This story is an excerpt from Empire of the Elite, a blockbuster new history of Condé Nast by New York Times reporter Michael Grynbaum.

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 Carter 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 — recently anointed as the new editor of Vanity Fair — seized his chance. What if VF 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, the satirical monthly he’d founded in 1986, he would reintroduce himself to a wary film industry as a welcoming, free-spending host. And he was certain that his new boss, Condé Nast owner 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.

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 co-host, 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, his VF predecessor Tina Brown’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 a sycophantic and embarrassing letter Tina had written to 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 25 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 10 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.

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.”

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 best-seller 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 to the party — making it easier for Vanity Fair to erect its security tents and giant Oscar figurines. Graydon, always an aesthete, got 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). Before the 2012 bash, 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.

Graydon 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 Jazz Age entertainment and society in his Park Avenue penthouse decades 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.

Excerpted from Empire of the Elite: Inside Condé Nast, the Media Dynasty That Reshaped America by Michael M. Grynbaum. Copyright ©2025 by Michael M. Grynbaum. Reprinted by permission of Simon & Schuster Inc.

This story appeared in the July 9 issue of The Hollywood Reporter magazine. Click here to subscribe.