Tara Reid, Xzibit, and a Spider Monkey: Waiting for Britney Inside the Playboy Mansion
In an exclusive excerpt of Jeff Weiss’s new book, ‘Waiting for Britney Spears,’ the music journalist and onetime tabloid reporter tells a story of early ’00s celebrity culture from inside Hugh Hefner’s Xanadu
America, 2003: a country at war, its shiny veneer beginning to crack. Von Dutch and The Simple Life dominate. And on the cover of every magazine, a 21-year-old pop star named Britney Spears. Years later, Jeff Weiss presents Waiting for Britney Spears, a gonzo, nostalgic, and “allegedly true” recounting of his years as a tabloid spy in the lurid underbelly of Los Angeles.
Below is an exclusive excerpt from the book, out Tuesday via Macmillan Publishers.
I’m awestruck as soon as I hop out of the Escalade. Mint, lavender, and flamingo pink lights cover the Playboy Mansion in a psychedelic tapestry. It looks like a French dauphin’s chateau devoted to shooting soft-core porn. The bunny logo is projected above the doorway. Ivy and vine smother the dignified gray stone walls. Twinkling dream light snakes through the trees. In the center of the driveway, a nude cherub perches atop a burbling fountain, complete with a wishing well to amplify the hopes of all who enter.
Chaos reigns on the manicured front lawn. Security guards and event staff entertain would-be attendees bargaining to swing open the gates of Xanadu. Everyone is always on the list, and yet there is always some mistake. I’m pretty sure I see Owen Wilson avoid the crowd and saunter in with four girls who look like they’re the centerfolds for the remainder of the year.
I press the Sidekick to my ear to pretend that I’m an esteemed guest whom Hefner personally called to ensure that I was coming. To my surprise, no one glances in my direction as I execute a screen action toward the eastern corner of the Gothic Tudor palace. I spot the security guard, Kerel, our man on the inside. He nods and directs me down a lightless servant’s path leading into the backyard.
It’s half past midnight and things are coming unglued. Tipsy older men in embroidered sport coats and trilby hats stagger across the grounds, their arms draped around surgically enhanced women in lingerie. A flash explodes from a photographer documenting three nude platinum blonds with tuxedos painted onto them. During the last shot, a wild black and white bunny rabbit scampers across the frame.
Wiping the sweat off my forehead, I spark another cigarette and float across the grass toward a massive party tent. The air smells like tequila and jasmine. Less than 12 hours ago, I was auditioning in the Nova offices. Now, my path is being blocked by Leonardo DiCaprio and his “Pussy Posse,” their arms interlinked with several Wilhelmina models. They’re wasted and honking back at an albino peacock revealing a starburst plumage.
Inside the white tent, a rambunctious dance party is underway. Giant silk roses and tulips droop from the ceiling. The bunny logo is everywhere. So are bombshells in bunny outfits bouncing to Sean Paul’s “Gimme the Light,” which is being spun by a DJ who looks like a Baywatch lifeguard. She happens to be topless. I feel like I’ve landed on Pinocchio’s Pleasure Island, except that you don’t turn into a donkey if you stay here too long—you just squabble with Kato Kaelin for the last skewer of grilled shrimp. He’s here too, with two playmates staring into his eyes like he’s about to tell them the real secrets of the O.J. murder.
About two dozen girls resemble Britney, but the genuine article remains elusive.
Might as well devour some sushi, tortellini, and miniature slices of pizza from the expansive buffet. Delicious. It’s probably not a bad idea to grab a drink at the open bar either, where I wait in line behind Jermaine Dupri and a voluptuous girl in Victoria’s Secret whom I think I saw once in a Ja Rule video. He’s explaining why L.A.’s strip clubs are inferior to Atlanta’s.
With a brimming glass of Black Label on ice, I resume my mission, crunching down pebbled pathways that extend into a thicket of lush redwood and fern trees. I’m only a few hundred yards from the tent, but it already feels like I’m in a rainforest. Toucans croak. An undisclosed primate screeches from the shadows.
“Yo, so you like cars, right?” I hear a familiar rasp lurking several feet away. “Oh my god, a spider monkey!” shrieks a blond woman with blue eyes that pierce the darkness.
She steps into a floodlight partially illuminating the animal cages. It’s Tara Reid and she’s talking to Xzibit. It is, in fact, a large New World primate leaping from branch to branch.
“I auditioned for Planet of the Apes,” Xzibit says. “Fucking gave my part to the Green Mile guy.”
Tara Reid is enraptured by the brown monkey doing trapeze swings from the tree limbs. An alarm-like squawk rips from my direction. It’s an African crane in the cage next door. Distracted, Tara Reid spins toward me and nearly spills her apple martini onto my shirt. Recovering her balance, she fondles the lapel of my coat.
“Oh my god, I love love this coat! Where did you get it?”
She’s wearing a ruby floral dress, bright red lipstick, and matching heels. A shattered somewhere-over-the-rainbow vibe.
“Uh, this like, vintage shop in Topanga Canyon.”
“Don’t you think this coat is bomb?” she asks Xzibit, box braided and fitted in dark denim.
The man who wrote “Paparazzi” nods his head, annoyed that my stupid fucking coat has interrupted his conversation.
From up the hill, the dankest weed fragrance that I’ve ever inhaled floats toward us. Xzibit squints in that direction.
“Yo, I think I see Snoop. I’ma catch up with him,” he smiles at the Van Wilder heroine. “My manager is gonna hit you about that video though.”
They exchange a big “let’s do this again soon” hug. Xzibit gives me a polite nod and rambles toward the house. Then it’s just me, Tara Reid, and the spider monkey.
“Did you know the Aztecs considered spider monkeys holy creatures connected to the arts?”
“Maybe that’s why I’ve always felt such a deep connection to them,” she draws closer to the cage.
“The males mate with three or four females at a time, but the females are incredibly selective and reject a bunch before deciding on their chosen one.”
“Are you a zoologist?” she asks.
“Just a big admirer of their work.” I gesture at the monkeys. She giggles and grabs my bicep.
For three months in the third grade, I was obsessed with monkeys. This is the first time it’s paid dividends. Things are vastly exceeding expectations. Bunny Lebowski is hanging onto me while I drink expensive liquor traipsing through a private zoo at San Simeon for “swingers.”
A buzzing rattles in my coat pocket. The text from Oliver reads “????”
I ask Tara if she’s down to head back toward the party. She agrees if she can “bum a stog.” On our stroll, we make small talk, with a few crucial details swapped for the truth. I’m a working novelist, here at the behest of Hugh Hefner, a family friend, who wants to collaborate with me on a memoir because he wants to tap into the perspective of the next generation. Anything is possible if you dream big.
Our excursion leads through the grotto, aglow in purple and rose like Sleeping Beauty’s Spring Break Castle. In the coral blue pool, three dozen girls in thongs and bikini tops frolic and caress each other, while photographers preserve the Ambers in amber. Underneath a rock waterfall, a soaked cover girl cries out “Hiiyee Tara!!!” She returns the greeting with a royal wave and pageant smile.
Ahead of us, a man and woman walk into the mansion holding hands. I can only see the back of their heads. He’s got rock star dirty blond hair and dresses the part. She’s a short blond in a shorter purple dress. Can it be? I take longer strides, careful not to look like I’m rushing. But before I get close enough to figure out their identity, they vanish upstairs.
“Let’s check out the house,” I tell Tara Reid, who is maybe a little more fucked up than I had first realized.
“Do you party?” she asks.
Of course. She grips my hand tightly, leading us into a game room, where partygoers shoot pool and play Space Invaders.
A hulking bodyguard guards the stairs. Tara Reid flashes him a wristband with a bunny emblem. He waves her up. When I try to follow, he throws a shoulder block.
“You can’t come up here unless you’ve got one of those bands.”
“Oh c’mon, Calvin, let him through!” Tara Reid bats her gumball eyes to no avail.
It’s not happening. Hef’s orders. No exceptions.
We gravitate toward a wall of Playboy pinball machines with illustrations of Hefner and his playmates: the girls completely fungible, his hair graying with each model. Getting older as they stay the same age.
Between shots, I furtively scan the room for evidence of what brought me here. For a second, I catch Jared Leto at the top of the stairs, looking like an Urban Outfitters Kurt Cobain. Then he retreats deeper into the estate. Britney is nowhere to be seen.
A rumor ripples through the game room. Everyone needs to get back to the tent. Someone MAJOR is about to perform. Tara Reid grabs my elbow with urgency. We practically sprint down the lawn into the glassy grey-pink night, past the near orgy in the grotto, back toward the tent festooned with a trellis of pale balloons and all the pretty lights and all the beautiful people.
Hefner is onstage now and thanks the crowd for coming: “Every night at the Playboy Mansion is a dream, but tonight is a fantasy,” Hefner says like a corny granddad. Everyone politely laughs. He’s wearing velvet pajamas and that goofy sailor hat and doesn’t look long for this world. The artificial orange tan gives him the look of a wrinkled lizard about to captain a regatta.
“The next performer has a special place in my heart because when he first came out, he had the message ‘let love rule.’ And that’s always been my philosophy too. And might I add, love as often as possible.”
Excruciating laughter.
“Without further ado, I want to bring to the stage one of the most soulful young poets in rock ’n’ roll. A Mr. Lenny Kravitz.”
Everyone in the room absolutely loses their minds. Standing applause. I’m pretty sure a playmate or two are going to pass out. Tara Reid looks like she’s about to kiss the sky.
Behold Lenny Kravitz. He looks exactly like Lenny Kravitz. Nose stud and sunglasses, leather jacket and leather pants. He pauses for dramatic effect before pulling out a guitar and sitting atop a stool. Then he plays an acoustic rendition of “Are You Gonna Go My Way.”
Tara Reid and several girls in tuxedo body paint are near tears, as if no guitar riff this gorgeous has ever descended from the heavens. Total strangers clink their drink glasses together to toast their fortune. Mini-Me is here with a different woman. Hefner is with his six girlfriends, arm in arm, swaying along, slightly offbeat. For a minute I feel depressed, as if I’ve shown up to the party a little too late, right when things are starting to get sad. And still, I wasn’t even invited.
Another emotion threatens to override my reflexive judgment. Even in the offhand shadows, the tricky light of celebrity can be transfixing. Adrenaline runs through me, a new world unlocked, the reflected glamor of trailing the earth’s most famous inhabitants to the places that seemed forever off limits only yesterday. The actress and I are still intertwined and a server in a sparkling camisole hands me a sparkling flute of Dom Pérignon and Lenny Kravitz is imploring a euphoric room to “love and rub-a-dub.” What could possibly go wrong?
My phone vibrates. A text flurry from Oliver:
“Where R U MATE!?!?”
“BRITNEY JUST LEFT.”
“GET OUT HERE NOW!!!”
Tara Reid is gone too. She’s slipped off my arm and followed the music. Standing up front, wrapped in a love puddle with a dozen playmates in next to nothing, singing every word like sacred psalms. There is no time to say goodbye. Besides, it would be too awkward. We’ll always have the spider monkeys.
Outside of the tent, I rush back into the teeming night, past the raucous grotto where clothes have become an unnecessary burden, crossing the laptop sentries and security at the entrance. Say goodbye to the mansion.
Oliver screeches into the valet area, hollering at one of the guards attempting to thwart this lunatic from driving onto the lawn. Spotting me, he furiously waves and I leap into the car. Slaloming down the hill, the gas pedal stomped in fevered pursuit, the chase replenishes itself anew.
Excerpted from the book Waiting for Britney Spears by Jeff Weiss. Copyright © 2025. Reprinted with permission of Macmillan Publishers. All rights reserved.