Making a Success of Failure

Writer and journalist Toby Young on How To Lose Friends and Alienate People

How To Lose Friends and Alienate People, which opened in cinemas across the country on the weekend beginning Friday, October 3, tells the story of Sidney Young, a small-time English journalist hired to work at a glitzy New York style magazine. 

Young, played by Spaced and Shaun of the Dead creator Simon Pegg, spends the film alternately wooing Kirsten Dunst, Megan Fox and Gillian Anderson and insulting, abusing and infuriating everyone in between. 

Directed by Curb Your Enthusiasm’s Robert Weide, and based on Toby Young’s memoir of his own Simon Pegg failed five-year attempt to make it in Manhattan, How To Lose Friends and Alienate People is perhaps the freshest and funniest British movie of the year.

Toby Daniel Moorsom Young was born in 1963, the son of Labour life peer Michael Young and novelist-cum-artist Sasha Moorsom. After receiving a first-class degree in philosophy from Oxford and attending Harvard as a Fulbright scholar, Young co-founded the ill-fated Modern Review – ‘low culture for highbrows’, says Young – with Julie Burchill and Cosmo Landesman in 1991. 

Four years later, with the magazine in ruin, Young returned to America, where he spent six massively counterproductive months at Vanity Fair, pricking publicists and celebrities and shaming himself with stunts such as sending a strippergram to a colleague on Take Our Daughters to Work Day.

Sitting down to interview Young in his suite at Dublin’s Merrion Hotel, I notice a couple of things: firstly, that he doesn’t resemble a rat, a snake or a raccoon, as Burchill has previously branded him, but rather a pot-bellied version of his slapstick cinematic self; and secondly, that Young is no longer the social pariah of his books, judging by the Merrion’s five-star swank and a PR with both eyes on the clock.

'I portrayed the character as being much less self-aware than I am, for comic purposes,' Young admits. 'But I think the time has come to draw a line under my whole schtick and come up with some new material which isn’t related to being a failure. It’s offensive to people who want to get their books published or, God help them, want to get into the movie business.'

Young makes no secret of his disdain for Hollywood. The Sound Of No Hands Clapping, his 2006 memoir, which has been optioned by Film4, concerns the author’s abortive attempt to achieve fame and fortune as a Tinseltown screenwriter. 

Despite penning a 33-page treatment for the big-screen adaptation of How To Lose Friends, which Young claims mined a similar rom-com vein to the finished work, he was usurped by an outsider. Peter Straughan, the Newcastle upon Tyne-based playwright who previously scripted Mrs Ratcliffe’s Revolution for Catherine Tate, was recruited to reshape Young’s catalogue of anecdotes into a filmable screenplay. He began by renaming the lead character.

Kirsten Dunst'When I saw the film for the first time I didn’t think of Sidney Young as being me at all,' Young continues. 'It came as a real surprise when my friends and family saw it and they all reacted as one: ‘My god, it’s uncanny.’ Until then I just hadn’t seen it – and I still can’t.'

Early in the production, Young had daydreamed about playing the part himself. Film4’s Stephen Woolley and Elizabeth Karlsen, who saw Young’s performance in a self-produced one-man stage play of How To Lose Friends, were unconvinced: 'I was expecting them to have a eureka moment and say, ‘Why are we looking around for an actor to play you? You should play you!’ But of course they didn’t.'

Instead, the role went to Pegg, the Gloucester-born star whose everyman looks, sarcastic wit and stage school-honed thesping chops have allowed him to corner the market in lovable, or at least vaguely likeable losers. 

Pegg’s portrayal of Young as bumbling fish-out-of-water is something of a comedy masterclass. Yet he wasn’t necessarily the first choice to play Sidney, as Young is only too happy - or naive - to reveal. 

'Sacha Baron Cohen was a possibility, but I think the problem with Sacha is that he’s got a commanding, charismatic, sexy quality, which wouldn’t have been right for the role – not to say that Simon lacks those qualities…'

It’s the first sign during our interview of Young’s famous foot-in-mouth fumbling, something the writer has described as ‘social autism’. 'I have difficulty grasping the appropriate way to behave in any given situation,' he says. 'But I probably have that in common with two thirds of the male population. Some men clearly have more difficulty than others and I’m probably at the most difficult end of the spectrum.'

It was a trait that followed him on set. 'Every time I went I was filled with anxiety. I was like an airline passenger who is convinced the plane is going to crash and tries to wrest the controls from the pilot and has to be subdued by security. I realised that if I wanted not to fall out with the filmmakers I’d be better off staying away. I didn’t want the events behind the scenes to echo the events on the screen.'

These events include a clash with Sharps editor Clayton Harding, played by Jeff Bridges and based on real-life Vanity Fair mogul Graydon Carter, and a show-stopping set piece involving Sidney, a skyscraper and a starlet’s pet Chihuahua. 

'Bob Weide did not want to kill the dog,' Young reveals. 'He’s a real animal lover. He has a menagerie of Jeff Bridgesanimals at his house in Los Angeles and is so attached to one of his cats that during filming he would call up his wife and get her to put the cat on the phone so he could whisper sweet nothings to it. I’m not making this up.'

It’s a strange existence for the 44-year-old father-of-four, who finds himself in the unusual position of giving interviews to promote a film based upon a book he wrote about his failings as an interviewer of movie stars. As turns of events go, it’s bizarre, complicated and most likely unique. 'I have somehow managed to forge gold out of base metal. I’ve snatched victory from the jaws of defeat.' 

Somewhat surprisingly, perhaps, throughout our conversation Young remains astute, engaged and articulate, giving considered answers to questions he must, at this stage, have been asked a thousand times. It’s a role reversal for the former celebrity griller. 

'I find myself sympathising with the people that complained about things I wrote about them out of context,' he says. 'I mean, I always thought, ‘Ah, that’s just a typical bit of spin. You’ve said it, I’ve got it on tape,’ whereas now I find myself being quoted out of context the entire time. It’s karma.'

Now living in London, where he is an associate editor of the Spectator and a regular contributor to the Evening Standard and the Guardian, Young has plans for at least one more volume of stone-turning confessional. 

'I want to write a prequel set at Oxford. I had a disastrous time there, socially. I was probably the most unpopular boy of my generation, but many of the people I knew have become prominent public figures – Boris Johnson, David Cameron, Michael Gove, Nick Robinson. I think I could write a funny book about that period.' 

How To Lose Friends and Alienate People is in cinemas now. Check out Culture Live! event listings for more information.

Andrew Johnston

Topics