The Gray Man Theory

On Graydon Carter's 'When the Going Was Good'

Francis Bacon, Study for a Portrait with Bird in Flight, 1980, Oil on canvas

A terrible thing has recently happened to me. I have become obsessed with the golden era of American magazines.

This grave affliction manifests itself in several symptoms. First, it causes one’s reading list to grow to enormous length. Just when you think you’ve discovered the last memoir about answering phones at the midcentury New Yorker, or cowering under the thumb of Anna Wintour at Vogue, or of late nights at Partisan Review in the hard-drinking glory days, or at the Village Voice in the high-flying Sixties, several more rear their heads, like martini-soaked Whack-a-Moles. And because the whole thing involves the settling of long-simmering scores and the clashing of titanic egos, you’re almost obligated to read everything in order to form a full picture of the personalities involved. Was the New Yorker’s William Shawn a gnomic sage, or a doddering fool? Did Tina Brown destroy high-middlebrow literary culture in America, or save it? The same person might be painted as a saint in one memoir and a tyrant in the next, and the same incidents might recur across different books with totally different causes and effects, so hell, you might as well read them all.

Second, and I promise I won’t spend too much time belaboring this widely-discussed point, to read about these days as a writer is to develop a longing for a level of financial and social status that can never be fulfilled. Every time someone writes one of these memoirs, there’s another round of consternation and wailing among the media set as eye-popping salary figures from the old days make the rounds, not to mention the first class accommodations, lavish expense accounts, and power lunches that accompanied a position at the top of the magazine world. This is a time when the world could stop for a splashy cover or a blockbuster article, and where readership numbered in the millions. Compare that to the denuded landscape of today, with its paltry salary figures, undignified rituals of repeatedly harassing a major media conglomerate to collect your few hundred freelance dollars, and ultimate reward of a few days of viral notoriety for a big piece, if you’re lucky, and one begins to understand how an Anglo-Saxon monk must have felt, standing among the ruins of some great temple to Jupiter.

One of the preeminent figures of this bright, gone world is Graydon Carter, a raffish man-about-town known for his stewardship of Vanity Fair, his hot-ticket Oscar party, and a memorable ongoing feud with a certain New York real estate developer-turned-politician. His entry into this crowded field of memoirs, When the Going Was Good: An Editor’s Adventures During the Last Golden Age of Magazines, chronicles his journey from working as a railroad lineman in rural Canada to reaching the top of New York society, first twisting the noses of the powerful with his satirical Spy magazine in the 1980s, then running Vanity Fair from 1992 to 2017. When the Going Was Good was hotly anticipated reading for me for several reasons. Not only would it fulfill my aforementioned appetite for magazine gossip, but I had also read and immensely enjoyed the diaries of Tina Brown, his predecessor at VF, cringing at her blithely quick trigger finger with her staff and her somewhat obsequious attitude towards the rich and famous yet relishing her immense tenacity and cool wit. I came away admiring her much more than I expected to; it was one of those books about a visionary and ambitious figure that leaves one bursting with energy of one’s own, so I was eager to see if I would find the memoirs of her successor similarly invigorating, or if he was merely, as Gore Vidal once said of Leon Wieseltier, a social climber with “important hair.”

Initial impressions were unpromising. The first thing that struck me about When the Going Was Good was the demure credit on the title page for co-writer James Fox, best known for wrangling Keith Richards’ memoirs into shape. No one expects literary coherence from a famously drug-addled rock star, but one would hope that a writer and editor of Carter’s experience could manage a vivid description or a memorable turn of phrase or two. Brown’s diaries, at least, are full of them. But alas — When the Going Was Good is written largely in the flat memoir-ese of the athlete or politician. Just after opening the book, which begins with Carter attending his wedding while negotiating a major scoop, the reader is confronted with this breathtakingly insipid paragraph:

The weather was decent, and the wedding party had assembled on our terrace and spilled out into the garden. After dinner, we made our way to our barn, which conveniently had a stage. There, Tom Freston and John Mellencamp had an incredible wedding gift for us: Otis Day and the Knights of “Shama Lama Ding Dong” and “Shout” fame, the band that had performed so memorably in the movie Animal House. When the night was winding down, Anna and I were about to drive off to the Mayflower Inn, not far from us, for the first night of our marriage when we found Fran Lebowitz sitting beside our driver in the front seat. Fran was a big part of our lives.

Black and terrible visions begin to dance at the corners of one’s eyes at the thought of an entire book of such awesome banality. Thankfully, things soon kick into higher gear and even Fran Lebowitz is mercifully mostly absent. Carter’s account of his middle-class Ottawa childhood is more interesting than the dull first sections of most autobiographies, providing as it does a fascinating contrast to his later life in the public eye. His father, a civil servant, was one of those somber prairie men for whom practicality is pursued to the point of fanaticism; the kind of man whose cocktail and bridge guests were ushered out the door at ten o’clock sharp, who would never think of stopping for hamburgers on a road trip, and who had his young children drag a gigantic fallen log out of the ice for hours in order to save a few dollars on firewood. So while Carter seems to have had a relatively happy childhood for which he bears little resentment, the shrink in me notes that in adult life he would reinvent himself as almost the complete opposite of his father, becoming a figure out of Evelyn Waugh or Anthony Powell: cultured, urbane, intensely sociable, and impeccably dressed.

Carter drifted through a series of nondescript government jobs in Ottawa before landing at The Canadian Review, a literary magazine which quickly folded, sending him to New York in hopes of finding more stable media employment. In one of those instances that seem so common in 20th century memoirs and are so difficult to imagine happening now, he finagled his way into a meeting with a top editor at Time who, in violation of the usual protocol, hired him on the spot. He describes those days at Time in the late 1970s, when the magazine was still one of the voices of America, as “magical realism,” and indeed, there is a Wonkaesque feeling to his descriptions of working in the enormous Time-Life Building.

Time was a weekly, and on Friday closing nights, staff in uniforms brought dinner (with wine) to writers’ offices on tea trolleys. There was a bar at the end of each corridor. I went five years without ever turning on my oven . . . . The magazine’s offices were spread over three floors. There was a series of long hallways, with the writers’ offices along the window side and the researchers’ offices on the inside. At one end sat the editor (they were generally men) and his secretary. The other end was where the bar appeared at the end of the week.

Chafing after a reassignment to the moribund Life, where he admits he mostly “stayed in my office and read Wodehouse,” he and his partner Kurt Andersen eventually left to form Spy magazine, a elegant satirical monthly that skewered the Wall Street-American Psycho era of “big hair and egos and long stretch limousines.” Spy was the right magazine at the right time, combining a beautifully jazzy and arresting design with an insolent attitude towards the rich and famous. They wrangled quotes from congressmen condemning the situation in Freedonia, the fictional country from Duck Soup. They assembled and published the complete client list of the “pathologically secretive” Hollywood power agency CAA, which caused its megalomaniacal founder Michael Ovitz to briefly contemplate closing it down (Ovitz would later go down flailing in a famous 2002 Vanity Fair profile, blaming David Geffen and a secretive “gay mafia” for the demise of his career). They sent checks for 13 cents to New York’s billionaires to see who would bother to cash them. And they made numerous enemies, which they would refer to by their trademark recurring prefixes: “churlish dwarf billionaire” Lawrence Tisch, “socialite war criminal” Henry Kissinger, and, most famously, “short-fingered vulgarian” Donald Trump.

Spy grew too big too quickly and couldn’t sustain itself, so after a short stint at the New York Observer, Carter found himself offered Vanity Fair when Tina Brown left to take on the New Yorker (though it should be noted that Carter and Brown have differing accounts of who was promised what in this transfer of power). Brown had masterminded a formula during her time at Vanity Fair: glitzy celebrity covers and society gossip combined with deeply researched, lengthy journalism covering politics, the arts, and true crime, and reading her account in The Vanity Fair Diaries of developing a vision for the magazine and securing regular contributors like Dominick Dunne and Annie Leibovitz is never less than fascinating. Not to downplay the difficulty of running the magazine day-to-day — I certainly couldn’t do it — but here Carter can’t quite match Brown for drama, having been handed the keys to a well-oiled machine instead of building it nearly from scratch.

But there are still interesting dynamics at play, as Carter stumbles through his first two “pretty dreadful” years at Vanity Fair. At Spy, he could heckle New York’s smart set from the cheap seats; now he finds himself in more luxurious confines, with the eyes of the audience upon him, and he has to be careful who he angers. His role becomes something like a statesman; he must navigate the process of establishing diplomatic relations with figures he has previously mercilessly attacked, while at the same time signaling to those figures that he can’t be pushed around. When he receives a lazy and substandard piece from Norman Mailer reporting on the 1992 Democratic Convention, he decides to take his stand. The Graydon is not for turning, he declares, and kills the piece. Aside from his literary fame and fortune, Mailer was known, even at an advanced age, for walking up to his enemies and socking them on the nose, so it did take a certain amount of courage to poke this particular bear (although, in another characteristic example of VF largesse, he did still receive the full $50,000 he was promised, which must have assuaged him somewhat).

It is to Carter’s credit that he manages to hang on and stabilize things; before the eight-year Brown regime, the floundering magazine had sent two editors packing within a year. Slowly but surely, his reputation among the staff begins to grow, he becomes accustomed to the monthly rhythm, and When the Going Was Good begins to take on a buttery tone, as he starts to enjoy life at the top. He struts around in suits from Anderson & Sheppard. He has a company car with a driver, a hulking Siberian called Sergei. Vanity Fair staff can expense everything from lunch to dry cleaning. Photo shoots are smoked-salmon-and-champagne affairs. Condé Nast even offers interest-free loans for buying houses. He does acquit himself well in his stewardship of the magazine, hiring Christopher Hitchens and Nick Tosches, breaking major stories about dirty tricks in the tobacco industry (a story later adapted into the Michael Mann film The Insider) and the true identity of Watergate’s Deep Throat, among others, and running some of Dominick Dunne’s best work, including his blockbuster series on the O.J. Simpson trial.

But it’s the social world that Carter seems to reserve his true passion for. A long chapter details the genesis of the now-famous Vanity Fair Oscar Party, giving Carter the opportunity to purr about seating arrangements, gatecrashers, and gift bags with the satisfaction of a man who is never happier than when he is gliding his way around a room full of big, bright, shining stars. Similar attention is devoted to the purchase and refurbishing of his West Village restaurant, the Waverly Inn, a nondescript pub which Carter turned into a celebrity-studded Jazz Age fantasyland. And when the whole magazine industry goes into free fall, bleeding from the twin blows of the 2008 financial collapse and the rise of the internet, Carter seems uninterested in diagnosing the decline, or documenting what it was like to experience it. His final years at Vanity Fair are dispatched within a few perfunctory pages, and his exit is described in terms of a power struggle with Anna Wintour at a reshuffling Condé Nast, with hardly a mention made of plummeting subscriber numbers or evaporating advertising dollars.

That’s all fine, so far as it goes — we’re here for the stories of the good times, after all. But there is something missing from When the Going Was Good, some larger sense of drive or vocation. What makes Graydon Carter tick? Again, the comparison to Tina Brown’s diaries is instructive. The Vanity Fair Diaries is fairly unabashed about her titanic ambition and ego, and the ruthlessness it takes to survive in New York high society. Her relationship with Condé Nast’s mercurial billionaire patron, S.I. “Si” Newhouse, is wary and calculated, that of an ambitious Roman senator trying to please Caesar or Claudius. And despite her appetite for fame, she surprised me with her nerd’s appreciation of the magazine as a form — she can quote Harold Ross’ New Yorker and the Vanity Fair of Condé Nast (the man) chapter and verse. Meanwhile, When the Going Was Good presents Carter as a dapper, genial guy who just happens to have found his way to the top. His descriptions of Si Newhouse, perhaps smoothed over by the passage of time, are never less than adulatory. And while he clearly enjoys the magazine world and loves the position of editor, one also gets the sense that he thought of it as a one-way ticket to a life of elegance and ease. He says so himself, early on.

And so, somehow, in my case, with a lot of mishaps and a dollop of good luck along the way, things just worked out. It wasn’t easy all the time, but step by step I managed to achieve the four things the twenty-five-year-old me thought would bring me happiness in my adult years:

1. Living in New York. Greenwich Village specifically.

2. Becoming the editor of a big, general-interest magazine.

3. Being one half of a wonderful marriage.

4. Having a large, happy family and a dog.

Well, I’m happy for you, Graydon, but those are not exactly the words of a man with an unquenchable fire in his belly. Throughout the book, one can detect a strange tension between the anachronistic dandy figure that Carter has fashioned himself as and the bland narrator of When the Going Was Good. Where’s the wit? Where’s the pizazz? Where’s the glinting diamond edge one needed to survive in this ruthless world? And what made this middle-class kid from Ontario want to reinvent himself as Cyril Connolly, anyway? He clearly worships a certain set of iconic aesthetes, and envisioned himself eventually joining their ranks. But these figures continue to compel us not just because they were quick with a line or went to a lot of parties but because their public personas constitute blows in a magnificent, doomed battle against life’s inexorable forces of sorrow and despair. Oscar Wilde’s fizzy social comedies hid a radically queer subtext, and Dorothy Parker cracked wise in order to conceal an abyssal melancholy. If there exists such a productive tension between mask and man in Carter, When the Going Was Good fails to shed any light on it.

In the end, one is forced to assess him as a capable mediocrity. When the Going Was Good is enjoyable enough reading and will no doubt be an able companion to its target audience on their first-class flights and in their upscale hotel rooms. Perhaps you had to be there to experience the true brilliance of his editor’s eye. But it seems to me that when the great mechanism of the golden age of magazines was humming along, a man like him, who could ably navigate the social world, take the temperature of the times, and identify talent and stay out of its way, could be mistaken for the equal of singular 20th century figures like William Shawn or even Tina Brown. Break the power of that mechanism and one begins to see who really had a brilliant, ambitious vision for the world of American letters, and who was just happy to be there, in the company of the rich, famous, and beautiful, quaffing negronis at the Waverly Inn.

Henry Begler writes the Substack newsletter

A Good Hard Stare

. He lives in Los Angeles, CA.