Toby Young looks remarkably like William Hague, a fact which most people would try to keep quiet. It seems typical that he has drawn attention to the similarity in at least five articles, "although I've retired it now, and at least I don't look anything like the new guy", he says. It's not just the bald head (there's two of us in that particular boat) or the scrunched-up, slightly pugnacious features. There's also the question of dismal failure. Young's book, How to Lose Friends and Alienate People, charts his own failure to achieve his dream of becoming a successful journalist in New York, and highlights his talent for saying the wrong thing to the wrong people at the wrong time. It is fitting, therefore, that at this magnificently inappropriate moment, he has just published a book about how dreadful New Yorkers are.
Back in the early 1990s, Young was one of the brightest young things of the London media set. The Modern Review, the magazine he co-founded with Julie Burchill, with its tagline, "Low Culture for Highbrows", tapped into a general tendency to take pop culture more seriously. Some of the claims made for the Modern Review were over-stated, but it helped to redefine media attitudes in this part of the world.
"It seemed to help other people's careers a lot more than it helped mine," says Young. "A lot of film critics and book critics for national newspapers got their start with the Modern Review. These days it's not at all novel to lavish attention, in a fairly smart-arse way, on popular culture, but it was more novel in 1991. People wrote about blockbuster movies in a rather snide, intellectually superior way. The most direct influence it had was that Andrew Neil based the Culture supplement of the Sunday Times on it, and recruited a few Modern Review writers - but not me."
A highly public and acrimonious quarrel with Burchill in 1995 (her last words to him: "I never want to see your ugly face again. You've been an embarrassment to me for years") led to the closing of the magazine. The two haven't spoken since.
"It looks like we've finally patched things up after six years," says Young. "We've struck up an e-mail correspondence. I e-mailed her and asked if she could supply me with a quote for the dustjacket."
That quote is now emblazoned on the cover: "I'll rot in hell before I give that little bastard a quote for his book".
When the Modern Review folded, Young was invited to come to New York by Graydon Carter, the editor of Vanity Fair, the ultra-glossy, ad-packed jewel in the crown of the CondΘ Nast publishing empire, which also includes Vogue and the New Yorker. His sojourn with what he dubbed the "CondΘ Nasties" makes his lookalike's leadership of the Tories appear a triumph in comparison. In the course of almost two years, he managed to contribute a total of 3,000 words to the magazine before being shown the door, and sliding further and further down the publishing food chain. All this is recounted in giddy detail in How to Lose Friends and Alienate People.
The book is full of juicy anecdotes, most of which, to be fair, show the author in a less than flattering light. But one of its central themes - that the people who work for a magazine like Vanity Fair are shallow, humorless and status-obsessed - hardly comes as a shock. The most surprising thing about Young's reaction is that he himself should have been surprised. Had he never read Vanity Fair, with its fawning interviews, its prurient (and incredibly long) features about the seamy side of socialite life and its shameless plugging of designer baubles? Is he having us on?
"To a certain extent, I've exaggerated that surprise," he acknowledges. "But I was still a little bit na∩ve. I was expecting that the journalists on Vanity Fair and the New Yorker would be very reverent and deferential to celebrities' faces, but incredibly heretical behind their backs. What was so surprising was that even behind closed doors, in the privacy of their offices, they were almost as reverent.
"What really surprised me was how uncynical they are. And how formal. There were so many unwritten rules that I wasn't aware of. People had told me all my life that I was far too bumptious and pushy to go over in London and that New York was the place for me - everyone was far more direct - and I was expecting to fit right in."
It sounds rather as if he made that most fundamental error of the newly-landed New York immigrant - he confused the US of movies and fiction with the reality. An easy mistake to make, if your first landing point is the exalted heights of Madison Avenue. On one level, How to Lose Friends and Alienate People is another meditation on that threadbare theme, Look at the Weird Americans. In this case, rather than right-wing loonies and gun-toting fundamentalists, it's political correctness, odd social rituals and rigid social structures.
The problem for Young was that he was as fascinated with celebrities as any of his colleagues. The book is full of wearying tales about our anti-hero's attempts to make it past the velvet rope into the VIP areas at parties and clubs, where he can rub shoulders with the likes of Jim Carrey, Ralph Fiennes or Mel Gibson. He is inevitably humiliated by the "clipboard Nazis" at the entrance, or else makes a fool of himself as soon as he opens his mouth to the objects of his fascination.
What on earth could possess an intelligent, well-educated man in his 30s to waste so much energy making a fool of himself?
"I could try and rationalise it by saying I wanted to write about the subject of celebrity, that it was intellectually fascinating - but it's much more primitive than that," he says. "It's wanting to get close to them to try and master the power they have over me. Trying to resist the primordial appeal of celebrities, particularly Hollywood superstars, is like trying to resist the sexual appeal of supermodels. One part of you knows that they're never going to have anything interesting to say, that the morning after you're going to be embarrassed and tongue-tied, but at the same time the part of you that's attracted to them is insulated from your critical intelligence. So I inevitably found myself drawn towards them."
The reason he upset so many Americans, he says, was that he seemed unconcerned about making a good impression. "If you make a self-deprecating joke about how unsuccessful your sex life is or how your career is in the toilet, they look very suspiciously at you. They interpret it, probably correctly, as a form of hostility. You're saying, 'unlike you, I'm relaxed enough to poke fun at myself'." There is a problem with this analysis. It's a clichΘ to say Americans don't do irony and, while it may be true of the CondΘ Nasties, it isn't the case in New York as a whole. To take the obvious example, hasn't Woody Allen built his life's work on self-deprecating humour and sexual anxiety?
"Well, yes," Young says. "If you're a nebbish-looking man from the Upper West Side, it's part of your culture. But if you're a Brit, they suspect, often rightly, that you're looking down your nose at them, so they're naturally on your guard."
I have some sympathy for the Americans on this one - how warmly could they be expected to greet a booze-soaked, coke-encrusted, self- pitying, overpaid, oversexed, lazy British hack with a talent for rubbing people up the wrong way? And that's even before you consider the short stature, bald pate and bad teeth (I'm not being gratuitously insulting here - it's all in the book).
He may be more settled now - he's recently married and teetotal - but there's still something about him of the affronted teenager insisting it wasn't his fault. It clearly rankles that he's been expelled from London's top media watering-hole, the Groucho Club, because of a story in the book about buying and taking cocaine in the club with actor Keith Allen and artist Damien Hirst during a photo-shoot for Vanity Fair's "Cool Britannia" issue in 1996. The crime, apparently, is not in the snorting but the telling, which breaks the club's code of silence. "I think that's a matter for the membership committee, who I hope will take a more lenient view of my crimes," he says. "My defence is that Keith Allen and Damien Hirst have never made any secret of their love of illegal substances. They've written about it and talked about it, so it's not as if I embarrassed anybody about anything that wasn't known."
He's still a magazine man. These days, he's theatre critic for the Spectator, contributing editor at Tatler and a special correspondent at GQ, the last two both CondΘ Nast publications. "Both of which jobs I thought I might lose when the book came out," he says. "So far, at least, that hasn't happened. The powers-that-be at CondΘ Nast are too cunning to blackball me immediately, because then it would look as though they were in some way troubled or upset by my book, but maybe in a year or two I'll be fired." Watch this space.
How to Lose Friends and Alienate People is published by Little, Brown (£9.99 in UK)