The loser takes it all: The strange career of Toby Young

When Toby Young dreamed of how his glittering journalistic career would be immortalised on celluloid he had in mind an updated version of the 1940s films His Girl Friday and The Philadelphia Story. The raincoat and porkpie hat-wearing hacks played by Cary Grant in these films were the types Young had expected to meet when he crossed the pond to work in New York in the mid-Nineties. He was disappointed by the much-changed industry he encountered, now the subject of How to Lose Friends and Alienate People, the film adaptation of his account of several years at Vanity Fair, starring Simon Pegg as Young, Kirsten Dunst as his love interest and Jeff Bridges as the editor Graydon Carter.

The book excoriates the diminished journalistic standards Young found in New York, where writers and editors, hidebound by their relationships with influential publicists and the desire to solicit the best invitations, have entirely abandoned old-fashioned skills like digging up stories and gathering facts.

"Journalism in the UK," says Young, "as far as it's a profession at all, is still a profession for ne'er do wells and fuck ups. That isn't the case in America."

Comparing the magazine he had edited in the UK to the one he joined in the US was far from analysing like with like. In 1995 he closed The Modern Review when its co-owner, Julie Burchill, tried to replace him as editor with her own lover. Its motto had been "low culture for highbrows". It stuck two fingers up at the serious agenda of the traditional press by giving lengthy editorial by big-name writers to pop culture icons such as Arnold Schwarzenegger and Adrian Mole. It had a niche, appreciative fan base and was pasted together on Young's kitchen table by a barely paid staff.

Young expected to inject a little of this chutzpah into Vanity Fair, assuming that Carter glimpsed his younger self in his new recruit, and was reminded of his days running Spy, an American satirical publication which inspired Young to pursue journalism. Instead, he found himself inside (just) the glossiest of New York's glossies. Vanity Fair was a pillar of American media society and instead of shaking it from its slumber he failed miserably, getting little published in the magazine and annoying everyone who crossed his path.

Young has always been desperate to be a star, or at least friends with the stars, so his enthusiasm for the dazzling magazine world was deflated when he learnt that to even hang out with them you had to play by a set of archaic social rules which undermined honest journalism at every turn. What is baffling is Young's claim to have had no inkling of the humourless Condé Nast that awaited him. For someone so astute, did he really expect to wander into the world of Woodward and Bernstein when he pitched up at a luxury goods-led magazine? His experiences pre-date The Devil Wears Prada. Would he have been better prepared had he watched that before his visit?

Frequent run-ins with image conscious celebrities – he managed to infuriate Nathan Lane by asking him whether he was gay or Jewish – means Young has since sworn-off celebrity profiles. "When it comes to journalism about celebrities," he reflects, "the lower down the media food chain you go in New York, the more likely you are to read the truth. You are more likely to read the truth about Madonna's relationship with Guy Ritchie in the National Enquirer than in Vanity Fair, because the Enquirer is not interested in access." When he discovered Claudia Schiffer had been given copy approval over an interview he was writing for Tatler, Young refused to complete the piece, only relinquishing the tapes after some begging from the Tatler editor.

The same access he came to despise was desperately needed by Young in New York to make it on to the best party lists. Ultimately, he could not stomach the humiliating sacrifices required and muddled through as best as a short, bald guy in a sea of stiletto-shod supermodels could. Now his life story is a Hollywood romantic comedy he can claim a little of that sparkle for himself, even if he had to sup with the devil to get here.

He is not quite having the last laugh. His own star might be in the ascendant, but he is played by Simon Pegg, not a latter day Cary Grant, and he managed to annoy Kirsten Dunst on set by commenting on her acting. Nor have his revelations about the cosy relationship between New York media and their subject matter caused any great waves. Carter is still in situ at Vanity Fair and magazines everywhere have to bend over backwards to secure access to celebrities.

For a man whose own father coined the word meritocracy and invented the Open University, it was painfully disappointing to discover that America was further from the land of opportunity than gulag Russia. This same father, though, of whom Young was fond, made a call to get his son into Oxford when he failed the entry requirements and was also a friend of the editor who published Young's first article, advantages he makes no attempt to conceal. Even now, despite his disdain for the world of Vanity Fair, Young still aspires to fame. "Admitting to wanting to be famous is a bit like admitting to being a child molester," he says. "People have a desperate desire to be famous but know it's not something they can admit to. I am open about it to contrast myself with them and say, 'Why are you being so mealy-mouthed about it?'"

His New York stint was not a failure. He met his wife Caroline there, with whom he now has four children, and dressing it up as a shameful disaster was a great ploy to win publicity – everybody loves a loser. What happened was that Young behaved like an ass and didn't fit in at Condé Nast.

Actually he is as deft at playing the publicity game as his sworn enemies. Even Julie Burchill's oft-repeated quote on the dust jacket of the original publication of How to Lose Friends and Alienate People – "I'll rot in hell before I give that little bastard a quote for his book" – was an invented comic touch. The new edition features the revised: "The funniest, cleverest, most touching book I've read for as long as I can remember" Julie Burchill, Spectator.

Journalism goes to the movies

How to Lose Friends & Alienate People (2008)

Based on Toby Young's struggle to make his name in America while working on 'Vanity Fair', the movie is an adaptation of the 2001 book of the same name. It features Simon Pegg in the lead role (playing a certain Sidney Young) with Kirsten Dunst as his love interest. Jeff Bridges plays a magazine editor very loosely based on legendary 'Vanity Fair' editor Graydon Carter.

The Devil Wears Prada (2006)

A naive journalist comes to New York to work on a women's magazine and finds herself in thrall to ruthless editor played by Meryl Streep (possibly US 'Vogue' editor Anna Wintour?)

The Killing Fields (1984):

Story of 'New York Times' reporter Sydney Schanberg's Pulitzer Prize winning coverage of Cambodia, it also features a portrayal of 'Sunday Times' journalist Jon Swain.

All The President's Men (1976)

Based on the book by Bob Woodward and Carl Bernstein, the 'Washington Post' reporters who broke the Watergate scandal and brought down Nixon.

The Front Page (1931)

An Academy Award-winning comedy, based on a Broadway play and featuring the attempts of an investigative reporter, played by Pat O'Brien, to cash in on a big story.