I’d just smoothed my tuxedo and taken a sip of my first martini when I saw them. It was February 27, 2011, and as I began my initial tour of the Vanity Fair Oscar party, taking a quick inventory of the famous faces in my field of vision—Larry David, Cameron Diaz, Mick Jagger, Anjelica Huston, Sacha Baron Cohen and his wife, Isla Fisher—I noticed a group of well-turned-out guests forming a loose perimeter around two instantly recognizable men. A starstruck Justin Bieber, whose careful handling of his career suggests he understands the fleeting nature of fame, had sought out one of the wise men of the entertainment business and one of its biggest stars, Tom Hanks. As Bieber’s date, Selena Gomez, stood by, I watched the boy wonder listen intently to the two-time Oscar winner, who offered a bit of wisdom wrapped in his usual self-deprecating wit. “Stay grounded,” Hanks told Bieber, slipping into ironic-pompous éminence grise mode. “Don’t become a jaded professional actor.”

A bit later that night, Hanks sounded amused when I mentioned to him that I’d observed his conversation with Bieber. “Did you feel the Zeitgeist shudder—the tectonic plates of our culture shift?” he said in a mock breathless voice. It was the actor’s way of saying, Don’t make too much of two guys making small talk at a party—even if those two guys are a teen heartthrob and, well, Tom Hanks.

Throughout the Tower bar and Terrace of the Sunset Tower Hotel, in West Hollywood, as well as the elegant structure that had been pitched over the hotel’s outdoor terrace and pool, moments like the Hanks-Bieber parlay were a dime a dozen. Before the night was over, Taylor Swift would have an intense conversation with her ex-boyfriend Jake Gyllenhaal, who reportedly inspired at least one entry in her lengthy breakup-song canon; Jane Fonda would commune with a group that included her brother, Peter, and Glee actress Jane Lynch; and comic and HBO Real Time host Bill Maher would bond with Mick Jagger over the latter’s treatment in Keith Richards’s autobiography, Life. “I had just read it, and we were comparing notes about how shitty it is to work with someone who’s fucked up on drugs,” says Maher, referring to Richards’s fabled heroin addiction. Jagger hadn’t fared well in Richards’s account of his life, and Maher says, “I remember telling him, ‘I’m on Team Mick,’ because I once worked with a heroin addict on a sitcom and it wasn’t fun.”

On the other hand, “more fun than anything,” according to Maher, was the 20-minute conversation he had the following year with then Denver Bronco quarterback Tim Tebow at the 2012 Vanity Fair Oscar party. It was not a chat you might expect to end pleasantly. “We’ve made jokes about him on our show, and, obviously, he and I do not exactly see eye to eye on the subject of religion,” says Maher, who is an outspoken atheist and critic of religion, while Tebow is a banner-waving Christian who strikes prayer poses at games and is saving his virginity for marriage. “But you know,” Maher says, “he was a sweet kid, and we just talked football.”

It’s this potential for unlikely, even odd encounters that makes the Vanity Fair party sui generis, says Anjelica Huston, who has been attending Oscar parties for decades, going back to Swifty Lazar’s annual event in the 60s and 70s. “You look across the room and you see Monica Lewinsky or Anna Nicole Smith or any number of people that you’re just dying to talk to and whose paths wouldn’t coincide with yours at any other point in your life,” she says. “These are people who enter your dreams occasionally, but you don’t ever expect to rub shoulders with them.”

Lewinsky provided just such a thrill in 1999, when she was invited to the Vanity Fair dinner and party and became the star attraction of the night. At dinner, which starts at five P.M. and takes place during the Oscar ceremony (shown on screens throughout the dining room), she sat with the actress Ellen Barkin and Hamilton South, formerly of Vanity Fair and then an executive with Ralph Lauren. When Gwyneth Paltrow won the best-actress award for Shakespeare in Love that night and stepped up to make her acceptance speech in the pink taffeta Lauren gown that would set the media reeling, Lewinsky, who had dished about her infamous blue dress at the table, turned to South and thanked him.

When he asked the reason for her gratitude, Lewinsky replied, “Now there’s a dress more famous than my dress.”

Having covered the Vanity Fair Oscar party as a working journalist for 11 of the 18 years that it has taken place—and attended one year as a guest when I worked at the magazine as a contributing editor—I can attest that there are moments at the party that feel like a waking dream. It’s not just that the room looks like the celebrity equivalent of the Milky Way as seen through the distortion-free lens of the Hubble telescope, but that these famous and wealthy and powerful guests are behaving in a remarkably relaxed way. There is no V.I.P. section at the Vanity Fair Oscar party; it’s not the easiest invitation to get, but once you’re in, you’re in the same room as everyone else. Celebrity handlers, bodyguards, and even agents are virtually nonexistent. The media are kept on a short leash as well. (Being caught at the party scribbling into a notebook is a one-way ticket to expulsion, and so I spent a good chunk of time at each party quietly jotting notes in men’s-room stalls. But that had its own rewards. In 1999, I was in the men’s loo when Goldie Hawn emerged from a stall to the surprise of Madonna’s brother Christopher Ciccone, Vanity Fair writer Kevin Sessums, and actor Andy Garcia and declared, “Never been better.”)

In this democratic and relatively free-spirited setting, Hollywood once again becomes high school with money, as the cliché goes, but in a fun, revealing, John Hughes kind of way. The tense, tightly wound business that Hollywood actually is, where everyone seems to be wearing Kevlar and carrying a scorecard, feels as if it were a world away. Instead, glamour, sophistication, romance, and fun—those ethereal qualities that the film industry is so adept at portraying (if not always exemplifying)—rule the night. It’s the kind of party where, in 1996, Mel Gibson arrived with an Oscar in each hand for Braveheart and a bagpiper hired by his friend Jodie Foster, where Monica Lewinsky also hit it off with Sir Ian McKellen in 1999, and where, in 2005, Tom Cruise pulled up to the back door on his sleek, black Ducati motorcycle.

The party has served as the playground for some of the most hotly discussed serial romances in contemporary Hollywood. “We’ve had Jennifer Aniston come with Brad Pitt, with John Mayer, and with Justin Theroux,” says Vanity Fair features editor Jane Sarkin, “while Brad has also come with Gwyneth Paltrow and Angelina Jolie.” Relationships have even been launched at the Oscar party: Ellen DeGeneres and Anne Heche famously fell for each other there in 1997, and in 1999, Ronald Perelman met his future, now former wife Ellen Barkin during the festivities.

And yet, though stars and starlets give the night its incandescence, the Oscar party has, from the start, cast a wide net. “You want the party to look as glamorous and as gorgeous as possible, but you also want to get that mix where the worlds of sports, art, literature, music, fashion, society, and politics collide,” says Sarkin.

In 2012, that meant a crowd that included not just movie stars and moguls but also art dealer Larry Gagosian, business magnate Carl Icahn, TV journalists Anderson Cooper and Christiane Amanpour, designer Tory Burch, hotelier André Balazs, biographer A. Scott Berg, former senator Christopher Dodd, socialite Betsy Bloomingdale, Amazon founder Jeff Bezos, and tennis greats Serena and Venus Williams. One of the more memorable guests ever was hero pilot Chesley Sullenberger, in 2009. General Tommy Franks came in 2004. “It’s sort of like Vanity Fair Live,” says the party’s host, Graydon Carter.

Before the Vanity Fair Oscar party, there was Swifty’s. Irving Paul Lazar was arguably the most powerful literary and talent agent of Hollywood’s postwar, pre-CAA era, and on April 13, 1964, he and his wife, Mary, threw an Oscar-night party that demonstrated his clout in social terms. For most of the next three decades Lazar’s was the hottest ticket to celebrate Hollywood’s holiest night.

Dubbed “Swifty” by his client Humphrey Bogart after Lazar orchestrated three deals for the actor in a single day, the bald and boldly bespectacled agent chose the Bistro restaurant, in Beverly Hills, for his relatively modest first bash. Approximately 40 people were invited to dine on beef stew and watch the Oscar ceremony on two televisions set up in front of an array of folding chairs. Those first guests included Jimmy Stewart, Gregory Peck, Jack Lemmon, director Billy Wilder, Tonight-show producer Freddie de Cordova and his wife, Janet, and artist David Hockney. Another 30 to 40 guests, including some Oscar winners, were invited to attend after the awards, at which point the parsimonious Lazar ordered sandwiches from the nearby deli Nate ’n Al to keep his entertaining costs low.

From these intimate and not-so-glamorous beginnings, Swifty’s party—as it became known despite Lazar’s apparent distaste for his nickname—evolved into the social apex of Oscar-night parties. And after a couple of venue changes, including a cross-country move to New York and Warner LeRoy’s Tavern on the Green in 1977, Lazar’s party landed in 1985 at Spago, the Sunset Strip restaurant opened by proto-celebrity chef Wolfgang Puck.

The guest list evolved, too, into a heady mix of Hollywood’s Old Guard, high society (and its disco-era iteration), the power crowd, and the entertainment industry’s latest sensations. But Lazar’s Oscar parties were not known for their relaxed attitude. Especially during the telecast, he did not like his guests mingling or even going to the bathroom. “Shut up” and “Sit down,” punctuated with “Goddammit,” were not uncommon orders from the host.

“Swifty was very, very stern,” says author Jackie Collins, who has the distinction of being a regular at Lazar’s parties as well as at Vanity Fair’s. “You wanted to socialize; he wanted you in your seat, and you weren’t going to argue with him. He would scream at everybody. God forbid you were late.”

When it came to Hollywood’s Oscar-night identity, the death of Lazar on December 30, 1993, left a void and a somewhat daunting opportunity. According to Vanity Fair director of special projects Sara Marks, it was then that Graydon Carter, who had attended Lazar’s party in its final year, “decided that maybe we should go out to L.A. and have a small dinner on Oscar evening.”

“When Swifty died, I had been the editor of Vanity Fair for about a year and a half,” Carter says. “I had seen what he had done, and I thought this would be a very good thing for the magazine. But I wanted to do it in a very small way. My feeling is, if you’re going to fail, do it in small company.”

At the time, the Oscar ceremony was held on Monday nights. Carter thus wanted to hold the dinner at Mortons, where Hollywood’s power players amassed on non-Oscar Mondays, but when he called the restaurant’s owner, Peter Morton, he learned that producer Steve Tisch (Risky Business, Forrest Gump) had beaten him to the punch.

“When Irving Lazar died, I felt there was an opportunity to create an Oscar party for a younger generation,” Tisch says. “I picked up the phone and called Peter, who was very open to the idea. Literally, probably 24 hours later, Peter called me and said, ‘You’re not going to believe this, but Graydon Carter called with the same request. Do you think you guys could do it together?’ ”

Tisch joined with Carter and a team that initially included Hamilton South, Sara Marks, Jane Sarkin, West Coast editor Krista Smith, and director of public relations Beth Kseniak, and the party was born.

The first one, in 1994, was an intimate affair, although the guests were greeted with the pomp and fervor of an old Hollywood premiere. Kseniak had stacked approximately 20 camera crews and 25 photographers at the entrance to Mortons, and the steady explosions of flash units and celebrity shout-outs proved to be a giddy amuse-bouche for the proceedings inside. Donald Sutherland, Lee Radziwill, Nancy Reagan, Oliver Stone, Gore Vidal, Gene Hackman, Barry Diller, Diane von Furstenberg, and Michael Stipe were among the 100 guests who came for dinner. That figure doubled for the after-party, which brought out the best of the Oscar ceremony, including Robert De Niro, Anthony Hopkins, Tom Cruise and Nicole Kidman, and Liam Neeson and Natasha Richardson. Prince drew attention to himself by, paradoxically, sitting quietly in a corner.

The media were reluctant to declare that Vanity Fair had succeeded Swifty’s as the premier Oscar party. But, as someone who did business daily in Hollywood, Tisch knew that the party had been a success. And that was not necessarily going to be good for his business.

“Look, my life was not threatened, but there were people who said to me, and I’m trying to quote, not paraphrase, ‘Well, listen, Tisch, if you don’t send me an invitation to your party, that decision is going to challenge our business relationship.’ I didn’t need that aggravation in my life.” So, the producer says, when Carter asked him in 1996 if Vanity Fair could go it alone, “it was literally like an 800-pound gorilla jumped off my lap.”

That gorilla quickly grew into King Kong. By 1998 the Oscar party had become such a hot ticket that the New York Post reported that Sean Combs, who was then answering to the name of Puff Daddy, was so intent on making the scene that he was willing to face possible arrest—he was scheduled to testify in a New York court on the same day that the party took place in L.A. He chose the Oscar party.

That year, Titanic won best picture, and the guest list surged 50 percent, with invitations to the after-party staggered over the course of the evening. Brad Pitt, single again after Gwyneth Paltrow and he had called off their engagement the previous summer, ended up in the sights of both Madonna and Demi Moore. “I was just giving him motherly advice,” Moore told me that night. “Just keeping an eye on him.”

The party needed to grow, and so, in 1999, Carter brought on board architect Basil Walter (who had helped him design Vanity Fair’s clean-lined offices) to work with Marks to expand the available space at Mortons. As Walter remembers the assignment, “We wanted to create an environment where when you walked into the room you didn’t think, I’m in a tent, but rather, Where did this building come from?” Engineers were employed, and Walter designed a structure for the top of the uneven parking lot next to Mortons, adding 7,500 additional square feet to the party. From the inside, the new space looked like an elegant nightclub with translucent bars and white overstuffed couches. The addition required literally pulling down a wall at Mortons before the party to facilitate crowd flow and then putting it back up after Oscar night. One year, a guest who had been at the party went to dinner at Mortons the following evening and was baffled when he couldn’t access the now vanished “nightclub.”

With the addition of this glamorous space—and, for the next years, the Cuban band Adalberto Alvarez y Su Son, brought in from Havana—the Oscar party was outfitted for the new millennium. Kseniak says that once the party became the destination for post-awards revelry the press hordes grew to 40 camera crews and 80 paparazzi as media outlets began to realize that they could fulfill virtually all of their Oscar-night needs by staking out a spot on Vanity Fair’s red carpet.

Inside, under the watchful eye of Kseniak and her team, a handpicked group of print and TV journalists are allowed to observe the party, where, in 2002, Gwyneth Paltrow could be seen, in an Oscar gown, squealing “Daddy!” as she ran across the room to hug her father, the director Bruce Paltrow (who would pass away in October of that year) and where, a year earlier, I had watched Combs give some serious shade to his ex-girlfriend Jennifer Lopez and her new beau, choreographer Cris Judd, as they passed by him. When a friend of the rapper’s called after Lopez, Combs gave him a shove. “Stop staring,” he commanded. That was a tall order.

“The party is almost like those tours of Hollywood homes that people take,” the writer-director J. J. Abrams says. “But it’s one where you can remain stationary and have a drink and the tour goes by you.”

Even Elton John, who was initially considered a contender in the post-Swifty Oscar-party derby, has become a regular, moving over to Vanity Fair’s event once his own annual Oscar-night dinner, an AIDS benefit, winds up. He has also made a tradition of auctioning off at least two invitations to the magazine’s party to raise money for his eponymous AIDS foundation. (The invites are regularly auctioned off at other benefits as well and, to date, have raised millions for charity.)

In 2009, after a one-year hiatus due to the screenwriters’ strike, the party moved from Mortons, which had closed in December 2007, to the Sunset Tower Hotel (owned by Jeff Klein, who is also Carter’s partner in Manhattan’s Monkey Bar). The on-site command center, which becomes operational approximately 10 days before the party, is called, inevitably, the War Room, and early this past December I sat in as the magazine’s equivalent of seal Team Six met at Walter’s Lower Manhattan offices to finalize production plans for the 2013 event. Sara Marks sat at a conference table, thumbing her BlackBerry. To her right was Walter, whose job entails working with the team on not just the look of the party’s physical space but also smaller details such as the design of the mini-lampshades that adorn the tables. Also at the meeting was Pete Barford, a London-based event planner who has functioned for 17 years as the Oscar party’s on-site production manager. En route to the meeting was Keith Duval, who oversees security for the event, and missing in action were Patrick Woodroffe and Adam Bassett, who design both the interior and exterior lighting but were tied up this day with another client, the Rolling Stones.

Spread before the trio and projected onto the conference-space wall was a blueprint of the Oscar-party space. The party is a collaborative effort all around, and when the meeting concluded, the team would have a final working draft for the 2013 party that they would then present to Carter. Adjustments would be made per Carter’s notes, and then, in much the same way that a major rock show is mounted, the elaborate “stage” for the event would commence construction at 11 A.M. on Friday, February 22, less than two and a half days before the first guests would arrive.

At the meeting, as the team proceeded through its checklist, I was reminded of something that the magazine’s senior West Coast editor, Krista Smith, had told me a few weeks earlier: “There is nothing accidental or haphazard about that party.”

The agenda included traffic patterns, the Vanity Fair topiaries that stand at the entrance to the party—and “brand” the evening in all the red-carpet photos—and the solution Walter had devised to make the helium-filled-weather-balloon-lined ceiling of the nightclub-like space that’s temporarily erected over the hotel’s pool more responsive to changes in lighting.

Inevitably, the subject of guests—both those staying at the hotel and those who will be invited to the party—was tackled, before the official meetings with Carter. Oscar-weekend guests at the Sunset Tower Hotel who aren’t invited to the Vanity Fair event are required to come and go from the hotel via a special entrance and sign a waiver that they will not attempt to join the party. Marks explained that last year, however, a would-be crasher whose room faced the red carpet climbed out of her window and dropped down onto a landing that put her perilously close to a lighting setup that carried a potentially lethal electrical current. In order to help ensure that nothing like that happens again, Marks has booked many of the rooms that might impact the party because of their proximity.

The total number of guests invited each year is something of a state secret, but by all accounts the party has shrunk since it last took place at Mortons, in 2007. If there is one constant to the guest list, it is that on the day the Oscar nominations are announced invitations with handwritten notes from Carter go out to the major nominees. The rest of the guest list, for both the dinner and the post-ceremony bash, coalesces as planning ramps up in the fall and winter. Marks, deputy director of special projects Matt Ullian, and a number of Vanity Fair’s editors and contributors—including Sarkin, Smith, Kseniak, deputy editor Punch Hutton, contributing editors Reinaldo Herrera, Lisa Robinson, Elizabeth Saltzman Walker, and Betsy Kenny Lack, Los Angeles editor Wendy Stark Morrissey, and special correspondent Bob Colacello—discuss potential guests with Carter. In essence, the team members ask themselves: Who would I like to meet?

The seating chart usually goes through a half-dozen drafts—one trick is to make sure that rivals or former lovers don’t end up next to each other—and, at last year’s party, the dinner consisted of 15 tables, each with 8 to 10 guests. Every year, a custom-engraved Zippo lighter is placed at each dinner guest’s place setting; last year’s bore the words of longtime Vanity Fair writer Christopher Hitchens, who had died the previous December: “Everyone has a book inside them, which is exactly where I think it should, in most cases, remain.” For those who wanted to fire up those lighters, there were cigarette girls standing by dressed in uniforms designed by Mick Jagger’s longtime paramour L’Wren Scott.

At Table Two, Twitter founder Jack Dorsey sat with Tower Heist director Brett Ratner, investor Vivi Nevo, SpaceX founder Elon Musk, and venture capitalist Yuri Milner and his wife, Julia. At Table Three, Carter and his wife, Anna, sat with a group of Oscar-party regulars, including Michael Douglas (who cut out early to go and present an award at the ceremony and then returned); screenwriter Mitch Glazer and his actress wife, Kelly Lynch; designer Carolina Herrera; author Fran Lebowitz; investor and art collector Jean Pigozzi; and billionaire Ronald Perelman. At Table 11, designer and filmmaker Tom Ford dined with Modern Family star Sofía Vergara and her then boyfriend (now fiancé), Nick Loeb; art dealer Larry Gagosian; Homeland star Claire Danes; director Sofia Coppola; and Coldplay front man Chris Martin, whose wife, Gwyneth Paltrow, was presenting at the Academy Awards in one of Ford’s creations.

Over the years, the Oscar-party team have seen some valiant efforts made at snagging an invitation. Staff members have been offered substantial financial rewards in exchange for entry to the party, as well as a number of non-cash incentives, all of which have been turned down. In the days when the party was held at Mortons, bomb-sniffing dogs would occasionally find someone dressed to the nines hiding beneath the metal scaffolding over which the tented structure had been built. “They’d been there since the night before with bags of food and small coolers,” Keith Duval, the security chief, says with an incredulous smile. Entry was once guaranteed to anyone who arrived at the party with an Oscar, guest list or no, but Duval says that changed when people started showing up with “fake Oscars and a bodyguard, or a real Oscar that they’d bought at a pawnshop.”

Matt Ullian has been the point person at the party’s door for the past 10 years. Among his duties are handling the “plus-one,” “plus-two,” “plus-you’re-kidding-me” questions that arise when, on occasion, guests try to finagle friends into the party at the last minute. “You wouldn’t believe how often someone shows up with extra people who we can’t let in, but the car’s already been valeted so the guest just leaves his or her excess friends standing on the sidewalk,” Ullian says, laughing. Actual Oscar winners are cut a little slack. In 2004, the year Charlize Theron was a favorite to win best actress for Monster, her publicist asked for flexibility. As Ullian remembers it, the deal was: “If she loses, she’s coming with a girlfriend. If she wins, she’s bringing a gaggle.” Theron won, and the magazine was happy to accommodate her.

A stickier issue concerns those who have been invited to the party but then engage in behavior (with staff or other guests) that ensures Carter will not invite them back—sometimes permanently. In 2001, Courtney Love was at one point inside the Vanity Fair Oscar party. I know because I asked her if Hollywood was becoming a more conservative place in the wake of George W. Bush’s election, and the former Hole front woman’s response was to flash me. “Do you see my nipple?” she asked. “That’s your answer.” Later that evening, Love demanded that her manager be admitted to the party. Carter told her to talk to Marks, who was out front. When Marks turned her down, Love tromped out to the video cameras stationed on the red carpet and said that she had an important annoucement. With cameras now focused on her, she declared that Marks was a “cunt.” She has not been back since.

Nevertheless, a scant few uninvited guests have been granted entry. The first year of the party, Carter says, he was informed that actor Martin Landau had shown up in a tux but without an invitation. Carter agreed to let him in, and the following year, 1995, Landau returned with an actual invitation as well as the best-supporting-actor Oscar he’d won for playing Bela Lugosi in Tim Burton’s Ed Wood. “I thought that was good Karma,” says Carter.

Another year, Lou Palumbo, who headed security for the party prior to Duval, approached Carter during dinner to tell him that a crasher had managed to install herself at a table between John Cleese and Faye Dunaway. Before the party, the woman had sneaked into Mortons by passing herself off as a staff person, then stole off to the bathroom and stood on a toilet for hours, and finally changed into a swish dress and joined the party as it got under way. The unflappable Palumbo defused the situation without drama by taking Dunaway’s seat and quietly identifying himself to the woman and explaining that, after a few moments of small talk, she was going to follow him out of the restaurant. But later, Carter remembers, “somebody came over to me and said, ‘Listen, she’d just love to come back in.’ I said, ‘If she went through this much trouble, we’ll let her in, but tell her to come back at 10:30.’ And she did.”

During the strategy session in New York, Walter, Marks, and Barford gave me a glimpse of a new feature they’re working on for the 2013 party: on one of the Sunset Tower’s walls, a faux bay window will be created. The “windowpanes” will consist of video screens carrying live feeds of Oscar winners and other guests arriving on the party’s “red carpet.” (It will be green and white stripes this year.) Cameras will shoot the guests from behind so that the view from the window will be of dozens of photographers and camera crews recording each arrival.

“We’re trying to get some of the buzz of the carpet into the space,” Barford tells me later, which, to be honest, given all that goes on inside the party, sounds like overkill. Then I remember what Anjelica Huston told me about stars watching other stars, which could almost serve as a motto for Oscar night. “Nobody likes a celebrity more than a celebrity,” she said. “They’re fascinated by the genre.”