"How to Lose Friends and Alienate People" by Toby Young

A would-be member of the media elite describes his hilarious misadventures trying to succeed in the shallow, celebrity-obsessed world of glossy magazines.

Published June 17, 2002 9:32PM (EDT)

Toby Young's gossip-strewn memoir of failure in the vicious world of glossy Manhattan magazines doesn't seem like a book to take very seriously, especially right now. In 2002, the idea of an autobiography of ambition and substance abuse in the big city feels only slightly less exhausted than, say, a lament decrying the placidity of peacetime prosperity or an exposé about Ecstasy use. Memoirs might not be dead, but the subgenre of memoirs about briefly misguided middle-class writers and their thwarted dreams of literary glory is an ailing one. Dave Eggers acknowledged as much in the second half of "A Heartbreaking Work of Staggering Genius," when he half-apologized for exploring a hopelessly overexposed and clichéd milieu. Calling the last section of his book, which dealt with hip young magazine writers, "kind of uneven," he wrote that such people are "very difficult to make interesting." And that was more than two years ago.

Toby Young has neither Eggers' wit nor his engagingly heartbreaking history going for him. Yet, amazingly, Young's "How to Lose Friends and Alienate People," which is the story of being fired first from Vanity Fair, then from London's Evening Standard, then, most humiliatingly, from Gear, is a very funny book that's also quite revealing about those elite segments of American media culture that orchestrate the stuff filtering down to the rest of the country. Somehow, it almost seems important. As in Ted Heller's "Slab Rat," a roman à clef about Condé Nast that came out in 2000, there's a persuasive critique of American careerism hidden beneath its broad comedy.

On the simplest level, Young's book is about totally fucking up at Condé Nast. But it's also about a country -- or at least a city -- where all other values have been subsumed by ambition and status. "Why do New Yorkers attach such importance to the state of your career?" he asks. "To a certain extent, they define each other according to the usual demographic categories -- gender, ethnic origin, religious background, etc. -- but these things pale into insignificance besides the jobs they do. It's as if there are no alternative sources of identity."

Young eventually reveals that it was his own father, Michael Young, who coined the word "meritocracy" in his dystopic 1958 novel "The Rise of the Meritocracy." According to his father, he says, "If everyone starts out on a level playing field then the resulting distribution of wealth, however unequal, will be regarded as legitimate." When people feel like they deserve their ill-gotten riches, there's no such thing as noblesse oblige.

Young's outsider's take on America's status fetish does a lot to illuminate the cult of work that has given us such things as the 60-hour week, celebrity CEOs, magazine editors and chefs, and the demise of old-school journalists' blue-collar sympathies. In this regard, he's part of a cultural backlash against the garish plutocratic values of the '90s. As a recent New York Times article pointed out, there's currently a wave of exposés about New York bosses published by former underlings, including Nicola Kraus and Emma McLaughlin's "The Nanny Diaries," Nicholas W. Maier's book about James Cramer, "Trading With the Enemy," and former Vogue assistant Lauren Weisberger's "The Devil Wears Prada," which comes out next year.

What makes "How to Lose Friends and Alienate People" distinct from these books is that instead of simply ripping apart Vanity Fair editor in chief Graydon Carter, it attacks the entire cultural and intellectual milieu that Vanity Fair and magazines like it are a part of. Young imagines himself a beer-swilling, coke-snorting lad mag Tocqueville, and occasionally, that's just what he is.

He is very good at detailing the process whereby smart, philosophically sophisticated people learn to nihilistically celebrate flash and triviality. For Young, it's precipitated by irritation with the recondite enthusiasms and ironic disdain for mass culture of his college friends. "Popular culture was strictly divided between stuff it was okay to like -- independent films, alternative rock, any form of cultural expression associated with minorities -- and the mindless pap produced by the American entertainment industry," Young writes. If mainstream pop culture was "enjoyed at all," he says, "it was strictly in a spirit of camp condescension."

Young's whole personality becomes a reaction against this attitude, a way of advertising his "hostility to the liberal intelligentsia." Of course, this pose is itself a kind of post-ironic irony, a Warholian irony that cloaks itself in gee-whiz earnestness. Yet Young's carefully calibrated faux-enthusiasm for celebrity culture becomes indistinguishable from the real thing. "Some form of transference had taken place and I'd ended up fully embracing the belief-system I'd only flirted with before," he writes. "I couldn't wait to strut around in my Armani dinner jacket, waving around the gaudy symbols of my success for all the world to see. Check out my Rolex! Get a load of the tits of my girlfriend! Am I cool, or what?

This kind of anti-culture-snob snobbery, cheerful embrace of hype and refusal of all distinctions save degrees of hotness defined the '90s. It was the thing that bound together Britney Spears and Salman Rushdie, Monica Lewinsky and Damien Hirst in one big Prada-sheathed daisy chain, and it was a mood that Vanity Fair did more than any other publication to promote.

Thus a gig at the magazine is clearly a dream for our author. In 1995, he writes, Graydon Carter invited him to come to New York for a trial period as a Vanity Fair contributing editor. What comes next will be familiar to anyone who has ever entertained notions of anti-patriotic universalism only to feel fuel-injected with national identity upon traveling abroad. Arriving in the capital of the American values he rebelliously championed in Britain, Young is gradually suffused by continental horror. He had believed that alienation from mainstream culture was tired, but that idea was partly responsible for the death of bohemia in the '90s, which Young quickly learns to mourn.

Of course, part of Young's turnabout is spurred by humiliation resulting from many foiled attempts at social ascendance, and he knows there's a danger that his whole book will seem like sour grapes. At one point, he tells his far more successful friend Alex that he wishes he'd made it to the top so "I could condemn it more convincingly."

His failure isn't even a result of any kind of cynicism or intellectual superiority. Besides making idiotic if hilarious gaffes -- like hiring a stripper to come to the office on "Take Our Daughters to Work Day -- Young sometimes demonstrates a bizarre cluelessness that makes one wonder what Carter ever saw in him. The rejected pitches he reproduces might be intended to demonstrate Vanity Fair's priggishness, but all they really show is that Young's sense of humor is less Evelyn Waugh than Benny Hill.

One query says, "How hard is it in this day and age to become a social pariah? Why don't I try and find out. The idea would be to antagonize as many people as possible by indulging in various forms of anti-social behavior in a twenty-four-hour period." Such a project might have exposed the minute, byzantine rules governing New York social life, but only if it was done with a degree of subtlety. Young's ideas were crude and blundering -- he proposed to crack open a Budweiser at an AA meeting, let his pager and cellphone ring during a play and smoke a cigar at a health food restaurant. Such stunts would have proved nothing save that people disapprove of extreme rudeness.

Nor does his book as a whole demonstrate the kind of scintillating insouciance that he seems to believe New York editors failed to appreciate in him. His imitations of what he annoyingly calls the "glossy posse" feel strictly secondhand, often involving use of the word "dahling." He makes the same references -- to Dorothy Parker, the Algonquin Round Table and the newspapermen of '40s films -- over and over again. He insists on using stupid names for cocaine like "devil's dandruff" and "Bolivian marching powder."

That said, he's an immensely sympathetic narrator in large part because he's so inept and, in a strange way, so naive. Despite his initial craven enthusiasm for American corporate media, he had absolutely no idea what it really meant. He can't seem to get over the idea that contemporary newsrooms don't resemble the one in "His Girl Friday."

"The old-fashioned New York journalist, a harum-scarum roustabout whose status is 'somewhere between a whore and a bartender,' has been replaced by a clean and sober careerist with a summer house in the Hamptons," he laments. It's as if an eager B-school grad went to work for Enron only to be shocked when Ken Lay turned out not to be a benign social benefactor.

That innocence works for the book, making it a kind of parable of the American media world during the last six or seven years, with all its market-driven credulousness, slavering celebrity obsession and smug sense of entitlement. Young's insight is about the way the American myth of total class mobility and equal, endless opportunity -- apotheosized in the anointing of the famous -- justifies "abhorrent levels of inequality" and ensures that anyone who's not materially successful will be viewed as defective. "The casual, unthinking cruelty with which successful New Yorkers treat cab drivers and waiters, not to mention their personal assistants, was something I witnessed every day," he writes. "In contemporary Manhattan, the concept of 'the deserving poor' is an oxymoron."

In escaping this world, Young achieves a kind of salvation -- and not just by writing a book that was a bestseller in England. He marries the lovely Caroline, an English law student with no patience for the world of Vanity Fair. His experience with the ugly side of beautiful people disabuses him of his affection for shallowness.

Many people, including Graydon Carter, briefly thought that Sept. 11 would do something similar for America as a whole. They turned out to be utterly wrong, but the momentary hope revealed that it's not just incorrigibles like Young who long for something better than the breathless mainstream sideshow culture. Celebrity worship may never go out of style, but perhaps alienation is coming back in.

By Michelle Goldberg

Michelle Goldberg is a frequent contributor to Salon and the author of "Kingdom Coming: The Rise of Christian Nationalism" (WW Norton).

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