‘Waiting for Britney Spears’: A Tabloid Writer Comes Clean

Jeff Weiss has a lot to say. He’s in the middle of a Zoom, which has swerved from the early-2000s Los Angeles club scene, to his favorite hard-boiled detective novels, to what it was like in the pre-iPhone era when we all had to print out directions on MapQuest. Charlie Brown has been referenced, as has Twin Peaks, more than once. More generally, though, he’s talking about his upcoming book, Waiting for Britney Spears, out June 10 — a semi-autobiographical, semi-fictional, almost 400-page look into America’s most famous pop star at the dawn of the 21st century, as told through the eyes of a young, hungry, ethically conflicted tabloid journalist. “I certainly wouldn’t call it a Golden Age,” Weiss, 43, says as his tabby’s tail swipes into the frame. “But that was an era, right?”  

Starting with the filming of her breakthrough “Baby One More Time” video in 1998 and finishing with her entry into a conservatorship a decade later, Weiss takes a reader on a journey through Britney’s story, offering vivid scenes of her meeting and marrying various ineligible men, navigating paparazzi chases, and trying to be a good mom, to differing degrees of success. Talking with Rolling Stone, Weiss is hesitant to say what in the book is real, and what is well-researched fantasy — though the cat, described in Waiting as a creature whose “gargling meows… didn’t endear her much to female visitors,” seems to be one of the more realistic details. Partly the veil is there so as to not break the magic — former Vice columnist and How to Murder Your Life author Cat Marnell blurbed that it “reads like a juicy long-form magazine story that you never want to end,” and she’s absolutely correct — but it also mirrors the tabloids he’s skewering. “Everyone always wants to know what really happened. How much of this is true?” he says. “I think we’re in a world right now where it’s very post-truth, post-reality. And I think this tabloid sensibility was kind of a canary in a coal mine, a harbinger of where the world was going.”

The unnamed protagonist in Waiting is a more “wide-eyed” version of himself, Weiss says, though he points out that he was, in fact, a tabloid reporter for a few years after college, and despite being mostly a fan of rap, he did have a thing for both Britney Spears and her music. (He would go on to write for alt papers like LA Weekly, and in 2007 founded his own rap blog, Passion of the Weiss, which is still publishing today; he has also contributed to Rolling Stone.) As in the book, he was often paired up during his tabloid days with a smooth-talking British paparazzo a few years his senior, identified in the book as Oliver. In real life he was named Mel Bouzad. (“He insists that I mention his name,” Weiss says.) Though they fell out of touch for a few years, this project has brought them back together; the photographer is even lending his Cockney-tinged voice to the audiobook.

Even 20 years ago, Weiss had a constant, nagging feeling that the magazines he worked for were exploiting the people they covered, and making the culture worse in the process. When he approached Bob Saget on a red carpet, for example, the late actor was enraged by a recent story Weiss’s employer had run about Mary-Kate Olsen. “Tell them that Bob Saget says that they can go fuck themselves with a rusty pink dildo,” Weiss recalls him saying in the book, another one of the few anecdotes he readily admits came directly from real life. Though the protagonist is taken aback, real-life Jeff gets where Saget was coming from. “From his perspective, he’s the hero in the circumstance. He’s standing up for people that he cared about.”

Weiss ultimately feels that the tabloid press exploited not just the celebrities they covered, but the writers, too. As he explains in Waiting, he was arrested, though not charged, after trespassing onto Brad Pitt’s Malibu property for People in 2005, trying to confirm the star’s relationship with Angelina Jolie. “That was the worst day of my entire life,” he says now. “I look back with contempt and disgust and wonder, and a dazed amusement that all these things happened, not just to me, but in real life.” In thinking about it, he concluded that there was plenty of blame to go around. “I thought I was the worst person on the planet,” he says. “But also, you know, thought People magazine was terrible for setting me up. And I thought Brad Pitt’s security was kind of not fair.”

The book was not a recent development; Weiss has spent almost two decades thinking about his approach to writing it. “One of the questions I got when I was pitching the book was, who are you to tell the story? I understand that from an intellectual level. And of course I was like, ‘Well, I kind of did live through this world,’” he says. “I think anybody’s vantage point can be valid if it’s executed well.” At certain times, he’s had what he admits were some “grandiose ambitions.” The title is a reference to Samuel Beckett’s classic play about a pair of drifters stuck waiting for a visitor who never shows, while his blend of fact and fiction takes a page from Gonzo classics like Fear and Loathing in Las Vegas. (“I really wanted to try not to rip off Hunter Thompson,” Weiss says.) During our conversation, he jokes that this book is his Slaughterhouse-Five (“It took me 20 years to write about the firebombing of Dresden, and then my firebombing of Dresden was, like, having to be in the tabloid trenches”) and that he initially was hoping to borrow from the format of Moby-Dick, though instead of inserting chapters about the history of whales and whaling, he thought about having mini magazines throughout the book, as a sort of primer to the times. He gave up on that idea early in the process: “There was no way the publisher would have been like, ‘Oh sure, we’re gonna just pay for all this.’”

To write the book, Weiss revisited journals he kept at the time, as well as copies of the stories he’d published. (In the book, he writes for Nova; it doesn’t take much sleuthing to discover that it’s a pseudonym for Star.) Another part of Weiss’ research process entailed ordering old tabloid magazines on eBay, spending what he estimates to be thousands of dollars for the blind items that never made it onto the internet, or had long since disappeared from it. “I am the greatest eBay collector now of tabloids from ’03 to ’07,” Weiss says. “And yeah, they were excruciatingly evil. Just deplorable. A complete absence of any kind of decency, anything remotely resembling humanity.”

In reliving the early Aughts through the tabloid media, Weiss made some unnerving discoveries. “The Trump stuff actually surprised me a lot — I did not realize how much he was just this main character in the tabloids,” he says. “Like, his family and Melania, you’re like, ‘Oh, my God, it’s all here.’ It was actually part of this laundering of him as this great business genius.”

Despite its source material, the book itself doesn’t feel exploitative; a deep love and respect for its titular star comes through. “I tried to make it a sympathetic portrayal of Britney,” says Weiss, who was in the courtroom when she spoke for the first time in her conservatorship case, in 2021. “I didn’t want to be condescending to her.”

In the end, the biggest villains in the book are the tabloids themselves, and they are ultimately destroyed by their actions. “We’ve cannibalized ourselves,” the character Oliver says towards the end of the narrative. “Rats in a fucking barrel…. Eventually, it’ll just be random nobodies taking pictures of celebs on the street, or the stars will just stage fake scenarios to post on their own. Cut the middleman right out.”

Though it’s a fictionalized phrasing, this is a conversation Weiss very much remembers having with Bouzard towards the end of their time together. “For 15, 20 years, those words rang in my head,” he says. The middleman has been cut out; we are now each the tabloid writers, as well as the tabloid fodder. Privacy is a memory, and our lives are an act. “So much of this is based on slippery, tenuous morality,” Weiss says. “We live in a world that’s obsessed with morality — but also completely amoral at the same time.”