TOBY YOUNG still finds it difficult to explain why, on his first day on the job at Vanity Fair in New York, he chose to wear a T-shirt emblazoned with the slogan, "Young, dumb and full of come" to meet the magazine's legendary editor, Graydon Carter. "Um, I guess I thought he'd find it funny," he tells me unconvincingly, shrugging his shoulders with an awkward laugh.
Happily he's not wearing it today, when we meet to discuss How to Lose Friends and Alienate People, the film version of Young's book of the same name, which explores in excruciating detail his time working at – and eventually getting fired from – Vanity Fair. However, he does concede that watching the scene re-enacted on screen – with Jeff Bridges playing the Graydon Carter role and Simon Pegg as Young – still makes him cringe.
"You know when you tell a self-deprecating story at a dinner party, everyone's laughing along with you? But then when someone else repeats that same story at another dinner party you feel they're all laughing at you? That's how I feel watching the film compared to writing the book," he says.
This neatly sums up 45-year-old Young's existence. While he may believe that his friends and colleagues are laughing with him, for the most part they're very much laughing at him. Yet his buffoonery has very much worked in his favour. He founded the Modern Review with Julie Burchill in 1991, moving to New York to work for Vanity Fair shortly after shutting down the magazine in 1995. He spent two-and-a-half years working under Carter, during which he wrote just 3,000 words but earned $85,000. How to Lose Friends and Alienate People chronicles nearly three years spent screwing up a phenomenal opportunity in a myriad of amusing and downright creative ways.
Young has built a successful career out of being a complete failure. He may have spent a lifetime being ignored at parties (those he manages to gain access to at all, that is) but, as a producer on a film based on his life with an A-list cast, surely he's finally "arrived"? Well, no. He can't quite seem to shake the "loser" label and still finds himself on the outside looking in. He was banned from the set of the film, he tells me remorsefully, after Kirsten Dunst, who plays his love interest, overheard him making suggestions to the director as to how one of her scenes might be improved. She in turn suggested that he be removed.
"I don't think she knew who I was," he says mournfully, going on to recount yet another wince-inducing encounter: "Halfway through filming I strode up to her and said, 'So, have you fallen in love with me yet?' referring to the fact that she does just that with my character in the film. She just looked at me blankly like I was some crazed fan. She definitely didn't know who I was."
Not only was he snubbed by Dunst, banned from the set and excluded from the director, Robert B Weide's wrap party at London's stylish Groucho Club ("He didn't invite me. I considered gatecrashing it disguised as a woman, but in the end decided it would be beneath my dignity"), but despite his best efforts, he still doesn't feel like a celebrity.
"I think I've been wishing for celebrity for so long that I've got used to being someone who's petitioning the establishment for acceptance," he says. "And now that that petition has finally been accepted I feel slightly wrong-footed, as if my whole schtick, my whole identity, is so wrapped up in being a petitioner that I don't really know how to react now that petition has been granted."
And yet, he's already enjoying some of the perks of fame. He's off to the GQ Man of the Year Awards after our meeting, he's been asked for his autograph a grand total of once and he's enjoyed more than one night on the town with bonafide celeb Simon Shaun of the Dead Pegg. "We were out in Cannes and suddenly were hit by this wall of flashbulbs as everyone started photographing Simon," he says. "Simon turned to me and said, 'Oh god, I really hate this,' and I said to him, 'Simon, I long for the day when I can moan so sincerely about being hounded by the paparazzi.'"
It's difficult to know whether Young really does hanker after the celebrity lifestyle, or whether the crawling protaganist of How to Lose Friends is a bit of a money-spinning creation. The man in front of me is friendly, measured, a little reserved, even wary – although that could be because "I've stitched so many people up in my time as a journalist I think karma dictates that that's what they're bound to do to me" – and I find it difficult to imagine him crashing around the offices of Cond Nast, offending everyone he encounters.
He is, quite simply, normal, and I'm not the only one who's been a little disappointed that he's less of an arrogant imbecile than he suggests: when Pegg first met him, after reading the book, he expressed disappointment that he wasn't "more of a c**t".
However, there are flashes of the slimy Young that his readers know and love to hate. During the interview he takes a call on his mobile from a friend, his voice suddenly in schmooze mode: "Hello? Cosmo! (Could it be Cosmo Landesman, journalist and ex-husband of Young's erstwhile friend Julie Burchill?] Yah, I could certainly write about it. Spectator, yah, I'll write about it in the Spectator. I might write about it in the Independent as well. The book party would be at a West End venue; I'd find a liquor sponsor and invite about 100 people. Literary editors. Journalists. Staaars..." The final word is long and purring. I wonder in which category he places himself these days.
"Sorry about that. A friend. I have to throw a book party for him. He's too modest to do it himself." The bold Toby, of course, isn't too modest to do anything, yet it's hard not to like him. He is arrogant but loveable, a bit of an underdog but, in the end, he gets the cheques. And the girl.
He lives in London with his wife, Caroline, (others have compared her to a young Jane Birkin, he has described her as "Baywatch tits" and she is said to be a very levelling influence) and their four young children, more concerned with nappies than film premieres. As he describes a life of domestic bliss, it's hard to imagine that he once hired a strippergram to visit the office on Vanity Fair's 'bring your daughters to work day' and told an actress at an awards ceremony that she "should have won the award for best supporting dress". I don't imagine that he could still be capable of making such gaffes. But, he assures me, he is.
"I recently boarded a flight from New York to London with my family and noticed that Salman Rushdie was on the same plane," he begins, rubbing his temples as he recalls the latest faux pas. "I thought to myself that the last person you'd want on a flight from JFK to Heathrow when your wife and four children are on board is one of the biggest terrorist targets in the world. The next day I happened to be introduced to Padma Lakshmi (Rushdie's estranged wife] at a party. And I thought it would be funny to tell her the story." How did she respond? "She just sort of smiled and nodded." Does he get that a lot? "Um, yes."
• How to Lose Friends and Alienate People goes on general release today.
TOBY Daniel Moorsom Young was born in 1963, the son of Michael Young, the Labour life peer, and Sasha Moorsom, the novelist, sculptor and painter.
He went to Brasenose, Oxford, where he started a magazine named the Danube. After graduating in 1986, he joined the Times for a while, but was later fired.
He then went to Harvard as a Fulbright scholar, before returning to the UK in 1988 to work as a teaching assistant. In 1991, he founded and edited the Modern Review with Julie Burchill and her then husband, Cosmo Landesman. Its motto was "low culture for highbrows". In 1995, with the magazine in financial dire straits, Young shut it down. He moved to New York shortly afterwards to work for Vanity Fair.
Now living in London again, he is an associate editor of the Spectator and a regular contributor to the Evening Standard and the Guardian.