Sidney Young () is a disillusioned intellectual who both adores and despises the world of celebrity, fame and glamour. His alternative magazine, Post Modern Review, pokes fun at the media obsessed stars and bucks trends, and so when Young is offered a job at the diametrically opposed conservative New York based Sharps magazine its something of a shock! It seems Sharps editor Clayton Harding is amused by Young’s disruption of a post-BAFTA party with a pig posing as Babe. Thus begins Sidney’s descent into success – his gradual move from derided outsider to confidante of starlet Sophie Maes – and a love affair with colleague Alison Olsen (Kirsten Dunst), that will either make him or break him.
The movie “How To Lose Friends And Alienate People” is based on the Toby Young memoir of the same name.