So I’m smoking a joint with Seth Rogen and Danny McBride. This might sound like the setup to a joke, and it would probably be a good one, but this is what the Oscar party was like. At least for me.

Over the years, whenever I told anyone I worked at Vanity Fair, 9 times out of 10, their first question was, “Have you ever been to the Oscar party?” The Oscar party grew to be so successful, so monolithic, that it became as big as the magazine itself. I only missed one between 1995 and 2017, in 2005. (In 2008, it was canceled due to the writers’ strike.)

At a few of those early Oscar parties, clipboard in hand, I worked the door, a miserable rite of passage for Vanity Fair assistants. Once you’d served your time as a grunt on the front lines, you graduated to fill-in, although sometimes you weren’t called on, eating dinner while leaning against the bar with fellow fill-in rejects and other staff members. After a few years of that, if you were still around, you became an invited guest, sitting in front of a place card with your name on it.

Leonardo DiCaprio, Sharon Stone, and Ellen Barkin, photographed by Dafydd Jones at the 1994 Oscar party, at Mortons.
Paul McCartney and Heather Mills, photographed by Becker at the 2002 Oscar party.

So I’m smoking a joint with Seth Rogen and Danny McBride, a really bad decision because I was on duty that night. Not only was I on duty, but I was doing something I had never done before, something that I had never wanted to do before, and something that I refused to ever do again after that night. I was working the red carpet.

Kate Winslet at the 2009 Oscar party.
Barry Diller, photographed by Becker at the 2009 Oscar party. David Geffen, second from right, sneaks a kiss in the background.

It was Oscar night in 2009, our first year at a new location, the Sunset Tower in West Hollywood, after 14 years at Mortons, which had closed the year before. A few weeks earlier, as we were trying to find new ways to cover the party for Vanity Fair’s Web site, the idea of having our own red-­carpet reporter asking celebrities questions, and live-streaming it to the site, seemed like a good one. We were getting with the times.

Michael Douglas and Kirk Douglas, photographed by Jones arriving at the 2009 Oscar party. Larry Fink and Becker hold cameras at center.

Somehow, Graydon Carter, then the editor of Vanity Fair, thought it was a good idea for me to be on the red carpet. (Carter is the founder and a co-editor of AIR MAIL.) I thought it was a terrible idea, and I made it known. I have never had the desire to be on-camera. I’m naturally shy, at least without massive quantities of booze in me, and to be a successful red-carpet interviewer you need to be an extrovert and outgoing.

I pleaded with Graydon to find somebody else.

“I think you’ll be great,” he said.

“I promise you, I won’t. I’ll only be able to do it if I get properly loaded, and I might do something stupid.”

“As long as we get it on-camera, that’s fine with me.”

Graydon was taking joy in watching me squirm, and I could tell he wasn’t going to let me off the hook.

The 4-1-1

The Oscar party happens in waves. The first to arrive are the dinner guests, maybe 150 of them or so, at around 5:30. These are usually not the biggest celebrities of the night—most of those are at the Oscar ceremony—although there might be one or two. It’s more a mix of L.A. social figures, producers, studio and agency heads, faded stars who are still locally viable socially, and some old-­Hollywood stars or starlets dragged out of the old-age home for the night.

Dinner guests sit at tables of 10 or 12 and spend the next three or four hours watching the Oscar telecast on televisions and screens set up around the room. When the Oscars are over, the tables are cleared away, and the party opens up to the next wave of guests, which are staggered by the hour, the time on your invite depending on your status.

Sidney Poitier and Cornelia Guest at the 2009 Oscar party.
Billy Wilder with his wife, Audrey, photographed by Becker at the 1999 Oscar party.

If you were a major movie or television star, or you were nominated, your invitation would be for nine P.M. This is when the real celebrities begin to arrive. Some are coming straight from the ceremony, others from home or wherever they happened to watch it. As the night goes on, the caliber of stars arriving lessens by the hour, until the Oscar winners start getting there, closer to midnight.

We always had two press pens set up outside the party. One was for still photographers from all of the major photo agencies; the second was the long line of news- and entertainment-show red-carpet reporters, who would broadcast live throughout the night. (“Let’s go to Janice at the Vanity Fair Oscar party.”) The interviews and photographs would travel around the world over the following days—it was a global event.

Joe Pesci and Robert De Niro at the 2009 Oscar party.
Larry David and Jerry Seinfeld, 2009.

It was right in the middle of that second pen, among all the news- and entertainment-show reporters, that I would spend what was going to be a miserably long night.

If you were a major movie or television star, or you were nominated, your invitation would be for nine P.M. This is when the real celebrities begin to arrive.

I put on my tux. I took a Xanax. I chased it down with some vodka. Then some more. I was staying at the Sunset Tower, so I didn’t have to go far, just a quick elevator ride. I took my place behind the velvet rope, right in the middle of the red carpet.

Sean Combs, Madonna, and, photographed by Becker at the 2006 Oscar party.
Nicole Kidman and Valentino Garavani at the 2009 Oscar party.

I couldn’t help but think back to my first Oscar party, in 1995. I had no formal role. I just kind of hung around, watching all the action.

It was the year of Forrest Gump and The Lion King. Tom Hanks won his second consecutive best-actor Oscar, while the film took home the Oscar in the other major categories: best picture, best director, and a handful of other categories, including best adapted screenplay. Quentin Tarantino won the best-original-screenplay Oscar for Pulp Fiction.

The scene outside the 2010 Oscar party, at the Sunset Tower Hotel, photographed by Becker.

Graydon would stand out front as the dinner guests arrived, in his bespoke Anderson & Sheppard tuxedo and dark sunglasses, hugging, shaking hands, being introduced to people. He was still relatively new on the Hollywood scene in 1995, but that first Hollywood Issue, which was still on newsstands, displayed prominently around L.A., had shaken Hollywood like an earthquake.

The issue was like a yearbook or a house organ for the industry. It was the beginning of a long relationship between Vanity Fair and Hollywood that would only grow in the coming decade. We even put the cover on a giant billboard on Sunset Boulevard. You couldn’t miss us—we were everywhere you looked. While we didn’t own the town just yet, we’d made a sizable down payment.

I put on my tux. I took a Xanax. I chased it down with some vodka. Then some more.

As I was watching Graydon doing his hosting duties, I found myself standing in front of Mortons, next to then Condé Nast owner Si Newhouse. I had never really met Si. I’d obviously seen him around the building, in the elevator, coming down to Graydon’s office or to look at layouts on the planning-room walls. He was small and unassuming. He’d smile at me, although he seemed to smile at everyone. He had the reputation of being a cruel mogul, talked about as that monster in the closet, firing editors or shutting down magazines on a whim, but he actually seemed friendly.

Si was always wearing a beat‑up pair of khakis and a sweatshirt around the office. I once asked Graydon why Si dressed so poorly. He was a billionaire; surely he could afford better clothes. “When you own the company, you can wear whatever the fuck you want.”

Carter and Si Newhouse, photographed by Ron Galella at the 2000 Oscar party, at Mortons.
The author and Becker, photographed by Larry Fink.

Si was quiet and soft-­spoken, shy. He and I just stood there, marveling at all the photographers and camera crews crowded in front of Mortons, staff running around making sure everything was perfect, Graydon, Si’s newest star, the conductor of this orchestra, beaming in the L.A. sun. It was an impressive display.

After Graydon had finished greeting the latest arrival, who was escorted into the restaurant, he came over to check on Si, who asked him who the man he had just greeted was. It was probably a producer or a powerful agent—someone important, but not a recognizable face to anyone outside the industry. Graydon told him. Then he turned to me. “Dana, why don’t you tell Si who everyone is as they come in.”

What? I literally had no idea who any of these people were. “But …” Si turned to me and smiled as Graydon rushed off, back to his greeting duties.

In a lifetime of humiliating and uncomfortable experiences, the next half an hour was certainly a contender for the top spot, as I stood next to not just the most powerful man at Condé Nast, but one of the most powerful moguls in the media world, without a clue who anybody was.

From right, the author; restaurateur Brian McNally; Carter’s son Ash; McNally’s daughter, Jessica; and Carter’s son Max. Photographed by Dafydd Jones.

Si would lean over and quietly whisper, “Who’s that?” I would shake my head slowly; “I don’t know, Mr. Newhouse.” “Who’s that?” “No clue, Mr. Newhouse.” “Who’s she?” “Jeez, your guess is as good as mine, Mr. Newhouse.” I was hoping that at some point he would figure out that I wasn’t up to this task, but he kept on asking.

I must have gone 0 for 50 and was sure that Graydon would get a call the next day: Get rid of that kid, he’s a complete moron. But I don’t think Si really cared, or at least he didn’t mention it to Graydon, and I lived to see another day.

Now, almost 15 years later, in 2009, at least I knew who everybody was. As the dinner guests arrived, some of them would do the press line; others would just smile and walk on by. I managed to interview a handful of celebrities, mostly of the wax-­museum variety: Sidney Poitier, Jay Leno, Joan and Jackie Collins, Robert Evans.

I made a few decent jokes and asked mostly stupid questions, like, “What are you most looking forward to tonight?” “Who are you rooting for?” “Is Meryl going to win again?” (Meryl Streep was nominated for best actress in Doubt, although she would lose out to Kate Winslet, who was nominated for The Reader.)

Winslet and Meryl Streep celebrate Winslet’s best-actress win at the 2009 party.

After all the dinner guests were inside and seated, and the awards had begun, I was off the hook until after the ceremony. I hopped over the velvet rope, earning envious stares from the other interviewers and crews, and walked into the party. I sat at the bar with other staff and rejected fill‑ins, had dinner, and watched the awards.

By the time I returned to the red carpet, a few hours later, when the awards were over, I’d gotten a little sloppy. I had a drink in my hand and a cigarette in my mouth. I was like the Dean Martin of the red carpet as I interviewed Jonah Hill, Jason Segel, Jon Voight, Harvey Weinstein, David Frost, Judd Apatow, and a handful of others.

After the red-­carpet interview with Judd, I needed a break before the final wave—the Oscar winners—so I hopped over the velvet rope and went into the party for a while. I was outside, on the terrace in the back, when I ran into my friend Matt Labov, a publicist who worked with Judd and a lot of the generation of young comedians who appeared in many of his films.

Oprah Winfrey, Mary J. Blige, and Kendu Isaacs at the 2007 Oscar party. At the table beyond, from left: David Geffen, Anna Carter, and Lapo Elkann.
Jonah Hill, Jason Segel, Daniel Craig, and Danny McBride at the 2009 Oscar party.

Matt was standing with Seth Rogen and Danny McBride, who are as funny in real life as they are on-­screen. Matt introduced us, and we chatted for a few minutes. At some point, a joint appeared. It would have been rude to say no.

I spent another half-hour on the red carpet. I could barely speak. Seth Rogen smokes really strong weed. I was getting distracted by all the bright lights, like a kitten or a baby. I somehow managed to interview Winslet and Dustin Lance Black, who had won an Oscar for his Milk script. Then I just gave up.

The next day I got a few calls and e-mails from friends in London. To my left on the red carpet that night had been a BBC crew and reporter. Because of the time difference, they were live on one of the morning shows in the U.K., and because of where I was standing, I was in their shot, drink in hand, cigarette in my mouth, often staring off into space as the night went on. Apparently I stole the show.

Dana Brown is a writer and producer and a former deputy editor for Vanity Fair