After our interview, Graydon Carter emailed me.
“Oh God, did I do okay yesterday? Too boring? Too indiscreet? Drank too much? Didn’t drink enough?”
This was something I had failed to notice about Mr. Carter during his plummy, powerful quarter-century astride a glittering Vanity Fair. This one-time social arbiter, who ran a wildly successful magazine in the peak era for glossies, has social anxiety.
How could the man who caused so much social anxiety, when he mercilessly decided who was in and who was out for the most exclusive parties on the planet, including his white-hot Oscar parties, have social anxiety?
“I’m not cool — I’m the squarest person you’ve ever met,” he says, unconvincingly.
We both started at Time magazine in the early ’80s, a louche era of bars in offices, clouds of cigarette smoke, cascading illicit affairs, sumptuous dining carts of roast beef rolling down the halls and expense accounts so lavish that a top editor would think nothing of sending someone from Paris to London to fetch a necktie he had left in a hotel room.
I knew Mr. Carter only slightly back then, but he sure looked confident and debonair to me. Unlike a lot of the men at Time, he wasn’t condescending to the few women writers there. My impression, when I met him, was of a Canadian who seemed to want to dress and talk like a Brit, with dandy aspirations and an upper-crust pronunciation of rather as rah-ther.
“It was a British suit,” he affirmed, laughing. “Well, you know, nobody’s going to buy a Canadian suit.”
As Walter Isaacson, the biographer and a former head of Time and CNN who was also part of our class at Time, recalled: “Graydon had both more style and more of a sense of adventure than any of us. I always envied the fact that he spent his time huddled with Kurt Andersen figuring out how to start Spy magazine when the rest of us were just typing away.”
Mr. Isaacson said that Mr. Carter belongs to the pantheon of illustrious editors who followed in the footsteps of Clay Felker at New York and Jann Wenner at Rolling Stone — journalists loaded with flair who defined the golden age of magazines.
Mr. Carter’s new memoir, “When the Going Was Good,” recounts his odyssey from the Canadian provinces to Manhattan, where he started Spy with Mr. Anderson, edited The New York Observer and landed at Vanity Fair in 1992. For the next 25 years, the magazine was at the pinnacle of media, politics and celebrity, helping to shape the culture. It was the home to distinguished writers (Christopher Hitchens, Dominick Dunne, Michael Lewis) and photographers (Annie Leibovitz, Herb Ritts, Mario Testino.)
Mr. Carter’s book — written with guidance from James Fox, the author of “White Mischief” and the co-author of Keith Richards’ memoir — goes into what it was like to be a celebrity editor when such creatures were more common. He tells a charming tale of how he navigated the Empyrean kingdom of Condé Nast while managing the egos of his beloved, neurotic stable of writers and palling around with and sometimes angering the media titans in his magazine’s orbit.
He also describes his decades-long relationship with a certain real estate developer turned two-time president. And, yes, there are some juicy pages about his fellow celebrity editor, Anna Wintour.
“Tina Brown brought magazines into the world of high-low,” Mr. Isaacson said of Mr. Carter’s predecessor at Vanity Fair, who conjured the template for its 1980s comeback. “What Graydon added to the party is, he brought magazines into the world of insiders-outsiders. He can be the most clubbable guy at the Waverly Inn but also retain his amusement at looking in from the outside.”
Once the young man from the Great White North had Cinderella-ed his way into becoming a Manhattan insider, he guarded that image. Jim Kelly, a former colleague of ours at Time who became the top editor there, recalled that once, after the two men had gone to Paul Stuart to buy shirts (striped, with a white collar, for Graydon), Mr. Carter asked his friend to carry his shopping bag back to the office. “He never wants to look like a tourist,” Mr. Kelly said.
When another writer at Time said that he had bought five suits for $100 each, so that he could wear a different one each day of the week, Mr. Carter noted to Mr. Kelly: “Here’s the difference between that person and me. He buys five suits for $100 apiece and will look shabby five days of the week. I will buy one suit for $500 and look great at least one day of the week.”
Mr. Carter has been compared to Jay Gatsby because he reinvented himself, going from a Canadian railroad lineman and gravedigger (for a day, until he realized how hard it was to dig frozen ground) to a Manhattanite who grew accustomed to flying to London to buy bespoke Anderson & Sheppard suits. But he didn’t have a nefarious fortune backing him, only the largess of Si Newhouse, the former Condé Nast chairman.
These days, the 75-year-old Mr. Carter works with Alessandra Stanley coediting his online creation, Air Mail, a weekly confection that hits your inbox Saturday mornings like something wrapped in cashmere. Air Mail would have been a delicious target for the wicked eat-the-rich satirists at Spy.
“They definitely would have focused on Graydon’s obsession with handkerchiefs,” said Mr. Kelly slyly.
The Air Mail office — chronicled in Architectural Digest — occupies a 19th-century brownstone on West 9th Street in the same stretch of the West Village as his apartment, the Air Mail Newsstand shop and the Waverly Inn, of which he is a co-owner. Mr. Carter’s friends have dubbed the area “Graydonia.”
“We have a no-hoodie policy in the office,” he said, wrinkling his nose.
Some people still call him to reserve a table at the Waverly, a throwback restaurant with red banquettes, jazz soundtrack and Edward Sorel mural of celebrities from Dylan Thomas to Bob Dylan. Mr. Carter continues to pore over the seating chart to create what he considers a lively mix. The menu proudly leads with a quote from Donald J. Trump: “Waverly Inn — worst food in city.”
Mr. Kelly told me: “More than anyone I can think of, Graydon has invented his own environment, his own presence, his own time period. He’s a romantic at heart. He’s filled with nostalgia. He loves handkerchiefs. Who loves handkerchiefs? At his house in Connecticut, he’s got enough canes and walking sticks to outfit a sizable hiking club. He’s got a great eye, a fantastic eye.
“He’s taken all these things, from 1940s black-and-white films about New York to nostalgia for the Chrysler Building to Barbour wax jackets to a love of English manor houses before World War I. He’s created his own snow globe, a hermetically sealed, perfectly arranged environment, and we all get to look at it. He inhabits that vision in terms of his apartment, his clothes, his Air Mail store, Air Mail itself. Like Ralph Lauren, he creates a world that you want to live in and you invite other people to live in. Who else would run long stories about restaurants or nightclubs that are no longer around?”
Mr. Carter is allergic to many modern devices. He doesn’t use a swipe card to get into the Air Mail office; for security, he just keeps an ax there, given to him one Christmas by a fellow Canadian.
A college dropout and the grandson of a British fur trapper from Moose Jaw, Saskatchewan, Mr. Carter has his own internal barometer of what’s cool. He feigned being a Jewish intellectual when he worked as a teenager as a railroad lineman because he thought it made him seem more intriguing.
He yearned to be like Walter Burns, the dashing newspaper editor played by Cary Grant in “His Girl Friday.”
“I have a very emotional connection to old Hollywood,” he says.
With print vanishing, he started a chain of Air Mail newsstands. Lena Dunham, who lives in London part time, is a habitué of the newsstand there. Soon, Mr. Carter will open one in Los Angeles.
He took me to the shop on Hudson Street, which sells newspapers, magazines, books and knickknacks inspired by his magpie obsessions: model trains, pencils, parchment paper. There are also red-white-and-blue lapel buttons that say, “I didn’t vote for him,” a reference to his longtime nemesis, Mr. Trump, whom he and Mr. Andersen memorably christened a “short-fingered vulgarian” in the early years of Spy.
Mr. Carter was not only a maestro of parties, the New Establishment list and the International Best Dressed List, he was an impeccable editor of the written word, right down to the captions, according to those who worked for him. Whether it was stationery, a menu, a place setting, or the Zippo lighters with quotes from everyone from Billy Wilder to Fran Lebowitz that he used to give as party favors at his Oscar dinners, he likes to design things down to a granular level.
Two years ago, he teamed up with the media mogul David Zaslav to host a party that was the social highlight of the Cannes Film Festival. It took place at the Hotel du Cap-Eden-Roc in Antibes, France, to celebrate the centenary of WarnerMedia, which Mr. Zaslav’s Discovery had recently acquired. The attention to detail was painstaking, with Robert Risko illustrations everywhere and old movies from the Warner Bros. vault like “Bonnie and Clyde” and “A Clockwork Orange” beamed onto the surface of the pool.
At Vanity Fair, Mr. Carter had a bit of a temper, people who worked with him said. He could be abrupt at times and insistent that employees be up to snuff — one staff member used to double his pace when passing Mr. Carter’s glass office to suggest he was racing to get a scoop. But Mr. Carter was also extravagant with praise, reflecting his own joy in editing a magazine. (I wrote a few stories for Vanity Fair over the years and can attest it was a smooth experience.)
In a farewell-to-Graydon piece in Vanity Fair, David Kamp, an editor and writer, recalled being gobsmacked by the boss’s “regal mystique” when he arrived at Spy “from middle-class New Jersey” as a summer intern.
“He spoke like someone out of Kipling, referring to cigarettes as ‘gaspers’ and a pee as a ‘squirt,’ and requesting that I make more coffee by gently placing a hand on my shoulder and saying, ‘David, can you fetch me a cup of your world-famous java?’” Mr. Carter turned out to be “a natural mentor figure,” Mr. Kamp wrote.
Mr. Carter has also produced several acclaimed documentaries about Robert Evans, the 9/11 attacks, Elizabeth Holmes, Jerry Weintraub, Fran Lebowitz and Hunter S. Thompson. He — and his wild hair — have also popped up in cameos in movies and on TV (“Wall Street: Money Never Sleeps,” the remake of “Alfie,” “The Paper,” “Arbitrage,” and “She’s Funny That Way.”) In 2013 he produced “I’ll Eat You Last,” a one-woman play about his hilariously profane friend, the superagent Sue Mengers.
Bette Midler, the star of that show, found Mr. Carter to be an excellent producer, and they got to be friends. “You can’t remain intimidated very long by someone with bat wings for hair,” she said of his curvilinear white mane. She and her husband visited Mr. Carter and his charming wife, Anna Scott Carter, at the home that they rented in the South of France, where, according to Ms. Midler, guests were allowed to stay no more than three days.
“He’s an original, an old-school wit,” Ms. Midler said. “He’s like a 19th-century English country squire gone to seed.” She calls him a versatile social critic: “He sees the fun in skewering the rich and famous, and he’s sees the fun in skewering the know-nothings.”
Mr. Carter’s book starts with an account of Vanity Fair’s scoop about the identity of “Deep Throat,” the anonymous source who helped The Washington Post crack Watergate. He goes on to detail the thrill of breaking the internet with the first cover story on Caitlyn Jenner, who appeared wearing a satin corset from Trashy Lingerie in a portrait by Ms. Leibovitz. He also takes readers through the two-year libel case brought by Mohamed Al-Fayed in response to an exposé by Maureen Orth, a story that went off like a bomb in London.
The night I interviewed him was a moveable feast. We began at his chic apartment in the Village, where Graydon made me one of his famous martinis — even Fidel Castro knew his favorite cocktail when they had lunch in Cuba years ago — serving it with a dish of quail eggs.
“They’re more expensive than Fabergé eggs,” he said.
I admired his stove.
“It’s a Lacanche,” he said. “You could put five kids through school for the price of that stove.”
A noted clotheshorse, he described what he was wearing. His cream pants were from “my guy on 39th Street,” he said, adding about his corduroy Navy jacket: “I just designed these jackets, based on a Givenchy shirt. I’ve had 30 of them made — in linen and wool also. I wear a version of the same thing every day.”
He showed me around the duplex. The bookcases featured bound copies of Spy and Vanity Fair and magazines that don’t exist anymore, like The Smart Set and Night & Day. There was a picture of a DC-3, his favorite plane, which he chose as the logo of Air Mail, and a 1920 map of Paris in 3-D with each house drawn by hand.
The bar was modeled after the one in a favorite movie, “Ford v Ferrari.” It was decorated with Churchill memorabilia, a collection of miniature Lock & Co. hats and a letter written by Condé Nast himself to subscribers in 1936 to announce that he was folding Vanity Fair into Vogue, because it was “unremunerative.”
Mr. Carter has a lot of interests, from canoeing to calculating the number of days he has left to live. He car collection ranges from a 1951 Chevy woody to a 1967 MGB in British racing green with wire wheels. His playlist includes “Stardust” by Hoagy Carmichael, “Skokiaan” by Louis Armstrong, “Brazil” by Django Reinhardt and “C’est Si Bon” by Eartha Kitt.
He has a chapter on “rules for living” in his book. His friend Henry Porter, the former London editor of Vanity Fair, dryly calls it “Magna Carter: How to be More Like Me.” The list includes:
If you like something, get two before they stop making them. (He stocked up on white Lacoste shirts with a white-on-white logo.)
For dinner parties, make double-sided place cards, so guests don’t have to circumnavigate to figure out where to sit.
Whom you don’t invite is as important as whom you do. (See: Kardashians.)
Monograms are idiotic.
His self-deprecating humor undercuts any pomposity. He once told me he hated hotel mirrors. I asked why.
“I remember being in a hotel in London,” he recalled. “They had a mirror behind me. My apartment in New York had only one mirror. All of a sudden, I noticed that I had a bald spot on the back of my head, which I had never seen before, so it horrified me. You don’t want to see any angles other than the angles you designed. If I could shower in a wet-suit, I would.”
I was looking forward to reading the memoir because I had always considered Mr. Carter the master of the stylish feud, and I thought he would have entertaining accounts of his jousts with Ms. Wintour, Ms. Brown and the restaurateur Keith McNally, who has Instagrammed his complaints about Mr. Carter not showing up for reservations and who once told Town & Country that all he wanted for Christmas was “Graydon Carter’s head on a platter.”
Mr. Carter always liked assigning stories on great feuds, and he had a few choice ones himself. But, unfortunately for me, he decided against score-settling in this book.
He had a good relationship with Ms. Wintour before he arrived at Condé Nast. He found her “enticing,” and he wrote for Vogue now and then. But after she was promoted to Condé Nast artistic director in 2013, he saw the “Nuclear Wintour” side when she called to tell him the company had decided to move almost half the Vanity Fair staff to a central unit that would report to her. She delivered the blow, he said, “as blithely as you would tell someone you wanted to change the color of their drapes.”
“I was almost speechless,” he writes, adding: “And from there, things began a slow decline.”
Anna aside, he could see that the internet was brutalizing the magazine business and the golden age was coming to an end. He left at the end of 2017.
“I have great affection for Anna, but she took to power rather than being the cozy, conspiratorial friend she used to be,” he told me. “We’re about the same age. Who wants to take on more responsibility? I’m impressed by her ability to take on more and more responsibility.”
The less reserved Mr. Carter writes: “As much as I liked her, I found Anna’s efforts to seem intimidating and powerful almost comical.” They had sons in the same class at the Collegiate School in Manhattan, and one time some boys put on a fashion show with a catwalk and dim lighting. Graydon saw Anna in the front row, wearing sunglasses: “I almost burst out laughing and had to turn my back.”
The Cersei-in-Chanel sunglasses would try to throw people off their game, he felt. She would greet him “either like her long-lost friend or like the car attendant.” And she is not the sybarite he is, certainly.
“Dinner with her at a restaurant is like something a McKinsey efficiency expert would admire,” he writes. “Seated at 8:00. No need to see a menu. Steak, rare. Not sure if she drinks. I think not. And when there are Vogue staff involved, the moment Anna has eaten the last piece of steak, there is a call for the check. Her dinner mates might be mid-bite. More often than not, after a meal with her, I’ve stopped off on the way home to get something to eat.”
Asked to comment on all this, Ms. Wintour didn’t bite. “It was wonderful having Graydon as a colleague, first at Vogue and then at Vanity Fair,” she said in an emailed statement. “We had great times together. I look forward to reading the book, and wish him nothing but the best.”
Mr. Carter and I talked about the rough transition from Spy, which maliciously mocked the rich and famous, to Vanity Fair, which more genteelly chronicled the rich and famous.
The people targeted by Spy, he said, were mostly “at the top of the game and we figured they could take it. We picked on overdogs rather than underdogs.” Still, when he went from throwing darts to darting to haute parties, he had to make some amends with offended celebrities. “I had to neutralize,” Mr. Carter said.
“It was horrible over the first couple of years, but I got through it,” he said of the period when he took over Vanity Fair from Ms. Brown, who moved to Mr. Newhouse’s other jewel, The New Yorker.
Mr. Carter writes that Si had initially offered The New Yorker to Mr. Carter but snatched it back and gave it to Ms. Brown after her insisting. But he notes: “I couldn’t really fault either of them in this decision.”
Ms. Brown disagreed with that version of events. Vehemently. She noted that she had recounted how she became the editor of The New Yorker in her 2017 memoir, “The Vanity Fair Diaries.”
“As you can see,” she wrote in an email, “Si first talked to me about editing TNY as early as 1988, and far from grabbing it out of Graydon’s clutches I was ambivalent about it all the way through to 1992, when he conclusively and directly offered it to me. As the diaries show, I was very attracted to it creatively, but with two small children, one of them with special needs, I was concerned it would add impossible strains to family life.”
Ms. Brown added that she accepted the job only after her mother agreed to move to New York to help with the children. “Never at any time throughout all this did Graydon’s name come up to me as a possible alternate candidate,” she wrote, adding that she was “so bedeviled by Graydon’s angry recollection.”
“Si was extremely secretive and precipitous in his decision making,” she continued, adding: “He never asked me whether I thought Graydon would be a good editor of Vanity Fair! Most people thought that if I left I would be succeeded by Adam Moss, and I was surprised by the Graydon pick as he had no experience with glossies, but he turned out wonderfully well.”
In a phone interview, Ms. Brown said, “I would like to point out that when I left The New Yorker six-and-a-half years later, why didn’t he give it to Graydon? He gave it to David Remnick!”
Mr. Carter said he worried during his first years at Vanity Fair that he would be fired. “By that time,” he said, “I had three kids and a fourth child on the way. I wasn’t even an American citizen, so I just wanted to keep my job. If I’d taken over Sports Illustrated, I’d be going to sporting events.”
In the book, he writes that, at first, advertisers and the staff were in revolt. A few holdover Brown allies — who dubbed Mr. Carter’s version of the magazine “Vanishing Flair” — were “deeply hostile and subversive,” making the workplace culture “poisonous.” Finally, he fired the loyalists, and a cloud lifted.
“Despite the fact that I am, at heart, a beta male, this moved me, at least in some eyes, closer into the alpha category,” he writes. After that, he climbed ever higher, procuring 300 pages of advertising at almost $100,000 a page, he reports — impossible to imagine now. Despite the fact that he had once spilled ice coffee on Mr. Newhouse’s white rug, turning it pinto, the two formed a close bond.
Mr. Carter has had a long and rocky relationship with Mr. Trump. His job helming Vanity Fair entailed meeting a lot of narcissists, but he calls Mr. Trump “a narcissist in a class of his own.”
“He was like an aluminum siding salesman, the fact that he would drop your name every third sentence. I didn’t dislike him, I’ll be honest. I’ve known him over the years, until he got elected. I don’t recognize this person.
“If it ever came out that he is a Manchurian Candidate, that this was a replacement, I wouldn’t be surprised.”
Reached for comment, Steven Cheung, the White House communications director, said in a statement: “President Trump is beloved by America and sits in the Oval Office every single day making the country better, while Graydon Carter is a washed-up has-been who can barely put a coherent thought together because he suffers from a debilitating case of Trump Derangement Syndrome that has rotted his tiny brain.”
Mr. Carter met Mr. Trump in 1984, when he spent three weeks in his company to profile him for GQ. This was the piece in which he noted for the first time that Mr. Trump’s hands seemed a bit small.
In a TV interview promoting the GQ piece, Mr. Carter predicted that Mr. Trump would either go all Howard Hughes, storing his urine in Mason jars, or go on to be the most powerful person in the world.
By the time Mr. Carter had become the editor of Vanity Fair, Mr. Trump had gotten over the hands thing and wooed him with Trump vodka and Trump ties “that were as stiff as a child’s toy sword,” as Mr. Carter put it. They had surf and turf at Mar-a-Lago.
In 1993, Mr. Trump invited Mr. Carter to his second wedding, to Marla Maples, at the Plaza Hotel. “He invited me to the one with Melania as well,” Mr. Carter said. “I wanted to go but I thought my friends would make fun of me if they saw my name in the paper as going, so I didn’t go.”
Mr. Carter assigned a story on Mr. Trump’s “comeback.” During the photo shoot, he writes, “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.” In the end, they scissored the cashmere sweater off, he writes.
The truce didn’t last. Mr. Carter couldn’t resist ridiculing Mr. Trump, and Mr. Trump went back to calling him “Dummy Graydon.” “In the days before Twitter, he’d write me really angry letters,” Mr. Carter told me. “With Twitter, he wrote angry tweets about me. He called me sloppy, a loser. He said the magazine was failing, the restaurant was failing, the Oscar party was failing.” Mr. Carter printed the more than 40 tweets. “I had them framed,” he said. “They were on a wall outside my office.”
Mr. Trump also claimed that Mr. Carter’s wife had called him “a major loser.” Pausing for effect, Mr. Carter said, “She never used the word ‘major.’”
He heard about the Twitter rants from others. “I’ve never gone on Twitter or Instagram or Facebook,” he said. “I go on TikTok because of my daughter. I love TikTok.” If he made a video for the platform, he might do an ironing tutorial: “I can iron a shirt like a French laundry.”
In 2015, shortly before his first presidential run, Mr. Trump sent Mr. Carter a tear sheet from an ad for a reprint of his book “The Art of the Deal,” with a picture of himself on the cover. In gold Sharpie, he had circled his hands and written, “See, not so short!”
“I wrote, ‘Actually, quite short’ on a card stapled it to the ad, and had it messengered back up to his office,” Mr. Carter said.
He said he finds Mr. Trump’s belittling treatment of Canada disturbing.
“People underestimate Canadians,” he said. “They mistake politeness and conviviality for weakness. Canadian winters are so brutal that after generations and generations of surviving those winters, Canadians have spines of steel. He would be wise to stay away from this in the same way Hitler made a mistake charging into Russia. If he does it in the winter, he’s going to lose. Canadians are good on ice.”
Even though he treads delicately about his two divorces and soft-pedals his feuds, Mr. Carter still has plenty of spicy opinions.
I asked what he thought Princess Diana — who came to one of his parties in London and wore her famous black “revenge dress” — would make of “As Ever,” the lifestyle brand from Meghan, the Duchess of Sussex.
“She’d be horrified,” he said.
He said that the Met Gala, Ms. Wintour’s version of his own Oscar parties, “wasn’t my thing. I mean, Halloween-type costumes. They might as well come dressed as SpongeBob.” The Greenwich Village Halloween parade, he said, “was classier, a better class of people. In the old days you’d go and you’d sit beside an architect or a writer, and now it’s all influencers and Kardashians.”
Mr. Carter told me proudly, “We never let a Kardashian into our parties.”
After we sat down to dinner at the Waverly — in his favorite booth, beneath the Sorel mural, and after he has ordered his favorite cabernet — he lit into Vice President JD Vance for being rude to Volodymyr Zelensky in the Oval Office.
“If he is the heir apparent, I would take Donald Trump Jr. over him,” he said.
About Elon Musk, he averred: “Tesla is going to die. No Democrat is going to go near a Tesla.”
Over Wellfleet oysters and a $34 bacon cheeseburger, he said he finds much of modern journalism “very hair shirt.”
“People with earphones, computers with partitions, no longer freewheeling,” he said. “Editors became clerks rather than editors, just at their computer terminals all day long. In the past, it was about moving around and talking to people.
“The magazine business was killed by the internet and the recession and the absence of newsstands. Now they sell slip flip flops and gum and Lotto tickets.”
I asked him what he thinks of Vanity Fair under his successor, Radhika Jones.
“Actually, I’ll say, the new editor took me off the comp list,” he said. “We used to have a comp list, advance copies that were messengered to 400 people. And the new editor took me off the comp list after I left. And I actually haven’t looked at it since.”
“You’re not curious?” I asked.
“I’m not going to buy a copy,” he said, laughing.
Ms. Jones said that wasn’t quite right. “We sent him a digital access code in 2018,” she told me. “Happy to re-up if needed!”
As we said good night, Mr. Carter wanted to insist once more that, all evidence to the contrary, his life is square, not spectacular.
“We watch ‘Frasier’ before we go to bed every night,” he said. “It’s like a nonalcoholic nightcap.”
The post The Not-So-Discreet Charm of Graydon Carter appeared first on New York Times.
