The Bill Simmons Podcast - Graydon Carter on Leaving Vanity Fair, Creating Spy Magazine, and Picking on Donald Trump (Ep. 275)

Episode Date: October 20, 2017

HBO and The Ringer's Bill Simmons is joined by former longtime Vanity Fair editor Graydon Carter to discuss working in a world of satire (6:00), the creation of Spy Magazine (11:00), Trump's threats against Spy Magazine (20:00), the prosperity of the '90s (30:00), the tabloid decade of the 2000s (38:00), Los Angeles as the top American city (52:00), the Vanity Fair Oscars party (1:04:00), and the "grass is always greener" mentality in society (1:12:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Spontaneous trades. Get in on these killer last minute deals. Download the Hotel Tonight app right now. All right, Graeme Carter, in the office studio. Been waiting to do this for a long time. You're a busy man. Not anymore. Yeah, when do you stop being busy? Well, you know, I'm retiring. No, I'm not retiring.

I'm stepping down from Vanity Fair at the end of the year. And yeah, after 25 years there, it seems about time. I was still shocked. Why? I don't know. I just, it was like a Lorne Michaels thing. We Canadians hold our jobs a long time. You assume at some point it's going to happen,

but you don't know it's actually going to happen. And it's like, yeah, great, it's stepping down. It's like, what? No, I thought, you know, I haven't had a break in 39 years, so we're moving to Provence for six months. We've rented a house, put our youngest daughter in school there. Some time to think, and I'm on a listing tour until the end of the year, trying to figure out what I'm going to do.

I have a million ideas. I've just got to winnow them down. So you've had one of my favorite careers. Oh, thanks. We've never done a podcast, but we've talked. I've never done a podcast. You've never done a podcast? Oh, wow.

It'll be a collector's item. I'll be gentle. Yeah. But I've told you this, but I'm going to say it again for the listeners. So you create Spy Magazine in the mid-80s with Kurt Anderson. Right. Which is one of my five favorite magazines of all time and came at a point. What are the other four?

Inside Sports. Okay. Sports Illustrated. Yeah. Early, not recent Sports Illustrated. Okay, yeah, yeah. Rolling Stone. Okay. Sports Illustrated. Yeah. Early, not recent Sports Illustrated. Okay, yeah, yeah. Rolling Stone. Right.

And. That's enough. That's good comedy. Probably Vanity Fair. Wow. Because I just, I always look at it from the standpoint of, I never really want to subscribe to magazines. I don't like it.

And then the mail, even when I was a kid, unless it was it was something i loved it's just clutter and then you feel obligated to read it right and there hit a point with magazines business on that yeah i know well there hit a point with magazines where i just didn't want to get them anymore and the only ones i really look forward to were sports illustrated until the early 2000s and vanity fair and new york magazine's another one that I do like but Vanity Fair I was always like I know there's going to be

two things that I love that I'm going to really enjoy I know I'm going to get 15 to 30 really good minutes

out of this magazine which I think is how all magazines Premiere Magazine used to be like that for me in the 90s it was really good yeah

Entertainment Weekly was like that for a while for me where it's like I'm getting this magazine Us Weekly in the mid 2000s okay I'm good, yeah. Entertainment Weekly was like that for a while. Right. It was like, I'm getting this magazine, Us Weekly, in the mid-2000s.

Okay. I'm going to get 20 minutes out of it. You almost know in your head how many minutes you need. That's almost before the Kardashians, right? Yeah. Wow, it's the Instagram

and social media really Us Weekly. Yeah, yeah, yeah. The celebrities became too available. Exactly. So anyway, Spy, which sometimes

what happens with these things is after they kind of have peaked or they've gone away then everybody exalts it and it'd be there's this mythology that it definitely happened with grantland i was like where were these people the first two years where were all of you as we were getting shit on um but with spy it was like in the moment. People were like, holy shit. Yeah, it was different. And I think one of the things that really stands out, just thinking back why it worked, what were the things that made people go, holy shit,

was celebrities just were not self-aware yet. And you guys flipped it. That's a good point, yeah. You know what I mean? The 70s, 80s, it was celebrities just behaving poorly, but nobody calling them out on it. We sort of redefined in New York what a celebrity was. We went after, wrote about the editor of the New York Times and the wife of the editor of the New York Times and socialites on Fifth Avenue. Trump.

And a lot of Donald Trump. Yeah. And you were the anti-establishment for a long time. Yes, in fact, we spent five years making fun of Vanity Fair. So coming to Vanity Fair, I was not welcome with open arms. I was going to ask you. So you go from anti-establishment to you're the establishment. Yeah, yeah.

But did it happen overnight? Or did you look at yourself and go, holy shit, what happened to me? It was a transition. First of all, I was really happy to get a larger salary. I had four kids by that time. And they're all in schools, very expensive schools in New York. So getting my salary went up by about 400% when I came to Vanity Fair. It's always a bonus.

That was huge. And so, but they, you know, the staff didn't, they didn't trust me at first because they thought we were either too mean at Spy or especially too mean about some of the people at Vanity Fair. But it took, after two years, they realized that I kept saying,

Kurt did the mean stuff, I did the funny stuff at spy he was saying the same thing right when he was transitioning to new york magazine so but after two years it all worked out and i've been happy for the last 23 it turns out you weren't that mean because then the internet came along and then we found out what real meanness was that's absolutely true yeah we were really soft when you look at it. Yeah. I think some of the stuff you did back then is just gone. Like, you'd write about, like, Trump, but you would describe him with, like, two or three just devastating adjectives. Yeah, we were good on epithets.

Like, you know, we'd call him a short-fingered Bulgarian. Right. But you had hundreds of those. We had a lot. Just little daggers. Tinyian. Right. But you had hundreds of those. We had a lot. Just little daggers. Tiny ones. A little factory that just manufactured these.

And there's a woman who was the wife of the editor of the New York Times. We called her a bosomy, dirty book writer. And these things just sort of stuck with people. It was great. I remember, especially like I was in college during the, I think, most of the heyday. Boy, you make me feel old. Yeah, go ahead. Yeah. Well, I remember like in, you know, I think, most of the heyday. Boy, you make me feel old. Yeah, go ahead. Yeah.

Well, I remember, like, in, you know, it's July. It's the summer. I have a lot going on. And it would be like, ah, it's been about a month since the last one. It started going in the mailbox. Like, is it going to be in there? People used to wait in line at newsstands because they would run out. Yeah.

Some of the stuff that was in there seems basic now, but it seems basic because you guys started it. Well, it was all pre-internet yeah so that made a big difference you know we did this thing where we sent checks for 32 cents to about 50 unbelievable really wealthy new yorkers they were millionaires at the time they weren't billionaires and then the ones who cashed the 320.32 check, we wanted to see if they would, if the ones who cashed the $0.32 check, we decided to send them a $0.16 check to see if they would cash that. And the ones who didn't cash the $0.32 check, we sent a $0.64 check, thinking that that may encourage them to take the time to write, do their signature,

and write for a deposit only on the back of the check and put it in the pile that goes to the bank. And this took a long time to do. It took you because you've got to wait for the check to come back, then you've got to remail new checks out. And we made up a name for some company like the National Clearinghouse or something. Right. It was written on the check.

And at the end of the day, just two people cashed 16-cent checks, and one was Adnan kashoggi then a very sort of notorious arms dealer and one was trump incredible you could say it was admirable that he cashed a he was cautious enough about his money that he cashed a 16 cent check 16 cents money rubbing yeah he was free money for it didn't matter how little it was i think he needed it at the time what was the other thing you did with when you would call the restaurants making fake reservations wasn't that no it was something like that we had a thing that basically um how how long it took for somebody to get back that's a measure of your your value to society and at times sebastian stallone like mike obitz would call call back the

number like two seconds because stallone was you know huge and you know joey bishop we just we did it and it wound up like 260 days and counting like it's just nobody had returned his phone call but yeah we're just like we're like mean Republicans used to call that sort of humor juvenile we just thought it was funny I thought it was hilarious you really flipped it on Hollywood too with the like Walter Monheit

one of my all time favorites the fake movie critic a 70 year old messenger that we used he was from Eastern Europe and he used to love going to nightclubs he was and uh anyway we needed we sort of put a monocle in his eye and his and took his photograph and and called him our messenger slash movie critic because they're movie critics like peter travers is still working today we just loved every movie he ever saw because

he loved seeing his name on the on the Thursdays and Fridays in the New York Times. Blurb specialist. So we didn't even get invitations to the screenings. We just based it on literature the studio issued and wrote our own little. David Camp, who was a writer at Spy and is a writer at Vanity Fair, he used to write the Walter Monheit reviews. And they were terribly corny. And yeah, but Walter was... Tommy, you know about this?

They used to be like, and here's another person that's coming, Oscar. You know, like all this stupid... Yeah, I know. It was a movie about a dog. And Oscar's going woof, woof over Benji. We used to laugh in college. We would just read all of them and laugh our asses

off that one worked and then um the log rolling in our time was another one again pre-internet and this guy howard caplan would spend days at the shakespeare and company and the old barnes and noble up in the upper west side looking for one critic who had given a blurb on the back of one book and then checking that author's books out and see if he'd written a book for for them and there was a ton of log rolling is just basically you scratch my back i'll scratch yours and it it still happens today yeah pre-internet this was tough work the other one occasionally you would do pictures would be like man at his best and it'll be pictures of guys from all different ages who just it looked like their cock might have been

or white guys dancing and susan morrison is now the deputy head of the new yorker used to do all of that that was great said she spent hours and hours like looking through pictures just to find the most embarrassing photographs of prominent New Yorkers. Separated Birth was another one that seems so obvious now. But at the time, I was like, oh, my God, yeah. I've always thought. Well, funny enough, I was going through the archives of Vanity Fair. And Vanity Fair did a version of that in the 1920s.

Wow. Yeah. And we had started because we were sitting at the bar at the algonquin at the blue bar the algonquin and there was a waiter uh who looked exactly like the shah of iran we thought oh my god let's just do this of like two people who look like each other we and this is we didn't have a big photo budget but it was amazing how how good some of these match-ups were yeah the spy list was another one that i would study and try to figure out. You just put like eight names together and I'd have to figure out what the

connection was. Well, it was a good way of not getting sued too. You know, um, it was like people who had reputations for really strange things, either enormous penises or they were coprophiliacs or something. But I felt it was,

it was libel proof because in order to sue us over that list, you'd be saying these other people had the same thing going on as well. Nobody would sue over the fact you were on a list of men with enormous penises. Or it could be like, I mean, I'm sure you had one week it was all people who had cocaine problems. Probably. I mean, that would be everybody in New York at the time. Especially in the mid-80s, yeah. The phone book.

Yeah, did you ever do a spy list where it was just, there actually wasn't any rhyme or reason to name names? No, no. It always had a reason? I go back, I look at it, if I'm looking through an old issue and I see a list, I have no idea why those names are together now. That's hilarious. You just forget.

I mean, even if I look back two months later, I wouldn't know. And then you guys did the spy list, i mean the uh like the top 100 spy 100 yeah 100 and uh which at a time when lists weren't really a big thing now it's like the internet is just filled with lists yeah this is yeah and i think the um chris elliott was on the first cover and we had we had a list of the 10 most annoying. Chris was just pretending to be annoying. But we started off with a list, the 10 most annoying New Yorkers, and Trump was on that.

Yeah. Trump was a target. Yeah. How much? Because drugs, especially cocaine, was so big, late 70s through the 80s, basically. Not at the spy offices but how much of it like in coverage and stuff did you um it sort of was because it was so prevalent it wasn't

that big of a thing and since we weren't we weren't part of the drug culture a we couldn't afford it b right you know some of us had young families and uh see that that you couldn't put out a magazine like that on with any kind of drugs how much so the first year you're doing spy how many people are working for you and how much did it cost how much did it cost to do an issue well i don't we i remember that the food budget of one annie leibowitz photo shoot when i got to vanity fair the the catering budget was equivalent to what we put an entire issue of Spy Off. Oh my god.

One issue, there was one issue that Kurt and I basically wrote the whole thing ourselves under various pseudonyms. Oh, I remember that from the book. So we had four or five major adults and then about 25

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Right now, my listeners can post jobs on ZipRecruiter for free. Go to ZipRecruiter.com slash BS. That is ZipRecruiter.com slash BS. We should put the fall internships on there. I never paid you for basically ripping off Spy Magazine in college. My freshman year in college, I did a dorm newsletter that was just all these different articles I wrote about everybody on our floor. And it was basically, I was just trying to be Spy Magazine.

I'm sure you had a million people trying to do that. The Statue of Limitations is still fun now. Yeah, I might mail you a commemorative copy. Yeah, I'd love it. It was called The Velvet Edge because the second week I was in college, everybody was watching some porn movie in somebody's room called The Velvet Edge. And our RA was in there, and some girl saw him in there and ratted him out and he got kicked off campus.

Okay, yeah, yeah. So The Velvet Edge became the obvious name for my version of Spy Magazine. Yeah, I like it, yeah. It's a pretty good name. I think it's a great name. But how did you get started, though, like what was your what was your job before spy i was at time magazine and like a like a fledgling writer fledgling writer time and um it was an amazing time and being at time in those days because you had um kurt was there jim kelly who later became the

editor of time was there rick stengler who later became the editor of Time, was there. Rick Stengler, who later became the editor of Time, then worked in the State Department, was there. Walter Isaacson, the writer, was there. He became the editor of Time. Michiko Kakutani, the chief book critic for the New York Times, was there. Maureen Dowd was there. Frank Rich was there. Frank Rich? Yeah, it was amazing.

And so, and we're all still friends. Yeah. And then you go. So then I'm at Time. And then I went to Life magazine. And then Kurt and I would have lunch. And we'd talk about this magazine. How did you know Kurt?

From Time. Okay. And we're godfathers to each other's children. And so then in 1985, we started really talking seriously about that. And we brought in a partner, Tom Phillips, who had worked at Rothschild Bank and at Goldman Sachs. And he helped us put together a business plan. What was the one-sentence pitch? It was a satirical monthly about the characters who made up New York.

And New York was filled with many more characters than it is now. It's now filled with bankers and lawyers. I mean, it's like Geneva with dirt right now. And a lot of them were acting, it's hard to believe this, but behaving much more badly than... Yeah, this was pre-internet, and they were showing off their money and showing off themselves in a way that made it very entertaining for a journalist. Like Gordon Gekko from Wall Street.

He's kind of heroic in that movie but he's actually a horrible person. It wasn't intended as heroic. Like Michael Douglas wins the Oscars. I kind of like this Gordon Gekko. He became a role model for Wall Street bankers. But people like Leona Helmsley who was a big

real estate force in the city at the time most of them are all but trump are pretty much gone did you feel like you ride this magazine for three to four years and it takes you somewhere better no what was your strategy actually we thought we're burning every bridge we could possibly imagine that's how i felt reading oh yeah no no and we thought we're burning every bridge we could possibly imagine that's how i felt reading oh yeah no no and we thought we'll just do this forever and uh without really thinking that that um there's basically no future for a standalone magazine in this world most magazines are part of larger companies we were so stupid we didn't know that you could go to a fashion company and borrow clothes for a photo shoot.

So we would like, when we had, I remember having Milton Berle on, we had to go shopping for clothes for Milton Berle. We had to buy them at the men's warehouse to find a suit that would fit him. Big underwear too for Milton. Huge

cock on Milton Berle. He was on that list, yes. Him and Secretariat. Man at his best. And so anyway, there were so many things we just didn't know. So you needed a COO, basically. We needed somebody who knew more about that aspect of the world than we did. We knew about our world that we were students of. That is, say, adult new york and then

california and it um and we used to just drive some of these people crazy because we'd we'd fact check things as much as we could but we didn't ask for comments so people would just the stories on them would just be in the magazine without any warning whatsoever. They have no idea. And Mike Ovitz would have conniptions. And he was the most powerful agent in Hollywood at the time he ran CAA. And he hired a private detective to try to find out who this person Celia Brady was. Who was not a real person. It was a pseudonym.

It was actually a man who was Celia Brady. Possibly. Yeah. Okay. And Celia tried to, at one point, we assigned a reporter and a friend of theirs. They worked on this for an entire year to do the CAA client list. CAA at that time represented everybody, but nobody had, even the partners there had, except for one, had seen the entire list of all their clients and they had everybody. So we worked for a year on this and ran it over,

I guess, a page or a page and a half. It was everybody you could imagine. It was big at the time. And they had to shut the agency down for about 10 days just to call the shock of the client seeing all the other people in their little category. Like if you represent both Al Pacino and Dustin Hoffman, Dustin Hoffman's realizing Al Pacino's getting these parts, he's not getting them, vice versa. So they had a lot of hand-holding for about 10 days after that list was published. You caused some chaos. Yeah, that was great.

Who was the maddest that you'd think? Ovitz is in the top five. Trump, I would guess. Trump, yeah. Trump would threaten a lot. Although, when I got to Vanity Fair, he invited me to his wedding, so he realized that he better...

Which wedding? Both. I was invited to both the Marla Maples wedding and the Melania Trump wedding. Well, because you took that... You had that one cover of Ivanka where it was just the all-time close-up of her face. That was really mean. Her face is... That was probably the meanest thing you did.

It was really... And she went and had everything redone after that. Oh, no. Everything. The silicone was on your hands. No. So she, I just lost my voice crack. No, she went on and did that.

And Vogue magazine did a photograph, a whole photo shoot of her sort of redone Bridget Bardot style. She had everything fixed. It peaked, I'm'm gonna say you had like a four-year apex five five-year apex yeah it ran for nine years we did when we did our history we call it spy the funny years and it was mostly the first five years what so tell the story of what happened that compromised the funniness no nothing happened we laughed you laughed we sold the magazine to charles sachi the advertising british advertising king and johnny pagazzi who was the heir to the simca car fortune they bought it and they wanted to turn it into vanity fair and i wanted to actually at that time

i want then i wanted to start up a twice a week newspaper in new york and so i was on a listing tour for that and um the fellow who owned the new york observer said look why don't you learn on the job i'm coming to edit this for me so i left and then kurt left and ran for another four years but why'd you leave because you know if you own something for five years and run it completely the way you see fit then all of a sudden you're working for somebody else it's just a different a change and i didn't want to work for did you have to sell or you just felt like it was the time we ran out of money okay yeah we did ran out of money like the magazine lost money it was too successful this is going to sound strange we had planned we had we haded, we raised the money and budgeted for a magazine that would have a circulation of 25,000 copies.

Because the magazine business is really rough. You spend all the money paying the writers and photographers. You print those magazines. You send them out to newsstands. And you don't get a check back from the ones you've sold for 90 days. So we planned to just do it in what used to be called platforming in the movies, where they'd open in a couple of theaters in New York and a couple of theaters in Los Angeles, and then spread as the reviews came in.

So we had budgeted for 25,000 copies on the newsstand or circulation in total. And within the third issue, we were getting requests from San Francisco and Los Angeles and London. And so we were printing 150,000 copies and waiting for all those sales to come back in, and it just became really difficult. Subscriptions couldn't help you? We had a lot of subscriptions. I know I subscribed. Yeah, we had a lot of you had i know i subscribed yeah we had a lot of subscribers but it uh you know that was a really um there was a lot of detail that went

into that magazine what would you do differently if you did it over again i would um i'd probably align with a larger company possibly from the get-go i'd also do you know this is a horrible thing i do fashion shoots because they're the people who advertise interesting and we weren't going to get ads from us steel or general tire but we could have if we had played our cards better gotten ads from you know ralph lauren and i think it would have been hard to juggle it would be in the all-time outsider but then also yeah i don't know how you do it it was impossible it was difficult because you know i think in that glass though oh it's amazing oh my god we had so much fun i think of that era and it's just letterman and it's like seinfeld and all those comedians coming

up and it's you guys and it's just comedy just shifted it was that johnny carson era of comedy that's true yeah all of a sudden gave way Letterman, the age of irony the age of being ironic about irony and then it just kind of and by the end of the decade we were in a totally different place and it was the place I wanted to be yeah, no it's funny looking back at the 80s it does look like

a real moment in time even movies look so different now all the men in their dockers or you know ralph laurencino's and a lot of people ties big ugly ties but wearing ties even you look at the comedies from back then and what was the movement that was going on didn't really transfer into the comedies the movie comedies until the next decade it It was almost like it took five years extra. We had like Franz and Seinfeld on NBC on Thursday night. Right, that was the 90s though. Cheers.

Yeah. Cheers was the 80s, wasn't it? Cheers was 80, but Cheers was old school. It was like the last great old school awesome sitcom. Yeah, it's still, you can watch Cheers now and it's still good. Yeah, yeah. It wasn't even a sitcom. It was like just a funny show.

Same thing with Fraser. It's beautifully written. Yeah. So when did you end up at Vanity Fair? I forget. 1992. But not running it, right? Yeah, I'm running it, yeah.

Oh, yeah, you're right. That's 25 years. Yeah, yeah. So you immediately got the job running it. Yeah. I was hired by Cy. He hired me, actually, to be the editor of The New Yorker. And I went home every night and canceled everything and planned what I would do for the first six months and came with a six

month, 12 month, 18 month plan. And then the day was supposed to be announced. I was told that it was going to be Vanity Fair. And I had no plan. And I didn't know enough that if I'd said, I need three months or a couple of months to figure out what I'm going to do, I wasn't sure whether they'd pay me for those two months or not. And I needed a paycheck. So I started right away.

You had 13 kids at that point. I had 13 kids at that point. Nurser schools and preschools. Yeah. So actually, yeah, my tuition bills were almost as much as my salary. kids at that point 13 kids at that nursery schools and preschools yeah yeah so i actually yeah my tuition bills were almost as much as my salary but what was vanity fair in 1992 what did you walk into it was a you know successful magazine had not made money but it was a successful magazine and it uh it was very emblematic of the 1980s. So that was the first thing.

And the 90s hadn't really defined themselves. So you're both trying to figure out your own vision and what time you're in. Decades don't really define themselves until you're probably halfway through them. So the 90s, as it turned out, the 90s were a curious, peaceful, prosperous decade. Yeah.

With a very decent president. Decent meaning competent. Right. And the Internet economy is starting to take off. That helps. Yeah. Russia has completely fallen apart and hasn't tried to rebuild itself. No, we were on top of the world

and then America and Britain were two great powerhouses so it took a while but then when I settled in Cy offered me the New Yorker again in 1999 and I was just turning 50

and all I could think of was getting this I'd ordered a sob convertible five five speed so i bet it broke down a bunch of times no no i and i was just i wanted to be delivered on friday so i could take it over the country i was so looking forward to it and then si offered me the job on the thursday and i realized after thinking about it for 24 hours that i was much more interested in getting this sob convertible than i was in changing jobs yeah so that was i loved my sob convertible by the way and you loved your job and i love my job so yeah one of the things i think when people think about the rain you had there is you just went after great writers and you paid them properly yeah did they

do that before you showed up or was that yeah no you brought to the table? Yeah, no, that was, I mean, Connie Nass was then starting to really assert itself. And most of the other magazine companies, like Time, Inc., most of the writers were house writers. You're paid a salary, you're a salaried employee. But I, you know, I immediately went after the first two people I called were Christopher Hitchens and Brian Burrell. And Brian then was the king of sort of business narrative journalism and he still is one of them and and and wanted Christopher then I Frank DeFord it was probably the third one I loved

Frank but he didn't it wasn't a fit event it was the wrong yeah it was the wrong time in his career yeah yeah he was better in 1956 he was good anytime but I and he was such a wonderful gent that 70s 80s long form yeah yeah it's almost like a short story that kind of started a fade yeah yeah no yeah so i mean i think of like dominic dunn that's the ultimate example of like i have to get vanity fair i want to read it i cared more about his oj takes than anyone in my life. I want to hear from him only. Well, that and then the Mendendez brothers. That's when he really... Yeah, before that, right?

He really made his name. And he was vital to the whole thing. And the care and feeding of Dominic was a big part of the job. It's funny. He was in the OJ FX series. Played brilliantly by Robert Morris. Yeah, and he was in it. And he was probably in it more than people understood why he was in the OJ FX series. Played brilliantly by Robert Morris. Yeah, and he was in it,

and he was probably in it more than people understood why he was in it. Yeah, yeah. I felt like he wasn't in it enough. You could have done his version, too. Yeah, he was. There was really nobody else covering the story correctly. Toobin did a good job with his book. Yes.

And I think he wrote some stuff, too, but Dominic Dunn, it was like he became the oj whisperer and everybody was just feeding him stuff and you never knew it was true and he looks sort of like like your friendly uncle you know he has that look you know i mean don was an interesting guy you know he he was a he was a d-day he was during fought in the battle of the bulge i mean his daughter got murdered got a daughter got married into the monday trial and the whole i mean it is griffin his son is you know he's a friend of mine he's doing really well it's just a really interesting family but they have a

they had a you know he had a long term falling out with his brother john gregory dunn but then they made up near the end of john's life and um but dominic was very much the dominic and annie leibovitz were the very much the franchise of the mid 90s did you steal any Leibovitz were very much the franchise of the mid-'90s. Did you steal Annie Leibovitz, or was she already there? No, she was there. Yeah, she left. She was a Connie Nass contract photographer and the principal photographer at the magazine. I remember I was living in Boston during the whole OJ thing

and obviously not really making any money, and I'm reading these Dominic Dunn. So then I was at this cocktail party at a famous yeah and just his life i was so fascinated by it was it was like the opposite of my life it's like every night he's in bel air in some mansion and yeah and i was just like man i i wished i was just cameras following this guy around so every day he's going to a different dinner and they're talking about oj yeah and I want to be at all these dinners. I just want to overhear it.

And that's what he became for a year and a half. Yeah, he was the guy. He was very high in high demand out here socially. You know, it's funny. Things are strange. I remember when Klaus von Bülow was tried for trying to kill his wife. You know, when he went back to london after that trial it was like you know a big social get there and in new york right it seemed like at some point

there became a recipe and i don't mean that as a negative way but like the typical vanity fair issue oh no absolutely it always hit a couple of formula yeah all right formula i guess you could say too but it's like every once in a while yeah you have to have some sort of european his wife mysteriously died yeah yeah no and then there's money missing and there's that one but then the big celebrity profile yeah yeah and then the gritty michael lewis yeah yeah things are about to go really bad in this way you hit like your seven buttons that you would just go to. It's a slight front that we try to vary from.

You want to be both consistent in a certain way without being too predictable. Maybe sometimes we got too predictable. There were certain stories that would happen, though, where we'd be like, I'm clearly going to be reading about this event at a fair four months from now. They will have some giant thing. When rich people kill other rich people, that's our turf.

One of our areas of turf. Well, the Tiger Woods car crash with the wife. Yes. I remember thinking, this is the ultimate Vanity Fair story. I don't know if they'll be able to get this one. Also, Annie had shot him for an American Express ad that never ran. And we were trying to figure what to do. And then she called and said, you know, I do have this photograph.

So she sends it over and him looking really menacing with his shirt off. And we ran it. And American Express would just live it with us because they had basically paid for the photograph. And I hadn't really signed off on it being used for anybody else. But yeah, you read something like Tiger, what do you say? Yeah, that's a good story for us. Do you have, like, is there a favorite issue you ever had at Vanity Fair? Because I know, like, at Grantland and at The Ringer,

I've had favorite days. I'm just like, we fucking killed it that day. Yeah, I mean. You don't have one issue where you're like, that is like the best issue we ever did. This is going to make me sound like a real ass. But I remember talking to John F. Kennedy Jr. on the phone and then telling him I had to get off the line because the Princess of Wales was on the other line. That I remember. Wow.

Yeah, that was something. Princess Diana probably made a few appearances in Vanity Fair. She did a lot, actually. Before and after. Her most famous photographs appeared in Vanity Fair. These ones taken by Mario Testino, which are sort of the defining pictures of her in the last, say, 10 years of her life. Hold on, we're going to take a quick break to talk about our friends at Rocket Mortgage by Quicken Loans.

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in place when you were there because you've taken advantage of it year after year you know the thing is the magazine has a big global audience we sell a lot of copies in europe and the far east and um and australia and canada and the only international language of celebrity right now is um with the exception of a couple of music stars or movie stars everybody has their own tv stars you go to italy they'll have the number one show you've never even heard of the people on it yeah and they wouldn't know who deborah messing is say and you can't sports stars are different in every country writing stars are different movie stars is the only it's the only international face currency and so we were stuck with that and we were stuck with um the position of having to sell, selling a lot of copies on the newsstand.

Who was the all time go-to celebrity that you're like, Oh, they're on the cover. I know this is going to sell the most. Well, we did. Well, it just,

I think Madonna was on probably six times. That was the nineties. Jennifer Aniston was the biggest selling cover of all time after she broke up with brad pitt post brangelina no is that what we're saying now that she broke up with brad pitt no when she broke oh when whoever broke up with who uh who you talking about now i just felt like brad pitt started kind of dating angelina jolie when he was married to Jennifer Aniston. I had known nothing about that. A little overlap? Yeah, I don't know.

I'm reading between the lines. That's a possibility. A lot of sexual tension on the set, and they just immediately start dating. He's a good-looking man. A handsome man. He has needs. She's on the front set. Who knows?

If I looked like Brad Pitt, I would be showering on YouTube every day. I think Brangelina was the greatest thing that happened to the magazine industry in the 2000s. Us Weekly had pushed to 500 levels. You know, Jan Wenner described it to me with just how Us Weekly would define something. So the first part is the getting together. So you've got them together, then photos together, and then what are they going to do together? So you've got like six months of that. Yeah.

Then when they break up. The tear. You've got alternating issues for like another six months or a year after that. Then who are they dating? So it just feeds like a giant amoeba. You guys wrote about that culture a couple times. No, about the celebrity culture, the Us Weekly, the whole... We wrote about the 90s, calling it the tabloid decade.

Yeah, yeah, yeah. Yeah, we never did... I mean, if you looked at a copy of Us Weekly... No, I'm not saying you wrote about, like, Brangelina. No. No, you wrote about the culture of that whole thing. Yeah, well, it's funny. If you check, like, a copy...

I'm just guessing a copy of us magazine or people magazine from 2003. You know, those are authentically famous people on the cover. Yeah, you look at it now you say I have no idea why I'm looking at this person and I don't know who they are. Yeah, they were trapped in a well. archives of all their stuff from the 70s 80s basically since they came out and it's really interesting to read how they wrote about people in the 70s and 80s and how much more forthcoming celebrities were you read about how like three's company suzanne summer's holding out right but the way they would write about it it was like reading a report well you're real in real quotes yeah i'm always fascinated to see how the trends train well you know it's funny because you look at life magazine in the in the 40s and 50s and photographers like william clackson to go spend like three weeks with steve mcqueen yeah it's very very different now it's like part of an industrial complex it's uh and that's what tv guide even would have stuff like that. But now, I think, and we see it in sports especially,

these guys are also savvy with who they're spending their time with and why. Well, the internet makes them have to be savvy. It's like, it's time for my magazine profile. All right, I'm going to call Lee Jenkins from Sports Illustrated. I'm going to give him four four hours and he'll write the magazine profile about me and then cross that check off and now we got to do a podcast which podcast and they just do this little playbook but in the 70s and 80s i i think a lot of the times people be like oh yeah i'll talk to you you know and well there's no eventually that faded away you

know the media was owned in large part by mom and pop operators. I mean, you know, it was like family-owned the LA Times, the New York Times, the Wall Street Journal, the Washington Post.

The networks were even owned were family-owned operations. So, it was a much, you know, it was a, not necessarily a better time, it was a simpler time.

Well, magazines are in a lot of trouble. Magazines are in a transitional period, yes. You must have been feeling some of that the last couple of years. Yeah, I mean, I think Vanity Fair has escaped the damage that's afflicted a lot of the other magazines, but we're not immune. But you're owned by Condé Nast, which I think has had some issues with some of the other properties. No, no, it's a very tough market right now.

When did you – Vanity Fair had this ability to just parachute in once a month, and they could tackle the big story but then also some evergreen story and just hit all these different things. When did you start noticing that the world, the content world, was just moving so fast? Like you might have this story coming but the way it was being dissected in real time was almost altering how that story like it was almost making it dated before it came out well it's funny because you know most of the um

running a monthly magazine in an internet age especially during this period of like this administration it's it's, it's a real challenge. You've got to choose something that might take two or three months to report and edit. Then it takes a couple of weeks to close it, going through legal review and fact-checking. And then it's going to be on a newsstand for a month. So you've got to choose aspects of the culture

that are very much in the air but that have a shelf space beyond the news blast you get on your phone. And you know, the New York Times and the Washington Post are just a rabid competition, very healthy over this administration. So you're phone is just pinging constantly with the Washington Post or the New York Times. And so we have to do, like Michael Lewis is doing this series for us right now, that I think will have a long and lasting impact.

So we don't chase news. We make news occasionally, but we don't chase the news because we're monthly. With a daily website, The Hive, that operates more like a newspaper. Right. And how's The Hive you really started investing in, I would say, three years ago? Two years ago. Two years ago?

Yeah. It's doing very well, and it's a young group with some three, four-star writers like Nick Bilton and Sarah Ellison and uh william d cohan and uh but it's it it does really well it goes up like i don't i don't know i don't know how many gets a lot every month and you feel like it has its own identity separate from yeah we invest more in it and we just hired gabe sherman uh it's a brilliant reporter and this guy joe pompeo so it's got a great staff yeah they're pretty good gabe sherman's good oh Pompeo. So it's got a great staff. Yeah, they're pretty good. Gabe Sherman's good.

He's amazing. He's got a story that's coming out at lunchtime today. Oh, really? Oh, God, yes. Well, we're not running this podcast. I mean, we're running it probably next week, so you can say. I think it's live right now. What's the story?

Bannon and Trump. I mean, just in. Yeah, I mean, anyway, anyway so did you ever write about harvey weinstein like in a in a really big way or not really no i knew those rumors were out there i never had any you knew that he's my next he's my cross the street neighbor in new york so i see him all the time oh what were your experiences with him when we became neighbors much better he we'd had a very antagonistic relationship up to that point i mean very antagonistic from vanity fair from vanity for and spy in fact i remember i would hear one spy oh yeah we wrote about him

and spy i didn't even know i didn't even know he really was out of the observer which is i was there in 1991 and um uh very antagonistic and uh when we became neighbors it became friendly because you can't have an enemy living across the street so yeah it's settled down dramatically after that but i'm sure you heard a lot of rumors and things out there i heard rumors but i never attached not ever attached to like a proper noun so it wasn't you'd i mean you could sort of guess i mean you know there's a british comedian called jimmy sabal once he was arrested as a pedophile you'd say like what you couldn't get this realize this beforehand he's all dressed in chains and tracksuit constantly and he's he was just it looked a bit like Marty Feldman he was a strange looking guy and

I had no idea that this was going on at this level but if I owned the Peninsula Hotel here I'd tear out all those bathtubs because you don't want to be sitting in a bathtub that Harvey Weinstein's been sleeping in like you know the

the the whole establishment that he was part of it feels like it's shifting like whatever has happened with the trump allegations last year the trump tape um the stuff that's happened with harvey just women coming out it does feel like this is this is kind of the pivotal sea change we're taping this uh october 10th pivotal sea change week for things are never going to be the same with this stuff now people are going to come out immediately they'd be good if that was the case and and um you know um weird thing is harvey has young daughters almost the age of some of these

girls and you know i have a 23 year old daughter. She worked at the Weinstein Company three summers ago when she was in college. And she said it was so chaotic that she never even saw Harvey. Yeah. She said they didn't even have desks for the interns. They had to work on their knees. They had to bring their own computers to work. Did you follow how The New Yorker and The Times

were basically competing to see who could get this story out first? Have you ever been involved with something like that? Oh, all the time. Constantly. Well, you know somebody else is doing the same thing. You always know. But you're on a monthly schedule. Yeah, but then we can release.

Now with the Internet, we can release it the moment it's ready. You have that at least once every couple of months. What's the best example of that? I can't even think of anything right now. But I know when we broke the Deep Throat story, that was a big thing, because that's one of the great mysteries of journalism. I was so upset that you broke that.

Why? I never wanted to know. I realized after I found out that I never wanted to know. It was so much more fun not knowing. Yeah, I get it. It's almost like the JFK assassination. I kind of never want to know. Well, so much more fun not knowing. Yeah, I get it. It's almost like the JFK assassination. I kind of never want to know. Yeah.

I always want to have my weird theory. Yeah, we'll probably never know. No, but this guy, this lawyer calls me and says, I represent a man who was a deep throat during the Watergate reporting. And I said, and we get a lot of not calls. So I turned it over to one of my editors, David Friend and he and I worked together forever, we used to work at Life Magazine together

and so we spent two years on this, we're like 95% sure that we had, that this Mark Felt was the guy and Carl Bernstein was on my masthead,

but I couldn't call Carl because I worried that he would then call Bob, and Bob would have the paper the next day. We have a monthly magazine. There was no internet to speak of at the time. This was 2005. And we closed the story. We secretly photographed him

using the husband of the head of the photo department and i go on my honeymoon and we my wife and i go to the bahamas for our honeymoon i forgot all about this we're on the in the airport coming back and i didn't even have a cell phone in those days and um my wife gets a ping on her cell phone and she has a little flip phone and it's my office saying the editor who'd been working on David Friend saying that we're releasing the story in about three minutes. And I

said, oh fuck, I forgot all about that. And so their plane was delayed and my wife's cell phone battery was going down and David called back. He said, it's gone up. Woodward and Bernstein say they're going to make a statement in a half an hour. So we have to wait there.

Oh, God. And I thought, if I get this wrong, I'm cooked. And just as we were heading towards the gate, my wife's phone rang again. And it was New York saying, they just said yep mark felt his deep throat so i got on the plane i was so happy i had on that short flight i must have had like five vodkas i was so relieved it's just it was a big thing i was i'm a huge watergate junkie i went through two different phases in the 90s i never i actually always thought deep throat was like three different people that

emerged. Yeah. That's what I thought. Because Mark felt was so obvious. If it was just one person, if you really studied it, it was like, all right,

if somebody is leaking this stuff to Woodward, like it's gotta be somebody that, that actually gains from this or is trying to get revenge in some petty way. And he was the guy who was, there was, it wasn't Al. Hey, that's true.

Mark Fowler was the only one who had a reason to be the leaker. And it was like, well the guy it was there was it wasn't al haig that's true mark fowl was the only one who had a reason to be the leaker and it was like well if it was him it would have come out so it had to have been four different people a lot of people a lot of people thought it was a sort of a narrative device dreamed up by alice may who the the editor of the book yeah who's a great non-fiction editor at simon and schuster and um yeah and mark by the time we ran the story mark was suffering from yeah he was that was one of the reasons he did it he wanted money for his family yeah and uh and then they i don't know you've seen the movie the movie is good i haven't seen the movie yeah i've read some somebody wrote a pretty good takedown of mark fell i can't remember where i read it that i actually agreed with like

kind of kind of undermine the country in some ways because he was being petty about the fact that he wasn't promoted yeah yeah i mean there there is definitely yeah the motives weren't as good as the as the result no and also the movie doesn't, and I love the movie and I've probably seen that movie it's in my top 20 of most times I've seen a movie, but it does discount, like he was also dealing with, I think it was the New York Times too, the New York Times.

And he was feeding stuff to them and it was really the Washington Post and New York Times together. But in terms of just pulling off that movie, it's still an amazing achievement. And the fact that, you know, an amazing achievement and the fact that you know the Woodward and Bernstein never ever laid eyes on

Nixon in real life ever once there's no confrontation which makes the whole thing even more remarkable that it could be so dramatic whereas if you look at the people from the Times like Maggie Haberman, she's wandering into Trump's office

five times a day. When did you feel like you were part of the establishment, officially? When you got the job or a couple years later? No, I don't feel like I am part of the establishment. Nah, you are. Let's be honest. You, Lorne Michaels, there's these certain guys that

are kind of... Canadian establishment. Yeah. I feel like I'm part of the Canadian. The Canadian in America establishment. Power players. I'm not a power player. And, you know, I... I would say you're a power player.

Okay. I mean, I don't know. There's certain people who have really great jobs. Many of them are based in New York. Yeah. You all know each other. Yeah, yeah, yeah. And I don't know.

It's a thing. No, yeah. It's funny. I remember when I first came to New York and I had a green card. Excuse me. And I remember applying for and then receiving in the mail,

going home and getting the letter and opening it. It was my Brooks Brothers credit card. That made me feel better than just anything that's happened since. Do you feel like New York versus L.A. is a thing? I think Los Angeles is the American city right now, not New York. I've been preaching this to... It's funny, when we started Gremlin in 2011...

And not just the weather or anything like that. No. When we started Gremlin in 2011, it was really hard to get people to move here. I bet. Young people. There was an Uber here. It was this big sprawling city, and it was intimidating. And over the course of six years, people want to move here now.

Absolutely. We can get anyone to move here. And it's a really fun place for a young person to live, which it was not six years ago. Cheap rents. Cheap rents. Uber. You can go everywhere you want because the new york thing if you're young in new york just hop in a cab and new york's up all night and la isn't up all night like that but it's got a lot of the other pieces though well you know my first apartment in new york was down in the in the

village and i paid it was a beautiful apartment had tall ceilings and a garden and a wall of leaded glass and and i paid $200 a month. And my daughter's apartment was right around the corner. And she was sharing with a friend. It was about the same size, but she was paying $5,000 a month. And so the rents in New York are just so atrocious that L.A. is a very attractive place. Also, I think, strangely enough, the overall decline of the movie business has allowed other industries to flourish here tech because it doesn't it doesn't hang over the city

like like like like a giant you know a cloud it's there's other life here there's the art world there's the tech world you know a huge tv business yeah and it just feels like a much more vibrant city and then you throw in everything else like the weather the palm trees you know and sounds like we should start looking for real estate yeah yeah where do you want to live should i start showing your neighborhoods you're the most you're the best looking podcast operator i mean oh yeah you and actually preet bahar in new york he's got a pocket he's pretty good looking the uh yeah i mean most of he doesn't have your blue eyes most of the attractive people in the US

live in LA I mean they have almost all the models and actresses yeah I know even the studio heads people like Bob Iger I mean it's like a movie star very good posture great the best you think he runs for president

I know I hope he does I think he's going to I think he runs for president i know i hope he does i think he's going to yeah okay i think you want to know an nfl team which explained a lot of the difficulties i had at my previous employer okay um and now i think he's going to run for president i hope he does it'll be interesting to see him versus trump i don't think trump will be there when this comes around really do tell i mean I give up making predictions after the election, but I can't in my life imagine this goes

on forever. Because we're all going to get blown up? You know, I think that there are people who will stop that little stubby finger from pressing the nuclear codes. I think that Little stubby finger? His fingers are like that long.

It's about half the length of a cigarette. He, he, of a long cigarette, you know, one of those Virginia slims. There's not a lot of nice things to say about him, but one,

one positive, if you're going to spin things into positives, he got you writing a little bit more. He got, yeah, he's been great. He brought your fingers out of retirement. no, I mean, they weren't in, they're in semi retirement. I love, a little bit more he got yeah he's been great he brought your fingers out of retirement yeah no

i mean they weren't in they're in semi-retirement i love writing about the guy oh yeah in fact you know i one of the things you know i'm planning my future i've got to plan it for a post-trump world it's too easy to you know for the new york times the washington post they are just like in in heaven right now with with this administration but they've got to plan how they're going to continue to be successful businesses when he's gone. First, I want to talk about Stamps.com, one of our oldest friends. Maybe we have some old friends on this podcast today.

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They'll even send you a digital scale that automatically calculates exact postage and helps you decide the best class of mail. I actually get mad whenever I hear people say, yeah, I got to run to the post office. Oh, I just got stuck at the post office. It's insulting. It's 2017. Nobody should go to the post office. Just go to stamps.com. Use my code BS for the special offer, a four-week trial plus postage plus a digital scale without any long-term commitments. Go to stamps.com. Click on the microphone at the top of the homepage and type in BS. That is stamps.com click on the microphone at the top of the home page and type in bs that is stamps.com enter bs sign up today stamps.com never go to the post office click on the microphone at the top of the stamps.com home page type in bs what do you think about uh

future networks all the stuff you talk about at the Vanity Fair Summit every year. Future TV networks versus the streaming and places like ESPN, even HBO. These old school powerhouses that now have these commerce. Netflix is going to spend $7 billion on content this year. And Netflix or Amazon, they're going to start writing checks to the NFL and professional hockey and professional baseball. NFL's 2021? Yeah. And Amazon just might say, we're taking this. Or the NFL, as you pointed out, they'll just say, we don't even need a network.

Yeah, we'll loan everything to ourselves. We'll find a young John Madden and do the color commentary ourselves. I do know that if you give a kid a DVD, they basically don't know what to do with it anymore. It's amazing. Nobody under 10, they'll look at a DVD like it's a UFO. Yeah, it's like a gramophone. I watched it change with my kids. Because my daughter, when she was born in 2005,

and we had this little DVD player that she could put the headphones in and she could watch it. And then eventually on demand started around 08 07 08 where it could be like oh your nickelodeon show put the on demand yeah and streaming was just it was like this whole world open so my son who's only he's almost 10 he only knows streaming like he doesn't know where cable channels are that my nine-year-old daughter's the same way yeah it's like he he goes to youtube and he goes to amazon yes i just wrote about this two weeks ago because we were there for ad week

and you know i talked to some of these big cmos these different places and they're they're concerned they don't know how to reach young people because young people are in places that they don't know how to advertise for how do you advertise for youtube when especially like if youtube does youtube red and you can just skip all the commercials how do they if you speed ahead most kids speed ahead through commercials totally i mean my daughter watches the simpsons on and on tv on demand and the ads are for such violent movies we just tolerate me to just skip ahead but if you were selling something and what i would do is i would design an ad that might be a 15 second ad but it's going to be seen in two seconds so that it's a stationary thing no matter how fast you go that right you don't try to get a lot of thoughts and you try to get one simple thought like if you were selling apple

you just like have the apple logo and nothing else so that when you speed like iphone 10 coming now and then it's over it's just that one logo yeah for the that when you speed ahead iphone 10 coming now and then it's over there's just that one logo yeah for the see when you speed ahead it doesn't i think that's where it's i think that we're heading you're seeing something in sports now you're seeing in during a football game the kickoff teams coming out and they stay in the field but they go split screen with the commercial yeah and now it's like it's not totally a commercial, but it's... I always wait 40 minutes before I start watching a game. You just zoom through it?

Yeah, always. That way a one-hour game lasts an hour. It is crazy. Games are the only time where I actually sit through commercials. I do through the Super Bowl. Yeah. But it's like you're watching an NBA game, and if you're watching live and you want to experience it on Twitter or whatever.

It is your business. Yeah. It's the only time I really watch commercials. You're tweeting and you're Facebooking whatever you do, you young people. We're starting to figure out ways to actually get content. You take a sponsor, something they want to do, and you actually do something that's fun content with it. We have this gambling podcast with my friend Sal sal and he has this make-believe casino captain morgan's make-believe casino because we love captain morgan's and he makes up a bet and

then the people on the podcast have to pick which side of the bet but it's a fake bet because we're in the make-believe casino and it's just really smart like it was his idea and it works and i just think it's more effective than saying, hey, drink Captain Morgan. It's like, not only drink Captain Morgan, but here, we're going to have fun with... This looks like a lot of fun to do, too. Oh, this is the best. Yeah. This is...

Yeah. I mean, you know, I... I want that job over there. He's got the best job. He's a conciliary. Yeah, yeah, yeah. Who was your conciliary at Vanity Fair? Oh, I have a lot of them.

I'm a firm believer that in life, 75% of the time you know what to do. 25% of the time you're not sure. And for that 25%, have a circle of trusted, wise people to talk to. Because that 25% is the difference between success and failure. So I have like five women in the office who are my, we've worked together for 25 years. One of them, I've worked together with her for 30 years. Wow. Yeah, Amy Bell.

And she's married to David Camp, the guy who used to write the Walter Monheit movie reviews. And so, you know, if I don't know what to do, I'll ask one of them. How would they describe you as a boss um i think you know i'm pretty i mean i'm a fair i mean um i never scream collaborative very yeah it seems like the most successful bosses are the collaborative ones i'm very appreciative of other people's talents. And I remember a friend, Dave Zaslow, said that Jack Welch, who was like one of the great business leaders of the last century, said that one of the things he really appreciated in an executive was gratitude. And I'm very grateful that they've been with me, mostly from almost from day one, the whole time. And we have, you know, one came over for breakfast this morning we've we're all very close and um and um that's the thing i'll miss when i take off what about you and kurt how did that relationship evolve over the

years you know we were so close we sat this far apart um five years and spent 10 hours a day together finishing each other's sentences. And then we still, friends still see each other. It's just not like sitting five feet away from each other every day, all day long. It's like you were married and then all of a sudden now you're just friends. Yeah, I mean, all the spy people are still very close. We had a reunion in October, our 30th anniversary. What happened at that? I didn't even know about that. We just did it back in the garden on the Waverly.

It was our 30th anniversary. I would have crashed that. Yeah, you could have. I just would have pretended. I would have pretended I was Celia Brady. I'm here. I was a 15-year-old kid pretending to be Celia Brady. Yeah.

So what happens when you guys all get together for that? There's a lot of, you know, well, first of all, we're all older. Everybody's, you know, really gainfully employed, which is nice. And they're all over. They're all doing newspapers and magazines. But by the way that's one of the reasons that magazine was great because it was all people who yeah who went on you were catching at the right time well there's a woman who writes out here nell scoble she does

a lot of tv oh yeah i know she went for grantland she she's wonderful and she came up with a line we did a story on really skin skinny socialites in new york the time. And I remember her first sentence was, why it seems so unfair that the woman who's a size 2 gets to live in a 14-room apartment and the woman who's a size 14 gets a 2-room apartment. Which I thought was very clever. Who was your biggest competitor during, let's say, the last 12 years? I mean, a magazine competitor yeah who did you measure yourself against well you know we compete against everybody and yeah but there had to be somebody you were

kind of monitoring the new yorker um the new york times magazine off and on um definitely had some off stretches even vogue because we competed with them for advertising. And Rolling Stone on occasion. That occasion's passed. No, yeah, but when Jan was... Jan is the finest editor of our generation. Yeah. Bar none. I mean, he discovered more talent.

When he was in the office, that magazine was tops. I agree. But by the same token, he wanted to live a life as well. Rolling Stone was a remarkable, remarkable achievement. We've serialized this book on Rolling Stone that Joe Hagan has written in our next issue. I heard he's pissed off about it. He is.

He kind of turned his life over to the guy and then the guy wrote a kind of a flattering and unflattering thing about it. Yeah, I mean, I don't notice anything that's inaccurate about the book, but I'll tell you, he was having a hell of a lot more fun than we were

at Time Magazine in the 1970s. But, you know, button-down shirts. Yeah. That was quite a time to be in the 70s. Oh my you know, button-down shirts. Yeah. That was quite a time to be in the 70s. Oh, my God. The 90s, too. I mean, the last three days, I found a photograph of my children. I can't even believe this. My older kids. I found a photograph

of my kids on the Concord. That was Connie Nass back in the 90s. You had the Oscar party was the great trump card for you guys. It was a good thing, yeah. You guys had this. They must have had it even before you had the oscar party was the great trump card for you guys it was good thing you guys had this when they would they must have had it even before you took the job no no it was they didn't okay no it was swifty lazara had a an oscar party up at the old spago and then i went to the last year he did it and then swifty died and i thought it'd be a good thing for the magazine if

Fannie Fair did it so I the then power restaurant in Los Angeles at the time was Morton's so I called Peter Barton and said I'd love to do it he said well the Trump's one of my best friends is Steve Tisch he's already called me so for the first so Steve and I did it together for a couple years

then he stopped doing it and we've done it ever since. And that really, what do you think was the key year that it really became, that it blossomed? You know, there was a year when Tom Cruise and Nicole came in. It might have been the Jerry Maguire year or something. It just, it grew organically. We started off very small, 150, 200 people,

and I'm a firm believer in not over promising something and making it small, let it grow in an arithmetic way rather than an exponential way and so now we had trouble trying to keep the numbers down.

I know for people who have said this about Lorne Michaels too that one of the toughest things about walking away from a job like that, other than the action and being around talented people all the time, is just kind of being the gatekeeper for some of this stuff. Lorne Michaels is like the man. And the moment he's not doing that show, maybe it flips a little bit. I'm sure you've thought about that, too, with Vanity Fair, right?

You know, the funny thing is the night of the Oscars, I love planning for something. I think it's really... I love marshalling all the troops and all the design and everything like that. The night of the Oscars rolls around, I just, I would kill to be in bed eating Chinese food, screaming at the TV.

Yeah, it starts late, goes late. It's a long day at the office for me. And I'm not a comfortable social gadabout. I mean, I like people, but I'm not comfortable in crowds. I actually, you know, I'm very claustrophobic. I have great social anxiety, so I'd have to take a beta blocker before the thing started.

And I'd want to, like, make sure I stayed awake through the most important parts of the evening. So I usually leave around midnight. It seems like that Vanity Fair Summit thing is your ideal two-day hang because of the ideas. Oh, I love all that. And I love it more than I thought I would. Yeah. I can tell.

The year I did it, you just seemed like you were like a pig in shit with the whole thing. Not a pig in shit. No, I mean in a happy way you just loved it i yeah or at least i showed i was looking like i loved it i would i felt like you loved it i did actually i felt like you're like this is great you're here he's this is coming really interesting people yeah what is life if not people yeah i'm glad you moved to tele i mean i'm in next year we'll come up with some sort of sports something yeah we did it was me and the year I did it, it was me and Macro did the future of sports media. It was great.

We were throwing bombs. Yeah, no, it was really terrific. And the two of you guys sitting there with like manspreading. Yeah, we were. It was like two people who don't really give a shit in those situations, which is what you want from a panel. You want people to kind of throw it around a little bit. Yeah, John's pretty. You're both pretty out there in a good way.

How long have you owned that famous restaurant in New York that nobody can get into? The Waverly, and we opened it in 2004, I think. Maybe 2003. So it's about 14 years old. It's been around forever, though. I mean, it's been there for 100 years. Yeah, you bought it and took it over. Yeah, and I live two doors down, so I can technically go home to pee rather than use the bathroom there.

Do you feel like this whole era of exclusivity with the Soho house, all these different places, it's hard to get in, that that's kind of going up a couple levels as we all get older here? I do think that unavailability is sort of one's, whether you're a company or a person, greatest asset. Yeah. Sports teams are starting to figure this out a little bit. By doing what? Like the little courtside clubs where at halftime only so many people can go underneath. It's like a Jerry Jones thing.

Yeah. Yeah. Yeah. And yeah, there's always, it's like, I used to have this sort of, sort of philosophy about New York that it's a, it's a house with seven rooms. And every time you figure, oh, finally I've arrived, I've gotten in this room, you notice there's a door at the other end and there's an even better room

and so I think life is a bit like that, that there's always you're really happy but there's that what's that door in the corner doing there? Let me open and see what that looks like and the people are better looking and the food is better and so that life's a

series of rooms and people are are monetizing that attitude what you young people say i would agree um best writer you ever edited um i mean this i'm going to ask you like four difficult questions in a row right christopher hitchens was the most um uh fluent writer i've ever met i mean we'd go for lunch and and when i said the observer and and amy bell and christopher and i would go out to lunch and we would uh he would drink they could make two-thirds of a bottle of wine and a couple of um after dinner drinks and we'd come back we'd sit him down in front of a typewriter, and he'd type out 1,000 words in 35 minutes. And you didn't have to do much.

Charlie Pierce was like that when he wrote for Grant. I bet he's still like that now. Oh, I guarantee you is. You'd be like, Charlie, an hour later, it's 1,300 words. Yeah, like short order cooks. Yeah. But those are people that are another species. I mean, James Walcott writes for me.

The thing is, a brilliant writer. I mean, he just, he, you know, he currents every single word and chooses whether that's the right one. And I think it takes him a good part of four or five days to write a thousand words. Who is the best writer you pursued heavily but could not pull off? Other than me. Other than you. I worked very hard to try to get you yeah um uh you're doing this hbo show and we're like really busy i know you're not busy anymore yeah yeah that level of business

now you're available i don't have a magazine anymore yeah look we missed our moment um A writer who I used to speak to sometimes three hours a day for years and years was Michael Hare. But he had written Dispatches. He was one of the great journalists of all time. And he became a Buddhist after Vietnam. He used to write all Kubrick's movies as well. And he wrote the narration for Apocalypse Now. He was brought in to fix

the things. And Michael was a wonderful peaceful person. I only got over 10 years of constant talking. I only got two pieces out of him. I would have liked more. But he said, I'm done writing. Did you ever make a run at Ta-Nehisi Coates? No. But I wish I had. That seems like somebody who would have liked more but he said i'm done riding did you ever make a run at tahtahasi coats no but i wish i'd had yeah that would that seems like somebody who would have been an incredible because he comes in he's got it seven eight nine times a year he parachutes in with the best take

on whatever's going on i agree he's brilliant yeah um so what's next for you you figured it out yet no i have a lot of ideas they say we're taking off to France for six months I love that part of the world of the simplicity and yeah I have a rough idea I know who I'm going to do it with roughly and it'll be you don't have to reinvent the wheel you just have to make a

really interesting wheel that doesn't exist now I've learned failure I always tell my kids you rarely learn from success you only learn from failures doesn't exist now. You know, I've learned, failure, I always tell my kids that, you know, failure is, you rarely learn from success, you only learn from failures. And I had,

I had a magazine in Canada when I was in college and it was basically, it was a literary political magazine, ran it for five years and it just folded. And then I had Spy, which I ran for five years

and was really successful. And the difference was, Spy had a point to it, whereas the magazine Canada didn't. We opened the Waverly Inn in the West Village, and at that point there were no American restaurants in the West Village. We had red banquets and white tablecloths, and they just didn't exist in the West Village at that time.

Then we opened another restaurant very similar to it, banquets, leather banquets, white tablecloths, same kind of food, American comfort food, blocks away and it didn't work because it didn't have a point the waverly inn had a point the other one was just there because we had a great space so whatever i do it's it's just gonna have to have a point i actually think that sounds simplistic but no but you know what it's it's it's a great point yeah and i think that's really... It sounds simplistic, but it's... No, but you know what? It's a great point. Yeah. And I think it's lost on a lot of people.

And I know at Grantland, I knew exactly what I wanted it to be. Yeah, yeah. And we had a point. Yep. And with The Ringer, we spent a lot of time in a house that we rented a few blocks away from here trying to figure out what is the point of this website. Other than a continuation of... We didn't want it to be a continuation you know and we and we wanted to react better to how the internet moved

but at some point you have to have a point and i think it took us about nine ten months to realize like the point of this other than trying to be a multimedia or whatever is you really have to double down on the three four five things you're great at and go all in on those things, and then everything else will fall into place. You couldn't take the Grantland name. Are they still using it? No. It's a good name. It was a good one.

And I think how it was playing out with Grantland was so good in so many ways, and yet they just didn't know what to do with it. So yeah, it just was the wrong place. I think if we had been almost anywhere else, I think it would have, you know, we hit this point.

It's funny. I hated the name. That was John Skipper. He was right. Yeah. Cause we had, it was the placeholder for the website. Oh,

that's interesting. We had this old, uh, this old legend, Walter Bernard, then I designed the first website, which we quickly changed. But he put Grantland in as the placeholder

because we didn't have the name. Yeah. And then there's this point where Skipper said, you know, that Grantland name's growing on me. And I'm like, oh, no, come on. That's terrible. And he's like, well, top it. Come up with a better name.

And I couldn't. Yeah. And then it turned out to be a better name. And I couldn't. Yeah. And then it turned out to be a great name. Great name. I'm actually glad we did that. Skipper used to hang around Spy Magazine all the time in the 80s. Oh, yeah. He loved it.

He was very good friends with Tom Phillips. He's a Rolling Stone guy, too. Really? Yeah, Skipper worked for Rolling Stone. Yeah, yeah. Yeah. I think all the right people seem like they hung around Spy. Some, yeah.

Yeah. 35th anniversary? Maybe I get the invite? No, that was the 35th no 35th maybe i'd sneak in it's like a bus boy like 2000 and something 30 years i know we're that's only three years off you know the first five years of my garage are you serious yeah those are the best years too those are the funny years i had some my mom because she's to be generous um maybe didn't realize to not be generous maybe it was being spiteful and didn't like having the magazines in the house but she

threw out the ones i had saved so i was kind of circling ebay for like three years yeah and then some jackass just put up the whole collection really the first five years for like 180 bucks or something i just i took it down like in a millisecond yeah and this giant thing comes this giant box with all these magazines and my wife was like what the fuck yeah what are you gonna do with these and i was like you don't understand jay abrams has a complete set yeah they're out there they're now they're more expensive yeah we have it now it's funny we did these grantland quarterlies that um we took a lot of shit for like everything else the first year and i really wanted to do them because you know i felt like we'd have

enough every three months for a book that i'd want to put in my bookshelf 10 years from now i'd want to read so we did 12 and the last four are really hard to get but just in general the set's hard to get and now the set goes for like 800 dollars oh and i was like this is this is cool this is exactly how we did this and you know i don't know how many are out there but i'm very big on making sure that if you've done something like that keeping a box aside could be surprised how quickly they disappear oh yeah i mean i'm sure if you had done a spy quarterly every six months or a bunch of books one of the couple books yeah we did one of the books we did spy high which treated like um american celebrity as a high

school yeah i remember that you act like i don't have all these okay well i have one copy left i mean it's funny. Really? Yeah. Yes. Yeah. I remember the Separated at Birth book was a thing. Yeah. It was a huge seller. Letterman did, I'm going to say he did top 10 lists as a book.

He did some sort of book in that book and your book. Both of them, like everybody had those books. Yeah. Actually, we did two Separated at Birth books. But yeah. You might have to bring that back. You don't own Spy anymore, though, right? No, it's owned by a man called Joe Coleman, who is the Coleman mustard heir. Let's tie him up and torture him.

We'll get it back. No, yeah. I'm too old to do it. Just take him somewhere for a weekend. We'll hire some thugs. You've got to be young and angry and 35. So he's just holding Spy and not doing anything with it? Yeah, yeah.

He bought it from Pagazzi and Saatchi. It's like ESPN just has Grantland. Yeah. It was this brand that actually probably was worth something at some point. And now it's just dead. I doubt it. I think they would give me VD before they gave me Grantland. You allowed to say that on a podcast? No, I don't know.

I don't know. Maybe. Who knows? Things stall over time. As you found out, you took over Vanity Fair. Everyone's mad at you. Yeah. And then within three years, everyone wants to come to your Oscar party.

Yeah. The invitation came around. Yeah. It took a while. How was it? We're done. How was your first podcast? Did you like it?

I loved it. It's good, right? It is a collector's item. You want to have one? I'm going to do this for a living. If you want to have a podcast, we'll have your podcast. I'm dead. Tommy, am I serious?

He'll book it for you. You can have guests. If you want to do one, we'll have your podcast i'm dead tommy am i serious he'll book it for you okay you have guests if you want to do one tell me are you the booker he's more than a booker yeah he's he's yeah he's one of the hottest talent relations people in the country even listen to this you i would say hundreds of thousands of people are listening to this yeah what's going to happen is over the next couple weeks people are gonna constantly say to you i heard you on that simmons podcast hey it was great yeah and you're gonna be like oh my god i should have done 20 podcasts say you sound like such an ass great simmons is smart no they're gonna say i heard you had the simmons then they're gonna say you had a Saab convertible? Yeah. I love that car. I might have had one, too. It was always in the shop.

Mine was... I bought a used one, and it was a disaster. Okay, now... Back when I had no money, either. It was the last sports car you could buy in America with five-speed transmission. Yeah? Yeah. That's impossible.

Yeah. All right. Graydon Carter, thank you. Thank you, Bill. This was fun. Okay, guys. Thanks. Thanks.

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