Toby Young's face confused New York. In London, his hometown, the author, playwright, actor manqu? and journalist was described as 'a balding, bug-eyed, skinny-chested opportunist with the looks of a punctured beach ball', 'a peeled quail's egg dipped in celery salt' and 'a noisome little tick', but Americans simply directed him to the service elevator.
How to Lose Friends and Alienate People, Young's best-selling memoir and now a highly amusing film, is a record of his failure to take Manhattan. In the book, he writes of being greeted at Vanity Fair by 'someone who looked like a male model'. The man had been 'discovered' by Graydon Carter, Vanity Fair's editor, who felt that he was 'so beautiful that it almost broke your heart'. Predictably, Young's countenance failed to inspire similar rhapsodies.
He has been ostracised for wanting to play out of his league and in this way he is something like Yoko Ono: confrontational in his non-conformity, a postmodern hero.
'I once made a pilot for a documentary about It boys,' he says, from the macho-literary minimalist garden shed-cum-study of the three-storey Victorian house he shares with his wife and children in Acton, west London. 'I'd just come back from New York and was going to transform myself into an It boy. It was a satirical commentary on the culture of celebrity. I bent over backwards to put this pilot together and got lots of famous people to appear in it ... I even organised a focus group of models! And - incredibly - even though the producer thought it was the best pilot he'd ever made, it didn't get commissioned.
'Afterwards, I had a conversation about it with him.' He clears his throat and, in a perfect Scottish accent, barks: ''Tob-eh! Ever heard of the term TUFTY? Too Ugly For Telly!''Asked if the comment hurt, he pauses. 'It's certainly true that had I looked more like Hugh Grant I would have had a much easier ride at Vanity Fair - in fact, quite possibly everywhere,' he says.
In How to Lose Friends, the 45-year-old Young depicts himself as a socially inept, impoverished, homely intellectual dazzled by celebrity and prestige. He is recruited by Carter only to find himself at the epicentre of what we understand as beauty - that sphere of supermodels and superstars. Young falters, encumbered by a peculiarly British sense of hierarchy (his father, the late Baron Young of Dartington, invented the term - and mocked the idea of - meritocracy). The film reshapes the narrative and changes every name to equal - if differently calibrated - comic effect, but the moral remains. Young can't shake the feeling he belongs on the other side of the rope.