If we could all fail so well. That, I imagine, is the reaction many readers will have to How To Lose Friends and Alienate People, British journalist Toby Young’s seriocomic memoir of his attempt to hit the big time at Vanity Fair, befriend as many celebrities as possible, and sleep with a staggering number of beautiful women. Or, as things actually turn out, get fired from Vanity Fair, be sneered at by the celebs, and get laid, oh, about once a year. But all‘s well in the end. He falls in love with an earthy English girl and returns to London a wiser and happier man. Now he has a book to his name and a job as theater critic for the London Spectator. He’s also a special correspondent for GQ and has sold the film rights to his book (a best-seller in England) for a princely sum. Failure rarely sounds this good.

By most people‘s standards, Young has always been a success. Being a loser is just his shtick, like neurosis for Woody Allen. His father, (Lord) Michael Young, founded Britain’s Open University and coined the word meritocracy; Toby quickly set off in the same direction. After establishing himself as a bright young thing at Oxford in the 1980s (he got a First Class degree in philosophy, politics and economics, and followed it up with a stint as a Fulbright scholar at Harvard), he went on to found The Modern Review, a highbrow journal dedicated to lowbrow culture that turned out to be remarkably influential, not to mention the literary birthplace of Will Self and Nick Hornby, among others. When Young ceased publication in 1995, after a feud with co-founder Julie Burchill, the press devoted almost as many column inches (1,705) to the resulting bust-up as it did to the war in Bosnia. Across the Atlantic, Vanity Fair editor Graydon Carter took note and offered the 31-year-old bad boy a trial job at the magazine for $10,000 a month. Young, whose idea of heaven was ”to roll around naked in a huge pile of money with Anna Nicole Smith without feeling the slightest pang of conscience,“ had just received his invitation to paradise. He didn‘t turn it down.

How To Lose Friends and Alienate People is funny. Not always hilarious or original, but consistently amusing, penetrating and astute. It’s a clown‘s-eye view of America’s media elite, print division, and pokes fun at the jester as well as his employers. Still, it‘s extraordinary how obtuse our hero is. (He’s like an updated Bertie Wooster without Jeeves.) Having been informed that Vanity Fair‘s dress code is ”casual,“ he shows up on his first day at work wearing jeans, sneakers and a Modern Review T-shirt with a picture of a bare-chested Keanu Reeves over the legend ”Young, Dumb, and Full of Come.“ As the English would say, brilliant — but maybe not too bright. The security guard puts him in the service elevator and sends him up to the Messenger Center. ”What the fuck are you wearing?“ Graydon Carter says when Young is finally presented to him. ”You look like you’re in a grunge band or something.“ Young protests that Carter‘s secretary had told him the dress code was casual, and is promptly informed that the correct term for ”secretary“ is ”personal assistant“ and that ”casual“ means khakis and a polo shirt.

But Toby’s just warming up. Sent to interview actor Nathan Lane, he opens with ”Are you Jewish?“ His follow-up question is ”Are you gay?“ There are no further questions because the interview is terminated immediately. ”You can‘t ask Hollywood celebrities whether they’re Jewish or gay. Just assume they‘re both Jewish and gay, okay?“ an exasperated Carter says afterward. (The book’s affectionately satirical portrait of Carter is one of its chief pleasures.) Appointed editor of ”VF Camera,“ a section devoted to celebrity snapshots, Young is handed a set of pictures of the artist Ross Bleckner and friends at an opening at Mary Boone Gallery. Unfortunately, he‘s never heard of Bleckner or his pals and can’t identify a single person in the pictures. He calls the gallery for help and, since he‘s phoning from Vanity Fair, is put straight through to the boss. What follows is priceless, and typical of the book:

”This is Mary Boone,“ a stentorian voice announced. ”How can I help you?“

I introduced myself and explained what I was doing. I decided to get the guest of honor out of the way first.

”Ross Bleckner,“ I asked. ”Man or woman?“

I genuinely didn’t know.

”I‘m sorry?“

”Is Ross Bleckner a man or a woman?“

There was a pause on the other end of the line.

”Are you really calling from Vanity Fair?“

”Yes, I really am.“

”Tell me, Tony,“ she said, a note of strain sounding in her voice, ”Why have they given you this assignment if you don’t know who anyone is?“

”I‘m not exactly sure,“ I replied hesitantly.

”He’s a man,“ she snapped.

”Okay,“ I said, ”Is he an old man?“

Again there was a pause.

”He‘s an older man, yes,“ she said impatiently.

”Good looking?“


”You do realize that Graydon Carter is one of my oldest friends?“

Now it was my turn to hesitate. What did that have to do with anything?

”What’s that got to do with anything?“

”Right, that‘s it,“ she replied. ”I’m calling him right now.“

Click. Dial-tone.

As that passage suggests, Young has an unerring ability to commit gaffes and disinter carefully concealed taboos, as he does most memorably when he hires a stripogram for his office mate, only to discover after the stripper‘s arrival that it’s Bring Your Daughter to Work Day. He also enjoys ruffling P.C. feathers, ordering Chinese food from the ultrachic clothing store Shanghai Tang. (The Asian-Americans on staff are not amused.) But although much of the book is taken up by set pieces and anecdotes (crashing the VF Oscar party, dates with gold diggers who make him feel as if he‘s at a job interview, a humiliating encounter with Martin Amis, etc.), there’s a more serious side to it as well. Having arrived in Manhattan as a wide-eyed, celebrity-besotted ingenue — or so he asks us to believe — Young gradually becomes disillusioned with the scene. Well, to place events in their proper order, first he‘s fired, then he’s disillusioned, but the disenchantment feels convincing nonetheless. How, he wonders, did his co-workers preserve their sanity ”while thinking up cover lines like ‘Jemima and Imran: The High-Stakes Marriage of Pakistan’s Camelot Couple‘? Were they all on Prozac?“ The answer, he adds in a footnote, is ”probably yes.“

It may not be news that America’s media elite is obsessed with fashion and status, but Young at least has a theory as to why. The all-consuming fascination with novelty for its own sake is a kind of degraded form of religion, he argues. From this viewpoint, the Zeitgeist becomes ”a mysterious, intangible entity that has many of the same properties as a divine being,“ and being in tune with it is akin to living in a Christian state of grace. Ultimately, this belief in the power of the new was one Young couldn‘t share, and his skepticism marked him as an infidel in the eyes of the Conde Nasties.

As for the obsession with status, American meritocracy is worse than the British class system because the latter allows for factors other than talent to explain people’s position. Despite its obvious demerits, class at least encourages the rich to be self-effacing and provides the poor with an explanation for their position. But in America the elite regards its wealth as ”completely legitimate,“ because self-earned, and can therefore condemn those who fail as losers. Whether or not Young is correct about this, it does help explain the American fixation with career. In the absence of all other influences, what you do translates to who you are. But the ”meritocracy,“ Young writes, is false anyway. ”To use a baseball analogy, America‘s most successful citizens were born on third and think they’ve hit a triple.“ The only personal assistants to be promoted while he was at Vanity Fair, he points out, both had famous parents.

Ultimately, this book is about the clash of two kinds of snobbery. There‘s the overt kind practiced by the fashionistas at Conde Nast, and the inverse snobbery of Brits like Toby Young. Coming from a much grander literary tradition, he instinctively looks down on reporters as ”hacks,“ despite being one himself. James Wolcott and Christopher Hitchens aside, he thinks of Conde Nast’s ad-packed flagship as little more than an upmarket tabloid. For Young, the joy of America‘s celebrity culture was that you didn’t have to take it seriously. It was frivolous, so why not enjoy it? But he soon discovered that New York‘s magazine world took celebrity culture very seriously indeed. So now he has returned to London, and, ironically, claims to have become more serious himself. Let’s hope not too much so. If there‘s one thing Young is good at, it’s being funny.

HOW TO LOSE FRIENDS AND ALIENATE PEOPLE | By TOBY YOUNG | Da Capo Press | $24 hardcover | 340 pages

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