel naked. It’s like going out without I don’t know, like pants, to me.

 

David Duchovny  35:38

You’re not suggesting to wear a hanky like your pants, but you’re saying could cover it.

 

Graydon Carter  35:41

But if you did go up without your pants, but you had a hanky, you can cover the naughty bag.

 

David Duchovny  35:45

Could be like number 21 and your 20 uses for the hanky, I think you had 20, but you say to your kids, you never learn from success, only from failure. Just try to keep the failures small and the success is big, which sounds great how?

 

Graydon Carter  36:02

Well even, like the very first Oscar party we did, I’d, I’d gone to Swifty Lazar, who, Lazar was a, you know, big, famous, or, you know, he’s a, sort of, one of the great, super agents of the period. And he invented the Oscar viewing party, and he invited me to to it one year, and it turned out to be his last one. He died in December, and I, I thought Fannie fair could step in and and do it. I thought, if I’m going to fail, I want to fail before fewer, as few eyes as possible. So we only invited about 120 or 130 people, 100 maybe 150 people, for dinner, and then about 150 or 200 people afterwards, who would come from the Academy Awards and and I did that simply because we could have made it bigger. But I did it simply because I thought, if we fail, I’d rather keep it to like 350 people talking about our failure, rather than 1000 and but we, we succeeded, and then it just grew and grew from there.

 

David Duchovny  37:09

I would love for you to talk about Trump, because, you know, in a way, you spent, well, that was more at spy, where you spent, you know, kind of taking shots at this ridiculous New York, New York City Real Estate Developer, but in some ways, you know, the the lore has it now that he was kind of humiliated into running for president as a you know, to get you, to get you all back, to get us all back for embarrassing him. But I’m wondering, if you ever think back on, you know, the DNA that you kind of created, I say with Lauren and Letterman, you know, back then. And I’m not saying in any kind of responsibility, but I’m just wondering,

 

Graydon Carter  37:57

I do not take response.

 

David Duchovny  37:58

No, and I’m not saying you should.

 

Graydon Carter  38:00

The Trump was it would be impossible for magazines like spy or comedians or columnists not to have written about Trump in anything other than a derisory way. It he, he was, he was ripe for ridicule because he was a narcissist and and narcissists are, are, are fascinating subjects to write about because they can’t get enough of themselves.

 

David Duchovny  38:27

Well, it’s true, but I think also that what, when I contemplate Trump, and, you know, I do, he does take up more space in my brain than I can’t

 

Graydon Carter  38:38

Got to see somebody for that.

 

David Duchovny  38:40

Um, there was some sense in in spy and in in Vanity Fair of I’m going to shame this person slightly or whatever, because they deserve it. You know, I’m going to puncture that balloon. And shame is this kind of a tool or a cultural phenomenon that brings people down to size would bring a narcissist down to size, and yet, that’s what I see running out of control on the internet, is everybody is shaming one another, aside from virtue signaling, you know, you have these two extremes where I signal virtue and I shame you, and Trump is just this guy who is impossible to shame.

 

Graydon Carter  39:29

I don’t recognize this Donald Trump in a way. I knew he could be vengeful, but not on this epic level of vengeance. Where that, you know, I mean, the destruction to the US government is so breathtaking into, you know, the weather service and at the time of crime, climate crisis, so and FAA, so just, they’re just making flying, which was a nerve wracking part of our lives. Anyway. Much less safe then you started dismantling the teams that handle our nuclear warheads, the intelligence communities, our relationships with our neighbors, and speaking as a Canadian, I’ve never been prouder to be a Canadian. I always have you too.

 

David Duchovny  40:17

I handle it well. I’ll be asking you for recommendation very soon.

 

Graydon Carter  40:22

Restaurants in Toronto?

 

David Duchovny  40:23

No, just on my on my passport. I’m going to try, and I’m going to try and become a Canadian. But I think the thing with Trump is, like, he’s a narcissist, but he’s also a nihilist and, and, to quote, Game of Thrones, Chaos is a ladder. This is a guy, you know, he’s just creating chaos. He’s just destroying things. He’s not creating anything. And, and as long as chaos exists.

 

Graydon Carter  40:44

He had three casinos. Oh, I know he had three business where people go there intentionally to lose money almost, and he get and they went bankrupt.

 

David Duchovny  40:52

Right? He’s the biggest loser of all time. And yet, there he is. But I know, I got to let you go in five minutes. So I just wanted to, just to touch on, you’re not just, you’re not done. You still got air mail and which, which is kind of a multimedia enterprise as well.

 

Graydon Carter  41:12

It’s like Vanity Fair, but a weekly digital Vanity Fair in a certain way.

 

David Duchovny  41:16

But let’s say, what was the point of, of Air Mail, if, if it needs to have a point, as you said.

 

Graydon Carter  41:25

Well, I thought I could. I thought I’d read the a lot of foreign papers I was living in France. I thought I reading all these stories that I know are not in the New York Times or the Wall Street Journal or the New York Post. And I thought I could pull something together that I think could be entertaining for my friends and but I wanted it to look beautiful, and I wanted to have I didn’t want programmatic ads, and I wanted to have the sort of advertising we had at Vanity Fair, like our mans and Dior and Ralph Lauren. I think it’s the most beautiful digital anything on on the internet, and because it was made by magazine people.

 

David Duchovny  42:02

So it was a it was an object of beauty, in a way, and yet it’s not really an object, because it does, it not exist in hard copy at all.

 

Graydon Carter  42:10

No, it’s just digital everything. I mean, you know, it’s funny, if the internet was at this stage when we started spy magazine, I doubt very much if we would have had a printed magazine. I think we would have done it digitally. And because there’s a million probably with magazines, you gotta there’s color correction, there’s going to the printer, there’s binding the magazine, there’s boxing the magazine, shipping the magazine to wholesalers. They sell it. They give it to retailers. The retailers have to open the box, put them on the newsstand, and then they sell, send all the covers of all the copies they didn’t sell back to you. It’s a process that could take months, and you’re not getting paid during that entire period.

 

David Duchovny  42:50

Absolutely and what strikes me about the transition from Vanity Fair, which was a beautiful looking magazine, and yet, and this is in contrast to your to your memoir, there’s something disposable about a magazine.

 

Graydon Carter  43:08

Well, they date. I mean, unless, unless they’re National Geographics, like when we were growing up, magazines date as physical thing.

 

David Duchovny  43:18

Did that ever was that ever a struggle within you as a human being on this planet was that ever sense of, oh, this is why I want to write a memoir. Because, in a way, this, you know, everything dates eventually, but this will date not quite as quickly as the June edition of Vanity Fair, you know.

 

Graydon Carter  43:43

The books don’t really date. And I it’s funny, because I very consciously did, I there’s no index in the book.

 

David Duchovny  43:51

I learned I wanted to call you out on that, because, you know, it was such a, it’s such a power move, I have to say, because everybody in Hollywood is, you know, Streisand did the same thing, right? There was no index, so you actually have to read the goddamn.

 

Graydon Carter  44:06

Andy Warhol did the same thing, but there’s no index and there’s no photographs. And I had this wonderful artist, Eric Hansen, do drawings to open each chapter, because I remember when I was growing up reading books with just drawings and to launch a chapter.

 

David Duchovny  44:23

And I agree with you, because when I started to write novels, I really had a sense of, well, yeah, this may date in certain aspects, but it’s also the fullest expression, in a way, of my experience as a human being on this planet in this time, right? And it is there for my kids. And in fact, like you and I, was moved by the fact that you said you wrote this memoir for your kids, in a way, not just because you don’t want to bore them anymore by telling the stories, but it’s really like, yes, you could poke the DNA of vanity, fair and spy and make it into a kind of soup, and that would taste. A little like Graydon Carter, but this is more like, This is who your father was, is, and beyond that to people who are not your children. This is, this is more who I am, what I saw, what was important.

 

Graydon Carter  45:15

And also a portrait of an era, both in New York and America. You know, when my wife and I watch, we watch Frazier most nights before we go to bed, because it was a night a non alcoholic night cap, and I reasonably much Frasier is because, you know, it was the time before social media, before the internet, the World Trade Center towers were still standing. And so it’s just a, I think I was fortunate enough to wind up in New York at a really good time the late 1970s so I saw the grit, and I saw that, you know, the glory, and then, you know, after this, the turn of this century, everything else.

 

David Duchovny  45:57

I understand that I often watch Star Trek reruns before bed, and it’s the same the original and and I felt very guilty about it for a while. And then I read an article because I thought, you know, what are you doing? And then I and then.

 

Graydon Carter  46:13

It settles the if it settles the nerves, it’s a good thing.

 

David Duchovny  46:17

And then I read this article about, you know, because they say you’re not supposed to watch television in bed or before bed, because it could be, you know, exciting in a way that would make it hard to sleep, but, but this, whoever was writing the article, said it’s actually good to watch things that you’ve seen before, because there’s no surprises. There’s nothing

 

Graydon Carter  46:37

That’s going to scare you, right? But it works for it works for us.

 

David Duchovny  46:40

I would end just by asking because, because what you said just a moment ago made me think of this, because we were talking about air mail. And you know the sense in which, you know I’m not done yet. I’m not done yet. I’m going to make this new thing. And there’s a point. Here’s the point. It’s not, it’s not just because I did Vanity Fair, and here’s this iteration of it again. No, it’s a new thing. It’s different. Is one of the points of air mail or of your work now, do you have anything to say to the present, or is it more an exercise in finding the audience of people like me or like you who want to kind of revel in the tone that they grew up in.

 

Graydon Carter  47:28

I mean, it’s a celebration. I mean, you’re we’re only here once, and to spend your life with a hair shirt on is probably not the best way to get the most out of life. And for most of us, you know, we go to a a restaurant in the evening, which is like, one of the life’s great miracles. People ask you, what you want. They bring it to you. They stir up afterwards. I think restaurants are simply amazing. Like, there’s so many good things in life, of like traveling in Europe, or, you know, swimming in the lake. And this is not about I just wanted, didn’t want something that was constant depressive politics, because politics is depressing nowadays, and there’s just got much more depressing over the last two and a half months.

 

David Duchovny  48:11

Well, I think what you say is very, I’d like to highlight that for a moment, because I what it makes me think is you spoke of a hair shirt. And I think we’re, we’ve kind of entered into a sense and culture where you’re not allowed to enjoy yourself in a way, yes, 100% at the office, especially. And I think that that’s a dangerous thing. And I think what you’re saying is profound, and that we are here, you know, and this is in no way saying that everybody has the same shot. You know, I’m not saying you and I aren’t privileged, or there isn’t such a thing as privilege, but there is such a thing as enjoyment, and that that it is, there’s a value in in seeking enjoyment. That’s not just a hedonistic value.

 

Graydon Carter  48:57

I agree. I mean, I mean life is life is Grab life now. Well, it’s good to just imagine if you were in Gaza, you know, five years ago, you’re, you know, looking out on the sea and and that’s gone now. So it take advantage of everything you can right now, because nothing is permanent yeah.

 

David Duchovny  49:17

Because I think what we’ve gotten away from in the last five or 10 years is any sense that that enjoyment is a good, you know, or something not to be ashamed of.

 

Graydon Carter  49:29

Especially nine to five, whether it’s work, work during the day, I do find most people take enjoyment in their evening, where their evening lives, and I just think they should spread that more to what they do during the day. I wake up every morning, and I think I’m so blessed at my and I feel very fortunate and that I figure out what the day is going to be like. And I think I’m living in New York City, in Greenwich Village, doing something I love, and with a wonderful family, and I. I think I’m really fortunate to have all that, and I’m not going to, I don’t depress easily. I worry all the time, but I don’t depress easily.

 

David Duchovny  50:09

Well, that’s a trick, right there. I’d like to learn that maybe.

 

Graydon Carter  50:13

Yeah, alcohol at the end of the day help.

 

David Duchovny  50:18

I was, I’m thinking, it’s constitutional, but there’s, there’s resilience in there, you know? It gets back. We can end with this. It can it gets back to how one deals with failure, or how worry is really just the contemplation of future failure really isn’t 100% so how, you know, and you raise kids, I raise kids, they’re very different constitutionally, but my son was a worrier about future failure, and we realized at one point, his mother and I that it’s a way of inoculating yourself against failure when it does happen. So because, because failure is coming for all of us, like.

 

Graydon Carter  50:53

Building up muscles.

 

David Duchovny  50:54

It is. It’s like you’re playing out the scenario, and you’re trying to see if you’re going to survive. Because that’s, that’s all of our fear is that this failure is the one that’s going to the herd is going to reject me. They’ve seen my true colors. I don’t belong here. I’m going to have to die on the savannah.

 

Graydon Carter  51:12

By and large. I like when somebody, somebody has something written about them in page six. I say, Listen, just let it and it’s, it’s not that flattering to them. I say how many years you’ve been reading pay stitch, and they’ll say 25 years. I said, Tell me one item about somebody else that you remember, and nobody can, because it just unless there’s, unless there’s 50 articles that say you have web feet and you walk funny, then maybe people start looking at your feet when they meet you and seeing if you walk funny. But if it’s one story in the in Page Six that says you have web feed and walk funny, nobody’s going to remember it.

 

David Duchovny  51:48

Well, that’s that’s one of my beefs with the internet, is that that things linger a lot longer then.

 

Graydon Carter  51:54

You got to do you got to Google the person’s name, and you got to Google their name and they put web feed and walk funny exactly. You got to know that they have web feed and blog funny, but the chances are you don’t, because you don’t remember that item from 15 years ago.

 

David Duchovny  52:07

Okay, I’ll buy that. Thank you, Graydon, for taking the time. It’s been a pleasure to get to know you a little bit and.

 

Graydon Carter  52:14

David, thank you so much. I’ll see you at the Waverly Inn. maybe.

 

David Duchovny  52:30

What a sparky talk with Graydon Carter. Time flew by. Really enjoyed that, and we got to it at the end. I’m not sure if it’s in the podcast itself, but I’ve had kind of a bit of a as I said, with great rancor, a bee in my bonnet, about the fact that air mail had never reviewed one of my novels, and great informed me that air mail does not review fiction. So there you have it. I’ve been harboring this kind of, you know, just little bubbling resentment against air mail because I’ve seen how they’ve reviewed Memoirs of actors. And they must be memoirs at this point, because I I’ve seen how they reviewed actors writing them like, why are they not addressing me? So there you go. Knowledge is power. Knowledge is forgiveness. I’m an idiot.

 

CREDITS 53:39

Thanks so much for listening to Fail Better if you haven’t yet, now is a great time to subscribe to Lemonada Premium. You’ll get bonus content, like my thoughts on conversations with guests including Alec Baldwin and Rob Lowe. Just hit the subscribe button on Apple podcasts or for all other podcast apps, head to lemonadapremium.com to subscribe. That’s lemonadapremium.com.  Fail Better is a production of Lemonada Media in coordination with King Baby.  It is produced by Kegan Zema, Aria Bracci, and Dani Matias. Our engineer is Brian Castillo.  Our SVP of weekly is Steve Nelson. Our VP of new content is Rachel Neel.  Special thanks to Carl Ackerman, Tom Karpinski and Brad Davidson, the show’s executive produced by Stephanie Wittels Wachs, Jessica Cordova Kramer and me, David Duchovny.  The music is also by me and my band. Lovely Colin Lee. Pat McCusker, Mitch Stewart, Davis Rowan and Sebastian […].  You can find us online at @LemonadaMedia and you can find me @DavidDuchovny.  Follow Fail Better wherever you get your podcasts or listen ad free on Amazon music with your Prime membership.