Graydon Carter, Vanity Fair’s big-spending editor for two decades, has written a star-strewn memoir. They were different times, he tells Hadley Freeman.
Graydon Carter, the last great bon viveur of American print journalism, has called his new memoir When the Going Was Good, and, oh boy, was it good. Reading
“No, I think it was the time I thought it would be fun to get all the Bond girls together in a group photograph. This was before the internet, so it was not easy to track them down, but we found them all except Claudine Auger. But eventually we track her down and we fly her over by Concorde, put her up at the Carlyle. And then we get her in the office and at that point we realise this woman is not Claudine Auger,” he says with a laugh. She was Claudine Longet – a French actress, yes, but not the one from Thunderball. So back she went across the Atlantic.
“So you flew to New York from London?” Carter asks me. Yes, in the back row of economy, I reply. He makes a sympathetic cluck: “Different times.”
We are sitting in a booth at the Waverly Inn, the chic West Village restaurant he opened in 2006, a few doors down from the des-res four-storey townhouse where he once lived with his second wife, Cynthia Williamson, and their four children, and around the corner from the apartment where he now lives with his third wife, Anna Scott, and their teenage daughter. Just down the road is the office for Air Mail, his digital newsletter. Launched in 2019, it is, like Carter, fun and gossipy (sample story: “Was Sean ‘Diddy’ Combs’s father murdered by the Gambino crime family?”).
Carter adores this neighbourhood, where whispers about the celebrity residents creep around every corner like ivy. Harvey Weinstein used to live across the street from the restaurant, “and the day the family moved out I was walking my daughter home from school and they had thrown out all the shag carpeting that had been in his screening room. I said, ‘Don’t touch that, sweetheart. You don’t know what’s been on that,’” he says. So Carter knew what Weinstein was up to? “The rumours were always there. But no journalist could make them stick until someone did.”
Carter, 75, still has his signature triangular Beethoven hairstyle – “No, I look like Barbara Bush,” he corrects me. He has the air of someone who knows absolutely everyone but he is also very good at laughing at himself, which I would not have expected when he was in his pomp, during his 25 years as the editor of Vanity Fair and one of the most influential media figures in the world.
He had a reputation for being unflappable, even when faced with the flappiest of A-list celebrities. One year, at the very invite-only Vanity Fair Oscar party – which he launched in 1994 – Courtney Love told him that he had to let her manager in too. “Why?” Carter asked. “He’s got my money, my car keys and my drugs,” Love replied. “I can’t deal with this right now, Courtney,” he said, and sent her to Sara Marks, Vanity Fair’s director of special projects and its chief party organiser. Marks said no, so Love went outside to made an announcement to the banks of photographers and video crews covering the party. “I just want to say one thing,” Love shouted. “Sara Marks is a c***.” “I felt terrible but I had to admire Courtney’s novel use of the technology available,” Carter writes in his book.
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Advertise with NZME.At another Vanity Fair party Russell Crowe grabbed Carter by the shoulder and snarled, “I have a bone to pick with you. Why have you never put me on the cover?” Carter steered him to the bar and they talked over a few drinks. A couple of years later he did photograph Crowe for the cover “but he was growing a beard, which was not working”. The cover was binned. Was Crowe mad? “I’m good at defusing situations,” Carter says.
The 1990s and 2000s were a golden age for magazines, although, as Carter writes, “You only realise it was a golden age when it’s gone.” He took over from Tina Brown as Vanity Fair’s editor in 1992, when the internet hadn’t yet cannibalised print journalism and Carter had “a budget with no ceiling – as in, it was unlimited”. Now that celebrities post selfies on Instagram every day, it’s hard to believe how interested people once were in who would be on the cover of his magazine each month. But they really were.
In 2015, when Caitlyn Jenner wanted to show the world how she looked after her transition, she didn’t go on any of the Kardashian reality shows with her family – she came out on the cover of Vanity Fair. The annual Hollywood issue, which Carter launched in 1995, was a talking point every year as people looked to see which young actors had made the cover. And its record was pretty good: Leonardo DiCaprio, Nicole Kidman, Joaquin Phoenix were cover stars, whereas the now much lesser-known Skeet Ulrich and Barry Pepper were tucked away in the gatefold.
In 2006 I rushed out to buy the magazine when it published its exclusive photos – taken by Leibovitz of course – of Tom Cruise and Katie Holmes’s new baby, Suri. Leibovitz’s photos were sent to the printers chained to the wrist of a security guard to prevent anyone leaking them to the tabloids. “Looking back at it now, I honestly find it difficult to understand what all the fuss was about,” Carter says today about the Cruise baby. “But, God, it was fun at the time.”
Carter has an amusing habit of introducing people by describing what their parents did, such as his assistant at the satirical monthly magazine Spy, the journalist Aimée Bell, whose “father had been a GE executive”. Or his wife, whose “father, Kenneth Scott, had had diplomatic postings in Washington and Laos. He was then appointed to be one of the Queen’s private secretaries. The job came with a grace-and-favour apartment in St James’s Palace, where Anna spent her teenage years.” And yet in his memoir, once Carter leaves behind his parents and his home country, Canada, he makes almost no reference to them again. Whereas others are defined by their background, he seems entirely self-formed. “New York was my focus from the age of 12 or 13 and all I could think about was how to get here. I just wanted to get in the melting pot and melt,” he says.
New York or bust
He grew up in Ottawa, the son of a pilot and a housewife. It was a pleasant outdoorsy life, but he longed for the glamour of Manhattan, which he read about in books. While drifting through his studies at Ottawa University, he joined the college magazine and soon became its editor. The magazine destroyed his brief first marriage “because I found something that changed my life and then I was never home”. But it gave him a route out of Canada, on to a journalism course in Yonkers, New York, and then a job as a trainee writer on Time magazine. He had no money for shampoo but he made sure to buy a posh suit “to look the part”.
It worked. Soon he was hanging out at the 21 Club where he spotted Frank Sinatra and going to Studio 54 with dancers from the Rockettes, just as he’d dreamt. “Back then, being a journalist gave you access to the entire city,” he says. It helped that the city was so cheap then too. His first apartment in Greenwich Village in the late 1970s cost $220 a month. Thirty years later his daughter and a roommate rented an almost identical apartment around the corner. The monthly rent? $5500. As Carter would say, different times.
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Advertise with NZME.In 1986 he launched Spy with Kurt Andersen, a former colleague on Time. Carter envisioned the magazine as an American version of Private Eye and he even flew to London to meet its editor, Richard Ingrams, about whom he still talks in tones verging on reverential. “Americans think of Canada just as America’s attic, but if you grow up in Canada half your culture comes from the United States and half comes from Britain, so in terms of journalism and humour it’s actually a great advantage,” he says. This explains his Anglophilia: when he later got to Vanity Fair he surrounded himself with British writers including Christopher Hitchens, AA Gill, Henry Porter and Andrew Neil. To help him write his memoir, he enlisted the British writer James Fox. His third son, Spike, is named after Spike Milligan.
British journalists, he says, have an irreverence mixed with erudition – but not all of them. In the mid-1990s Carter briefly hired Toby Young, “which was a mistake”. By Young’s own admission, he achieved little at the magazine as a contributing editor, but succeeded in turning his stint there into his 2001 memoir, How to Lose Friends and Alienate People, in which he depicted Carter as a bully and a snob. “The impression he gave was of a man who’d gone to a great deal of trouble to cultivate a particular image of a faintly bohemian Wasp with literary aspirations,” Young writes, “but was only too happy to contradict it the moment he opened his mouth.” Carter says he “absolutely” never read the book, although he did see the 2008 film of it, but only because his character was played by Jeff Bridges (Simon Pegg played Young). To be asked about Young all these years later, Carter says, “is like having long Covid”.
Whereas Private Eye focuses on politicians and journalists, Spy mocked the grandees of Manhattan. From the very first issue it went after Donald Trump “because he was already the noisiest of the parade floats”, Carter says. He had started teasing Trump before he even launched Spy, beginning when he interviewed him for the cover of GQ in 1984 and portrayed him as a tacky braggart – an “outer-borough sharpie”, as he puts it – with hands too small for his body. Trump was so enraged he got his staff to go out and buy up every copy on the New York newsstands so the public wouldn’t see it. Years later Carter was told that, because the issue had sold so well, a publisher commissioned Trump’s book The Art of the Deal, which later led to him being cast on The Apprentice, which turned him into a mega celebrity. “A butterfly’s wings,” Carter says with a shrug.
This tale is as revealing of Carter as it is of Trump. After all, he could have gone after Trump for his dependency on his family money or his stupidity – but instead he went after him for having no taste. “But his shirt cuffs come down to here and his cufflinks are this big and all this makes his hands look smaller. I could do a makeover in two seconds!” Carter protests.
Does he ever think it’s this kind of snobbery that kick-started Trump’s rage with what he calls the “elites”, despite his own inherited wealth?
“But it wasn’t real wealth – it was just Queens wealth,” he says, referring to the outer borough where Trump was born.
I give him a “yes, that’s the kind of snobbery I mean, Graydon” look. He laughs at himself again. I suspect that on some level he took against Trump from the start because the latter always had money but no taste, whereas Carter always had taste but no money. Does he now think he underestimated Trump?
“No. I don’t recognise this man. If it comes out in 15 years that this Trump was a Manchurian candidate, I wouldn’t be surprised. The Trump I knew was someone who just wanted to be liked. And in the absence of that, well, I guess this is how he’s gone.”
Wintour chill
After a brief stint as editor of The New York Observer, Carter took over Vanity Fair in 1992. Critics carped that the magazine was all puff and fluff, and that’s fair about the celebrity profiles. Tom Cruise was so pleased with his coverage in the magazine that he sent Carter a printed sheet encased in Plexiglass outlining the tenets of Scientology. But when I think of the magazine’s heyday I think of Dominick Dunne’s rage-filled dispatches from the OJ Simpson and Menendez brothers’ murder trials that made me want to be a journalist, or Christopher Hitchens’s screeds against Bill Clinton. Carter says his favourite story was the magazine’s 2005 unmasking of Deep Throat – the codename for the FBI source who leaked details about the Watergate scandal.
Carter’s handling of some stories has come under scrutiny. In 2003 he published a profile by the journalist Vicky Ward of Jeffrey Epstein. After the financier and paedophile died in 2019, Ward claimed Carter had refused to run quotes in her article from women who said they had been attacked by Epstein. Carter said her reporting simply wasn’t good enough and that the article didn’t meet their legal standards. Does he have any regrets about his editing of the story now? “I have regrets we didn’t have a better writer so we could have run the story. But I’m not going to talk about [Ward],” he says with a sudden flash of anger.
The financial crash of 2008 made journalism “more challenging”, as Carter puts it, but an even bigger force hit him eight years later: the Vogue editor Anna Wintour. The two of them had been mostly friendly rivals throughout Carter’s time at Vanity Fair, although she “tends to greet me either like her long-lost friend or like the car attendant”, he writes. But then she was promoted to Condé Nast’s editorial director, making her Carter’s boss. He “saw the writing on the wall” and in 2016 decided it was time to step down. “It’s funny, Anna’s job title has gotten longer as Condé Nast has gotten smaller. She’s like one of those Ruritanian princes,” he says. He includes some pretty cheeky anecdotes about Wintour in his memoir too, such as her leaving a meal as soon as she’s done, even if her “dinner-mates might be mid-bite. More often than not, after a meal with her, I’ve had to stop off on the way home to get something to eat.” Does he worry about her reaction to the book? “I think I was pretty generous! She might be a little more frosty. But she was always sort of frosty.”
Today’s Vanity Fair, under its editor Radhika Jones, is, in my opinion, less fun, less interesting and don’t even get me started on the dull covers. “You can say that, I never could. I haven’t held a copy of the magazine since I left,” Carter says cheerfully. He does, however, look at it online and he counts how many fewer adverts it gets than in his day. He knows that sounds “really trite and small”, but his satisfied smile suggests it’s worth it.
Carter insists he would have been happy to be a stay-at-home husband all his life looking after the kids, who now range in age from 41 to 16. But I don’t believe him. After all, he lasted only a few months of what was supposed to be retirement when he left Vanity Fair before he started planning Air Mail. If he was still at Vanity Fair, who would he put on the cover this month?
“Oh, I wouldn’t have a clue,” he begins. But then, as if despite himself, he bursts out, “Oh, Leo Woodall!”
Still got it.
Graydon Carter extract: My 30-year spat with Trump
My durably contentious relationship with Donald Trump had begun with an observation I made in a 1984 profile of him in GQ – his first major national exposure – to the effect that he had remarkably small (if neatly groomed) hands. This was ratcheted up to “short-fingered vulgarian” in the pages of Spy. When I got to Vanity Fair the transactional Trump realised that a strategy shift was in order. Notes complimenting me on an article or a particular issue began to come my way. He sent me a couple of Trump ties. They were a basic blue and a basic red, and they were as stiff as a child’s toy sword. He sent me bottles of Trump vodka.
An invitation to Trump’s wedding to the actress Marla Maples appeared. I went, out of journalistic curiosity – or at least that was how I reasoned it to myself and to my friends. It was in the Plaza Hotel, which Trump had recently bought, and we were in and out in a couple of hours. I’ve seen more honest emotion at an early morning Starbucks line. When I bumped into Trump in Palm Beach, he invited me to join him for dinner at Mar-a-Lago. We had “surf and turf”– something I hadn’t eaten in 20 years. Trump lived the way a poor person in a folktale might have imagined how a rich person lived – high up in gilded faux Regency and Louis XIV surroundings.
In the early 1990s he announced that he was making a comeback. In 1989, at his peak, at the height of the real estate boom, he had told Forbes magazine that he had a net worth of $3.7 billion, which Forbes adjusted to $1.7 billion. When the real estate market collapsed, Trump found himself almost $1 billion in debt.
Now he was back, he said. He was taking his casinos public in a deal that he claimed would net him billions. I thought a story on this purported comeback might prove interesting and ordered up an article and a photoshoot. During the sitting the stylist decided that the Loro Piana cashmere sweater she had given Trump to wear wasn’t right. She asked him to remove it. Trump refused to pull it up over his head, not wanting to muss his elaborately assembled confection of hair. There was a standoff. Finally, one of the assistants on the shoot was sent to get scissors to cut the cashmere sweater up the back so it could be taken off.
The Trump-Carter truce was not to hold. Try as I might, I couldn’t resist making fun of him and thus vanished our days of bonhomie and transactional friendliness. In time, with his new Twitter handle, he fired back after every perceived slight. At first, the hurt was palpable: “Dummy Graydon Carter doesn’t like me too much… great news. He is a real loser!” he tweeted in December 2012. And then, the next day: “Graydon Carter has no talent and looks like shit! Also, his food sucks”– this referring to the Waverly Inn, a restaurant I was a partner in.
Trump has variously called me “no talent”, “sloppy”, “grubby”, “dopey” and “sleepy”. He wrote that my wife thought I was a “major loser”. Just days before he launched his campaign for the presidency, Trump sent me a tear sheet of a nearly 20-year-old magazine ad for The Art of the Deal. In gold Sharpie he had circled his hands in the photo of himself and written, “See, not so short!” I almost admired the effort he put into his valiant attempt to show me the error of my ways. I wrote “Actually, quite short” on a card, stapled it to the ad and sent it back to his office. This ignited another frantic flurry of tweets.
Trump provided inexhaustible copy – as did so many of his type. Wealth, in a few hands, was growing exponentially and the people who had it were anything but shy about showing it off. Rich people were either stealing from each other or trying to kill each other and it was a great period for journalism. When there’s that much money at stake it brings out the charlatans and the grifters, like worms after rain.
© Graydon Carter 2025. Extracted from When the Going Was Good: An Editor’s Adventures During the Last Golden Age of Magazines by Graydon Carter (Grove Press).
Written by: Hadley Freeman
©2025 TIMES OF LONDON
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