Graydon Rides the Wave

Thirty years ago, long before he’d hatched the idea for Spy, reinvented the New York Observer, or emerged at the sunny peak of Vanity Fair, Edward Graydon Carter worked on the western railways of Canada as a lineman, stringing wire between telegraph poles in rural Saskatchewan. He stuck out like a tiger lily. Most of his co-workers were convicts, railroad lifers, or both; Carter was middle-class and already a bit of a dandy. When he arrived at the Winnipeg depot in the spring of 1970, he was wearing a pair of brand-new Adidas and carrying a big knapsack full of books – Kerouac, Brautigan, tattered copies of the National Lampoon. His foreman took one look and ordered him to get a haircut, which he did, at some whistle-stop town outside of Saskatoon.

Carter befriended a fellow named Craig Walls, the only other curious, underachieving 21-year-old in the bunch. “I was a high-school dropout,” explains Walls, who now works for the Ministry of Culture in Manitoba, “so Graydon really stands out in my mind. Imagine a guy with hair down to his shoulders and the whitest teeth you’ve ever seen, a guy who came from the East” – Ottawa, the Canadian capital – “and had all these books. It was quite exciting. He was an alien.”

Carter wasn’t an especially good lineman – “I don’t think he wanted to be good at it,” says Walls – but he made a strong impression: He had a flair for cruel nicknames; he worked on his tan a lot; and when the crew’s cook was fired, he whipped up the gang a little something … canapés. “Salmony things,” says Walls. “I think his mom served them at bridge club.”

Walls has plenty of vivid Graydon Carter stories. But one looms larger than most. The crew was eating some mysterious meat dish, “and Graydon said to me, ‘This is good – what is it?’

“And I said, ‘It’s pork.’

“Graydon is brilliantly self-invented, pretending to be someone until he became that person.” “If a person is useful to him, he’s loyal. But once that usefulness is gone, it’s ‘Next.’”

“And he said, ‘Oh, my God, my mother would kill me!’

“And I said, ‘Why?’

“And he said, ‘Because I’m Jewish.’ “

Walls lets the phrase hang.

“We never knew whether to tell Herbie, our foreman,” he says. “He’d been a German POW and was purported to have S.S. tattoos on his body.”

The story stands out in Walls’s mind for a reason: He’d never met a Jew before. But to anyone who knows Carter now – the bespoke suits from Anderson & Sheppard, the Connecticut country home, the Anglican bone structure, the Gray Goose martinis, the pilgrimages to London – it stands out for a different reason: Carter isn’t Jewish.

“I was reading a lot of Kerouac and a lot of Ginsberg,” says Carter, sitting on a bench in Bryant Park 30 years later, struggling to explain it. He smiles sheepishly and jiggles one leg up and down. “And … and I thought, If you’re going to be an intellectual in New York, you gotta be Jewish. It wasn’t some experiment, like Gentleman’s Agreement, or anything like that. It was just … I thought … I just found it …” He trails off. “I don’t know. It was so much more exotic than what I really was.”

Today, Carter no longer needs to trim his biography with extra filigree. He’s the Jay Leno of the magazine world, the king-size personality controlling the world’s glossiest showcase for the formerly, currently, and would-be famous. Nervous, ubiquitous, and impossibly fabulous, Carter, in the words of his friend Jim Wiatt, president and co-CEO of the William Morris Agency, “has transcended being a great editor – he’s really a celebrity.”

When he first replaced Tina Brown as Vanity Fair’s new editor in 1992, Carter was dismissed as a lightweight, a mere caretaker at the helm of his predecessor’s creation, like a replacement Grizabella in Cats. But since he took over, Vanity Fair has won four National Magazine awards and increased its advertising pages by more than 60 percent. This year, the magazine overtook Vogue to become the second-most-profitable in the Condé Nast empire. (Glamour is the leader.) And Vanity Fair’s annual post-Oscar bash, a Carter innovation, has replaced the late Swifty Lazar’s Spago party as the postgame destination of tout Hollywood.

How on earth did this happen? How did the creator of Spy, a magazine that made toothsome snacks of the same celebrities and power brokers Vanity Fair now so happily lionizes, wind up the darling of his former victims? How did a penniless military brat, a college dropout, a Canadian, wind up one of the best-paid editors (roughly $1.5 million annually) in the Condé Nast building?

“Graydon is endearingly, sort of brilliantly, self-invented,” says David Owen, a staff writer at The New Yorker. “And I mean in the way Cary Grant was self-invented: pretending to be someone until he became that person.”

Growing up in the suburbs of Ottawa, Carter fantasized about a perfect Manhattan life, one based on a diet of old Esquires, Damon Runyon novels, and classic movies – particularly Sweet Smell of Success, Alexander Mackendrick’s noirish paean to Gotham intrigue and celebrity dish. And that’s exactly what he’s got now.

Today Carter flies through Manhattan in a chauffeured car, wears custom-tailored shirts, and lights his cigarettes with a tarnished silver Zippo. He lives in a Bank Street townhouse, spends his weekends in Connecticut, and dines almost nightly at Da Silvano, usually in a cloud of smoke, usually in some Lazy-Susan combination of writers (David Halberstam, Fran Lebowitz, Michiko Kakutani), moguls (Barry Diller, David Geffen, Brian Grazer), fashion people (Diane Von Furstenberg, Kenneth Cole), and visiting Angelenos (screenwriter Mitch Glazer and his wife, actress Kelly Lynch).

“Graydon is a man who has decided to create the world he dreams of,” says Jim Kelly, incoming managing editor of Time and one of Carter’s closest friends. “And he has been more successful at it than anyone I’ve ever met.”

But his transformation – from celebrity spoiler to celebrity Boswell to celebrity himself – has produced its share of casualties too. In Carter’s breathless, perpetual forward ascent, he managed to disown not only much of his past but some of his friends as well.

In certain ways, Carter still remains an outsider, a tantalizing exception in the exclusive world of New York media. He hates Park Avenue sit-down dinners. At large parties, he doesn’t glad-hand his way around the room but remains off to the side, a grounded sailboat, watching, observing. And until recently, he was a deeply serious family man, eschewing most of the 25-plus invitations he receives each week to spend quality time with his wife, Cynthia, and their four children.

“He has always professed that the haute bourgeois pleasures – a good life and family and all that – are what satisfies him the most,” says Kurt Andersen, who co-founded Spy with Carter, “and that work, in some ultimate sense, is secondary.”

But this July, Carter’s wife of eighteen years packed her things and took the children to her sister’s place in Beaufort, South Carolina. Then publicists made it official: The Carters were getting a divorce.

For months, the talk of the publishing world had been that Carter was having an affair. He had also just turned 51. In October, it would be eight years since he’d started editing Vanity Fair – almost the same length as Brown’s tenure before she flew the coop – and Hollywood was tantalizing him with lucrative job offers. To the outside world, anyway, it looked clear: A midlife crisis was in full bloom, just when Carter should have been exulting in his success.

It would not be an exaggeration to say that it’s easier to penetrate a state dinner at the White House than the Vanity Fair Oscar party. This past March, as I pulled my rented Dodge Neon up to the first of three checkpoints, a man reached through my open car window – the car was still moving – and grabbed my purple parking pass off the dashboard. “That won’t get you valet,” he told me.

“I was told it would – “

He gave me a harsh, exfoliating stare and signaled me to keep driving.

For Carter, Oscar night is like Christmas Eve. He flies out a week early and hunkers down at the Beverly Hills Hotel like a field commander, finalizing seating arrangements, poring over the dinner menu, and making sure the Swedish roses are all in place. The point is to create the millennium version of Ciro’s in the forties, with its heady mix of the powerful and the glamorous.

At checkpoint No. 2, I am greeted by a friendly county sheriff. “I don’t think they’ll let you in with that,” he says, staring at my pass. He consults a color-coded chart. “Green gets you in. But what do I know? I’m just a flunky at the first checkpoint.”

“Second,” I tell him.

“Really?” he asks. “Wow.”

Spy often treated movie stars and Hollywood types with unfettered, delectable brutality. One of the magazine’s most memorable coups, in fact, was getting hold of a fawning note Tina Brown sent Michael Ovitz, hoping to lure him into cooperating with a profile – for Vanity Fair. (Spy ran the complete text with footnotes, making deconstructive jambalaya of her servility.)

Yet Carter’s Vanity Fair is more obsessed with starlets and moguls than it ever was under Brown – and is arguably more fawning. Carter invented the magazine’s annual April Hollywood issue, an inch-thick orgy of perfect skin and peerless talent. Every October, he offers the New Establishment list, a who’s who of movers and shakers that still leans heavily toward studio executives. This October, Carter came out with Vanity Fair’s Hollywood, an even thicker compendium of flesh and fantasy, this time between hard covers. (It is currently No. 35 on the expanded New York Times nonfiction list.)

I move ahead to the third checkpoint and give my name to a surgically modified brunette with a headset. Success. I hand my keys to the valet.

Morton’s is packed, a glittering seascape of 1,000-watt Somebodies, all gathered in happy clusters or streaming toward the back of the restaurant, which glows in an orange-red hue. People are pressed so densely together it’s almost impossible to move, much less scrutinize their outfits, and Carter is nowhere to be found. So I go with the flow: past Uma and Ethan; through Tom and Nicole; around Christina Ricci and Courtney Love and Jude Law.

Gwyneth, Matt, and Ben are standing in a knot. Paltrow is a West Village neighbor of Carter’s. I ask her if she has any good stories about him.

“He’s very charming,” she offers. Her makeup is bleeding slightly under her eyes. I find this strangely reassuring. “And he’s very sincere with his flattery.”

Affleck says he has “a great story” about Carter, but Paltrow cuts him off.

“He wouldn’t want you to tell that story,” she scolds.

“Why?” he asks, a bit guiltily. “It’s … true.”

She shakes her head.

I wend my way to the restaurant’s back room. Carter is on the dance floor, twirling a bushy-haired blonde. (His own curvilinear hairdo, as usual, is spectacular. Who’s his hairdresser, anyway? Frank Gehry?) I try to say hello, but before I get close, his publicist materializes, seemingly from nowhere, and requests I put my notebook away. When I turn back around, Carter has vanished, like a warlock.

It occurs to me at this point that it’s been easier to chat up Gwyneth Paltrow and Ben Affleck than Graydon Carter. The power he wields here is palpable. In Hollywood, says Bryan Lourd, a partner at CAA, “everyone is always courting Carter to some degree.” Back in March, when the Internet was still blooming with cash and possibilities, Brian Grazer, co-founder of Imagine Entertainment, tried to lure him out to run, his Internet venture with DreamWorks and Microsoft co-founder Paul Allen. “You’re the king of New York!” he gushed at the time. “You’re like the pretty girl in high school that everyone wants!”

Carter declined – wisely, since subsequently imploded – and he dismisses all talk of a future move to Hollywood. “He’ll edit Vanity Fair for the rest of his life,” says Jim Kelly. “It’s the ultimate puppet theater.” (Besides being an amateur watercolorist and amateur magician, Carter is an amateur puppeteer.)

But Carter can’t resist dipping at least one oar in the West Coast’s warm waters. He is currently producing a documentary about film producer Bob Evans (The Godfather, Chinatown), whose delicious autobiography is a cult favorite in Hollywood. It’s a modest project, tailor-made for Showtime or A&E. But because Graydon Carter is Graydon Carter (and Vanity Fair is the ultimate puppet theater), he plans to first screen the film in … Cannes. (Who knows? Carter could even collect an Academy Award the following March – and then attend his magazine’s Oscar party as both host and honoree, statue in hand.)

Arnold Schwarzenegger, as debonair and structurally formidable in person as he is in the movies, is just off to the left of the dance floor, giving an interview to a Washington Post reporter about his political aspirations. I take a chance and whip out my notebook. Arnold smiles gamely. Does he have any stories about Graydon Carter? “Only spiiicy ones,” he answers.

Really? Seriously?

“Yah.” He nods. “But I’ll haf to check with heeem first.”

Even the Terminator is slightly afraid of Graydon Carter. I wave my near-blank notebook at him. Is there nothing he can say right now?

“No!” he barks. “I must get his permeeession.” His eyes twinkle. “But you ah doing an excellent job at your profession! Have you met my wife, Maria Schrivah?”

As I head for the door, I see Jay Leno standing alone with his wife, Mavis. Maybe he has a Graydon Carter story? Leno looks at me apologetically and says that sadly, he does not. Then he stops himself. “You know,” he says, “Graydon amuses me. I like how he moves – like a true patrician. Not in a bad way. He’s a breed of New York-Connecticut Yankee patrician you didn’t know still existed.”

I smile, thank him, and tell him Carter is from the suburbs of Ottawa.

“There’s probably a half-dozen movie actors I really like,” says Carter six months later, on his way to lunch, sitting in the puff-pastry comfort of his chauffeured Lincoln Navigator. “But a lot of them just aren’t that interesting.”

So who’s a movie star he likes?

“Tom Cruise. Very cool guy. Great company. Beyond that … he’s more the exception than the rule.”

He lights a cigarette. “But Robert Redford – very self-serious. He was in my office to scout locations for The Horse Whisperer. At one point, he was standing at my door – he was with some woman – and he said, ‘Could you excuse us for a second?’ So I said, ‘Sure, absolutely.’ And he said, ‘No, no: I mean, could you leave your office?’ “

Carter’s eyes widen.

“I was totally taken aback. I said, ‘Yeah, okay.’ Can you imagine saying that? I was horrified. It was just rude.”

Sergei, his handsome Russian driver, pulls the SUV to a stop outside Da Silvano. All the waiters give Carter a warm hello. One shows us to his table, located in the restaurant’s high-rent district (front corner, just to the left as you walk in the door). Carter helps me off with my coat and orders us two $18 glasses of wine. “Love the cod here,” he gushes. “There’s a book that came out about how cod changed the world. Cod is more responsible for the discovery of the New World than almost anything else. Drove the Vikings across the North Atlantic, and John Cabot discovered America by looking for cod. The stirrup! The stirrup was a huge thing; people could engage in battle properly on horseback …”

All Carter’s friends say he’s the most entertaining person they know. He has a gift for making people feel larger and lighter than they are, and smarter too, like a drug; this quality would be intoxicating to anyone but is especially intoxicating to the company he keeps – journalists and Hollywood people – whose egos, as a rule, tend toward the fragile.

“… how air-conditioning changed America! These little things, they have huge effects on life. Much more so than the personal computer, almost. Is my smoking bothering you? Are you waving away my smoke?

“Graydon is someone of unbridled enthusiasms, multiple enthusiasms – enthusiasms, in fact, that change, and change suddenly,” says Kelly. “He’s like your favorite camp counselor. He’s always got projects going; he’s always got ideas about what to do. As far as I’m concerned, that’s the key to understanding him. His enthusiasms are a terribly seductive thing.”

Planes. Mid-century American architecture. Movies from the forties. Thumb carefully through Vanity Fair, and you’ll see it’s an art-directed manual to Carter’s obsessions. The nostalgia stories, for example, about old Hollywood joints, gangsters, and movie stars: pure Carter. And the magazine’s fizzy visual quality and fanatical attentiveness to design are all a product of Carter’s own abiding sense of style. He was a fop long before it was fashionable for heterosexuals to be foppish, gussying himself up in crisp English shirts and Nathan Detroit pinstripes. (Kurt Andersen calls his former colleague “one of the best-dressed men on Planet Earth.”)

Yet for a creature of such studied elegance, Carter is surprisingly excitable. The first time he sat down with S. I. Newhouse, the owner of Condé Nast, Carter was pulsing with so much nervous energy he sent a glass of iced coffee flying across the publishing mogul’s immaculate white carpet. “Nervousness,” shrugs Walter Isaacson, the new editorial director of Time Inc., “is part of the charm.”

He’s also an epic gift-giver, deluging friends not only with stationery, bound volumes of blank paper, and other writerly accoutrements but quirky, highly personalized curios collected at flea markets. For his closest friends, he flies off the deep end: Stacks of china. Ancient bottles of port. Rare, human-size plants. And he knows how to bolster the confidence of his anxious writers. After each story, Carter sends them notes, either by fax or on Bennetton Graveur Paris stationery, isolating some special aspect of their work he enjoyed.

But if he has a hawkeye for people’s tastes and talents, Carter also has a merciless eye for their weaknesses. Just as he can build people up, he can make them feel quite small.

“He’s funny about people’s mannerisms,” notes Henry Porter, the London editor of Vanity Fair. “And he’s quick to spot other people’s delusions and motives: why they bought the new car, why they got the trophy wife.”

“Some of Graydon’s humor is based on making light of your foibles,” adds Kelly. “To your face.

“If you trip up somewhere in the world,” agrees Mitch Glazer, “he’s there gloating about it. He misses nothing.”

Most people know Carter is from Canada. After that, the details get fuzzy. One former colleague heard he was raised in Moosejaw. Another seemed certain it was Toronto. A third thought Carter split his time between Ottawa and London because his father was a diplomat – in fact, wasn’t he partially raised in the Savoy Hotel?

Carter was born on Bastille Day in 1949. He did live abroad between the ages of one and 6, because his father was stationed in both England and Germany as a flier of Lancasters with the Royal Canadian Air Force. But he spent the rest of his childhood in the middle-class suburbs of Ottawa.

This is how Carter describes himself as a kid: “I was just, just out of control. I don’t mean on drugs or anything like that – just out of control.”


“Too many grand plans.”

For instance?

“Just – plans! You know, I’d come up with some grand plan to build something, and my mother would be like, ‘No, you can’t, we need that furniture.’ “

This is how Carter describes his father, who died in 1991: “A fucking character. Like Basil Fawlty. I have a feeling he was Basil Fawlty, and I was his Manuel. I really do. He looked sort of like David Niven, pencil-thin mustache, funny, eccentric, sort of a sportsman. Loved bridge, loved my mother, loved having beer. And, um, he loved wood. He had this obsession with wood …”

Nailing down the particulars of Carter’s past is a tad difficult, especially the period between high school and college. “I did a bunch of blue-collar jobs,” he says, “because I knew I’d wind up with a white-collar job at some point, and I wanted to, I don’t know, I just wanted to taste life. I dug graves for a while, I worked as a stock boy in a big department store, I worked in a bank …”

This was during a one-year period? “Yeah. And I worked for the railroad as a lineman in Western Canada. Best seven months of my life.”

There’s just one problem: The University of Ottawa has no record of Carter until 1974. That would have meant an interregnum of seven years between high school and college, not one.

Carter attempts to clarify the discrepancy by explaining that Canadians spend five years in high school, not four, and he’d been such a lousy student it took him six. Then he adds that he spent nine months as an assistant to a deputy minister in Parliament, though he can’t remember the man’s name (“Alec … um, Alec, fuck, um, it’ll come to me”) or his political party.

Carter does give some specifics about his young-adult life. At 22, he got married to a French-Canadian museum worker. Three years later, he enrolled at the University of Ottawa. Within months, he was spending all of his time at the offices of The Canadian Review, a tiny literary rag started by a classmate. Carter quickly took charge, and by the time the Review folded in 1977, he had transformed it into a full-fledged, New Republic-style culture-and-politics magazine with a circulation of 50,000.

“It was a really courageous thing to do,” says Bruce Maclennan, a childhood friend of Carter’s. “Here he was in Ottawa, and he was starting a magazine. I mean, Ottawa! It’s a horribly drab place.”

Of course, Carter was also failing out of school at the time (“I had, like, a record number of incompletes”) and didn’t do any better, in the winter of 1975, when he transferred to Carleton University. The magazine, when it finally sputtered out, left Carter almost $50,000 in the red.

By that point, he was ready to move on. In the summer of 1978, he left for New York in an old BMW, leaving his soon-to-be ex-wife and some furious investors in his wake. Carter gave himself one month to find a job, and on the last day, he talked his way into the managing editor’s office at Time magazine and got himself an offer. God knows what he told him.

“We all edit our pasts,” shrugs Tom Phillips, another co-founder and the first publisher of Spy. “Graydon just does it with more flair and fanfare. I actually admire this about him – his ability to move beyond The Canadian Review and whatever life he had in Canada to create a new life, a new marriage, a new career, and to become, in his way, the king of New York.”

He ponders this point a moment.

“It’s a very practical set of lies that he tells,” he continues. “Vanity Fair is all about creating an aura, a version of the world. If you’re going to be good at that, you’re going to have to create your own fiction and communicate it in an appealing way. So the fact that he doesn’t deal head-on with reality, or that he doesn’t exactly feel encumbered by the truth, works to his great advantage. In fact, I’d go further: I’d say it’s a prerequisite for him to do his job well.”

His very first week as a writer-trainee at Time, Carter went out to lunch with Jim Kelly, another writer-trainee, and told him that he wanted to launch a magazine called Spy. Seven years later, over the course of many lunches and jaunts to the video arcade in Times Square, he and Kurt Andersen, also a member of the Time tribe, planned the launch of their new magazine together.

Both men had the same journalism lodestars: Esquire from the sixties, The New Yorker from the thirties, Mad. What they produced, with Spy, was an odd hybrid of tough reporting and mordant satire that, despite its brief, six-year life span, left an indelible mark on the magazine world. Besides ridiculing the shiny-tied brutes of the eighties (Trump, Ovitz, Tisch), Spy created a trademark set of features and columns, including “Separated at Birth,” which paired unflattering photographs of celebrities caught in similar poses, and “Logrolling in Our Time,” a chronicle of who was scratching whose backs in book blurbs.

The magazine could be ferociously cruel. Liz Smith, for example, was a routine target of their ridicule, once referred to as “the old doughy one kissing everybody’s ass.” (Says Smith today: “It was kind of unpleasant. They seemed to be on my case about things I couldn’t help, like my age or how I looked. But it was what it was, and it was funny, some of it.”)

As co-editors, Andersen and Carter were equally engaged in molding the content of the magazine, but their styles differed significantly. Andersen was the quieter, more serious one; Carter was the office motivator and bon vivant. If people’s moods were flagging, he’d drag them all out to the San Genaro festival. At Spy’s boozy, bacchanalian Christmas parties, he’d dress up in a Santa suit (probably the only non-bespoke suit of his adult life) and sit his employees on his lap for a year-end evaluation of their behavior.

For the staff, Spy was a way of life. It meant working until midnight, great parties, and boozy idea lunches at Buffa’s and Jerry’s. “It was like being on The Dick Van Dyke Show or something,” recalls Tad Friend, a former Spy senior editor.

Then, in February 1991, with the magazine’s financial future in doubt, it was sold to Jean Pigozzi and Charles Saatchi, two publishing neophytes with money to burn. Carter started foraging on his own for funding for a new newspaper venture. One of the people he spoke to was Arthur Carter, the publisher of the fledgling New York Observer. Arthur invited Graydon to come edit his paper instead.

While Andersen was attending a family reunion in Colorado, Carter called to tell him he was leaving. His partner was stunned. “I wish,” admits Andersen, “in some ideal world – I guess I wish that, you know, there’d been some conversation beforehand. But we all had our own lives. Clearly, the bomb-bay doors were open. He jumped first.”

Was Carter apologetic, at least?

“Apologetic? No.”

The move bewildered Andersen. “Before Graydon transformed and reinvented the Observer,” he explains, “it was kind of a dopey thing. I mean, it wasn’t like, ‘Whoa, the brass ring!’ It wasn’t, ‘Do you want to be editor of The New Yorker?’ Not remotely.”

He smiles. “So at least whatever sense of surprise I had was not compounded by great jealousy.

“It’s funny,” continues Andersen, now a co-founder of “On the one hand, you could say Graydon’s temperamentally a conservative, kind of a Tory in his bones. On the other hand, he does make these radical breaks in his life, whether it’s leaving Canada, starting Spy, leaving Spy, living on the Upper West Side, living in the Village, all these things. And at the moment Graydon’s doing whatever he’s doing, it is the greatest thing in the world. He can’t imagine living any other way.”

Carter transformed the Observer almost overnight. Founded in 1987, the paper started as a sleepy little attempt to cover local community-board meetings; Carter turned it into a gossipy, characterful rag about Manhattan’s defining professions: the media, the law, real estate, entertainment, Wall Street. “He was a story-generating machine in those days,” says Helen Thorpe, the writer who did the paper’s media column at the time. “I got a lot of credit for ‘Off the Record.’ But what no one realized is that I got only half the items myself. Basically, Graydon would go out for these long lunches, and he’d come back slightly flushed, and then he’d dump in my lap the most unbelievable media gossip I’d ever heard.”

Carter was thriving. Before even the first year of his tenure was up, S. I. Newhouse called to invite him by for a little talk. He revealed that Tina Brown wanted to leave Vanity Fair. Then he mentioned that he was also thinking of making a change at The New Yorker.

Carter jumped. The prospect of editing The New Yorker got him so excited he went home and drew up a plan to reinvent the weekly, then stuck in a murky, post-William Shawn amber. But it was not to be. Newhouse wanted Brown for the job. And when she finally said yes, he offered Carter second prize – Brown’s vacated Vanity Fair post. Carter accepted. Privately, he was crestfallen.

“I blew my relationship with Tina,” Carter says. What I should have done was ask her advice more.”

Newhouse insists he wasn’t trying to use Carter to leverage Brown’s interest in the job. “I talked about both jobs being open,” he now admits, sitting in his spare, lunar office in the Condé Nast building. “At the time, it was not clear that Tina felt she could handle The New Yorker, that she was ready to deal with a weekly, so there was some uncertainty. However, my feeling at the time was that Tina would accept The New Yorker, as she did, and I was thinking of Graydon more in terms of Vanity Fair.

Graydon Carter announced he was leaving the Observer. Arthur Carter was furious. A decade later, he’s still furious. “I was surprised,” he says. “But, uh, it might have happened anyway. Truthfully, I found him to be homophobic and anti-Semitic.”

He can think of only one example.

“He would use the expression, over and over again, ‘Oh, he’s just an old fruit,’ or ‘He’s just an old Jewish fruit,’ ” he explains. “The first few instances, I thought it was just a bit of a joke, but when it was repeated over a period of time, I saw it was beyond that.”

When I tell Graydon Carter about this at Da Silvano, he seems perplexed. At this point in our conversation, he has just named Arthur Carter as one of his seven or so major professional influences. “Well,” he says, “I can easily see calling someone that as a joke. That’s a holdover from Spy.” He doesn’t sound particularly defensive. “I’d say most of my friends are Jewish,” he adds. “I don’t know. I have no idea. I never even think about it.”

“I’m sorry that Arthur feels upset,” he says, a few minutes later, as the bitterness of the accusation sets in. “Because I have nothing but warm feelings for him.”

The former editor of slash-and-burn Spy and the cheeky New York Observer at the helm of the celebrity-worshiping Vanity Fair? It was like the fox taking over the henhouse. Why did Newhouse do it? “Any editor is a gamble,” he explains today, “but I think that between Spy and the Observer, Graydon had a flair for a kind of journalism that was important to Vanity Fair. Vanity Fair is a strange animal. It’s popular, yet it appeals to a very cultivated taste.”

And Newhouse seemed to understand something else. Carter was ready for the change. He wanted it. As soon as he accepted Newhouse’s offer, he began frantically distancing himself from his past. “Spy is long behind me,” he told USA Today. “Spy was a day job.”

His former colleagues didn’t appreciate it. “Given that I was still at Spy,” says Andersen, “I felt as though he sort of defined Spy as a youthful indiscretion, which didn’t particularly please me.”

“Let me tell you something,” Carter says now. “No one at Spy had three kids and a fourth on the way. That’s the basis for almost all of it – I had to make a living. If I’d been hired by National Geographic, I’d have learned about science and nature.”

Even as Carter was airbrushing his years at Spy out of the picture, he was hastening to mend fences with the magazine’s victims. He called Donald Trump, whom Spy relentlessly referred to as a “short-fingered vulgarian,” and later became so friendly with him he attended his wedding to Marla Maples. At a party at Barbetta, Carter also sheepishly extended his hand to Liz Smith. She graciously accepted his apologies. “I admire him for it,” she says in a drawl thick as soup. “Why should he go on being a professional shit if he could get out from under it?”

Ironically, Carter was also now the target of media coverage himself, and often it was his former colleagues who were writing about him. He hated it. Every item, no matter how trivial, was viewed as a betrayal. “I think he wished that the Observer wouldn’t cover Vanity Fair at all,” says Susan Morrison, who started with Carter at Spy and took over the Observer when he left. “But because of Graydon’s own innovations at the paper, the Observer was fueled by media stories, and the credo of Spy had always been ‘no sacred cows.’ “

After Andersen became editor of New York in 1994, he started hearing from Carter, too. At one point, he received a note about an impending “Intelligencer” item, telling him that if the item ran, their friendship was over. But their friendship had mostly evaporated by then, anyway. “The threat,” says Andersen, “was moot.”

Two years later, when Morrison and some other former Spy graduates tried to organize a reunion dinner for Spy’s senior editors, she discovered that one of Carter’s editors at Vanity Fair, clearly with his blessing, was organizing a competing Spy reunion for the same evening – for assistants and interns only. That’s the one Carter attended.

Carter insists he isn’t the only one to blame for the unraveling of his old friendships. “You know,” he says, “at some point, maybe you feel that they’ve abandoned you, as well.”

It’s clear, though, that Carter feels every slight acutely, perhaps too acutely. When he becomes angry at friends or colleagues, he frosts them – in the office, at parties, wherever – leaving them wondering what they’ve done. “He has his virtues,” says Ann Louise Bardach, a former Vanity Fair contributing editor. “But courage is not among them. Anything unpleasant is delegated.”

Those on the receiving end of his indifference feel the hurt for a long time. “If a person is useful to him, he’s loyal,” says Arthur Carter. “But once that usefulness is gone, it’s ‘Next.’ I’d say it parallels what’s going on with his marriage, frankly.”

Carter described the jump from the Observer’s cramped East Side townhouse office to Vanity Fair’s spread on Madison Avenue as “going from Menudo to the Metropolitan Opera.” The first year was a disaster. Advertising pages plunged. Right from the start, the rumor mill began spitting out squibs about Carter’s numbered days. He started to gain weight. He lost sleep. Each morning, he checked the building directory at 350 Madison Avenue to make sure his name was still there. Then he’d wander into his office and flip on Frank Sinatra.

“I think he was terrified that he wasn’t really equal to the task,’ says Jesse Kornbluth, then a Vanity Fair writer, who left seven months after Carter’s arrival. “So he hid behind his door like the Wizard of Oz, closeted himself in his office with some of his aides-de-camp, and ran the operation by remote control. Morale was through the floor.”

Gossip was flying. The office was still filled with Tina Brown loyalists, and they burned the phone lines, telling Brown and all their media friends about Carter’s latest missteps.

A formal animus quickly developed between the two editors: They were both gunning for the same writers and advertisers; both were trying to prove themselves in climates where fear and skepticism about their talents ran high. It could get petty. Even last year, when Brown started Talk magazine, Carter reprimanded his columnist Christopher Hitchens for attending a dinner she threw for Martin Amis. (Brown wouldn’t return New York’s calls.)

Today, the tension between the two may finally be easing. “I blew my relationship with Tina,” Carter admits. “What I should have done was just asked her advice more.” At the very least, he may feel less competitive. “There was a great concern within Condé Nast when Talk started,” says James Wolcott, Vanity Fair’s culture columnist. “But by the second or third issue, it had all pretty much died away. She’s lost her Jesse James status.”

After eighteen months at Vanity Fair, something happened to Carter. “One day,” he says, “I realized, Look, don’t feel sorry for yourself. You can make this magazine anything you want. Then a few staff members left, all in a one-week period. It was like opening the windows. Nothing against them. I gave them two years to fall in line about me, and to be a sport about me, and they couldn’t do it.”

Wolcott remembers how Carter tried to woo him back from The New Yorker (where he’d followed Tina Brown). “Graydon was telling me what a fun, attractive place Vanity Fair was to work,” he recalls, “and he said, ‘Because one day, I picked up a stick and drove all the snakes out!’ “

Carter began to remake the magazine in his own image. Brown loyalists still say it remains her creation, that all the essential DNA – the nifty photos by Annie Leibovitz, the high-society crime stories by Dominick Dunne, the gauzy, adulatory cover stories about hot actors – came from her. But Carter has given the magazine a much richer visual design, and he has added a whole new kind of feature, the glamorous piece about the high life of bygone eras. And Carter has greatly expanded Vanity Fair’s fetishistic coverage of Hollywood, an arena where’s he’s managed to out-Tina even Tina.

“We publish too much of that inside-showbiz-tycoon crap,” says Hitchens. “I just don’t believe that huddles form around the country, wondering how Barry and Mike and Captain Jeffrey” – that’s Diller, Ovitz, and Katzenberg – “are getting on. I don’t believe such huddles have formed, and I don’t believe they ever will. By the way, I still can’t tell those fuckers apart.”

This new interest in the tinsel behind Hollywood tinsel coincided with a transformation in Carter’s social life. In the past, his friends were fellow journalists; now his dance card began filling up with new best friends like screenwriter Mitch Glazer and producer Brian Grazer and mogul Barry Diller.

Not surprisingly, Diller gets extremely favorable coverage in Vanity Fair. In a story about Paramount in this year’s Hollywood issue, seven out of eight “pull quotes” – lines from the story that hover in large letters next to the text – were about him, five of them very flattering. (Example: “Barry was king.”)

As it turns out, one of Diller’s companies, USA Films, is financing Carter’s documentary on Robert Evans.

Now, that’s logrolling in our time.

But Carter’s writers are quick to salute his bravery. He allowed Marie Brenner to spend several months pursuing a story about tobacco whistleblower Jeffrey Wigand – later the basis for the movie The Insider – even though millions of Brown & Williamson advertising dollars were at stake.

“He let me trash Princess Diana while her body was barely cold,” says Hitchens. “At the time, that made people very upset.”

“I wonder whether each of his jobs has brought out the best and the worst in him,” says George Kalogerakis, a former Spy editor and a current contributor to this magazine. “At Spy, he used his wit to make it as funny as it was, but Spy also provided an outlet for his cruel streak. And if Vanity Fair allowed him to draw on his social graces, it’s also indulged the side of him that, I think, always envied some of the people he enjoyed mocking.”

Unfortunately, Vanity Fair’s sweetest public triumph comes during one of the bitterest years Carter has ever had. Just when he should be savoring the moment, he’s trying to conceal his anguish. “When you’re the editor,” he says, “people want you to be strong. Your children want you to be strong. Moping is an unattractive attribute in a man. So, you know, I’m like Jerry Lewis. I’m laughing on the outside and crying on the inside. It’s been the toughest period of my life.”

Carter met Cynthia Williamson, a paralegal at a midtown law firm, in 1982. She was 23 years old and positively lovely – she still is – with Helena Bonham Carter hair and a relaxed, porcelain demeanor. After knowing her for less than three weeks, Carter proposed at the Empire Diner. It was 3:30 in the morning. She first told him no.

“She thought I was drunk,” he explains.

Was he?

Of course. It was 3:30 in the morning.”

By pretty much all accounts, they had a model marriage – a marriage so decent, in fact, that it deeply depressed many of their friends when they split.

What ended it? A not-very-unusual combination of things. Briefly, there was someone else – an employee – so people talked about it a lot; it seemed out of character for Carter. The papers showed surprising restraint. “Not a single gossip columnist asked him about the breakup of his marriage,” marvels Liz Smith. “I just thought, ‘If I write a word of this …’ I could have written a lot. I had a ton of stuff.”

Anna Wintour, the editor of Vogue, certainly never got that kind of white-glove treatment when her marriage went to pieces. Does Liz know why? “She’s not friendly to people,” she says. “I think maybe she has gotten a bum rap. But she had no – what do you want to call it? – bankable emotional love from people in general.”

Though he may have been spared, Carter still admits that the recent turmoil in his private life has chastened him: He has second thoughts about having allowed his writers at Vanity Fair to delve into the infidelities of public figures, including Rudolph Giuliani’s.

The past four months for Carter have been the toughest of his life. “Diane Von Furstenberg told me something that was very smart,” he says. “She said that when a parent is with their child on their own, they connect with that child in a very different way. But it hasn’t been liberating so far. I’ve just been quietly miserable.”

Until recently, Carter was determined to lure his wife back to New York. Every day, he speaks to her on the phone. A few weekends ago, he took her and two of the children to see The Music Man.

But Cynthia has a new house in Beaufort now. The two youngest children are enrolled in school there, and the two eldest are away at boarding school. “She’s happy down there,” says Carter. “My children are happy. And, you know, what do I do? It’s impossible to get back together when you’re five states away. I’m resigned to the fact that this is the way it is.”

He finds himself entertaining more. “I have a nice house,” he notes. “I just discovered cooking. Nothing fussy. Brian McNally came over the other night – we were heading out to dinner – and he just thinks I’ve turned into a complete fag, like cooking and doing the laundry. So I made sure, just as he came in the door, to be rearranging the flowers, Martha Stewart-like.”

But at this point in his life, it isn’t Martha Stewart whom Carter brings to mind. It’s Jay Gatsby. After all those fabulous evenings at Da Silvano, and after all those fine parties on Bank Street, Carter’s friends shuffle away, sated and paired off, and he’s left in the big house alone.

But for the first time, Carter also seems eager to connect to friends who’ve fallen by the way, particularly the old gang from Spy. “I think about them,” he says. “I should correct it. I probably should. Don’t know how, exactly, but I think it’s probably more up to me than them.”

Two weeks ago, Carter had a long, boozy dinner with Andersen. It was the first spirited, relaxed interaction they’d had in years. “The ground,” says Jim Kelly, “has shifted under Graydon. “I wouldn’t be surprised if it has caused him to stop, look around, and reevaluate what’s important.”

Graydon Rides the Wave