Vintage Young

His book How To Lose Friends and Alienate People describes the hysterical ups and downs of New York's media industry and his disastrous attempts to interview Hollywood's A-List stars.

The 39-year-old emerged unscathed, a firm public favourite, because he approached every job with a foolhardiness, dry sense of humour, sarcasm and innate ability to commit faux pas, that only someone from this side of the channel could master, gaining gasps of awe in the process.

After all, this is the man who was thrown out of the Oscars party for upsetting mega stars, and messed up every interview he was commissioned. Suffice to say, he didn't last long in the Big Apple.

When interviewing Nathan Lane, who was about to play Robin William's boyfriend in The Birdcage, Toby dared ask if Nathan was Jewish and gay.

"His jaw hit the floor and, for a second, I thought he might hit me," Toby recalls.

"Instead, he simply got up and walked away. His publicist came over: 'Will you please leave? You're making Mr Lane uncomfortable'. As soon as I got back to the office I was hauled before the editor. He said: 'What were you thinking? You can't ask Hollywood celebrities whether they're Jewish or gay. In future, just assume they're all Jewish and all gay, okay?"'

While he might play the fool, Toby's CV speaks for itself.

He graduated with a first in PPE (Philosphy, Politics and Economics) from Oxford University in 1986 and then got a scholarship to Harvard.

Now big on the talk circuit, Toby is coming to the Oxford Union on Wednesday to discuss his past antics. Affable, well-spoken and articulate, his seemingly inexhaustible stream of anecdotes have something to please every palate.

But as a journalist he's in the ironic position of now being famous in his own right by cashing in on the fame market.

His book, which was translated into eight languages and appeared on national best seller lists in Britain, America and Canada, was optioned by FilmFour last year and has been turned into a one-man show starring Jack Davenport, which is transferring to the West End.

Toby auditioned for the part of himself but was turned down, a situation that could have come out of his book.

"After seeing me do a run-through, the producer decided the show would have a greater chance of success if it was performed by a professional actor. I was a little disappointed, obviously. The producer gently explained it wasn't my acting abilities she was worried about, so much as my physical appearance. She thought the play might be more appealing to women if someone a bit easier on the eye was cast in the lead.

"She was essentially saying I wasn't good-looking enough to play myself. I'm now being played by Jack Davenport. He played Miles in This Life - it's a bit like getting Julia Roberts to play Janet Street-Porter," he sighs.

So while Toby continues writing his restaurant review for the Evening Standard and theatre column for the Spectator from his London home, audiences are packing the aisles to chuckle over his former life.

Now married, Toby is also known for exposing New York's vociferous dating scene, which he innocently joined when he lived there. Toby has waxed lyrical on many an occasion, both in print and on TV, about surviving the terrifying arena.

"On the few occasions I managed to persuade an American girl to go out with me they'd fire these questions: 'What kind of car d'you drive?' 'What's your relationship like with your mother?' 'Why are you single?' It was less like a romantic encounter than an extremely tough job interview," he recalls.

What next? One senses that while Toby is enjoying all the interest How To Lose Friends and Alienate People has generated, the second novel is proving something of a sticking point.

"I did want to go to the West Coast and do the sequel, but my wife had no interest in living in LA. I think it might be a novel next," he says vaguely, before heading off for a media lunch.

Toby Young will be appearing at the Oxford Union on June 4 at 8.30pm.