The not-so-discreet charm of Graydon Carter

“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 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 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.”

Isaacson said 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.

Carter’s new memoir, “When the Going Was Good,” recounts his odyssey from the Canadian provinces to Manhattan, where he started Spy with Andersen, 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.)

Carter’s book — written with guidance from James Fox — 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,” Isaacson said of 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.”

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 suits. But he didn’t have a nefarious fortune backing him, only the largesse of Si Newhouse, the former Condé Nast chair.

These days, Carter, 75, works with Alessandra Stanley co-editing 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,” Jim Kelly, a former colleague of ours at Time who became the top editor there, said slyly.

The Air Mail office occupies a 19th century brownstone in the same part of the West Village as his apartment, the Air Mail Newsstand shop and the Waverly Inn, of which he is co-owner.

Some people still call him to reserve a table at the Waverly. 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 Trump: “Waverly Inn — worst food in city.”

Carter is allergic to many modern devices. A college dropout and the grandson of a British fur trapper from Moose Jaw, Saskatchewan, 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.

With print vanishing, he started a chain of Air Mail newsstands. He took me to the shop on Hudson Street, which sells newspapers, magazines, books and knickknacks. There are also lapel buttons that say, “I didn’t vote for him,” a reference to his longtime nemesis, Trump, whom he and Andersen memorably christened a “short-fingered vulgarian” in the early years of Spy.

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 that he used to give as party favors at his Oscar dinners, he likes to design things down to a granular level.

Carter has also produced several acclaimed documentaries about Robert Evans, 9/11, 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: superagent Sue Mengers.

Bette Midler, the star of that show, found 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 Carter and his charming wife, Anna Scott Carter, at the home that they rented in southern France, where, according to Midler, guests were allowed to stay no more than three days.

“He’s an original, an old-school wit,” 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 sees the fun in skewering the know-nothings.”

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 Leibovitz. He also takes readers through the two-year libel case brought by Mohamed Al Fayed in response to an expose by Maureen Orth, a story that went off like a bomb in London.

The night I interviewed him was a movable feast. We began at his chic apartment in the Village, where Graydon made me one of his famous martinis.

Carter has a lot of interests, from canoeing to calculating the number of days he has left to live. He has a chapter on “rules for living” in his book. His friend Henry Porter, a 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.

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 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.

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.

Carter 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.”

Carter has had a long and rocky relationship with Trump. Carter’s job helming Vanity Fair entailed meeting a lot of narcissists, but he calls Trump “a narcissist in a class of his own.”

Steven Cheung, the White House communications director, said in a statement: “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.”

Carter met 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 Trump’s hands seemed a bit small.

In a TV interview promoting the GQ piece, Carter predicted that 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 Carter had become the editor of Vanity Fair, 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 Carter put it.

Carter assigned a story on 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. Carter couldn’t resist ridiculing Trump, and Trump went back to calling him “Dummy Graydon.” “In the days before Twitter, he’d write me really angry letters,” 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.” Carter printed the more than 40 tweets. “I had them framed,” he said. “They were on a wall outside my office.”

After we sat down to dinner at the Waverly, he lit into Vice President JD Vance for being rude to Ukrainian President Volodymyr Zelenskyy 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, 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.”

As we said good night, 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.