A Writer Remembers His Astonishingly Well-Paid Gig With Graydon Carter’s Vanity Fair

Vanity Fair embraced New Journalism, but as Graydon puts it in his book, it also “had an asset that no other magazine had in Annie Leibovitz. Annie was already a legend, a photographic visionary of huge gifts.” Leibovitz pushed the boundaries of what made a newsstand cover, from the arresting group photography showcased on Vanity Fair’s annual Hollywood Issue to its iconic image of a pregnant Demi Moore. The magazine mattered, especially in Hollywood and New York.

It left not only a legacy of glamour but also one of notable journalism. On the page, it excelled at—and really owned—the dramatic exposé that unfurled like a thriller. There weren’t many articles in each issue, maybe eight or nine, but they were very long, typically definitive, and they carried the unmistakable scent of the highest-end tabloid: well-sourced tales of Washington intrigue, of fallen royals and CEOs, of Silicon Valley shenanigans and whatever scandal was befalling Michael Jackson at the moment. Also, dead bodies. Lots of bodies. Many pieces made news. Maybe its finest moment, which Graydon orchestrated and which opens the book, was its unveiling of Bob Woodward and Carl Bernstein’s fabled Watergate source, Deep Throat, whose real identity had remained a mystery for more than thirty years.

These stories and the striking look and feel of the magazine lured advertisers in droves—at its height, Vanity Fair featured a couple hundred pages of glossy advertising and around 140 pages of editorial content. Given this success, it’s surprising to be reminded that when he was handed Vanity Fair in 1992, Graydon was a complete afterthought, the player-to-be-named-later in the magazine shake-up of the decade; the big news was that his superstar predecessor, Tina Brown, who had made the modern Vanity Fair into a zeitgeisty book, was taking over The New Yorker. As it happened, Tina lasted only six years at her new post. Graydon, despite snide chatter that he could never fill Tina’s Jimmy Choos, lasted twenty-five at his.

I was the second writer he hired in those hectic first days, after the late Christopher Hitchens, the pickled British iconoclast who could never remember my name. Graydon and I both had much to prove. After cofounding and selling the snarky Spy magazine, he had landed at The New York Observer, a drowsy broadsheet whose readership spanned the expanse between Fifth Avenue and Lexington. Although he remade The Observer into a gossipy morsel for the power-lunch crowd at Michael’s and the Four Seasons, it was still of only marginal significance. I was thirty-one. Graydon wanted to beef up Vanity Fair’s business coverage, and I was one of the top business journalists at the time. I had spent almost a decade at The Wall Street Journal and coauthored a number one bestseller, Barbarians at the Gate. I had also promptly followed it with a book that sold about seventeen copies.

When I started in 1992, Vanity Fair had only been on newsstands for eight years. It was far more popular in Los Angeles and New York than the spaces in between, and working there was a rarefied gig. I started out telling friends the magazine was for the jet set and those who aspired to it; later I took to calling it a guilty pleasure for the intelligentsia. To the bicoastal, to ladies with tiny dogs, to those who clinked glasses in the Hamptons or Hydra or Beverly Hills or Gstaad, it was already all but required reading. These people were fascinated by my world. They usually knew my name, or at least my articles. They always asked what Dominick Dunne—Vanity Fair’s marquee writer—was like.

To folks in my Texas hometown, though, to my cousins in rural Arkansas, to our plumbers and delivery people and yardmen, Vanity Fair was something they vaguely understood to be some kind of “women’s magazine.” From them, I recall the occasional look of pity.

It didn’t bother me. If you knew, you knew, and pretty much everyone whose opinion I valued during the 1990s and 2000s knew.

a hopeless sophisticate, as tweedy as any character imagined by his beloved P. G. Wodehouse, Graydon started out as the quintessential kid from the hinterlands who dreamed of making it big in New York—and then did. He grew up middle-class in Ottawa, a government worker’s clever Anglophile son, and from an early age found escape in the allure of magazines. A lot of the book’s early chapters focus on hockey, summer camp, movies, and his father’s oddball hobby, woodchopping. This is all about as compelling as, well, woodchopping. I confess, I began flipping pages. There are many.

While in college, he started a magazine and was able to sell it, if not graduate. Yearning for New York, he was admitted to a publishing course at Sarah Lawrence College in Bronxville, the kind of program where top magazine editors speak. Afterward, Graydon peppered them with job queries. To his amazement, the editor from Time invited him on board.

Graydon proved an underused cog in a bloated corporate wheel, but he learned the trade and made lasting friends. In the mid-1980s, he and one of them, Kurt Andersen, got so bored they mused about their dream magazine, which of course became Spy. The Spy chapter is one long giggle, if only for the epithets the magazine’s catty young staff attached to the rich and powerful. You may remember a few. Donald Trump, then an up-and-coming real estate mogul, was a “short-fingered vulgarian.” The wife of a New York Times editor was a “bosomy dirty book writer.” This kind of needling was unprecedented. Spy’s targets practically frothed at the mouth in outrage. “I actually have very long fingers,” Trump protested, a rebuttal he has now repeated for thirty-plus years. My favorite irruption came from Laurence Tisch, slighted in Spy’s pages as a “churlish dwarf billionaire.” His PR man fumed to Graydon that Tisch was “not technically, medically, a dwarf.”

To this point, When the Going Was Good is a lark, a familiar tale of a cheeky kid in thrift-shop blazers making his way in the city. It’s not until a quarter of the way through, when Graydon is offered Vanity Fair, that the book begins to hum. For the first time, he is at serious risk, on a national stage, over his head a bit, facing an entire tier of the upper crust still livid at their treatment by Spy. In the office, he is plagued by the sniping of Tina Brown holdovers, his imminent demise occasionally predicted on Page Six. He calls this period “pretty dreadful.”

By the time he dreams up Vanity Fair’s glittering Oscar gala, though, you begin to sense his genius. The Oscar party, with its star-packed Hollywood edition and the New Establishment list of movers and shakers, nudges many of them—plus lots of aspirants—to engage with the magazine and its writers. But it’s Graydon’s savvy handling of people—the schmoozing, hiring, and even firing—that proves decisive as he alternately burns and builds the bridges that shape what Vanity Fair becomes. Almost overnight, he lets go of three malcontents, including my first editor, transforming Vanity Fair’s culture from poisonous to pleasant. Office drama dwindles. People begin saying please and thank you. They actually smile. It is refreshing.

Graydon’s outreach beyond the office was breathtaking. Not all bowed to his post-Spy charm offensive—Hollywood bigwig Mike Ovitz never forgave or forgot Spy’s digs at him—but scores of others did, notably the influential columnist Liz Smith and Ralph Lauren, a crucial Vanity Fair advertiser. In time, Graydon amassed a stable of pals and advisers we called “friends of the magazine,” including Diane von Furstenberg, Barry Diller, David Geffen, the restaurateur Brian McNally, the producer Mitch Glazer, and the fashionistas Reinaldo and Carolina Herrera. He had a special weakness for reclaiming bygone celebrities, including Billy Wilder, Artie Shaw, and especially the onetime superagent Sue Mengers, who introduced him around Hollywood. All of them graced Vanity Fair’s parties, posed in its pages, and opened doors for its writers, including this one.

At his desk, Graydon knew who he was and what he wanted. He had a nose for the provocative and a winning self-confidence. And for a man who prizes antique canoes and suits tailored on Savile Row, he was a master at skewering pretensions. When Graydon took a call from the office of some studio chief, only to have that exec’s assistant place him on hold to say, “Let me get him for you,” he hung up, religiously. Early on, he banned dozens of words from the magazine, many feints toward insiderness: abode, glitzy, A-list, eatery, flat, flick, honcho, schlep, Tinseltown.

His instincts were mostly dead-on. His ideas could be eccentric. He hired a barback named Dana Brown, who became an assistant and then a valued editor, in part because Graydon liked the way he walked. When other assistants struggled, he suggested that they try walking like Dana. (Must’ve been some stride; I never noticed.) He once told me he could never trust a man who perched sunglasses atop his head. I haven’t risked it since.

It took him a few years to find his footing, but once he did, the dark rumors and predictions of failure fell away. By 1994, Vanity Fair was “hugely profitable,” and Graydon received unyielding support from the magazine’s parent company, Condé Nast, and its owners, the Newhouse family—especially the enigmatic Si Newhouse, who adored magazines and adored Graydon. Not to mention the river of Newhouse cash that flowed Vanity Fair’s way. Oh, the money. Good Lord, the money.

as i look back today, Graydon’s Vanity Fair does feel like some lost world, a gold-encrusted Atlantis ultimately inundated by economic and technological tsunamis, its glories only now being picked over by media anthropologists. I’ve never talked much about what it was like to write there. Because I have always worried about how I’d come off. I mean, the money alone. I’m probably breaking some unwritten law of publishing, but here it is: For twenty-five years, I was contracted to produce three articles a year, long ones, typically ten thousand words. For this, my peak salary was $498,141. That’s not a misprint—$498,141, or more than $166,000 per story. Then, as now, $166,000 was a good advance for an entire book. Yes, I realized it was obscene. I took it with a grin.

Then there was the Hollywood money. Every third or fourth article I wrote ended up optioned for the movies. Most were in the $15,000 to $25,000 range for a renewable eighteen-month option. A handful crossed into six figures. (You haven’t lived until you’ve sat across from Robert De Niro on a film set as he reads your own words back to you—although, sadly, that adaptation of my piece “The Miranda Obsession” never made it past development.) This was an era when management allowed writers to keep that movie money. These days? One magazine I love takes 90 percent off the top.

I am aware of peers who did just as well. Nowadays, though, such windfalls are a distant memory. Today, for a rare magazine article, I’m lucky to receive two dollars a word, or $20,000 for that same ten-thousand-word story. (Don’t even ask what they’re paying me for this piece.) People sometimes wonder why I don’t write more. It’s a chore to explain that, at these rates, it is hard to get that excited.

I was treated like a prince. Stepping off the elevator at 350 Madison, and later at the Condé Nast Building in Times Square, almost everyone on the floor greeted me—Bryan!—and had a glowing word. That review in The Times! Fabulous! Saw you on CNN! Fabulous! Can you sign my book? Fabulous! Can you believe that shitstorm at Goldman Sachs? It needs the Bryan Burrough treatment! The flattery was so uniform I wondered whether it was mandated in an employee manual.

In Sydney, they put me up in a Four Seasons suite overlooking the opera house. In London, it was Claridge’s. I’ll never forget the photographer who stood me high atop a Times Square trash can overlooking traffic for an author photo, which never even ran. Passersby gawked as if I were a celebrity, and I kind of felt like one. There were presents on my birthday and Graydon’s handwritten mash notes after each story.

The staff’s perks were posher still. Breakfast—any breakfast—could be expensed. Dinner parties at one’s home could be catered on the company’s dime. Town cars famously stood ready to whisk you anywhere. Editors received interest-free loans to buy new homes; Condé Nast even covered moving costs. Cash advances were a signature away. There was an “eyebrow lady” who swanned in to tweeze everyone’s brows.

Every few months I’d attend one of the magazine’s parties. The Oscar gala was the hallowed ticket. Once, I took a friend, a civilian, and she ended up stuck in a cramped hallway chest to chest with Warren Beatty. I had to beg her not to touch De Niro’s backside. (Alcohol may have been involved.) One year, I was seated at a table behind the singer-songwriter Gwen Stefani, who was at the height of her career. A line of directors inched by—Cameron Crowe, Martin Scorsese, and Steven Spielberg I remember clearly—and while leaning in to speak to her, they thrust their rears against the back of my head. Such were life’s challenges. For my thirty-fifth birthday, a studio sent me a cake.

Keep in mind, this was never even a full-time job. Vanity Fair stories took maybe six months of my year; the rest I spent on a book. I worked at home, rarely attending anything like a meeting. Every few weeks, my longtime editor, Doug Stumpf, took me to a pricey lunch.

The editorial process, in fact, was simplicity itself. It did evolve over time, though. For the first few years, Doug and I had struggled to come up with ideas that excited Graydon. The stories that resulted were seldom memorable. Looking back, I realize we had not developed a keen sense of Vanity Fair’s worldview. We were both homebodies. Living in New Jersey with my wife and two young sons, I was one of only two people on the masthead who deigned to occupy such an unhip zip code. The requisite party aside, I didn’t hang with celebrities, supermodels, or CEOs. I wasn’t on Page Six. The quiet life afforded me only a narrow slice of Graydon’s milieu, and I didn’t know what he expected from it.

I remember the moment everything clicked. It was one of the final days of 1998, just before New Year’s. Graydon called me directly, a rarity at the time. A violent storm had struck an ocean regatta off Australia; half a dozen people were dead. The Silicon Valley billionaire Larry Ellison had survived. I flew to Sydney, saw Ellison on the way back, and in three weeks came away with a harrowing narrative, one of the best articles I’d produced to that point.

A connection of sorts was forged. After that, Graydon began calling me regularly; over the next fifteen years, probably three of every four stories I wrote were his ideas. I told myself, grandly, that I was “Graydon’s guy.” I’m sure others thought something similar.

His story ideas were simple. They often consisted of a single word. If, say, Rupert Murdoch was involved in something scandalous, he would call and say, “Wanna do Murdoch?” We both knew what he meant, what I was to deliver. My specialty became dramatic reconstructions of events we skimmed from the headlines. A cruise ship sank off Italy: “Wanna do the cruise ship?” That was usually all it took.

In the following year alone, he sent me to London and Florence to sit with Gucci executives as they fought a takeover attempt—“a perfect Vanity Fair story,” he calls it in the book—then to Nepal when the body of a legendary climber who vanished in the 1920s was found, then to the South of France, where a serial killer’s mutilations seemed based on Dalí paintings. The climax was Graydon’s tip about a mysterious woman who spent years silkily cold-calling and befriending celebrities as varied as De Niro, Billy Joel, Quincy Jones, and Ted Kennedy. A sort of catfisher, avant la lettre. I managed to track her down and confront her: an angry, overweight social worker at a Baton Rouge community center. “The Miranda Obsession” remains the most popular article I’ve ever written.

It was glorious. Not because I felt the work was important but because the work was so enormously exciting. I was crafting narratives that I was genuinely curious to explore—and I had unlimited resources to do so. After years in the dark, I had figured out what Graydon wanted—not just the kind of story but the kind of writer he wanted me to be. At Condé Nast, writers were described as either showhorses or workhorses. Showhorses were known as much for their social visibility as for their stories. Workhorses kept their heads down and cranked out copy. I became a consummate workhorse, avoiding office politics and any hint of drama. At the few functions I attended, I watched what I drank.

Unlike some, I never phoned or pestered Graydon; I understood he didn’t care what reporting or writing challenges I faced. Once I accepted an assignment, I simply disappeared for a month or two and returned with the story he wanted—on time, every time. If for some reason I couldn’t deliver, I let him know with plenty of notice. My mantras became “low maintenance” and “no surprises.” Simple.

In the 2000s, we hit a stride. He gave me teams of writers, and I led us to produce pieces on 9/11 and the run-up to the Iraq War. There was an exclusive profile of the reclusive billionaire Steve Cohen, at the time a focus of insider-trading investigations; after the 2008 financial crisis, defining stories on the fall of the trading house Bear Stearns and the “mini-Madoffs” Marc Dreier and Allen Stanford; and, notably, a massively buzzy piece detailing Ovitz’s immolation, in which Ovitz blamed it all on a “gay Mafia.” The Times actually did a story about our story.

Not that any of this drew me deeply into Graydon’s world. I did not visit his homes or see him socially. Our office meetings were perfunctory. He sat behind his desk or on a low couch. I sat with Doug, straining to say something clever. The closest we came to a more personal connection were droll comments he made about my attire. Once, after I spoke at a Vanity Fair conference, he said, “Maybe not your best socks.” I didn’t mind. Not remotely. I understood how good I had it, how good we all had it. And I never thought it would end.

vanity fair’s best moments read like a digest of popular culture from 1995 to 2015. There are Maureen Orth’s investigations of Michael Jackson’s preoccupation with boys. Dominick Dunne’s operatic coverage of the O. J., Menendez, and Phil Spector trials. Marie Brenner’s discovery of the tobacco-industry whistleblower Jeffrey Wigand. Michael Lewis’s outside-the-box financial narratives. Buzz Bissinger’s introduction of Caitlyn Jenner. Deep Throat. The back stories are all there.

As you’d expect, Graydon’s celebrity gossip in the book is stellar, if a tad dated. Jean-Claude Van Damme kicking down a bathroom door to free an editor. Graydon dancing with Madonna until her brother cut in—to dance with him. A dinner where he errantly brushed Dolly Parton’s breast, which she waved off as something that happened all the time. Another dinner where newspaper columnist Peggy Noonan bumped knees with Princess Margaret, who wailed, “You’ve wounded me!” The time Si Newhouse’s beloved pug couldn’t sleep in a bright Hollywood hotel bungalow, so the staff painted over a skylight.

If the book has a flaw, it’s that it can feel a bit Canadian, a bit nice. Assistants, receptionists, and even drivers are extolled at length. Not that Graydon doesn’t name names or settle scores. He banned Harvey Weinstein—okay, easy target—from Vanity Fair events for boorishness. As an adviser at Spy, Clay Felker—okay, long dead—urged him to fold the magazine mere hours before taking the top job at a rival. “I never spoke to him again,” Graydon writes.

It’s only late in the book that he brings out the knives, and mostly, surprisingly, for his own writers. Gossips will probably home in on Dominick’s meltdown. He was Vanity Fair’s first and brightest star, a onetime Hollywood producer who reinvented himself as a ringside observer of headline trials. In Graydon’s telling, it eventually went to his head, and Dominick developed a compulsive, if not addictive, need for fame, appearing on television relentlessly. He died a day after Ted Kennedy in 2009, and Graydon takes a bit too much relish, for my taste, in detailing his own suggestion to Dominick’s family that they delay the announcement of Dominick’s death in order to escape the shadow of Kennedy tributes.

Vanity Fair was still thriving when the first tsunami—the 2008 financial crisis—hit. In the ensuing years, advertisers grew twitchy. Meanwhile, more and more readers were being drawn to free offerings online. In 2009, Condé Nast alone folded five print magazines, including its landmark epicurean magazine, Gourmet, which had been around for nearly seven decades, and its chic home decor glossy, Domino, which lasted less than four years. Weeklies like Time and Newsweek struggled to remain relevant as consumers pivoted to reading online rather than waiting for news digests to arrive in their mailboxes seven days late. Time’s parent company, Time Inc., cut 6 percent of its entire workforce, or more than six hundred employees, across its slate of magazines.

By the mid-2010s, Vanity Fair was noticeably thinner. I remember a creeping sense of foreboding, and the inertia. Graydon was out of the office a lot in those years; I don’t recall a surfeit of memorable articles. His attention increasingly appeared drawn elsewhere, to several Manhattan restaurants he had opened, as well as to a series of documentary films he produced.

I expected his book to dwell on this period, which I imagined as a kind of death by a thousand cuts. I thought he might grieve the changed media landscape—how practically every publication without a rich benefactor is in danger of shuttering, or how young people seldom seem to care about, or engage with, writing of any length. Instead, he tells the story of his departure as a crisis brought on by a single decision in 2016. His frenemy, Vogue’s estimable Anna Wintour—it’s complicated and all in the book—had been elevated to Condé Nast’s magazine czar and suddenly ordained that Vanity Fair’s independent photo, art, and copy departments were to be merged into a centralized Condé Nast–wide unit. Reporting to her.

As he tells it in the book, “from there, things began a slow decline.” His contract was up for renewal. He threatened not to sign it unless Vanity Fair was exempted from Wintour’s changes. He eventually signed a nine-month contract, but the damage was done. He had sensed the shift in the winds and planned his departure for December 2017. When he announced his retirement, The New York Times ran the story on page one.

Graydon wafted off to the South of France for a time. He has since started a mini–Vanity Fair, a newsletter called Air Mail. It’s done well. He is now seventy-five, an age when so many hark back to their glory days. His memoir makes for a breezy read that will mostly interest media junkies. It’s a well-deserved valedictory, though, and will no doubt serve as a Rosetta stone for literary archeologists yet to come.

for me, alas, it didn’t end as well. In the early 2010s, I went through a torturous divorce. For a long time, my emotions sat way too close to the surface. In 2012, I reluctantly accepted leadership of a team tasked with crafting a narrative around the techie turncoat Edward Snowden. For reasons I still can’t explain—perhaps just that period of unhappiness in my life—I loathed this assignment and performed poorly, sleepwalking through reporting trips to Hawaii and Hong Kong. At one point, meeting in Graydon’s office, I teared up as I begged in vain to back out. You don’t tear up in Graydon Carter’s office. (I am grateful that none of this appears in the book.) He did not react to my plea; he only calmly insisted I finish the piece.

And then his calls stopped.

For the next four years, I struggled to get things in the magazine. At a low point, the business side stopped my monthly payments until I furnished the necessary pieces. When Graydon announced his departure in 2017, many on staff left. I was relieved. It gave me the cover I needed to scuttle away at a time when I sensed my contract wouldn’t be renewed anyway.

Afterward, it took time to reset my career. With little interest in cut-rate magazine work—these days I write the occasional piece for friends at Texas Monthly—I briefly considered academia or public relations. Neither was remotely appealing. In the end, I found that you can still live a nice life on book advances, royalties, and investment income.

The funny thing is, I never looked back. I never mourned the end of Graydon’s era, or all that money. Not once. I understood the gift I’d been given. I said it then, and I still say it today: We had a great run. In the vanishing world of American magazines, I suspect there will never be another like it.