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Words: Joseph Bullmore
Noël Coward once said that “work is more fun than fun”. I have always thought that this rather depends on the work. And the fun. And also whether or not you happen to be Noël Coward, come to think of it.
Graydon Carter is not Noël Coward. He is Graydon Carter, which is possibly even more enjoyable. Across the span of half a century, he has variously been the editor of Spy, the New York Observer, Vanity Fair, and now co-editor of Air Mail. He has produced documentaries and thrown world-famous parties. He owns the Waverly Inn in Manhattan’s West Village, where he still does the table plan at the restaurant every night. He recommends the chicken pot pie.
His new memoir, When the Going Was Good, is a reference to a collection of Evelyn Waugh’s travel essays, but also to the shimmering heyday of magazines and old media. Quite possibly to the heyday of everything, actually. Hurtling through the book as a magazine editor in 2025, one has an eerie sense of having turned up to the party in one’s best suit – one’s hair neatly parted, a bottle beneath one’s arm, an anecdote or two polished – only to find the room deserted, the lights turned high, and the Krug souring on the coffee table.
Photograph by Nikolai Von Bismarck
At many points throughout the book, I jotted an exclamation mark in the margin. The passages set at Vanity Fair in the nineties and early noughties are peppered with them. Sixty Concorde flights a year. Assistants with assistants to manage their assistants. An eyebrow lady effectively contracted to the office. A driver in each city. Town cars (is there a sweeter type of car?) everywhere. Exquisite private bathrooms in personal offices. Every few hours, a woman in an English maid’s outfit would come around to make fresh coffee. “Flowers were sent out to contributors at an astounding rate,” Carter writes, “sometimes just for turning a story in on time.” Senior figures were provided with interest-free loans by the company to buy houses or apartments. “My passport picture was taken by Annie Leibovitz!” writes Carter, providing an exclamation mark of his own. “This, in essence, was Vanity Fair,” he concludes. “Younger people would never understand the expense-account stories of the time, because that all disappeared with the Great Recession, in 2008.” (The first day of my working life happened to be 15th September that year, the morning that Lehman Brothers filed for bankruptcy.)
“It was kind of like boiling a frog,” Carter says now of those golden days, as we chat on a video call in early March. “You sort of get used to it. When I first got there, I thought: ‘My god! I couldn’t believe it’.” The catering budget at an Annie Leibovitz cover shoot for the crew alone was more than the entire editorial budget for an issue of Spy – the magazine with which Carter and his co-editor Kurt Andersen made their name in the eighties. “It was like moving from a youth hostel to a five-star hotel,” he writes of his career trajectory. (And there were plenty of hotels – The Connaught, The Ritz, Hotel Bel Air, the Hotel du Cap-Eden-Roc.) But the largesse, Carter points out now, “only worked if you were successful and you made money for them. And Vanity Fair cost a lot to produce, but it made money for years. It was the most profitable monthly at Condé Nast, and therefore probably one of the most profitable monthlies in the world. There were issues when we’d have more than 300 pages of advertising, at close to $100,000 a page. So it was hugely profitable.” (Cocktail napkin maths: $30 million in ad revenue per issue.)
Carter during his last day in the office of the New York Observer, 1992. Photograph by Dafydd Jones
This is fair enough. Work can be more fun than fun when the work is really working. So one races through the book not with generational resentment (though whiffs of $43,000 Upper East Side apartments might sting anyone of any age today) but with a sort of wide-eyed wonder. Nostalgia tourism. This is made all the easier by the warm, bright, Manhattan morning light in which Carter bathes the stories and anecdotes, not to mention the natural self-deprecation that’s common to all good raconteurs. “Somehow, in my case, with a lot of mishaps and a dollop of good luck along the way, things just worked out,” he writes.
The other thing that helps is the picaresque mood of the book and of Carter’s own career. The going was good, but it was rarely straightforward. There are adventures and scrapes; heroes, villains and “an eye for the main chance”, as PG Wodehouse’s bounders would say. Gives one hope, in a funny sort of way. It is easy now to imagine that Graydon Carter emerged into this world with a martini in his hands and a Dorothy Parker quote on his lips. A debonair toddler in a velvet smoking romper; a whip of white hair on his head like soft-serve ice cream. As it happens, though, he was raised in a suburb of Ottawa, Canada – a place where ice hockey was a religion and “everyone had a frostbite story”. Growing up, Carter writes, “I worried at times that I was destined to become little more than one of those faceless, nameless men in the scenery of someone else’s better life.”
"I was the least popular candidate that could have ever been presented before them. The office was poisonous..."
“I knew nothing until I turned about 19 or 20,” he says now. “No ambitions. No passions beyond hockey, skiing, music and reading.” But he loved magazines and was a good draughtsman, and so soon enough became the art editor, and later editor proper, of a magazine called The Canadian Review while he was at college. “The magazine was really good, considering that nobody knew what they were doing, but also objectively not very good,” he says now. Its circulation of around 50,000 would make many national magazines weep in 2025. “Yes, it was surprisingly large, but it never stopped losing money,” Carter says. “And after three years, we just ran out of money in the end”.
Before this, Carter had worked for six months as a lineman on the Canadian railroads. “That was sort of a tradition in Canada that middle-class parents send their kids out,” he says. “We were white and soft.” On the first day, he spotted a chart that showed workers how much they’d be paid for any limbs they lost on the job. You’d get $500 for a leg. “So I spent six months climbing telegraph poles way out in western Canada, living in a boxcar where almost all the other crew members had minor criminal records. But it was one of the great experiences of my life,” he says. “And, as it turned out, one of my favorite jobs.”
“I actually think it strengthened me in a way… I can talk to almost anybody as a result. I had a great time with the other guys in the boxcar. We lived in bunk beds. It toughened me up,” he says. “And to survive in the magazine business for over half a century – I was one of the youngest editors when I started, and I think I’m probably one of the oldest editors now – that is not without its bumps.” On his final day on the tracks, a train slowed down to pass by in the twilight, and through its soft-lit window Carter spied a handsome couple drinking cocktails. “I knew one thing,” he writes: “I wanted to be on the other side of that window.”
Carter at the Vanity Fair Oscar's Party, 1997. Photograph by Dafydd Jones
And so, after The Canadian Review sojourn, Carter travelled down to New York, and to the centre of the universe. There were bumps, then foothills, and later the glossy Olympian peaks of Vanity Fair and beyond. But first, there was a stint at Time magazine while it was at the very height of its power. “It was hugely successful, had a vast circulation, and was highly influential,” Carter says of the publication he joined in the late-seventies, just after moving to New York. “There was a magical realism to Time in those days,” he writes, and there’s certainly a Wonkaesque wonder to the passages set there. Great pneumatic tubes sucked artillery shells of copy from floor to floor. There was a bar at the end of each corridor, and “staff in uniforms brought dinner (with wine) to writers’ offices”.
“It was wonderful,” Carter says. “We had vast expense accounts. It was a lot of very smart people thrown together who were all starting to find their way. And so many of them became heads of magazines, Pulitzer Prize winners, esteemed producers, columnists.”
One of these very smart people was Kurt Andersen. “Kurt was doing very well at Time, and I was floundering,” says Carter, “but at the same time we had a similar sensibility. We were good friends and he was the perfect partner for me.” The pair started dreaming up a new type of magazine, on their lunch breaks and in the gaming arcades of the city. A publication that might capture the peculiarities of life in New York in the power-shouldered 1980s – an island filled with exotic new species and apex predators that required, Spy’s founders felt, a certain taxonomy or field guide. Or, in some cases, a dart gun.
Spy magazine launched in 1986 with the tagline “fun, funny, fearless”, and I have always liked that distinction between fun and funny. (How many funny people do you know who are actually quite hard work? And how many good-time people do you know who are eerily humourless?) It seemed about right: the magazine was funny in a way that many sincere American magazines weren’t (a great early inspiration was Private Eye), and yet had a helter-skelter sense of play that was eminently attractive. “We had a hoot,” he writes. It was also good looking, with refined type and handsome layouts that lent a sophistication to the tomfoolery.
But it’s the fearless thing that’s most intriguing today, in an age where most slights and skewerings are met with social media pile ons or ruinous lawsuits from on high. Carter and Anderson – aided by that outsider-insider viewpoint; the Canadian and the Nebraskan in New York – were goading some of the most powerful people in the city on a monthly basis. One of their trademark weapons was the use of devastating recurring epithets. Donald Trump (more on him later, in all senses) was a “short-fingered vulgarian” based on his tiddly, well-groomed paws. Laurence Tisch became a “churlish dwarf billionaire”. And, most gorgeously of all, Henry Kissinger became a “socialite war criminal”. Did they feel truly fearless at the time?
With Diana Princess of Wales, Serpentine Gallery Gala, 1994. Photograph by Dafydd Jones
“Strangely enough, we didn’t have that much in the way of anxiety,” Carter says. “I mean, we tried to choose our subjects carefully. We were in our thirties, so you’re a very different person than as you get into your forties or fifties. We did take on The New York Times, which was then the centre of the entire intellectual universe in New York. We wrote every month about the editors there, which would drive them slightly crazy. And that was probably the most dangerous thing we did on a regular basis.” It was a practice, he writes, that would usually “court certain career death”. But the reports were also hugely influential, and gave a delicious glimpse of life inside the ivory tower. “The day the column came out, work would all but shut down at the Times while the reporter-level hands photocopied and passed it around,” Carter writes.
“We also made great fun of people like Donald Trump, who became a recurring character/villain in my life,” Carter says. His first collision with Trump was a cover profile he wrote on the real-estate, nepo-baby for GQ in May 1984. Trump hated it, and so sent his minions out into the city to buy up and destroy every copy they could find. The story goes that the inflated newsstand sales convinced Condé Nast’s owner Si Newhouse that Trump was a bona fide star, and that this was part of the reason he pushed through the Trump memoir, The Art of the Deal, in 1987 with his publishing entity Random House. As of 2025, there have been no further repercussions.
Trump was a constant figure of fun at Spy, who threatened to sue the magazine repeatedly and would seed rumours of its imminent downfall to other publications. In response, the editors put together a story called ‘Death be Not Short Fingered’, which gave an insurance actuary Trump’s “height, weight, his eating habits, his age,” Carter says. “The actuary gave us an estimate of when Trump was going to die. So we started a sort of countdown clock.” Later, while at Vanity Fair, as Trump was running for the Presidency in 2016, Carter assembled all the vitriolic tweets Trump had posted about him in the corridor outside his office. He would joke that it was the only wall Trump ever built. Spy’s “sheer shock value” made it a huge and pretty much immediate hit. The magazine, which had been created to write about New York, soon expanded its horizon and distribution to cover the whole country. It was massively successful. Too successful for its own good, in fact. “The math just didn’t hold up,” Carter writes. “The gap between when we had to spend the money and when we would get paid for advertising and copies sold was still uncomfortably wide.” And so Carter and Andersen courted an offer from Charles Saatchi and Johnny Pigozzi to buy the company in 1991. Their involvement saved the magazine, but spelled the end, in many ways, of its precious editorial independence and nimbleness.
Soon, Carter was poached to run The Observer, a “weepingly dull” Manhattan newspaper that for some reason ran a map of New York City on the second page of every issue. Carter gave it bite and colour, and sent it to all the editors and interesting people he knew. Meanwhile, as Si Newhouse prowled the various outposts of his empire, he began to notice its salmon-coloured pages on many of his people’s desks.
And so a year or so later, when the time came for a ritual shake-up of Condé Nast’s editor posts, Newhouse happened on the idea of Carter for either The New Yorker or Vanity Fair, which had been resurrected in the eighties by Tina Brown. Carter said he wouldn’t mind taking on The New Yorker, thanks very much, and for several weeks it looked like he would – until Newhouse told him, on the day of the announcement, that Brown would get the post instead, and Carter would take over at Vanity Fair. The appointment appeared as something of a poisoned chalice. After all, Carter had spent the past half decade poking fun at the magazine’s powers-that-be, and his arrival at the office was met with both bewilderment and bile. “You could feel the venom in the corridors,” he writes.
“I was maybe the least popular candidate that could have ever been represented before them,” Carter says now, noting that a new editor was often accompanied with a rapid clearing out of staff. “The office was poisonous; it was very combative. I prefer a collaborative, collegial, appreciative office. I don’t like drama. The first two years at Vanity Fair were pretty dreadful.” Rumours circled constantly that the new editor would be ousted almost immediately. Every morning, Carter would check to see whether his name was still on the address board in the lobby of Condé Nast’s Madison Avenue headquarters. “That’s how tenuous I felt my residency at Vanity Fair was.”
Carter and John Scanlon at the White house Correspondents dinner, 1994. Photograph by Dafydd Jones
Advertisers were unhappy. Readers were allegedly “horrified” by editorial choices. “In those early days and months, pretty much everything went wrong.” And the workplace was a “viperish nest”.
After two years of rumbling hostilities, Carter let three particularly sour apples go, all in the same week. They had, he says, mistaken politeness for weakness. “It was more people than I’d ever fired before in my life,” he says. “But the clouds cleared, and for the next 23 years I had the office I wanted to have.”
After those rocky early days, Vanity Fair as we know it began to emerge – a whirl of shimmering celebrity, delicious scandal, powerful rooms and friends in high places. Carter’s stature and acclaim grew with his trademark flourish of hair. His principle was that “if you take care of the talent, you’ll get better work”. And under his tenure, the publication’s talent – from Christopher Hitchens (his first signing) to Dominick Dunne to Annie Leibovitz to Herb Ritts to AA Gill to Michael Lewis to Mario Testino – routinely produced work that was singular, excellent and provocative. The pages had style, flair, and a knowing world-view – clubbable, but never cloying – which stemmed from the sensibility of the editor.
One of Carter’s biggest innovations was the Vanity Fair Oscars Party – for a time the shining Everest of social bashes. It was a gargantuan affair organised with the ruthlessness and elan of a military coup, descending on LA each February in a flurry of publicists, PRs and planners. “It hinged on having more movie stars per square inch than any other party in the world,” Carter writes.
At the party’s height, the team would knock out the entire back wall of Morton’s, the LA restaurant where it was held, in order to fit enough people in. They’d rebuild it the next day. The head of security for the event was a former NYPD counter-terrorism expert – a worthy match for the many wily gatecrashers who would attempt to sneak in. There was a great deal of thievery, not all of it encouraged. The organisers hoped people would steal the beautiful bas-relief ashtrays to display on their desks and coffee tables as proxy-advertisements for evermore. They were more surprised when the guests smuggled out “decanter-sized” bottles of Dior fragrances from the bathrooms. One night, Adrien Brody was spotted pinching an exquisite bespoke table lamp. “He’s a gentleman, and a charming one at that, and he still apologises any time I see him,” Carter writes.
"If you're my age, not a day goes by that you don’t factor out how many years there are left”
The party was Carter’s Vanity Fair made flesh. Its success and cachet was reflective of the magazine’s supremacy, but also of the supremacy of magazines in general across the 1990s and early 2000s. We all know what happened to the industry next – those twin terrors of the internet and the 2008 recession combining to slowly strangle the publishing world.
Things declined “gradually, then suddenly,” as Hemingway would have it. Carter stayed at Vanity Fair for another nine or so years, and the magazine sometimes felt like one of the last holdouts from the old world. It introduced franchises such as ‘The New Establishment’ that reflected the shifting power centres of the internet age: Silicon Valley; the flash boys of Wall Street; the new crowd in Washington; the latest cadre of internet-era celebrities. A landmark cover story, crafted in military-grade secrecy, revealed to the world Bruce Jenner’s reassignment surgery to become Caitlyn Jenner – a scoop that made headlines globally and prompted a supportive tweet from then-President Barack Obama.
And then one day, when he was preparing to leave for the Vanity Fair New Establishment Summit in 2016, Carter received a call from Anna Wintour, Condé Nast’s newly minted editorial director. “As blithely as you would tell someone you wanted to change the colour of their drapes,” Carter writes, “she informed me that there were going to be some changes at the company”.
The adjustments were “dumbfounding”. Many departments at the magazine would be folded into a central unit at Condé Nast, representing “almost half my staff,” Carter writes. He felt it was “an unnecessary and potentially catastrophic move” which would undermine the uniqueness of the publication, as well as its journalistic integrity. He had a meeting with Wintour in which she hymned the “glorious efficiencies” of her plan, and Carter “got a bit heated” and said that nobody in the editorial department had even been consulted on the move. Wintour said she had discussed it with many others – though mostly people in Silicon Valley. “And from there, things began a slow decline,” Carter writes. “You never know you’re in a golden age. You only realise it was a golden age when it’s gone.” He left Condé Nast in 2017 after a quarter of a century at Vanity Fair. (Media commentators have been sceptical of the title’s relevance ever since.) When the news of his departure broke, friends saw his name on the alerts and assumed he had died.
After such a glittering and all-consuming tenure, many people would have simply put up their feet and relaxed. And for a while, Carter did just that. He moved to the South of France for an extended break with his family, and set about replying to the 2000 or so people that had written to him on the news of his retirement from Vanity Fair. But after a month or so of pootling around Provence and swimming laps in the pool, he began to get a “bit itchy”. Reading the local papers one day, he formed the idea of a private newsletter for his friends in the USA, which snipped up the best and juiciest bits of the European and international press and passed them on. This humble dispatch soon became Air Mail, which launched in the summer of 2019 as an exquisitely formed weekly newsletter, and which now exists as a fully fledged and heavily subscribed media entity (The New Yorker estimates it has about 400,000 paid subscribers.) It has somehow managed to take the gloss and gumption of the golden days into the often inelegant digital realm. In 2023, Air Mail threw a party at the Hotel du Cap during the Cannes Film Festival that rivalled even those in the heady Vanity Fair days. The going ain’t too bad, even now. But I ask Carter why he didn’t decide to lie on a beach somewhere and work on his tan; why he felt the need to tough it out in the brutal world of digital media startups.
Photograph by Nikolai Von Bismarck
“Because I don’t play tennis and I don’t ski anymore,” he says. “There’s only so many hours in the day you can read. I love doing what I do, I’ll probably do this until I drop and I can’t think of anything better than being an old-fashioned editor. Even though I’ve been doing this off-and-on for more than half a century, the job is not appreciably different than when I first started out. I’m just much better at it.” I tell him that I asked a similar question to Johnny Pigozzi, his old associate, a few years before, and that Pigozzi had replied: “I do as many things as possible so I do not think about death.”
“That’s Johnny,” Carter says. “Everybody thinks about death on a regular basis; any sane person. If you’re my age, not a day goes by that you don’t consider how many years there are left,” he says. “I was sitting in my bed the other day, and I thought, ‘Thank God I don’t suffer from sentility’. No: sensility. No: sensilly,” he laughs. “And it took me 30 seconds before I got to ‘senility’. I get the irony that I’m having trouble remembering the word senility while thinking I’m blessed in not having it…”
“So I appreciate every day and morning. I wake up to think, ‘OK, what does the day ahead look like?’ And I think: ‘OK, I’m really lucky.’ I look out the window and I can see the rooftops of New York…”
The days remain busy and full. Running Air Mail, he says, is as enjoyable as any job he’s ever had. “I simply love being an editor,” he writes, and while he jokes in the closing pages of the book that he could well have “moved to Florida” to concentrate on his golf game, he much prefers instead to “get on with the life I have chosen and the life I love”. At the end of his memoir, Carter offers “Some Rules for Living”. The chapter gives various bits of decent advice, from using double-sided place cards at parties (simple but ingenious) to how to pick a life partner. (F.I.S.K is the watchword here: funny, interesting, smart and kind.) The final rule is to “always carry a handkerchief,” and Carter outlines 25 justifications for the item – a jolly throwback to a gentler time. “When all else fails,” he concludes, “it is something to wave in the air when it is time to surrender.” But not yet.
Before I spoke to Carter, I stumbled on an old iPhone note from 2018, when I’d just started working for Gentleman’s Journal. It was about Carter’s ideal editorial mix for a magazine issue. Alongside a decent literary story and a high society scandal, it advocated for “a proper narrative piece about someone’s life”. The reason, set in bold in the note, is one that’s borne out by this bright, rich book and the career it captures. “Big lives are life-affirming.”
For more from 90s New York, discover Dafydd Jones's party photographs...
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