A British writer struggles to fit in at a high-profile magazine in New York. Based on Toby Young's memoir "How to Lose Friends & Alienate People".
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Simon Pegg pulls away from the ridiculous humor of zombie killing & crime fighting. Into the ackward hilarity of social climbing in "How to Lose Friends & Alienate People." Directed by Rob Weide & adapted by Peter Straughan from Toby Young's semi fictional book "How to Lose Friends" focuses on Brit-born Sidney Young (Simon Pegg) & his year long adventure into the red carpet world of magazine publishing.
Ever since he was a young lad Sidney has dreamed to be amongst the famous of the movies, to live in the lap of luxury he believed the actors dwelled in. In first- person voice- over narrative the film starts present day where Sydney is wearing a fancy tuxedo & designer watch, attending an awards ceremony with newly inaugurated starlet Sophie Maes (Megan Fox). The movie then flashes back to a year before the sparkle & influence of Sydney's life as production manager at the highly regarded Sharps Magazine.
When not trying to crash his way into film premieres & after parties, Sydney runs a counter - culture style of publication called Post Modern Review. After talking up Thandie Newton & making an array of flash photography at a party Sydney charms up Sharps Magazine's founding editor Clayton Harding. He manages to land a job offer & off to NYC he goes. No more than four months into the job Sydney manages to overstep his position on the professional ladder & repeatedly irritates coworker Alison (Kursten Dunst) the closest thing he has to a friend. A somewhat misleading title for Sydney doesn't have any friends to lose his personality & behavior are completely socially inept noticed by all except himself. But poor Sydney can't help but be himself even if it's totally offensive & inappropriate. This film will have you laughing but also feeling empathy for him. Sydney is one of those who has an underlying innate charm that you can't say no to.