Greta Gerwig fangirls and Billie Eilish’s new gold accessory: My surreal night at the Vanity Fair Oscar party

I’m standing in between Usher and Emily Blunt, who is telling her husband John Krasinski that she’s cold. Not too far ahead, I spot Jennifer Lawrence chatting to a friend. Then I see Sydney Sweeney. And Kim Kardashian. All of us are in a queue. Not just to get into the Vanity Fair Oscar party but to have our photos taken on the red carpet that currently stretches between us and its entrance. It takes longer than it should for me to realise that nobody needs to take any photos of me. So I tiptoe past everyone trying not to look too much like the Pink Panther until I reach the door, where I wind up having to wait because Jessica Biel and Justin Timberlake are getting a photo with the Haim sisters.

Tina Brown, doyenne of the magazine industry and former Vanity Fair editor, once said that a journalist should always “feel like an outsider”. Nowhere does that sentiment feel more appropriate than when that journalist is at a Hollywood party. Not just any Hollywood party, though. The Vanity Fair Oscar party is the behemoth of A-list soirees, attracting the starriest celebrities from every industry spanning film, fashion, music, sport, and politics.

Tonight, the gamut ranges from Nicolas Cage and Roger Federer to Nancy Pelosi and Kylie Jenner. A post-Oscar buzz fills the room alongside them. As predicted, Oppenheimer sweeps the board, garnering seven wins including best film. More surprising, perhaps, is Emma Stone’s best actress win – many had their bets on Lily Gladstone – which is accompanied by a major wardrobe malfunction: “My dress is broken,” she whispers into the microphone when accepting her award. Understandably, she changes outfits for the afterparty.

Having started as a post-ceremony dinner in 1994, the event has long-been renowned as the hottest ticket in Tinseltown. It started after the death of legendary talent agent Irving “Swifty” Lazar, who had hosted an exclusive Oscar afterparty since 1964. Noticing a gap in Hollywood’s social calendar, Vanity Fair’s then-editor Graydon Carter decided to team up with producer Steve Tisch to co-host an event at Morton’s Steakhouse, a restaurant in Beverly Hills now occupied by Cecconi’s.

Back then, there were only around 40 guests. Tonight, there are upwards of 500, many of them clutching those famous gold Oscar statuettes – Billie Eilish, who, at 22, makes history tonight by becoming the youngest person to win two Academy Awards, walks past me with hers lodged in her elbow. I tell her it’s a great accessory. “That’s all it is!” she laughs before walking off to talk to Euphoria’s Hunter Schafer.

“It’s like the magazine Vanity Fair brought to life,” says Radhika Jones, editor in chief at Vanity Fair and host of its famously exclusive afterparty. “We’re celebrating the Oscars, so of course Hollywood is well represented,” she says of the guest list. Each year, Vanity Fair brings out a special issue ahead of the ceremony, cherry picking some of the seasons standout stars for the cover; the current crop includes Bradley Cooper, Natalie Portman and Barry Keoghan, who arrives this evening with his rumoured girlfriend, Sabrina Carpenter.

Radhika Jones, editor in chief at Vanity Fair and host of its famously exclusive party

“Of course the movies change every year, which is nice because it keeps things fresh,” Jones says. What does it take to earn a place on the guest list, aside from getting an Oscar nomination? “We keep a close eye on the cultural conversation, and look for people from across fields who are intriguing and influential and fun,” she adds. “We’re always looking to strike a balance between party regulars and first-time guests.”

Unlike most celebrity events, which are, let’s face it, just another extension of the job, with endless streams of interviews, photo opps, and branded content creation, the Vanity Fair Oscar party has maintained a somewhat nostalgic, old Hollywood environment free from all the pomp and pageantry that might otherwise make attendance taxing. Once inside, the only obligation is to enjoy yourself.

“For all the nominees who’ve been on the awards circuit, this is finally a moment to let their hair down,” says Jones. “The mood is celebratory, but with zero pressure. And for those who arrive with an Oscar, this night represents the culmination of a dream. It’s one of the most memorable nights of their lives, and we lean into that vibe.”

It feels particularly significant, too, given that this year marks the Vanity Fair Oscar party’s 30th birthday. As a result, the event has become somehow even glitzier, with tighter security (I’m given multiple passes just to get near the entrance) and a new artistic edge, with creative director and designer Will Cooper having been enlisted to assist the party’s long-time architect Basil Walter to take things to the uppermost echelons, decor-wise.

The result is a breathtaking custom-built crimson-lit, Mughal tent at the Wallis Annenberg Center for the Performing Arts in Beverly Hills. Inside, the proceedings revolve around an enormous oval-shaped bar serving white negronis, espresso martinis, and what tastes like the very best champagne money can buy. Venture outside and you’ll discover a heated courtyard with a decked-out pizza bar at the back. It’s here where I find someone who kindly offers to light my cigarette; it’s later on in the bathroom when I realise that someone was filmmaker and son of Francis Ford Coppola, Roman Coppola.

Such is the calibre of the Vanity Fair Oscar party that guests are said to spend months preparing, undergoing every possible treatment and tweakment you can think of in order to look good on that red carpet. I have three days. So after I arrive in LA, my first pit stop is to facialist to the stars, Dr Barbara Sturm, for her special Oscars facial, which involves lymphatic drainage (reduces puffiness), cryotherapy (improves muscle tone), and a device that provides oxygen to my face (to plump and firm). Her other clients over the weekend? Florence Pugh, Mark Ruffalo and Issa Rae.

The Hollywood experience continues at my hotel: the impossibly plush Waldorf Astoria in Beverly Hills, which is flanked by a regular stream of blacked-out SUVs, chevvying various important industry people around the city ahead of the big night. Walking into my capacious room, which is decked out with Aesop toiletries, a private terrace, and one of those bedside buttons that controls the curtains (just like the one in The Holiday), is enough to make me feel like an Academy Award winner. It’s here where I pace around furiously for several hours, preparing for the most surreal evening of my life.

The dress code is simply “black tie”. For my outfit, I enlist the help of Net-a-Porter, settling on a sheer floor-length gown from The Attico, which earns compliments from both Meghann Fahy and Allison Williams, paired with a Manolo Blahnik clutch and Nodaleto shoes that are high enough to pass as smart, but not so towering I risk tumbling over in front of Ryan Gosling. Following a stellar rendition of his eponymous Barbie track at the ceremony, Ken himself is sadly not in attendance at the afterparty; “It was great,” says Mark Ronson of his performance with Gosling in between mouthfuls of an In-N-Out burger – they are famously served to guests throughout the night.

There isn’t a huge amount of dancing – Vanity Fair Oscar party stalwart Emily Ratajkowski tells me this is normal – but I do catch Callum Turner looking lively as Dua Lipa’s song from the Barbie soundtrack, “Dance the Night Away”, plays out on the speakers. The two are rumoured to be dating.

Suffice to say, my evening with Hollywood’s finest is a lot of fun. But being at a party where you know no one is not easy. The social anxiety is on par with how it might be at the wedding or barmitzvah of a distant relative, except that relative could be Steven Spielberg, Emma Stone, or Christopher Nolan, who has nothing to say about Oppenheimer’s astonishing success aside from that he’s “having a fun night”. Later, I see him observing the dance floor from a booth with Matt Damon, two gold statuettes standing tall on the table in front of him.

There are slivers of normality, though. Like seeing guests getting star-struck by one another – I overhear two musicians gushing to Greta Gerwig outside – and losing track of their plus-ones: Trevor Noah, Chloë Sevigny and Kate Berlant are all looking for theirs when I meet them. Then there’s the A-list actress’s assistant who comes up to me in the bathroom to ask if I have a tampon.

It’s refreshing to see that everyone truly seems just as happy to be there as I am. “No one here is any better than you are,” whispers an older woman I befriend by the bar as I loiter nervously. “Go out there and know that you’re on the same level as everyone in this room; deep down, they’re all just as overwhelmed as you are.” It’s advice I manage to cling onto for most of the night, though it wanes a little when someone introduces me to Donatella Versace.

By 1am, people start to filter out. There are other parties, with a group of models who’ve kicked their high heels off telling me they’re off to one that Beyoncé and Jay-Z are hosting at the nearby Chateau Marmont. Others are venturing to one laid on by Madonna and her manager and pal Guy Oseary. I order a taxi and call it a night, waiting it out in a dedicated “Uber lounge”, keeping my arms tightly crossed. Because Blunt is right: outside the party, it’s a little cold.