Being a magazine editor in 2025 can sometimes feel like being a carriage driver in 1925. Even as we forge new paths into the brave new world of “content,” there’s an inherent allure to a time when you could print a magazine that millions of people would just… buy. No one embodies the chasm between that golden age and now more than Graydon Carter, the founder and co-editor of Air Mail whose twenty-five year run at Vanity Fair placed him firmly within the pantheon of editors-in-chief. His recent memoir When the Going Was Good feels like it was designed to extract FOMO from those of us who were in diapers during the era when Conde Nast was cutting writers six-figure checks for a single article. In this sense, the book occupies a similar terrain to Tina Brown’s Vanity Fair Diaries, which was the required reading for the wannabe editors of my generation.
As much as he’s known for his tremendous soft power (google: Vanity Fair Oscar Party), Carter is an editor’s editor. When I ask what gave him an edge during the newsstand arms race of the 1990s, he points to the way he was able to surround himself with a world class cadre of writers. Even today—in the age of TikTok, ChatGPT, and the overarching “en-shittification” of media—Graydon Carter still believes in writing, so much so that he launched a new prize for emerging talent in both fiction and nonfiction. We talked about that before he indulged me in questions about back issues of Spy magazine.
Thom Bettridge: I have some editor-to-editor type questions, but first let’s talk about the Tom Wolfe Prize.
Graydon Carter: Well, the idea came from three young staff members in the office. We wanted to give an emerging fiction prize and an emerging nonfiction prize, and we named them after an old friend of ours, Tom Wolfe. Tom wrote fiction in the most unique way and wrote nonfiction in the most unique way. We worked on it with his estate, and with his wife Sheila and his daughter Alexandra. We’re really thrilled with it. We’re doing it with Montblanc, the pen company. We will have $10,000 prizes. We’ve got great judges like Wes Anderson, John McWhorter, and Emma Roberts.
And is the prize for people who write in a Tom Wolfe-y way?
Nobody writes like Tom Wolfe. And the people who try generally fail. No, this is just about great fiction and great nonfiction.
Do you feel like you’re actively trying to keep writing alive? Magazines now are so visual. Our online culture is so visual. Let’s not even talk about AI.
I think the literary scene in New York is very much alive. We do a lot of things at our newsstand on Hudson Street. We throw a number of book parties, probably five or six a year, at the Waverly Inn. Then there’s obviously things like Substack, which have become refuges for people who left traditional media.
Something I like about Substack is the democracy of it. If people read you, you get paid. There isn’t a magazine in the world where editors get paid based on how much traffic they create—and usually it’s the younger editors who have to generate the lionshare of traffic.
Well, there’s definitely a certain amount of pressure on you if you’re a Substack writer. At least in the old days of magazines you sort of went home at the end of the day and had dinner with your family, or read, or relaxed a bit. Substack people are at it 24 hours a day.
Because you’re often selling a persona. I feel like a lot of these newer mediums have brought back the columnist in a real way. Everything is voicey. Everything is autobiographical.
It’s funny because the other day my older son Ash mentioned at dinner that people worked as journalists for like 40 years before they became a columnist. Now becoming a columnist is sort of the entry level to the whole thing. You have people like Kevin Sessums, who used to work with me at Vanity Fair. I can’t believe how well done his Substack dispatch is and how often he files.
Forcing yourself to write is harder than it looks.
You know, editors really have no point in life other than we sort of bring order out of chaos. I think that a lot of Substack writers could use an editor to perhaps trim the fat a bit. Some of them get a little long.
A lot of media people from my generation read your memoir with a kind of ravenous envy—of how well-paid and high profile writers were in your Vanity Fair era. You were almost more like a movie executive than a guy commissioning articles, in terms of the massive things you were green-lighting.
It was very much like that. Some of these projects did cost as much as small movies. But there was also a lot of pressure because it was a golden age in those days. Everybody was good. The magazines I competed against were at the top of their game too.
Who was your biggest competitor?
I used to tell the staff not to talk about stories in the elevator at the Condé Nast building because a lot of our competition rides up and down there. You had The New Yorker and Vogue. We were also competing against The Atlantic, the New York Times. And you’re not only competing for readers. You’re competing for stories. You’re competing for advertising.
What did you feel like your edge was?
If I had an edge, it’s that I created a circle of writers that other writers wanted to belong to. Same thing with photographers. If you join a masthead that has Michael Lewis, Annie Leibovitz, and Sebastian Junger on it, you feel like you’re in good company.
Your book really fed into the FOMO people my age have of wanting to have contemporaries like that. Most of the editors I came up with wanted to model their lives after these old war stories.
When I came to New York in the 1970s, we had FOMO for the people who were already there—because they had bought apartments for like $25,000, and by the time I got to New York in 1978 that wasn’t possible. So I’m sure that at a certain point, 15 years from now, people will look back on this period and think this is a golden age.
I was once at a bookstore in Harlem that was in the process of closing, and there was this guy in the store who was moaning about how New York was ruined, and how all the cool stores were disappearing, and how it used to be better 30 years ago, and all those things people always say. The owner of the bookstore pulled out this old book and read a passage from 1880 where two guys were talking about how New York was ruined and was so much better in the 1850s.
It’s a cycle, for sure.
If you were in your twenties now, would you be drawn to a career in legacy media?
A version of it, probably. There’s a market for magazines again, because I think young people have come to appreciate them the way they appreciate vinyl. It’s not the broad market it was last century, but if you do something well, you can make a living.
When we relaunched i-D this year we really thought long and hard about why people need a magazine today. I feel like whereas magazines used to transmit information, they’re now more like cult objects. They’re physical totems for people’s homes.
If you look at Casa Magazines on 8th Avenue, there must be a thousand very cool magazines that people worked very hard to produce.
You know, the way I learned about making magazines when I was young was I would go on eBay and buy like 80 old copies of GQ for $20. Spy was a really important one—I bought like 20 issues of Spy that got sent to me in a dusty cardboard box. That was a huge inspiration for me. The edge and the tone of voice that magazine had feels so relevant today, actually.
And some of the characters, like the current inhabitant of the White House, are still in our lives.
One of my favorite Spy stories was the one where you guys sent checks for one cent to billionaires and waited to see who cashed them.
It was 13 cent checks! Well, we started off with 32 cent checks, and then if they cashed that, we thought we’d see if they would cash a 13 cent check. It took months and months because you had to send the checks out, wait for them to endorse them, and then wait for the checks to come back. In the end, two people signed 13 cent checks: Adnan Khashoggi, who was then the world’s leading arms merchant, and Donald Trump. Very happy day at the Spy office.
Something I love about Spy was how it leaned into the haters, which is such a currency online today. I remember you guys did another issue where you ranked the US states from best to worst—it was the kind of thing that was pretty much designed to generate an online argument, but before the internet.
I do think if somebody could start a magazine like that now it would be a huge hit.
Well, now you have my email.