One day in 2006, Graydon Carter touched down in Venice to attend a global retreat at the Hotel Cipriani for high-ranking editors and executives at Condé Nast. The launch of Portfolio, Condé’s new high-end business magazine, was a few months away, and a handful of copies of a dummy issue had been printed and distributed on a strictly confidential basis.
Jon Kelly, a twentysomething then working as one of Graydon’s assistants, had flown in on a redeye from New York, and he was in his hotel room when the telephone rang. Graydon was on the other end. The editor couldn’t find his copy of the Portfolio prototype. He must have misplaced it on a boat ride in town.
“Look,” Kelly recalled Graydon telling him, “you’ve got six hours to find this thing. Otherwise, we’re screwed.”
Kelly was jet-lagged, newly arrived in a foreign city, and he needed to locate a single issue of a magazine that was sitting in the back of one of hundreds of boats that spent the day crisscrossing 150 canals. He figured he had one option: bribery. Hanging up, Kelly opened the safe in his hotel room and removed an envelope that contained 10,000 euros in bills—his usual allotment of petty cash for an overseas trip. Given the uncertainties of international travel, it was standard practice at Condé for assistants to carry a significant amount of money, the better to ease the burdens of important editors in chief.
Kelly slipped a 1,000-euro tip to the head gondolier at the Cipriani, who agreed to ferry him to what seemed like Venice’s equivalent of a maritime parking lot. Another hefty tip convinced the on-duty clerk to rummage for the missing issue. The Condé gods were smiling that day: the Portfolio turned up, and a grateful Kelly shelled out another 1,000 euros as a finder’s fee. The issue was returned to Graydon with time to spare.
In his quarter century as editor in chief of Vanity Fair, Graydon Carter surfed the crest of Condé Nast decadence. He established himself as an impresario of Hollywood, Washington, and Manhattan, famous for his double-breasted suits, flowing white hair, and seven-figure salary. This identity, and the highly agreeable lifestyle that accrued to it, was almost entirely a product of his own invention. Like his forebears at Condé Nast, Graydon was a conjurer: he dreamed of a fantasy Manhattan life, willed it into being, and made himself the star of the show.
Edward Graydon Carter was born on July 14, 1949, to a middle-class family in Toronto. His father had been a Royal Canadian Air Force pilot in World War II, who, after a short stint as a shopkeeper, returned to the service to fly Lancasters and Sabres. When Graydon was a toddler, the Carters sailed to Europe, where his father trained pilots in Germany; the family spent time in England and France, returning to Ottawa the year he turned seven. Graydon, who shared a bedroom with his younger brother, was the kind of child who was impatient to become an adult. He admired the well-dressed neighbors who sipped cocktails at his parents’ weekly bridge games and studied the wry sophisticates of screwball comedies like My Man Godfrey and Twentieth Century. At eight years old, he watched Sweet Smell of Success, the Burt Lancaster film set in the world of Manhattan gossip columnists. Graydon was intoxicated by its vision of ice-cold martinis, private telephones at the 21 Club, and rain-soaked New York streets glowing in neon light. “I could hardly wait,” he recalled, “until I could smoke cigarettes and have cocktails and get dressed up and play bridge.”
Academics were an afterthought; he preferred learning from magazines like Esquire, Life, and Time. After Graydon graduated from high school, an aunt referred him to the Canadian National Railway, where he worked as a telegraph lineman in rural Saskatchewan. He rode in a boxcar with ex-convicts; at the time, his hair was grown out hippie-style, and a foreman forced him to shave his head. Graydon, who traveled with a knapsack of books by Kerouac, calls this one of the great periods of his life, and it’s clear, looking back, that he was experimenting with new identities. At one point, he informed his railroad compatriots that he was a Jew. (He isn’t.) “I thought, if you’re going to be an intellectual in New York, you gotta be Jewish,” Graydon explained years later. “It was so much more exotic than what I really was.”
Self-invention became the project of Graydon’s youth. He spent a few years working at a government accounting department, then helped draft speeches for the office of Pierre Trudeau, then the prime minister of Canada. He pitched himself to publications as a political cartoonist and wrote a spec script for the sitcom All in the Family, in which the Bunkers inherit $1,500 from a dead aunt. Along the way, he took classes at the University of Ottawa and Carleton University, but never earned a degree. Instead, Graydon, then known to friends as “Gray,” found his footing at The Canadian Review, a tiny magazine about literature and politics. He joined as the art director in 1974 and eventually became editor, growing circulation to a respectable fifty thousand readers. At the Review, Graydon added an E. to the front of his byline and set up a spacious office with a fireplace and a long leather couch. A colleague later remembered him wearing white pants to the office, so regularly that they wondered if he owned a single pair that he cleaned and pressed at night. “Carter had an understanding I’ve always admired,” said Jonathan Webb, an editor at the Review, “that you can create a reality by creating the trappings of it first.”
His stewardship of the Review reflected an entrepreneurial streak that Graydon had long nurtured. In a prescient 1975 essay, written when he was twenty-six, Graydon reflected that he had “always fluctuated on the edge of a career in journalism, or one in business. There are possibilities of course that ‘the twain might meet,’ but for the most part, one would have to combine the most outrageous set of talents to nimbly walk the tightrope that divides the two fields.” He added, “The thought of spending my nights lounging around the Rideau Club,I with favourite cronies, sipping Port and smoking cigars, while organizing and putting through profitable mergers and takeovers, really brought out the Dow Jones in me.”
In 1977, however, the Review went kaput, with tens of thousands of dollars in debt.II Undeterred, Graydon drove a beat-up BMW to Manhattan a year later, where he talked himself into a job at Time magazine. An outsider among Ivy Leaguers, Graydon wore his ambition literally on his sleeves, going to work in neatly tailored suits. (He once showed up to a party wearing spats, although, years later, he claimed he had done so as a joke.) Restless to move up in the world, Graydon left for a senior editor role at a start-up magazine called TV-Cable Week, only for it to fold weeks later. He ended up at Life, where he spent lunch breaks with his friend Kurt Andersen mapping out Spy, which they hoped would blend the insouciance of The New Yorker in the 1920s, Esquire in the 1960s, and Rolling Stone in the 1970s. Named for the gossipy magazine that James Stewart’s character works for in The Philadelphia Story, Spy would cast an irreverent eye on Gotham, skewering the city’s potentates in politics, publishing, and finance. “New York bristles with power and hubbub, glamour and squalor, extravagant effort and astonishing rewards,” Graydon wrote in his business plan. “It is a spectacle, packed to overflowing with rascals and entertainers and madmen and geniuses.” Among the inspirations was Graydon’s old childhood favorite, Sweet Smell of Success, in which all of Manhattan’s elites live in fear of a powerful newspaper columnist; Spy winked at the movie by attributing some articles to J. J. Hunsecker, Burt Lancaster’s role in the film. It wasn’t long until Graydon became a fixture of the New York social whirl, a well-dressed imp with a poison pen.
By the early 1990s, Condé Nast was a charter member of the media establishment that Spy loved to needle. But Si Newhouse could not help but appreciate Graydon’s gumption. He loved the same old Hollywood films as Graydon, whose WASP affectations hit a Condé-friendly note of gently ironic grandeur. Plus, Graydon was funny: Spy once knocked Canadians for being so polite that they said “thank you” to their bank machines. So Si was receptive, in 1991, when Graydon called and asked to meet.
On a cold morning, around 6 a.m., Graydon arrived in Si’s spare, all-white office, ready to pitch him an idea for a newspaper. The meeting went fine, until Graydon stood up to leave and the tail of his whipcord Chesterfield coat caught his drinking glass, which was filled with iced café au lait. Graydon watched, in a kind of slow-motion existential horror, as coffee and ice cubes arced through the air and splashed, Pollock-like, onto Si’s pristine carpet.
Fuck, fuck, fuck.
“Everything I could ever humanly want to do in life, he owns,” Graydon remembered thinking. Near tears, he looked at Si helplessly.
“I’m so sorry.”
“That’s okay.” Si shrugged. “I do it all the time.”
The newspaper idea never took off. But a year later, Si would tap Graydon as the next editor of Vanity Fair. The kid from Ottawa had clawed his way to the inner circle. It was the start of one of the most miserable years of his life.
CONDÉ NAST’S ANNOUNCEMENT, in June 1992, that Graydon Carter would succeed Tina Brown at Vanity Fair did not go over well in Hollywood. At a James Taylor concert, Warren Beatty told a journalist that people were uneasy and that VF was ceding its Los Angeles territory, “now that Tina’s gone.” Beatty’s response was typical of the showbiz royalty who were worried about the fate of their favorite magazine, whose soft-focus cover stories were seen as a reliable driver of box office sales. Under Tina, Vanity Fair had come to play an important symbiotic role in the Hollywood celebrity-industrial complex. Now Si had put a fox in charge of the henhouse.
Graydon wasn’t particularly thrilled about the situation, either. After leaving Spy in 1991, following its sale to outside investors, he had spent a year remaking The New York Observer. (His first issue foreshadowed some future preoccupations, like an article about “Two Brothers from Queens”—Harvey and Bob Weinstein—who “resemble car salesmen in both appearance and manner.”) Then came Si’s bait-and-switch with The New Yorker. Now Graydon had to prove himself capable of succeeding arguably the most famous magazine editor of the era. He quickly recruited the acid-tongued British essayist Christopher Hitchens and the crack investigative financial reporter Bryan Burrough, a coauthor of Barbarians at the Gate. But Graydon knew it was Vanity Fair’s access to Hollywood that kept the magazine in the zeitgeist, reeling in readers and ads. The skepticism of stars like Beatty represented a serious threat.
Graydon had also come to believe that Tina’s loyalists were plotting against him. A VF mailing list of celebrities, media machers, and other VIPs who received advance copies, maintained by Tina’s PR guru Maurie Perl, disappeared during the transition. The advance issues stopped going out, and the VIPs got the impression that the new editor had gone out of his way to snub them. Tina was also a conspicuous no-show at Si’s big welcome party for Graydon, and her allies who remained at VF sniped to the gossip pages about the stumbles of the new boss. The whole thing still rankled Graydon thirty years later. “I always thought she left them behind,” he said of Tina and her acolytes, “just so they would be able to tell her how fucking catastrophic I was.” Graydon’s early issues included a memorable cover of the singer k. d. lang being shaved in a barber’s chair by Cindy Crawford, a witty Herb Ritts image that captured the trend of lesbian chic. But it was obvious to the outside world that VF was struggling. Advertising sagged, and The New York Times declared the magazine “out of the spotlight.” Critics called it Vanishing Flair. Four months into his tenure, Graydon admitted to an interviewer that he sometimes felt “a little bit like the new bride in Rebecca.”
Everything changed when he decided to throw a party.
Since 1964, Irving “Swifty” Lazar had hosted Hollywood’s premier see-and-be-seen soiree, an annual Academy Awards watch party that by the early 1990s was held at Wolfgang Puck’s Spago. Swifty was a legendary talent agent who had represented icons like Humphrey Bogart and Lauren Bacall. He masterminded his party like a Lilliputian Stalin, enforcing a seating chart that separated A-listers from B-listers, and chastising guests who attempted to stand up and use the restroom during the ceremony. Entry was coveted and sternly policed; in 1983, on assignment for Time, Graydon himself donned a tuxedo and tried to sweet-talk his way past the door. The valet refused to even park his car.
When Swifty died in 1993, Graydon seized his chance. What if Vanity Fair sponsored a shindig of its own? Graydon imagined the party as a marketing coup for the magazine and a way to repair strained relationships on the West Coast. Instead of being the scary guy from Spy, he would reintroduce himself to a wary film industry as a welcoming, free-spending host. And he was certain that Si Newhouse would approve. Like Graydon, Si was intoxicated by the romance of the movies, telling friends that “if I’d had my choice of what to do with my life,” he would have been a magazine editor—or a film director. (Si’s remark, recounted by Robert Gottlieb, helps explain why he conceived of Condé Nast as an old-fashioned movie studio—and hints at the pressure he felt from his father to set aside artistic longings in order to become the custodian of the family business.)
For the venue, Graydon zeroed in on Morton’s, the West Hollywood power restaurant popular with studio moguls and both of the powerful Michaels—Ovitz and Eisner—who loomed over the business at that time. But when he called the restaurant’s owner, he discovered he was too late: a producer named Steve Tisch had already booked the venue for an Oscar party of his own. Tisch, the scion of an East Coast corporate dynasty, had once been described by Graydon’s Spy as a “primogeniture loser.” Perhaps Tisch hadn’t read that issue, because when Graydon called and suggested he serve as cohost, the producer agreed.
In a sense, Tisch acted as Graydon’s Trojan horse, a Hollywood player with real credibility—he had co-produced the Tom Cruise megahit Risky Business—whose presence sent the message that VF’s new editor was now willing to play nice in the celebrity sandbox. It was just one salvo in a charm offensive launched by Graydon shortly after he took over the magazine. One of his early gestures was to invite the powerful gossip columnist Liz Smith to lunch, where, by her account, “he extended to me these abject apologies for the way he had treated me at Spy.” The old Graydon had derided Smith as “an egregious bum-kisser to the famous and the wealthy” and “the best argument for licensing journalists.” Condé-ized Graydon invited her to pose in Vanity Fair, where she appeared, in Converse sneakers and an Anna Sui dress, in a splashy Steven Meisel photo spread on grunge.
Graydon also wanted to enlist Jane Sarkin, Tina’s longtime celebrity wrangler, who was well known for her formidable Rolodex of agents and publicists. At Spy, Graydon had alienated Sarkin in spectacular fashion when he obtained and printed Tina’s sycophantic and embarrassing letter to Michael Ovitz. Sarkin, who was on her honeymoon in Bermuda when the issue appeared, had to leave the beach to take calls from a furious Tina, an incident she later described to me as “the worst moment of my career.” When he took over VF, Graydon believed it was imperative that he keep Sarkin from departing, and he quickly fell on his sword. “Oh my god,” he told her, when they met face-to-face. “I’m the worst person in the world.” Sarkin stayed.
To repair his relationship with Barry Diller, the entertainment tycoon that Spy often referred to as “gap-toothed,” Graydon called on a friend of his: Diller’s wife, Diane von Furstenberg. “If it hadn’t been for my wife, I probably wouldn’t be speaking to him twenty-five years later,” Diller told me. Within a year of Graydon’s arrival at VF, Diller agreed to lend his star power to a party that the magazine was throwing in Washington before the 1993 White House Correspondents’ Dinner. There, the mogul said to a reporter the magic words:
“Graydon’s been rehabilitated.”
The inaugural Vanity Fair Oscar party, held in March 1994, would be the capstone of this latest reinvention of E. Graydon Carter. Sarkin persuaded Tom Cruise and Nicole Kidman to show up. Then came Liam Neeson and Natasha Richardson, Candice Bergen and Anjelica Huston, Nancy Reagan and Gore Vidal. Prince mingled with Lee Iacocca and James Carville as Annie Leibovitz snapped photos. Graydon stood at the entryway and personally greeted everybody who walked in. There were some snubs—Jack Nicholson and Demi Moore were no-shows—and none of the night’s big award winners made an appearance. But one important guest was pleased: Si Newhouse, who shared door-greeting duties with Graydon and was thrilled to see the Hollywood he had worshiped since childhood brought to glamorous life.
It was immediately clear that the VF party had pull: one producer showed up despite the fact that the magazine had accused him, in its current issue, of illegally importing rare antique coins. Doubling down, Graydon devised a special “Hollywood Issue” that he timed for the following year’s Academy Awards. It included a gigantic photography portfolio of stars, studio bosses, directors, and screenwriters, shot by Leibovitz and Herb Ritts, and a foldout cover featuring ten of the world’s most in-demand actresses, including Kidman, Uma Thurman, and Julianne Moore, posing in slinky lingerie. One newcomer on the cover was Gwyneth Paltrow, whose breakout role in Seven was months away; she was still obscure enough that VF’s publisher had to explain to the ad sales staff how to properly pronounce her name. Paltrow, who was photographed in a gown, was the only actress on the shoot who did not strip down to her underwear. “I can’t,” she told the VF team. “My parents will kill me.”
The Hollywood Issue was a huge seller, but it also drew accusations of racism, for featuring too few Black directors and actors, and sexism, for the way it had depicted one of Hollywood’s most powerful women. Sherry Lansing, then the chairwoman of Paramount Pictures, had agreed to appear, but when the shoot fell through, Graydon decided to use a years-old picture, shot by Leibovitz for an American Express campaign, in which Lansing posed poolside in a revealing swimsuit. Lansing never received a heads-up, and the photo ran, pinup-like, under the headline “Working Girl.” Lansing, the first woman to lead a Hollywood studio, was furious. “I started to scream when I saw it,” Lansing told the Los Angeles Times. “It diminishes the accomplishments of all women, not just in our business, and it shows a great insensitivity to the changing role of women in the world today and how we feel about ourselves.” And yet, when that year’s Oscar party kicked off at Morton’s, there was Lansing, smiling and posing with the editor in chief. The two had made up over lunch a few days before.
Like his Condé forebears, Graydon had learned to weaponize exclusivity. “It’s not just about those you invite,” he liked to say about his party. “It’s about those you don’t invite.” In the mid-1990s, there were no social media platforms for celebrities to advertise their decadent lifestyles and A-list friend circles. With dozens of news crews from around the world covering the red carpet, an appearance at the VF Oscar party became a coveted symbol: a modern version of Mrs. Astor’s old Four Hundred. The saturation of star power in the room—what the writer Frank DiGiacomo called a “panorama of encyclopedic celebrity”—confused even the pros: when the talk-show host Regis Philbin saw Cate Blanchett at the party, he exclaimed that “Gwyneth” looked great. (His wife, Joy, had to correct him.) Will Smith and Sandra Bullock queued at the entrance like any other bridge-and-tunnel partygoers. Even Warren Beatty became a regular at Graydon’s table.
Entrée was tantamount to a cosmic signal that one’s achievements—or notoriety—had resonated in the culture. “Everyone’s trying to get on the front page here,” said Matt Drudge, who attended in 1998, two months after he broke the Monica Lewinsky story on his website. Lewinsky herself was invited to the 1999 edition, where guests remarked upon her physical similarities with another attendee, Shoshanna Lonstein, Jerry Seinfeld’s much-younger former girlfriend. When Lonstein clumsily delivered a tray of coffee to Graydon’s table, Fran Lebowitz was audibly unimpressed.
“I’m sorry,” she told Lonstein, “we asked for Monica.”
Lonstein left in a huff. “You mean to tell me,” Lebowitz said, “Jerry Seinfeld’s ex-girlfriend doesn’t have a sense of humor?”
Civilians and celebrities alike went to elaborate lengths to gain access. One year, a woman snuck in posing as a service worker, hid in a restroom stall for hours, and then wiggled into a formal dress, only to be discovered by security guards who hauled her away. One VF editor was offered $30,000 for a pair of invitations. Bronson van Wyck, an aspiring party planner, took advantage of VF’s policy of allowing in all of the night’s award winners. In 1998, van Wyck rented an old Oscar from a pawnshop, affixed a custom plate with his name and “Best Sound Editing” (not a real category at the time), and showed up in a white stretch limousine. The bouncers waved him in, and he returned the statuette the next day.
Jane Sarkin, holder of the official guest list, was once approached by a woman in a formal gown who demanded entry.
“I need to come in,” the woman explained to Jane. “I’m Jane Sarkin.”
When Ernest Lehman, the screenwriter of Sweet Smell of Success, attended one year, it was a neat bookend to Graydon’s youthful fantasies. Vanity Fair’s editor had manifested this night out of raw ambition and a hustler’s nerve, the same combination that had driven another outsider, Condé Montrose Nast, to gather the leading lights of entertainment and society in his Park Avenue penthouse seventy years earlier. By the time the Oscar-shaped topiaries were dismantled from the Morton’s driveway, and the 3 a.m. stragglers stumbled into the predawn California chill, a new status marker had been carved in the cultural bedrock. Condé Nast was once again the proprietor of the most famous celebrity party in the world.
BACK AT CONDÉ HQ, Si was pleased by all the buzz—and the happy symbiosis between the party and the prestige of his magazine. Graydon’s Hollywood Issue became a perennial bestseller and a magnet for advertisers, with agents and publicists demanding spots for their clients. “People needed that cover to get their price up for a movie, to compete with other people in the movie, to explain why they couldn’t be on a panel because the other actor on the panel wasn’t in the same league,” Sarkin recalled. “It was so powerful.” Si took advantage, asking Graydon to arrange breakfasts with his favorite movie stars during Oscar week; one VF veteran recalled seeing Si, Graydon, Cruise, and Kidman dining together at the Hotel Bel-Air.
For all these reasons, Si was happy to approve the party’s ever-expanding costs. At one point, Condé Nast paid for residents who lived next to Morton’s to vacate their homes and stay at a hotel in the days leading up to the party—making it easier for Vanity Fair to erect its security tents and giant Oscar figurines. Graydon, always an aesthete, now had the budget to indulge his more fanciful whims. Invitations were sent on watermarked Benneton Graveur stationery, printed in Paris. Cigarette girls in dresses designed by Mick Jagger’s girlfriend L’Wren Scott paraded around the room. The famed chef Thomas Keller of Per Se provided hors d’oeuvres (caviar macarons, truffle lasagna). In 2012, VF arranged for an apple farm to fit a custom-built vise around hundreds of budding Red Delicious fruits, applying pressure that interrupted the natural flow of the crimson pigment. The vise, molded in the form of two Art Deco letters, compressed the apple as it grew, leaving the mature product imprinted with a distinctive monogram: “V.F.” Packed into straw-padded boxes, the apples were then flown to California to be used as centerpieces on the Oscar party tablescapes, in between the ironically served In-N-Out cheeseburgers. The coordination involved in creating this disposable party favor, for the fleeting delight of millionaires, was just one of a thousand details that Vanity Fair devoted to each year’s extravaganza.
Riddled with anxiety when he started at VF, Graydon now grew more comfortable with the trappings of his rank. By the mid-1990s, he had moved his family from a West End Avenue rental into a spread at the Dakota, which he decorated with model sailboats, an eighteenth-century French cherrywood dining table, and a bust of Napoleon. (Later, he moved to a West Village town house. Condé Nast provided loans to help secure both residences.) Always dapper, he amassed a collection of bespoke Anderson & Sheppard suits, and increasingly relied on his Condé-provided Russian chauffeur, Sergei. His tricorn swoop of silver hair became a calling card of its own; Graydon’s email signature includes an Al Hirschfeld sketch of himself, complete with a “NINA” hidden in his coiffure.
Vanity Fair’s floor at Condé Nast gradually became a physical expression of his exacting taste. Graydon’s blond-wood office resembled a set from mid-century Manhattan workplace movies like The Best of Everything; he didn’t have a pneumatic tube, but a glass panel in the wall could be discreetly slid open for his assistant to pass him notes. A constant hum of jazz—Stan Getz, Duke Ellington—wafted from a Bang & Olufsen speaker and a Camel Light was usually on Graydon’s lips or in a vintage ashtray, even after New York City enacted its indoor smoking ban in 2003. Rubber-soled shoes were banned (Graydon disliked the squeak); Dunkin’ Donuts cups were verboten (too gauche); Britishisms were always preferred (“dinner jacket,” never “tux”). His assistants had to keep a clutch of pencils in a cup on his desk sharpened to the precise point where they generated a satisfying scrawl, but did not disintegrate upon impact. Printouts had to be prepared with binder clips, not paper clips. Never paper clips.
A signal task for Graydon’s assistant was to fetch the editor’s briefcase from the town car he took to work. After a driver sent notice that Graydon was on his way, the assistant jogged to the elevator, descended to the sidewalk, and grabbed the bag from the back seat while Graydon swept into the lobby hands-free. When the workday ended, the process repeated in reverse. “Will you do the honors?” Graydon asked, and the briefcase would be toted down to the car. In an episode of the sitcom 30 Rock, Alec Baldwin’s character, Jack Donaghy, employs the services of an “office replication service” to construct an identical mahogany workspace for himself while traveling. In real life, Graydon achieved the next best thing. If he was staying a few days at, say, the Hôtel du Cap-Eden-Roc in Antibes or the Four Seasons in Milan, an assistant sometimes flew out ahead of time to prepare his hotel suite. The same meticulous tablescape of pencil cups, stationery, and ashtray that greeted him each day at his Condé desk would be awaiting him on arrival.
His assistants learned that one grave error was to allow Graydon to answer his phone and hear someone else’s assistant on the other end. According to a former employee, Graydon once picked up expecting to speak with the superagent Ari Emanuel.
“Hi, Ari.”
An assistant’s voice chirped back: “Please hold for Ari.”
“I will not hold for Ari,” Graydon replied. “He called me.” Click.
Some ego, perhaps, was to be expected. Graydon was enjoying his spoils. “The basic atmosphere of Vanity Fair is kinda like Spy, only with money,” he told a journalist after a few years on the job. Whereas Graydon was once eager to win the respect of celebrities, he now had a way of striking fear into their hearts. One year, when the Carter family rented a summer cottage in East Hampton, Graydon was dropping off his kids at the Jitney when he bumped into the Sex and the City actress Kim Cattrall, who was boarding the same city-bound bus. When Graydon got back to his office on Monday, he received an urgent message from Cattrall’s publicist: “Kim wanted to let you know that the reason she was on the Jitney was because her Bentley was in the garage.”
“That was the saddest thing I’ve ever heard in my life,” he recalled.III
As cutting as Graydon might be, he could also be generous and loyal, particularly with many of the younger editors and writers in his employ. Turnover in the top ranks at Vanity Fair was rare, and to this day Graydon still works closely with members of his old team from Spy. He sent Champagne to friends on birthdays and gave holiday gifts like linen pocket squares. When the political writer Todd Purdum, whom Graydon had recruited from The New York Times, wrote a controversial article for VF about Bill Clinton’s post-presidential carousing, there was fierce blowback from Clinton’s allies. Purdum and his family took a trip to Paris to get away from it all; Graydon called and told him to put a few hotel nights and dinners on Condé Nast.
There was a caper-like quality to life at VF. One year at the National Magazine Awards, Graydon was so put off by the rubber-chicken catering that he called his office and requested takeout for his entire table. Two assistants arrived in the Waldorf-Astoria ballroom with bags of gourmet sandwiches, which they proceeded to hand out to the magazine’s staff—“Who wants tuna?”—as less-flush competitors picked at their limp salads. But Graydon also sometimes surprised his minions by revealing a neurotic side, particularly when Si’s phone extension appeared on his office line. “There’s a 1 percent chance I’ll be fired,” Graydon would say before trudging off to see the boss. If Si had a specific request, it took precedence: once, when Si expressed curiosity about the Paris Hilton sex tape, a phalanx of Vanity Fair assistants was mobilized to find him a copy.
Amid this fussiness and frivolity, Graydon also ran a magazine that made news. In 1996, an investigative piece by Marie Brenner on Jeffrey Wigand, a former research executive who’d blown the whistle on Big Tobacco, inspired the Al Pacino film The Insider; Graydon published the article even when major cigarette brands pulled their ads. In 1998, VF published a glamorous photo shoot featuring Monica Lewinsky, shot by Herb Ritts on the beaches of Malibu. Lewinsky had bumped into Maureen Orth, the wife of news anchor Tim Russert, at a party in Washington and gushed about Vanity Fair; Orth, who wrote for the magazine, arranged an introduction with the editors. The pictures, which evoked 1950s-style pinups—Lewinsky wore blue jeans and a gingham shirt in one; in another she danced with a sunlit American flag—were dissected on all three network newscasts and Larry King Live. Maureen Dowd mocked the shoot as “sickening,” but she also acknowledged that “getting your own photo shoot in Vanity Fair has become the premier achievement in our celebrity-mad culture.”
The Ritts shoot is notable in light of the 2010s re-evaluation of Lewinsky as the victim of a global pile-on, when a new generation asked why the young intern had been subjected to so much cruelty. In one sense, Vanity Fair had gotten there first: in December 1998, the month of Clinton’s impeachment, the magazine included Lewinsky in its year-end Hall of Fame, recognizing her as a victim of a media that “project[ed] every dark wish, sociological cliché, and erotic fear onto her” and left her “deprived of her voice.” “This is a melancholy story,” VF concluded, “covered in shame.” In 2014, when Lewinsky wrote her first extensive public commentary on the scandal, she did so in the pages of Vanity Fair. The essay, “Shame and Survival,” came about after Graydon referred Lewinsky to a British public-relations adviser who had worked with Kate Middleton and David Cameron. The redemption narrative they crafted kicked off a campaign that turned Lewinsky into a sought-after speaker on cyberbullying and public shaming, and the heroine of a sympathetic Ryan Murphy TV docudrama. More than two decades into his tenure, Graydon was still shaping the zeitgeist.
LEONARD DOWNIE JR., the executive editor of The Washington Post, was onstage at a management retreat in Maryland on May 31, 2005, when the cell phone in his pocket started to ring… and ring, and ring. The buzzing was so persistent that Downie, trying to concentrate on his remarks, shut it off. Finally, he spotted the chairman of The Post, Donald Graham, whose family owned the newspaper, beckoning him from behind a door. Downie walked over.
“You better call Woodward,” Graham said.
That morning, Vanity Fair had published an explosive scoop: it unmasked Deep Throat, the famously anonymous source whose confidential tips fueled Bob Woodward and Carl Bernstein’s reporting that brought down Richard Nixon. Deep Throat’s secret identity was among the most enduring mysteries in American journalism, and, up until that day, was known only within a vanishingly small circle of Post journalists. Yet here was W. Mark Felt, formerly the number two official at the FBI under Nixon, revealing his critical role in political history—not in the sober newsprint of The Post, but in the pages of a magazine whose cover featured Nicole Kidman promoting the film Bewitched.
Woodward and Bernstein, who had promised to shield Felt’s identity until his death, were caught by surprise: Graydon never contacted them ahead of publication, to minimize the risk that they would publish first. John D. O’Connor, a lawyer representing Felt’s family, had first pitched the story to People magazine and the book publisher HarperCollins, requesting payment in exchange for the information; both turned him down. Vanity Fair reached a different accommodation: the magazine paid O’Connor roughly $10,000 to write the article, and the Felt family retained the potentially lucrative film and book adaptation rights. It was the biggest journalistic coup of Graydon’s tenure—ABC broke away from a live presidential press conference to report the news—and it underscored VF’s ongoing relevance in Washington. The magazine’s annual party after the White House Correspondents’ Dinner, which originated as a reception in Christopher Hitchens’s apartment, had become the apex of the capital’s social calendar, an infusion of glamour into a district of drab. The event even caught some blame for fueling Washington’s fixation with celebrity: in 2012, during the Obama years, George Clooney, Reese Witherspoon, and Woody Harrelson all attended. If Tina’s “Reagan Stomp” cover hinted at a coming fusion of Washington and Hollywood, Graydon’s annual soiree embodied it.
Back in New York, Graydon pursued other projects that blurred the line between his role as a chronicler of the culture and an active participant. He bought and revived a pair of classic restaurants, the Waverly Inn and Monkey Bar, that became living manifestations of his magazine’s “who’s in, who’s out” vibe, with seating charts curated by Graydon’s assistants on a daily basis. Condé Nast had no formal ties to these ventures, but the clamor for reservations (and the paparazzi regularly parked outside) added to the company’s mystique. With Barry Diller, Graydon coproduced a documentary on the producer Robert Evans, The Kid Stays in the Picture, that premiered at Cannes; later, he produced a Broadway show about the agent Sue Mengers with Bette Midler. Graydon’s social circle increasingly consisted of the wealthy moguls and Hollywood grandees whose doings he had once skewered in Spy and now often celebrated in Vanity Fair. At one point, he accepted a $100,000 payment from the producer Brian Grazer after he recommended a book about a math genius; the ensuing movie, A Beautiful Mind, had won the 2002 Oscar for Best Picture. That year, Grazer and the film’s director, Ron Howard, were included on Vanity Fair’s New Establishment list.
All this extracurricular activity raised grumbles inside Condé Nast that Graydon was distracted from his day job. Some readers noticed a staleness creeping into the magazine’s pages. In 2011, a reporter for The New Republic calculated that one out of every three issues of Vanity Fair since 2003 included at least one article either focused on a member of the Kennedy family, written by a Kennedy, or mentioning a Kennedy on seven or more occasions. Graydon proffered a defense—“They are the totemic figures of the last great years of the American Century”—but the survey fueled an impression that his magazine, ostensibly a champion of the vanguard, was overly fixated on the past.
Still, the allure of the Oscar party endured. For each new generation of Hollywood stars—many of whom had grown up absorbing the party’s mythology, and dreaming of one day attending themselves—Graydon’s invitation still counted as an official confirmation that, in the eyes of the town and the culture at large, one had arrived.
“I try not to be too aware of powers-that-be giving you approval,” said the actress Greta Gerwig, who first attended in 2013. “But I would like to think that somewhere, in the internal workings of Vanity Fair, they said: ‘Yes, Greta Gerwig. You can now be part of this.’ ”