Aspiring Expatriate HackEmbraces the Cult of Failure

How to Lose Friends and Alienate People , by Toby Young. Da Capo Press, 329 pages, $24.

We’re all familiar with the idea of the warts-and-all portrait, but Toby Young, in sitting for his own likeness, has followed a more extreme formula: all warts. There’s almost no form of triviality or obnoxiousness that he doesn’t confess to, and his not admitting to a particular sin doesn’t suggest innocence so much as lack of space. Mr. Young arrived in New York from London in 1995 after the collapse of The Modern Review (motto: “Low Culture for Highbrows”), the magazine he edited and co-owned, to serve an apprenticeship on Vanity Fair . From this auspicious beginning, he ruthlessly clawed his way to the bottom (unemployment, binge-drinking, ostracism).

How to Lose Friends and Alienate People was published in London last year, and it did pretty well. A number of British best-sellers in recent years, such as Nick Hornby’s Fever Pitch and John O’Farrell’s Things Can Only Get Better , have been distinctly downbeat by American standards, treating success as something that arrives by accident and at the last possible moment, at a point where it’s almost more traumatic than welcome. This kind of story is a much harder sell in a country without a cult of failure. If you can’t have a tragic fall, at least try to have a glamorous one-it’s not as if Toby Young was the head of a major studio when the self-destructive habits kicked in. He was an aspiring hack with a knack for overplaying his hand and giving offense to those who might have helped him.

When he met Tina Brown in 1985, for instance (he was a student at Oxford and she was editing Vanity Fair ), he rushed up to her and threw out his arms, exclaiming, “At last, the female Toby Young!” When this approach didn’t seem to work, he modified it by saying, “Only joking. I’m the male Tina Brown!” Here and throughout the book, humor is imagined to disguise the rancor from which it springs.

In Britain, Mr. Young championed mainstream popular culture largely as a way of getting up the noses of the elitists (the joys of nasal penetration seem never to have palled on him). But when he arrived in America, a love of the mainstream no longer marked him out as a maverick. He didn’t even like pop culture that much (or only at its most artful, in movies directed by Preston Sturges or written by Ben Hecht). When the book gets serious, Mr. Young starts piling on the references to Freud, Plato, Cicero, relying on high culture as a sort of jet pack to raise him above the herd.

The self-analysis gets particularly contorted when Mr. Young addresses his feelings about his mother. She makes her appearance rather late in the book, with a calculatedly stark section ending: “You see, my mother was dead.” This sounds like part of a chat-up routine, the shameless appeal to sympathy when other approaches have failed.

After a couple of years in New York, Mr. Young fell in love with a woman named Caroline, whom he’d dated for a while when she was staying in his apartment. It wasn’t while they were dating that he fell in love with her, but only after she dumped him for another man. This in itself is standard-his dealings with women were greatly affected by considerations of how much other men wanted them. In the case of one ex-girlfriend, Syrie Johnson, he mentions not just her acknowledged attractiveness but also the fact that her previous partner was “the most famous young novelist” in Britain. She had not only value, but a provenance.

Caroline, though, was different, and he set out to win her back. She had the advantage of being British (more than that, she laughed at his jokes), and she met international babe standards. For a page or so, it looks as if Mr. Young is going to moderate the crassness of his sexual assessments, contenting himself with describing the woman he eventually married as “a Loaded reader’s fantasy come to life: a ladette with the figure of a centerfold.” By his standards, this is courtly love, but then he goes and spoils the reverent idyll: “She had Baywatch tits, perfect 34Ds.”

What made Caroline the one for Mr. Young was that she disapproved of him in the same way his mother had. His mother being dead, she couldn’t forgive him, but Caroline could do the job in her place. All the women mentioned in How to Lose Friends and Alienate People are likely to wince as they read the book, since Mr. Young plays a particularly mean variant of Cyrano’s game, harping on about his baldness and lack of good looks without modifying his own demands. Does the dude with the big schnozz court the lady with the club foot? The hell he does. He pesters supermodels, telling them what a rotten world it is where people judge by appearances. But Caroline is a special case. It’s unusually degrading, surely, to be courted as a mourning aid, a shortcut to closure.

If Toby Young’s redemption by love sounds hollow, then it’s in keeping with the rest of the book. How to Lose Friends and Alienate People fails as a satirical portrait of New York because its author’s pathology is so comprehensively distorting. Some of his observations are convincing-about conformism, careerism and the tyranny of publicists-but it’s clear he wouldn’t care about these little details if only Manhattan had taken him to its heart. He doesn’t quite complain about “the lack of Marmite and HP sauce” like other Brits, but he soon begins to miss the good old class system that muffled his bad behavior.

Certainly there are differences between Britain and America as societies, but the crucial difference for Mr. Young is that in literary and journalistic London, however badly he behaved, there was always likely to be a person in the room murmuring, “You mustn’t mind Toby. It’s just his way.” In New York there was no such person, and he came across not as an erratic relative but an erratic stranger. He would have us believe that he finally fell out of love with the shallowness of New York when he realized that his eminent father, Lord Young of Dartington, a colossus of Labour politics and social thought, wasn’t appreciated in Manhattan (why should he be, exactly, so far from home?). It would be truer to say that Toby Young moved to New York hoping it would be different from London, and finally went home when he realized it was.

Adam Mars-Jones writes for the London Observer.

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