‘Waiting for Britney Spears’: Behind the Scenes of Her Infamous Summit With Paris Hilton and Lindsay Lohan

Britney Spears is Gatsby, Daisy and the green light at the end of the dock in a probing new book that posits the long-troubled pop star as the modern-day Marilyn Monroe. Waiting for Britney Spears is a gonzo tale of fluorescent noir, in which she’s the femme fatale who’s relentlessly stalked by hordes of paparazzi, along with a reluctant, shambolic Britney beat reporter — who may or may not be an exact stand-in for the author.

“I’m calling it a hybrid memoir,” says its writer, Jeff Weiss, who really did spend a stint of his 20s incurring PTSD on the front lines of the tabloid trenches at magazines like OK! and Star. (In the book, the slightly fun-house-mirrored depictions are referred to as HI! and Nova.) “My joke is that it’s my Slaughterhouse-Five,” he says. “My firebombing of Dresden was getting arrested on Brad Pitt’s property. It took me decades to process it.” These days, he’s known as one of America’s most respected music journalists. Weiss explains of Waiting: “It’s fictional, but it’s not. It’s 50 percent true, 100 percent honest. I had to add a subtitle” — A True Story, Allegedly — “for legal reasons.”

Weiss’ L.A.-native protagonist is on the scene at every iconic moment in the Spears arc, from the shooting of her 1999 hit “… Baby One More Time” music video and her 2004 wedding to Kevin Federline to her 2007 head-shaving meltdown at a Valley hair salon to her disastrous VMAs performance of “Gimme More” to the final 2008 at-home custody showdown involving police that precipitated her 13-year-long conservatorship.

The book contains genre multitudes, encompassing not just noir and memoir but elements of the spy thriller and historical fiction, too. Its plot often hinges on clandestine espionage — the donning of false identities, the infiltrating of restricted spaces, the handling of intelligence assets — while its analog milieu is a recently lost world. The paparazzi and tabloid outlets that dominate the book are now on life support, replaced by everyone’s smartphones and social media accounts posting their own celebrity content. “This is a love letter written in poisoned blood,” Weiss says. “I’m not nostalgic for that era, and yet it was better.”

He observes that, as with movie stars, Spears’ next-gen replacements haven’t come close to matching her. “They’ve tried to make another Britney, but they couldn’t,” Weiss says of the music industry. He points to Gen Z’s TikTok phenom Addison Rae, noting she’s talented, charismatic and seemingly succeeding even amid a now fractured zeitgeist. “But if Addison Rae walked past you right now, would you know it? You’d think: ‘That’s an attractive person who’s maybe an influencer.’ We just don’t mint icons the same way anymore.”

For years, Spears was mostly out of sight due to her conservatorship. Weiss sees its implementation as a forerunner for America’s hard-right cultural lurch: ” ‘Conservative’ is in the name. It’s revanchist.” Since a judge mandated her release from court oversight, most of what the public knows of her has been mediated through her unfiltered, unpredictable, sometimes unsettling Instagram feed. “The old mystique has been replaced by this Lynchian mystique,” Weiss muses. “Naomi Watts in Mulholland Drive.”

Now that she’s ostensibly free, and yet still appears to be struggling, Weiss thinks her messiness makes her the quintessential American public deity, at least for the generation that came of age with her and now often sees itself as caught in an inexorable downward spiral. “Britney is how millennials see themselves, subconsciously: dancing erratically with knives in your face. That makes sense to us.” — GARY BAUM

***

It’s a quarter to 10 on the weekend after Thanksgiving. Most of the HI! staff was back in their hometowns, which meant that my editor, Alice Van Bronx, was destined to call. This time she wanted to send me to the hottest club of the minute, Hyde. I could say no, but there’s never anything going on that week in L.A. Besides, getting in on a Saturday would require the hand of God. I’d most likely be rejected at the door and check an assignment off my monthly quota.

They want me there in case of a Britney and Paris pilgrimage. For the last 10 days, they’ve been inseparable. In the aftermath of the divorce, Britney took a trip to Kentwood to visit family. But on the way back to L.A., she hit Vegas to record at the Palms Hotel studio with Dr. Luke. It’s here that the resort’s owner George Maloof formally reintroduced Gatekeeper to Keymaster.

The Britney and Paris honeymoon in Vegas included a $10,000 Britney blackjack victory at the Playboy Club in a pink wig, and a sleepover. Back in L.A., Britney popped into Paris’ American Music Awards afterparty, a few hours after presenting a crystal pyramid to Mary J. Blige. Reports described her as “inconsolable” after an opening sketch where the host Jimmy Kimmel lowered a Federline mannequin into a sealed crate, placed it onto a truck (“no damage will be done to his cornrows”), and dumped the fake corpse into the port of San Pedro. “PopoZão” played the entire time.

In one week, the paparazzi caught Britney stepping out of cars without panties four times. Us called them “Girls Gone Wild.” Nova tried to make “Paritney Spilton” happen. The number of magazine spies embedded in nightclubs doubled. My own bottle-service days had been replaced by formal parties and awards shows, where I didn’t need to lie about my real reason for being there.

Within weeks of its formation in the spring of ’06, Hyde became the throne room at the end of empire. Being basic-cable famous didn’t ensure admittance. This wasn’t Studio 54; it was Andy Warhol’s broom closet. Capacity was 100, and even that risked a visit from the fire marshal. It was the Hollywood club in final form, an ingenious leverage of supply and demand, where being snubbed at the door could mean public humiliation. No need for a VIP section when only VIPs can enter.

TMZ was headquartered across the street. Each day, they would faithfully broadcast the melodrama from the night before. Hyde was where Shanna Moakler socked Paris Hilton for kissing her husband and MTV co-star, Travis Barker; in retaliation, a Greek shipping heir loyal to Hilton allegedly shoved the former Playmate down the stairs. Hyde was where Avril Lavigne spit on the paparazzi and where Nicole Richie collapsed before checking into a hospital.

Hyde is the city’s most high-end dive. Miniature crystal disco balls drip from a copper-leafed ceiling. Candles flicker in iron sconces. The side tables are made of petrified wood. Ultra-suede walls are dappled with pink and black paisley. The unapologetically beautiful gaze at their reflection in smoked mirrors. All the perfumed unguents and performative rituals of fame are present.

Stationed by the bar, I soak up industry gossip and hubristic pickup attempts.

I’ve been in these rooms so many times that it feels strangely natural. The DJ, Samantha Ronson, spins “L.A. Woman.” I order a third whiskey on ice because I’m reminded of something Jim Morrison once said: “Being drunk is a good disguise. It means I can talk to assholes.”

A Hungarian model with a Guess billboard humors conversation, but mostly wants to know if I think she’s too old for “Leo.” He’s sitting in a crocodile leather banquette with his Blood Diamond co-star, Djimon Hounsou. She’s 24. I tell her that I think he’s dating an Israeli supermodel, but she just says, “So?” Then she yawns and says that she’s thinking about moving to Miami.

To my right is Colin Farrell, his facial scruff meticulously engineered at 4.6 days’ growth. The Olsen twins are here too. One dresses like a beatnik gymnast; the other like a Romanian fortune teller. They greet Farrell with a hug and kiss.

When Britney and Paris arrive, the music plays but no one hears a note. The bartenders stop pouring, the light smears into a soft crimson fog. It’s slightly before the stroke of midnight, perfectly timed for drama. Paris leads, languidly floating, tall, slim and Sunset Tan bronzed. She’s wearing a ruffled white blouse over tight designer jeans, and a tiara headband. Her imperial blue contacts shield organically brown eyes. With a conqueror’s gaze, Paris coolly weighs the situation.

All necks, male and female, curve in their direction as Paris flashes her fugitive smile. The baby doll voice, the dumb blonde schtick, create a requisite layer of fiction. She always knows the right angle and understands the cardinal rules of iconography.

Being shrewdly attuned to the present allows her to see the future, in which the only talent required is the ability to advertise yourself. The medium is the message, and the medium is a Carl’s Jr. commercial where hamburgers are pornographically devoured by a platinum blonde nymph writhing in a bikini.

Right now, there is no more divisive pop culture figure than Paris, who’s been attempting to go from a reality star to a renaissance woman. Her self-titled debut album was only a modest success, selling 200,000 copies in August, and landing a Top 20 single called “Stars are Blind.” She’s the symbol of ugly entitlement: famous from a sex tape, parodied by Pink on the hit “Stupid Girls” and recently arrested for a DUI in Hollywood.

Britney follows after Paris, skipping in slow motion. The Princess and Empress pursuing opposite ends of the same story book, their paths perpendicular on Sunset Boulevard. If the Bel Air “celebutante” innately considered the entire world as her birthright, what was inside Britney awaited discovery. Her childhood was crawfish boils and auditions, not high society balls and cotillions. The hidden majick glittered whenever she went on stage or in the studio.

The world Britney was raised in encouraged the fantasies, but the one she inherited was cold and confusing, filled with love and contempt to frightening extremes. Something, somewhere had gone lethally askew, and she was chosen to be both weather system and weather vane.

Tonight, Britney wears a short black London-in-the-’60s dress, diamond earrings and black high heels. Around her neck is a snake pendant representing sex, rebirth and death. Her eyes are anxious but trusting. Her features are gentle, set off by a toothy and sincere smile. Paris escorts her to the bar, not far from me.

I overhear Colin Farrell ask his friend if that’s really Britney. It seems to be? It is? They haven’t spoken in over three years — since he sent her that stupid gag gift. Better to play it cool, the friend says. They remain sedentary.

With purposeful volume, Paris tells Britney, “Who gives a fuck about Colin Farrell?! He’s here every night trying to fuck a different model. He gets so wasted, he probably can’t even get hard.”

Britney snorts like a slumber party. She’s a creature of action, about to turn 25, and starting fresh once more. Maybe she’s a bit gullible, a little drunk, but not clueless. It isn’t lost on her that the room always parts, the bartenders bolt in her direction. You don’t just stop being Britney Spears.

Paris and Britney head outside to smoke cigarettes on the patio. The open-air space resembles a high school lunchroom hierarchy. Everyone here is a personage, but only these two are phenomena. A few clusters of the superlatively cool or well-connected feint toward joining them, but Paris’ contemptuous smile intimidates intruders. The few who know them personally — Mischa Barton’s ex-boyfriend, Cisco, and a blond guy who may or may not be Rod Stewart’s son — give them air kisses on each cheek.

Back in the interior, the sleazy pseudo-producer who made and sold the Paris Hilton sex tape has appeared with the heir to a hamburger chain. They take the table from DiCaprio, who has had enough and didn’t fall for the charms of the Guess girl. Rod Stewart’s daughter is here now with Paris’ assistant, Kim Kardashian.

The DJ spots Britney and Paris at their table and queues Elton John’s “The Bitch Is Back,” which they shout along to like the entire room is watching. It is. At least until quarter to 2, when Lindsay Lohan whorls through the door like a raspy chaos phantom. By now, the Hungarian model has returned to me. She just gave out her number to the actor Lukas Haas.

“I can’t remember what he’s in, but I know that I’ve seen him a bunch,” she tells me. Then she spots Lohan and whispers, “This is going to be ugly. Paris poured a drink on her last night at Guy’s.”

The Guess girl tells me about how Lindsay accidentally overdosed at the Chateau a few weeks ago on coke and Vicodin and Ambien and maybe a little nitrous. A friend found her unconscious at 9 a.m. and called a doctor who covered it up, but word still got out and now everyone won’t stop talking about it. Lohan attempts to speak with the burger scion, but he won’t entertain the conversation. She’s here all alone, scanning the room to see who she should talk to and who to avoid. Lost eyes searching vainly for an escape.

Lohan is the duchess, royalty but a rank below. The true aristocracy will never respect her because she is a striver, forever beneath their bloodless inheritance. Her mother was an ex-Rockette who dreamed of fame but never made it. Her father was a Wall Street trader currently serving a two-and-a-half-year jail bid. The tabloids say that he wants to become a minister when he’s free.

Paris sees Lohan’s distress and turns to Rod Stewart’s daughter. They point and laugh. Lohan senses the scorn and her face becomes redder. The bartender screams, “LAST CALL,” and she heads to the bar to order a drink. A fussy orange man in a suit — who the model tells me is a publicist — whispers something in Paris’ ear. She never breaks her haughty expression. Britney bops her head to Prince’s “Erotic City.”

After Lohan gets a tequila soda, the publicist hurriedly shuffles her to a different corner to sell her on something. The Hungarian model leaves me to talk to Tori Spelling’s brother, who tells her that he’s filming a reality show with Rod Stewart’s son.

Closing time. Security asks people to leave. Liaisons offer afterparty options to Paris and Britney. The house raises the lights, causing everyone to squint and the enchantment to break. Paris and Britney levitate toward the exit. The leathery little man drags Lohan back to Paris, who looks at her like a humbled servant. I can’t make out the conversation, but Lohan is talking a lot, and Paris says little. The uninspired nodding of a ceasefire.

For a few breaths, Britney is alone, halfheartedly wandering in my direction. She seems buzzed and distracted. This is the closest that we’ve ever been. I notice how regular she seems. Gorgeous, sure. But there’s something unmistakably disarming and pure. Not in the choir girl sense, but how she still remains unpolluted by the contrived poses of Hollywood.

She locks eyes with me and smiles. I must have done the same because my feet stutter in that direction. I rack my brain for anything interesting or witty. “Hi” is all I’ve got. She says hi.

Before I respond, Paris links arms with Britney to lead her away. Security clears a path out onto Sunset Boulevard, where 100 paparazzis gather. I see Tara Reid outside, waiting glumly at the velvet rope. She must have shown up after they hit capacity and been forced to wait. The Girls Gone Wild guy gives her a pity kiss on his way out. She doesn’t remember me from our night at the Mansion.

Oliver is outside too, trying to get a photo amidst the maelstrom. We briefly make eye contact, but another paparazzi jabs him in the ribs, jockeying for position.

An obsessive fan babbles, “Please, Britney, just one autograph. Please … Please! ” A female voice unleashes a banshee shriek. The valet is late bringing up Paris’ Mercedes. The paparazzi form a flashing ring, asking Paris over and over, “Lindsay Lohan accused you of hitting her last night. Is that true?”

Wrapping her arm around Britney, Paris walks to the Mercedes. The paparazzi creep. Security shove them away, “Guys, back up, back up!” Britney frowns, whimpering: “C’mon, guys, let us get in our cars.” With fear in her eyes, Britney signs the autograph for the superfan. She tiptoes toward the valet and jumps in the car. The photographers angle themselves for an upskirt shot. Paris snaps at them: “Guys, don’t be perverts.”

As Paris scurries to the driver’s side, the paps ask one last time, “Did you hit Lindsay?”

Spotting Lohan emerging from the club, Paris points: “There she is, you can ask her.” The cameras pan to Lindsay being escorted by the gnomish publicist. “Lindsay, tell them the truth!”

“Paris never hit me. She’s my friend,” Lindsay says robotically. Her head is lowered and one arm defensively crosses herself. “Everyone lies about everything. She’s a nice person. Please leave us alone. I’ve known her since I was 15. Please make us stop hating each other.”

To the delight of the paparazzi, Lindsay hops into the passenger seat. Britney sits the middle. Paris beams confidently behind the wheel.

“Oh, this is classic,” one paparazzi coos.

Mechanistic flashes. The girls are stationary in the car for only a few seconds, but in the morning, the photos achieve awe, scorn and eternity. The New York Post puts it on the front page with the headline “Bimbo Summit.” Paris favors the kinder appellation: The Holy Trinity. Forever bronzered in immaculate unwrinkled youth, with smoke-glazed irises, beatific smiles and blinding futures. The McLaren as a V8 Grecian urn, Paris driving off down Sunset, toward the edge of the earth.

Excerpted from Waiting for Britney Spears: A True Story, Allegedly (Farrar, Straus and Giroux). Copyright 2025 by Jeff Weiss.

This story appeared in the June 11 issue of The Hollywood Reporter magazine. Click here to subscribe.