A flashback to the tabloid culture that made and broke Britney Spears

Washington Post

11-06-2025

Jeff Weiss was 16 years old in the summer of 1998, when a then-unknown Britney Spears came to his California high school to film the music video for her upcoming debut single, '…Baby One More Time.'
Also 16 years old, weeks away from the onset of the fame that would eventually consume her, Spears was a goofy theater kid dressed in a schoolgirl uniform from Kmart, joking with her backup dancers.
Even to Weiss, who was more of a rap fan, it was obvious: Britney was magic. 'Britney was the opposite of everything I'd known,' a smitten Weiss writes in 'Waiting for Britney Spears: A True Story, Allegedly,' his incredibly entertaining and frequently insane debut book. 'A sequined mirage and airbrushed myth. It felt like I'd just watched a comet be born.'
Weiss wound up as an uncredited extra in the video and in the story of Spears's life. An acclaimed music journalist who runs the online magazine Passion of the Weiss (and has written for The Washington Post), Weiss began his career as a reluctant tabloid reporter assigned to the Britney beat.
'Waiting for Britney Spears' traces his and the pop star's intertwining paths in early-2000s Los Angeles. Its title draws from Samuel Beckett's 'Waiting for Godot,' except unlike Godot, Britney shows up. Everywhere, all the time, slaloming through L.A. nightlife, hell on stripper heels, trailed by an ever-present wolf pack of paparazzi, reporters and pitiless observers documenting her every move.
At least, this is how Weiss tells it. 'Waiting for Britney Spears' isn't strictly a nonfiction account. It's a throwback to the days of Hunter S. Thompson-like gonzo journalism, a kinetic, extravagantly written fever dream that lands somewhere between a memoir and a roman à clef. True in vibe, if not necessarily in detail.
For anyone who consumed pop culture in the '00s, 'Waiting for Britney Spears' feels as vividly real as any documentary account. All the Mount Rushmore moments are here: both of her weddings; the night she first hooked up with Kevin Federline; the time she shaved her head; the day she drove off with her baby in her lap, paparazzi in pursuit. The more prosaic moments are here, too: the court dates, the barefoot gas station Red Bull runs, the breakneck Westside paparazzi car chases.
Most of these vignettes are reported by Weiss as either first- or secondhand accounts. And while it's unlikely that even the most diligent Britney chronicler would have been present for all of them, they do coincide with contemporaneous published reports. Most of the events Weiss describes almost certainly happened, in other words, even if they didn't always happen to him.
At first, everyone was mostly having fun. Spears was the biggest pop star in the world. Her exploits at an endless series of bottle service nightclubs and awards shows were a welcome distraction from the country's post-9/11, Iraq War doldrums. When a walk to the beach with K-Fed turned into a national news story, complete with helicopters circling overhead, she seemed amused.
Weiss and his paparazzi sidekick weren't immune to Mission: Impossible-style maneuverings, either. One day, when the couple chartered a luxury boat, 'Oliver rented a helicopter and pilot and snapped $20,000 worth of photos while dangling from the chopper,' Weiss recounts. 'Britney waved.'
'Waiting for Britney Spears' peaks one night in 2006, at Hollywood club-of-the-moment Hyde. Everyone was there: Leo DiCaprio, Colin Farrell, Paris Hilton (imperious and blank, the only person there as famous as Britney) and her lowly assistant Kim Kardashian, 'raspy chaos phantom' Lindsay Lohan.
It was the pinnacle of '00s Ed Hardy culture; the Yalta conference, except everyone was in trucker hats. Later that night, Spears, Hilton and Lohan would drive off together in Hilton's car, photos forever memorializing what became known as the Bimbo Summit.
It was all downhill from there. As Spears tumbled deeper into whatever cocktail of mental illness and substance abuse eventually pulled her under, and the once exhilarating Britney beat turned into a 'trail of tears,' Weiss, who longed for literary seriousness and lamented his guest role in Spears's misery, grappled with his own self-loathing and guilt.
But when he wasn't assigned to Britney detail, things were somehow worse. He engaged in a death-defying car chase with Ben Affleck, only to realize it was Affleck's brother, Casey, behind the wheel. He was publicly admonished by Bob Saget over tabloid treatment of the actor's former 'Full House' co-stars the Olsen twins. 'What amount of money is worth losing all self-respect?' Saget asked Weiss, who wasn't sure.
He even became briefly famous himself after being detained for trespassing near Brad Pitt's beach house while on assignment for People magazine. He was scooped up by the actor's security crew and dragged before a disapproving Pitt. 'His skin is perfect,' Weiss recalls. 'His expression is wrenched with disgust. He shakes his head slowly, confidently, letting me know that I've lost.'
As 'Waiting for Britney Spears' draws to a close, Britney and the tabloid culture that birthed her seem to be disintegrating at the same pace. The advent of TMZ dynamited the established tabloid order. Traditional paparazzi, who at least had a vague sort of ethical code, were replaced by less professional, more menacing 'stalkers with video cameras, jumping in celebrity's faces,' lamented the old-school Oliver. The advent of citizens with camera phones would soon render both models obsolete.
Meanwhile, Spears was in her 'crack-up summer' era. She reportedly rubbed mashed potatoes on her face at the Chateau Marmont. She spoke in an inexplicable British accent. She appeared to hold her infant child hostage, leading to an extended police siege. She was utterly alone.
With great sympathy, Weiss recounts her devolution from an animated and sweet southern teen to a finger-snapping, assistant-terrorizing hellion clutching her tiny dog for comfort to, eventually, an empty-eyed zombie, submitting to an involuntary psychiatric evaluation.
During one of the book's most poignant passages, Weiss recounts Spears becoming trapped by photographers inside a Malibu Starbucks, pregnant, disoriented and terrified, clutching her newborn. 'In the glass cage, she begins sobbing. An excited gasp erupts from the photographers who know that tears pay double.' Are you not entertained?
Weiss saves his greatest distaste for the men who betrayed her: ex-boyfriend Justin Timberlake ('a horny doofus,' writes Weiss, which about covers it); her Rasputin-like minder Sam Lutfi, who Britney's mother suspected was drugging her food to keep her compliant; and Spears's scowling father, one of the overseers of her 13-year conservatorship. She would later claim he belongs in jail.
Weiss doesn't exempt himself from criticism. To write a book that grapples with Spears's exploitation while simultaneously providing an imagined interior monologue of her innermost thoughts and fears, the only private thing not taken from her, is itself a form of exploitation.
But still. The Britney of Weiss's recounting, which ends as her conservatorship begins, is a more 3D Britney than the one in her own, somewhat mechanical 2023 memoir, 'The Woman in Me.' And sometimes a more optimistic one. 'Her struggles were communal,' he writes. 'She's become a heroine for a malfunctioning society. If Britney can come back, hope can never fully be lost.'
Allison Stewart writes about pop culture, music and politics for The Washington Post and the Chicago Tribune. She is working on a book about the history of the space program.
A True Story, Allegedly
By Jeff Weiss
MCD. 402 pp. $19