Screenwriter, producer and director Bob Weide has spent his two score and ten odd years genuflecting at the altar of American comedy. A foremost knowledge on the life and work of the Marx Brothers (along with our own Simon Louvish) and, arguably, the nation’s greatest comic author – Kurt Vonnegut, Weide has also made documentaries about WC Fields, Lenny Bruce and Mort Stahl. If he’s known at all on this side of the pond, it is for his TV work directing and exec producing Larry David’s seminal Curb Your Enthusiasm series. In short, Weide has spent an admirably slow burn career walking, talking and standing on the shoulders of giants. And then he decided to make a film about a British celebrity journalist.

Based on Toby Young’s memoir of his failed five year effort to ‘break’ America as the contributing editor of Condé Nast Publication’s Vanity Fair magazine and starring Simon Pegg as the young Toby/Sidney, Weide believes that How To Lose Friends & Alienate People was the perfect project for him. ‘When I first met Toby – he was goofy, awkward and funny and when he left the producer Stephen Woolley asked me what I thought of him. I said, “I like him a lot.” Stephen started laughing and said, “I don’t think anyone has ever said anything that nice about Toby before’.” Weide became aware of Young’s more annoying tics and foibles later on but is still more benign towards the follically challenged writer than most.

‘You know all that stuff he writes in these newspaper columns about him being kicked off the set and not being shown drafts of the script, it’s all rubbish. He had access every step of the way but that story doesn’t fit with the belligerent loser persona/mantra he lives by.’

As it turns out the film version of How to Lose Friends … is a pretty broad adaptation of Young’s book. Adapted by Brit screenwriter Peter Straughan, (Mrs Ratcliffe’s Revolution, Sixty Six) many of the situations and names have been excised for comic and legal reasons, as its star Pegg explains. ‘The book doesn’t really lend itself to being a film in a sense, because it’s very anecdotal and it’s filled with huge tracts about philosophy. In order to make it into a film Peter [Straughan] had to shape it differently.’ Seizing a moment to set the record straight Weide elucidates: ‘Yeah, it’s a more tangible sort of love story now. What’s funny is I’ve been on imdb.com and I’ve seen people say, “oh, what character from the book does Gillian Anderson play?” Or “who in the book does Megan Fox play?” Well they play characters that were made up for the screenplay, they aren’t in the book at all. One of the elements we heightened was that this Sidney character comes to work for this magazine thinking not only that he’s going to take New York by storm, but that he’s really going to excel in this business, in this work place. He thinks he’s going to be allowed to do his sort of iconoclastic journalism and to really shake things up, and basically once he gets out there he realises that the whole idea is to get with the programme. He realises the extent to which the writers and even the editor, are sort of in the palm of the powerful publicist. He wants to write these satirical iconoclastic pieces on these celebrities, and basically what he learns is that he can’t do that because the publicist played by Gillian Anderson is very powerful and has a number of big celebrity clients, and if they piss her off, they’re not going to get any of her clients on the cover of the magazine which they need to sell it. So there is this game of not being able to rock the boat too much because you don’t want to upset the wrong people.’

Pegg also feels the film has a specific message, one maybe at odds with Young’s original missive from the land of opportunity and media humiliation.

‘It was interesting because I started the film directly after doing a big block of press for Hot Fuzz, so I had literally just been in contact with about 600 journalists. It was fascinating and funny and not as weird as you might think it was. Toby/Sidney is a specific kind of journalist, I think. It was originally set in the mid 1990s but I think now that kind of journalism – the sort of obsession with the material end of show business – is so rabid and ridiculous that the notion of the guy who is desperate to be in that world and at the same time deconstruct it, is very topical.’

Weide agrees with Pegg. He points out that Vanity Fair editor Graydon Carter (called Clayton Harding in the film and portrayed with long haired pomposity by Jeff Bridges), who Weide knew when he edited groundbreaking satirical magazine Spy in the 1980s, ‘was considered a serious satirist. Now by his own admission he has crossed to the dark side and become the sort of person he would have once despised.’

Pegg views celebrity journalism with an unsurprising disdain. ‘You know nowadays, you see so many photographs of journalists over their columns and it’s like, “well, what are you doing? Do you want to be famous or do you want to talk about being famous?” Of course some of them do want to be famous. It’s that position of having their cake and eating it. It’s what Sidney definitely wants to be.’

They both agree this version of How To Lose Friends … is a fish out of water story which aspires to be equal parts Billy Wilder’s The Apartment and The Devil Wears Prada. ‘It’s just a romp, an underdog story with some great set pieces and a loser hero.’ Pegg yelps before Weide sets off on a more languorous explanation.

‘You know years ago I adapted Vonnegut’s novel Mother Night into a screenplay which became a film starring Nick Nolte. When I was working on it, Kurt, who by that time was a good friend gave me some great advice. He told me to just let the book be a ghost around my house. To ignore it, or refer to it if I needed to but always to know that it is looking over me. So in adapting Toby’s book we had nothing more on our minds than extracting the essence, telling an interesting story and getting some laughs.’

Pegg concurs. ‘Peter [Straughan] made the decision to pull it away from being a straight biographical film, so for me it would have been silly to get bogged down in an impersonation of Toby because very few people know what Toby sounds like let alone what he looks like. My character gets off with Kirsten Dunst under the Brooklyn Bridge. Can you imagine the objectional steamroller that is Toby doing that?’

How to Lose Friends & Alienate People is on general release from Fri 3 Oct.