How to Lose Friends & Alienate People – 2008 | 110 mins | Comedy | Colour

Plot Synopsis

Liberal adaptation of Evening Standard restaurant critic Toby Young’s bestseller based on his brief tenure as contributing editor at Vanity Fair. This mirthless middlebrow romcom features Simon Pegg as the bumbling but lovable journalist, and he brings a degree of humility to the role, but along the way screenwriter Peter Straughen has relinquished the scathing catalogue of Manhattan insincerity for pratfalls and literal slip-ups. It’s an amiable comedy but one that disappoint fans of the book.

Cocksure British satirist Sidney Young (Simon Pegg)used to poke fun at celebrity culture in ‘Post Modern Review’, his left-field London mag, but one day he receives a job offer from Clayton Harding (Jeff Bridges) of high-profile New York ‘Sharps’ magazine where his dream of mixing with the rich and famous seems set to come true. Young immediately falls foul of two-faced office superior, Lawrence Maddox (Danny Huston), and subsequently falls further from grace by hiring a transexual strip-o-gram on bring-your-children-to-work day, crushing a starlet’s Chihuahua to death and delivering a coked-up football chant to the incredulous guests at a society garden party.

But the unthinkable happens and he sycophantically falls for starlet Sophie Maes (Megan Fox) and begins playing by publicist Eleanor Johnson’s (Gillian Anderson) rules. But Young finds to his cost that the vapid world of celebrity that he had always aspired to isn’t as glamorous as he always thought. It’s left to scornful co-worker Alison (Kirsten Dunst), who constantly arches her eyebrows in bemusement at Sidney’s antics, to bring him back to his true self.