The Fuckup

I can't remember when poking fun at Toby Young became a spectator sport in the Manhattan media. He once had an impressive reputation as the co-founder of an irreverent English magazine called The Modern Review (concept: "low culture for highbrows"). Having provoked two major lawsuits by the age of 30 from newspaper magnate Robert Maxwell and Elizabeth Hurley, Young caught the eye of Vanity Fair's Graydon Carter. But soon after his arrival in New York, Young squelched everyone's great expectations and ended up writing for the New York Press and ambulance-chasing Tina Brown and Harold Evans. He chronicles his meteoric fall in How to Lose Friends and Alienate People, a repellent yet surprisingly entertaining compendium of gaffes and humiliations.

Talking to Young in a West London café while he waits to be filmed for a TV documentary about celebrity misbehavior, it's hard to reconcile this almost charming, bespectacled guy with the Toby who got himself in deep shit by asking Nathan Lane if he was gay and Jewish, hired a stripper at Vanity Fair on Take Your Daughter to Work Day, and left a woman on his freezing doorstep all night while he slept off a coke binge. Why would an intelligent, Oxford-educated man act like a sidekick from The Howard Stern Show?

Young blames his downfall on lots of things: innocence, excessive drinking, "negative charisma." He says, "If I'd been a little more Hugh Grant-like when I was at Vanity Fair, I would've done better. I came off like too much of a hustler." Later he insists, "Years of failure have humbled me slightly." Perhaps very slightly. If you Google his name, you'll find that nearly every article Toby Young writes revolves around . . . Toby Young. A profile of Kofi Annan turns out to be Young's recollections of a dinner party at which he entertained Annan with his wisecracks; in an essay about New York in the Guardian, written a few weeks after 9-11, Young has the gall to plug his own book.

Young: a starstruck dunderhead panting to get Into A-list parties
photo: Sylvia Plachy
Young: a starstruck dunderhead panting to get Into A-list parties

Young's parents were members of the liberal intelligentsia—his father founded England's Open University to provide higher education for working-class people and coined the term "meritocracy." Young says, "It was partly a reaction to that background that led me to idealize American mass culture. The whole point of The Modern Review was to critically elevate some of the things English people looked down on as schlock. In the context of my upbringing, embracing people like Madonna and Schwarzenegger seemed iconoclastic." He worshiped at the altar of all things lowbrow, spending much of his time in Manhattan acting like a Porky's-damaged frat boy. As he writes in How to Lose Friends, America offered him the chance "to expunge the guilt I felt about not doing something more worthwhile with my life, like working for Unicef. My idea of heaven was being able to roll around naked in a huge pile of money with Anna Nicole Smith."

Young caricatures himself in the book as a starstruck dunderhead panting to get into A-list parties and toadying up to movie stars, while Graydon Carter comes off as an indulgent but elusive character who inexplicably gives Toby chance after chance to redeem himself. The more likely reality is that Carter intended to launch Young in New York, expecting that he'd start a provocative, Modern Review-style magazine here. "I should have done that, obviously," Young says now, wincing. "But suddenly I found myself at VF with an expense account, Lincoln Town Cars to take me to parties—and I didn't feel like giving it all up." He claims that at one point he almost landed the editorship of Spy magazine with Carter's full support, but they gave the job to somebody else. Within a few years Young had irritated Carter so much he was banned from the office.

After his expulsion from paradise, Young decided to write "a Malcolm Gladwell-esque book about Condé Nast" that mutated into How to Lose Friends, a memoir full of amusing dish on the media world. He writes of a Vogue fashion editor who furnished her summer pad known as "Petty Cash Junction" with stuff purchased on company funds, bemoans the rigid hierarchy at Vanity Fair("senior editorial staff treat the fact-checkers like uppity housemaids"), and recounts colleagues' foibles ("Graydon likes his underlings to move purposefully round the magazine's offices and occasionally snaps at people who walk too slowly, telling them to 'pick it up' ").

Young makes some astute critiques of American media and popular culture, but much of it seems hypocritical: He chose to immerse himself in frivolous effluvia, then proclaims horror at its superficiality. His greatest disappointments were the sobriety of Manhattan media folk and how class-bound New York is. "I imagined that it was this really informal open society," he says. "But I discovered New York was even more socially stratified and formal than London." This may be true, but Young's broad generalizations are based on the fashionista party milieu he frequented—a world where no one sets foot in the subway, and women get their hair blown out daily.

Many of his biggest faux pas stem from his inability to notice things going on outside his shiny head—as if Young is wearing an extra-thick condom that makes him insensitive to the vibrations around him. He admits, "When I started amassing the evidence, I did begin to think, 'There's a pattern here, I'm a self-saboteur.' " But instead of going into therapy, Young convinced a British newspaper to pay for a focus group session in which female acquaintances discussed his foibles. "I thought it would be humiliating but manageable and funny." Describing the scene, he begins to squirm in his chair. "I had been looking forward to the point when I'd come out at the end and we'd have a good laugh and I'd show them I didn't mind. But as the evening wore on and they became more insightfully brutal, I began dreading it. It really opened my eyes to how unattractive being drunk all the time was to women."

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