Jeff Weiss doesn’t quite know what he’d say if he got 10 quality minutes to talk to Britney Spears with no one around. He can’t even speculate what a real life conversation with her might even be like after everything she’s been through.
“The thing that attracted me to the story of Britney was that so much of it was a mystery,” he said of the star who burst into Americans’ lives as the 17-year-old schoolgirl in the “Baby One More Time” video before becoming the head-shaving woman forced into a 13-year conservatorship that didn’t end until last year.
“There still is a mystery at the core of her,” Weiss told Creative Loafing Tampa Bay. “Like, ‘What is going on?’ Nobody knows.”
That intrigue—and the years Weiss spent chasing the pop icon for his job at the Star tabloid—unravels and expands in his new book released in June.
“Waiting for Britney Spears” is organized by the Library of Congress under “Gonzo journalism” and categorized as creative nonfiction. The 388-page work’s subtitle is perhaps its best descriptor: “A true story allegedly.”
In so many ways, Weiss’ offering is a referendum on the impossibility of knowing the exact truth about anything—especially anything refracted and distorted through the screens sucking dopamine out through our eyeballs.
At its core, the work is a statement on the American dream and how the media distorts it. Almost an academic time capsule, the book also embodies escapism and self-examination all at once.
“My friend used to joke like, ‘Your beat is the fall of Rome,” Weiss said, adding that society might now be in the “Nero, everything is burning” phase.
“At the time, you could see the writing on the wall; it was encroaching. There was no concern for anyone’s humanity at that point,” he noted. “She was martyred for our own bloodlust for entertainment—and the irony is that now we’ll just martyr ourselves to make profits.”
On Wednesday, Weiss comes to St. Petersburg to talk about all of that. The conversation at Tombolo Books, naturally, will be conducted by Caroline Calloway. In 2023, the Sarasota-based author released “Scammer,” a memoir The New Yorker described as “funny, engaging, and full of genuine insight—mostly into the art of social-media influencing.” Calloway’s rise, in many ways, is borne of America’s obsession with celebrity, gossip, and folklore that can only be proliferated online.
Waiting for Britney Spears: An Evening with Jeff Weiss
Time Wed., Oct. 15, 7-8 p.m. 2025
Location Tombolo Books, 2153 1st Ave S., St. Petersburg
Weiss told CL he’s more likely to tell the real truth about what’s in his book in-person than he is on the internet. A revered hip-hop writer and alt-weekly legend for his music criticism, Weiss cited a lyric about Nas from Jay-Z’s 2001 album, The Blueprint. “Homie, you ain’t live it; you witnessed it from your folks’ pad. You scribbled it in your notepad, created your life,” Jay-Z says on “Takeover.”
“Rap is like, kind of this prototype of what people consider autofiction,” Weiss said “Sometimes you want to print the myth, and sometimes you kind of want to reinvent the myth—and I guess that’s what I was probably going for with this book.”
Britney’s story, he added, is already shrouded in so much lore, and also buried with the pages of tabloids stacked high in Sarasota housewives’ basements. Weiss knows—he spent thousands of dollars buying old magazines that now serve as a playground for his cat, Alice Coltrane The Cat.
When he’s done talking, Weiss plans on pulling the curtain back on his own perceptions about the Gulf Coast.
“I’ve never been to St Pete, and that’s always been on the kind of my bucket list,” he told CL, citing a desire to see the town that gave way to out-of-the-box homegrown rappers Chester Watson and Kent Loon, who’ve released music on Weiss’ heady and highly-influential POW Recordings. He’s also written about the Bay area’s own They Hate Change, a duo whose sound he described as “invigorating…both familiar and unlike anything else in rap.”
The Dalí Museum is on the itinerary, and so is the home of Jack Kerouac, Weiss’ first favorite writer. While he was at L.A.’s Occidental College, Weiss made the trip to Kerouac’s grave in Massachusetts. After a speaking gig at George Mason in Virginia, he went to the headstone of F. Scott Fitzgerald in Maryland. “To me, a great writer, home is sort of like a sacred pilgrimage,” Weiss said.
Eventually, Weiss will find his way back to L.A., a city where jacarandas bloom in the springtime, summer evenings are spent catching concerts at the Hollywood bowl, and nights get blurry while drinking at The Dresden Restaurant & Lounge. It’s the city that fed him dreams of becoming a journalist before serving up years spent chasing Britney Spears. And it’s also where he cut his teeth at The Occidental Weekly and L.A. Weekly—jobs he loved, with readers who looked to him to make sense of the community around them, even if he himself didn’t quite fit into that world.
“I think the writers always should be the outsider,” Weiss said.
Yes, an outsider that helps us make sense, or at least have fun with, the mysteries in our lives.
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This article appears in Oct. 2 – 8, 2025.