Illustration by Tim Robinson.

The labor of magazine-making has never been less glamorous, less stable, or less profitable. Prestige, as the union organizers at Condé Nast have said, doesn’t pay the bills. With the churn of digital publishing pushing magazines into the financial and cultural doldrums, the luster of the legacy media job has only gotten duller. Yet there is still a magic in print magazines that does not seem to exist in newspapers or book publishing. Be it a weekly, a biweekly, or a monthly, a magazine can give us a snapshot of cultural mores, a printed record of the present, and a forecast of the future. “The more fragmented we become as a culture,” Tina Brown once observed, “the more the media holds us together.”

There are, of course, many different kinds of magazines that help hold us together: Little magazines like n+1 and trade magazines like Variety, smutty magazines like Penthouse and general-interest magazines like The New Yorker, left-wing magazines like Dissent and right-wing magazines like National Review. Each obviously serves a different master and aspires to win over a different audience, but as revenue declines and subscription numbers shrink, each shares a common fate—and the glossy magazines, which once ruled the newsstand, most tellingly of all.

While Vanity Fair, Vogue, Elle, and the like still carry some cachet, they are no longer ubiquitous. Instead, they are relics of a vanished era of prosperity when their pages were bloated with ads and their editors in chief served as the feudal lords of competing fiefs. Today, when someone narrates the story of this heyday, it is hard not to feel like you’re reading an obituary. Legends of elephantine expense accounts, personal drivers, boozy lunches, palace intrigue, and incessant starfucking: These are supposedly what made the gilded age of celebrity editors and their glossies great.

Condé Nast was at the center of this lucre. Those who worked at its old offices in 4 Times Square, as well as those who observed its goings-on from the outside, have a habit of talking about this era in tones of world-historical seriousness, even if what they are talking about is really just the loss of all those late nights and hangovers, chance meetings with B-listers, and the occasional anecdote about an A-lister. Dana Brown, who rose from editorial assistant to deputy editor of Vanity Fair under the tutelage of its editor Graydon Carter is no exception. As he implies at the start of his new memoir, Dilettante, his book is not unlike The History of the Decline and Fall of the Roman Empire, but for editors with corporate credit cards:

This is a book about the rise and fall of a great civilization. A universal account of change. And my own personal journey through this fertile tableau and morass. Part memoir, part social history, part journalistic exploration and cultural criticism. A lament, celebration, and elegy. The biography, obituary, and capstone of an era.

Brown is only half-kidding about his memoir’s ambitions, but what follows is closer to a Horatio Alger story about a bootstrapping outsider’s rise to consummate insider. A college dropout and mediocre rock musician, Brown was not plucked from the usual stock of assistants who’d edited their college newspaper or been blessed with a sterling family name that opened doors. (He is unrelated, he notes, to Tina.) Unlike his peers, he was discovered as a cater waiter working a dinner at Carter’s apartment. But from there, Brown’s life takes a fateful turn: He lands a job as Carter’s assistant and climbs the ranks, going from answering phone calls to editing cover stories, working (really hobnobbing and binge-drinking) with literary luminaries such as Christopher Hitchens and smoking pot with Seth Rogen at red-carpet events.

Brown’s memoir, like those that came before it, reads like a typical insider’s account. He succumbs to the potted conventions and self-importance that infect this genre of writing: “It was the age of the glossy magazine and the celebrity editor—they were the arbiters of taste, translators of culture and style to the culture-and-style-hungry masses. They decided what was cool, what was important, what was necessary, what made it onto their pages, what people would be talking about, watching, reading, wearing, thinking.” Still, his book has its merits—dishy and gossip-filled (did you know that almost everyone who worked at Vanity Fair, apart from the boss, hated Fran Lebowitz?), it is an entertaining enough tale of partying and careerism. Having started out as an assistant, Brown can also tell a slightly different version of the company’s history than his bosses. Grabbing coffees, working the door at parties, babysitting Carter’s kids, and fulfilling all manner of inane tasks, he proves to be a capable court historian—a partisan of an ancien régime and celebrator of its excesses—while also offering his readers just enough self-deprecating punch lines and juicy tidbits to look past the terminal symptoms of the disease that killed his profession in the first place.

Brown began working as one of Carter’s assistants in 1994. By the time he was laid off, in 2018, he was a member of Vanity Fair’s senior editorial staff, working with writers like Buzz Bissinger and Nancy Jo Sales. The vast majority of the book chronicles not Brown’s later years as a deputy editor but his time as an assistant and the impostor syndrome he overcame by partying and hustling harder than any of his peers. It is obvious from the start that it was his loyalty and not his talent that recommended him for success: He worshiped Carter, was attentive to his needs yet never prying, and performed his obeisances in every sense. Without hesitation, he throws laurel wreaths at Carter as the tastemaker du jour: “The moment he took over Vanity Fair, Graydon became one of the most important and influential editors in New York and America, a kingmaker in the publishing business.” In Brown’s estimation, Carter was not just a king but an artist: The “G” in Carter’s signature, Brown believes, is Picasso-like.

In fairness to Brown, the world that Carter built around himself was carefully composed: The perfect swoop of gray hair and amiable smile, the apartment in the Dakota, the Connecticut country house, the rich and glamorous friends, lunch and dinner at the hottest restaurants, and a memorable catch phrase (“Don’t fuck it up”) were as much works of self-promotion as they were the signs of a hardworking editor. In Brown’s view, it was this force of personality that gave Vanity Fair its power. For him it was “the most influential general-interest magazine” during the two decades he worked there, all because Carter possessed an astonishing talent for image-making and magazine innovation. In Dilettante, we get pages upon pages of praise for the banality behind the scenes. We overhear Carter on the phone with Dominick Dunne as he files dispatches from the O.J. Simpson trial and helps cement a new lurid sensibility in American pop culture (“Reality was suddenly so much more interesting”); we see Annie Leibovitz snap a portrait of Caitlyn Jenner in what we are urged to believe was the most significant magazine cover in a decade; we see Carter supposedly landing the scoop of a generation by helping uncover the identity of Deep Throat; in a weird aside, Brown justifies Hitchens’s support of the Iraq War as stemming from a concern for human rights.

The recent past, cast in such a flattering light, looks strange: Was this really the height of taste and power? But the ardent reminiscences and unflagging devotion place Brown’s book in a subgenre of the publishing memoir that Francesca Mari, writing in Dissent, noted focuses on “the assistant economy.” In its fictional guise (The Devil Wears Prada) or its nonfictional trappings (Jon-Jon Goulian’s The Man in the Gray Flannel Skirt), the literature of the assistant often lampoons the bygone titans of an earlier era of magazine publishing, but it also makes the work at hand sound far more important than it really was, and it clarifies what makes the editor as well as his or her assistant more than dilettantes. “This mythologizing,” Mari writes, “is relentless and trifling, but it fills a real need: the need to justify your job by making your boss as big and as marvelous as possible. And that, after all, is what the boss always wanted.”

Indeed, the most fascinating character in Dilettante is not the author but Carter, whose inner life is out of reach but who remains an ever-present force in Brown’s life. Carter occupies the roles of mentor, dad, and deity all at once. We hear so much about his accomplishments, and about Brown’s dutiful work in making sure his life remained frictionless—and yet, like any good book from an assistant, it doesn’t tell us much about Carter as a person. We learn very little about the vicious gossip or critiques that were leveled at Carter over the years, nary a detail that might paint a more complicated portrait. The following passage from a 2000 profile of Carter provides more insight than Brown ever bothers to furnish: “He’s the Jay Leno of the magazine world, the king-size personality controlling the world’s glossiest showcase for the formerly, currently, and would-be famous. Nervous, ubiquitous, and impossibly fabulous, Carter, in the words of his friend Jim Wiatt, president and co-CEO of the William Morris Agency, ‘has transcended being a great editor—he’s really a celebrity.’” Brown’s only special insight is that Graydon hated paper clips and was a great gift giver. No complaints here!

All the nostalgia found in Brown’s memoir makes sense: His years working alongside Carter were his own personal zenith, after all. Mythmaking also pervaded his workplace—Carter’s Vanity Fair was premised on nostalgia and the longing for an earlier Golden Age of the United States. The magazine Carter produced was always less about the future or the present than about a constant conjuring of some better past: “Planes. Mid-century American architecture. Movies from the forties,” writes Jennifer Senior in New York. “Thumb carefully through Vanity Fair, and you’ll see it’s an art-directed manual to Carter’s obsessions.” In fact, the magazine under Carter did not do anything all that original, but instead replicated what Tina Brown had called “the mix”: “Celeb cover to move the newsstand, juicy news narrative…. A-list literary piece, visual escapism, revealing political profile, fashion. If we nail each of these per issue it’s gonna work.”

Carter did deliver one innovation as editor: He supercharged Vanity Fair’s sense of exclusion, turning the magazine into a feted event, and the accomplishments of his reign, according to Brown, include an issue devoted to new Hollywood stars, an issue that celebrated business leaders, and a party held every year in honor of the Oscars. Brown’s account of the creation of the first Hollywood issue, which featured a series of actresses across generations, underlines the unintentional comedy that pervades the book:

A mix of established stars and up-and-comers, familiar faces and new ones, and more than a few who would achieve a level of fame that would last until today. Okay, sure, in retrospect we dressed them up like tarts, and it looked like a police lineup of prostitutes more than a magazine cover, and we would rightfully catch some grief for that, and let’s not even talk about the lack of diversity. But it was a hit.

This crass register is one Brown luxuriates in. Describing his HR orientation, he cracks a joke about the absence of political correctness in the business world at the time: “There was no sensitivity training, as I’m sure corporate orientations nowadays are legally mandated to do.”

Brown’s perspective on the explicit classism of Vanity Fair provides plenty of fodder for mockery. But a dose of pathos creeps into his narrative as well. We all know what will become of Vanity Fair’s “simple business model,” which provided Brown with all these rich experiences: It will “run into a steamroller called the internet” and take with it the beautiful world he so cherished—emaciating the pages of the formerly ample magazine. It is not hard to sympathize with Brown when he describes the decline and fall: “Content and distribution,” he notes, “quickly meant something different from simply putting a magazine on the newsstands every month and hoping for the best.” Editors, he insists, need the space to put a finger in the air and read the wind, but can they now? At large-scale institutions like Condé Nast, this was no longer possible: The “number crunchers and MBAs,” he grumbles, began “to replace the creative class in New York’s media hierarchy, business-school acronyms taking the place of actual words in meetings with our corporate overlords…. Pitch decks, Excel spreadsheets, and PowerPoint presentations replaced casual meetings, conversations, and boozy lunches about what was going on in the world and how to cover it—those of us who created the content suddenly became less important than those whose job it was to find an audience for that content.”

Brown understands this shift as a generational problem as much as an economic one: “The office was being overrun by rows and rows of silent, headphoned, Invisaligned, and Warby Parkered twentysomethings on bouncy balls slurping slop in tiny cubicles, tapping away at their keyboards. The modern workplace was turning into a dystopian, Dickensian…adult nursery school.” And he is not all wrong, though the fun of magazines was sucked out less by the number crunchers than by the numbers themselves.

When I worked as a low-level editorial employee at a music website that Condé Nast purchased in the 2010s, there was no way around the blandness of our toil. But that wasn’t because boring young people had invaded the halls of Condé Nast but because under financial duress, magazine-making—in print or online—could no longer be an art form or a craft, assembled from sensibility and taste. To survive, it was seen as needing the validation of engagement numbers and page views. Yet optimizing writing and editing for an unknown audience is often a fool’s errand. It shackles you to clichés and received wisdom; it’s why so many headlines read the same, inane way (posed as questions, calls to action, and other prefab formulations) and why everything on the Internet looks so sterile. Yet what is going on in the media today is not really a changing of the guard but a generalized desperation in the face of market forces—something Brown seems to be aware of, even if his memoir avoids engaging with it. At a book party for Dilettante, he told a New York reporter: “There’s just no money in journalism now…. They pay these kids fucking nothing to sit on a computer all day and look at what’s trending.”

Given that Brown was axed, it’s no surprise that he is bitter about how things have gone and blames a generation rather than an industry-wide crisis. But a question remains unanswered: Was Vanity Fair ever a great magazine? Brown takes it for granted that his readers would agree it was. But is a magazine devoted to dead royals, dead Kennedys, and dead everything really all that interesting? The “Jay Leno of the magazine world” might be the most damning thing you can say about Carter.

When it comes to describing what an editor used to do, Brown offers us very little wisdom. He compares the work of a magazine editor to that of a film director, a therapist, a conductor. These are rote descriptions, and Brown doesn’t seem to evince a philosophy for his work besides finding “good writers” who are easy to edit. (He loves to admit that he barely edited many of the stories that came across his desk.)

When Carter finally retires and Brown applies for the job as his successor, the memo he writes is full of even more platitudes. As he sums it up: “Print was fading as a viable business, digital was the future, costs would need to be cut, there would have to be more integration between the print and digital staffs and writers, and new sources of revenue would have to be found…. The magazine had lost touch culturally, the readership was aging, we needed to get younger, more digitally savvy.” Brown knows that what he is selling is bullshit and admits that he was pandering to his corporate overlords: “I must have used the word diversity in every other sentence,” he wisecracks. For him, what makes editing editing is the clout that came with it: “I liked being a Vanity Fair editor…the lunches and dinners with writers, the invitations to parties and premieres, the cultural capital it gave me. People found me interesting and were nice to me based solely on my job title.”

But what happens when legacy magazines can no longer rely on their reputation to get readers, let alone party invites? Condé Nast’s magazines, especially Carter’s Vanity Fair, used a strategy of exclusion to generate a sense of luxury—which its editors enjoyed partaking in. Yet can any publishing project today succeed on that basis alone? Writing about Philip Rahv’s time as coeditor of Partisan Review, Irving Howe observed that what made Rahv “brilliant” was that he “wanted his magazine to constitute a public act…. Rahv saw cultural life as if it were enacted in a political arena…. He ran the magazine as if he were heading a movement.” Calling a magazine a movement might be as self-important as anything Brown has written, but in a profession that feels increasingly laborious, precarious, and dire—and certainly less glamorous—this definition of editing allows us to imagine the vocation as something more worthwhile. In the end, what can ultimately sustain magazines, as well as their employees, is this pursuit of a place in some kind of public sphere. On this, Tina Brown was right: As our lives become more and more confusing, a magazine and its editors still have a difficult task ahead of them—sifting through the shit of shared experience and finding the things that might still surprise us, might change our minds after all.