How to Lose Friends & Alienate Peopleis a 2008 British comedy film based upon British writer Toby Young's 2001 memoir of the same name . The film follows a similar storyline, about his five year struggle to make it in the United States after employment atSharps Magazine.The names of the magazine and people Young came into contact with during the time were changed for the film adaptation. The film version (adapted by Peter Straughan ) is a highly fictionalized account, and differs greatly from the work upon which it was built. It was distributed in the United States by Metro-Goldwyn-Mayer , and in the United Kingdom by Paramount Pictures and Channel Four Films (the former also distributed in Australia ).
The film was directed by Robert B. Weide and stars Simon Pegg as Sidney Young, Kirsten Dunst as Alison Olsen, Jeff Bridges as Clayton Harding, Danny Huston as Lawrence Maddox, Gillian Anderson as Eleanor Johnson, and Megan Fox as Sophie Maes. The cast also includes Max Minghella and Margo Stilley .How to Lose Friends And Alienate Peoplewas released in both the United States and United Kingdom on 3 October 2008.
Sidney Young ( Simon Pegg ) is a smalltime, aspiring British journalist who works for a left-wing radical magazine. Following an incident at a party where Sidney accidentally lets a pig loose he is hired to work for an upscale magazine in New York City. He is hired by Clayton Harding ( Jeff Bridges ), editor ofSharpsmagazine, a man Sidney had previously lampooned in his own magazine.
Sidney annoys the staff he works with, first Alison Olsen ( Kirsten Dunst ), who is only there to pay the bills whilst she finishes her book, then his boss Lawrence Maddox ( Danny Huston ). He also dares to target the star clients of power publicist Eleanor Johnson ( Gillian Anderson ). He then meets new rising star Sophie Maes ( Megan Fox ); however, he is told by Lawrence not to talk to her. Sidney makes it his mission to become something within the business; however, it is almost ruined when he accidentally kills Sophie's dog (Cuba), as he was able to stop the dog from going out the window but unfortunately could not stop a vase from falling onto the dog. Luckily, Alison covers for him and nobody else finds out it was him.
At a party, Alison and Sidney's relationship grows when she reveals she has just ended an affair with Lawrence. Sidney stops her from driving home drunk, causing him to miss his opportunity to sleep with Sophie. At a later party, however, just when Sidney was about to ask her out, it is revealed Lawrence has left his wife and that he and Alison are officially together. In a desperate attempt to up his career, he begs Eleanor to publish a piece on Vincent, a director he truly hates.
The next day at work Clayton reveals that both Alison and Lawrence have left, and he promotes Sidney. Sidney finally becomes successful, getting all the girls that were disgusted by him before and even catching the eye of Sophie. The night before the awards ceremony she stated that if he gave her his late mother's ring and she won best actress, she would have sex with him. Going to the ceremony the next day he sees Lawrence, now being someone he used to be, stating that he and Alison split as she was in love with him. When the winner is revealed (Sophie), as she is going to get her award, he realizes he does not really love her and asks for his ring back, then, after a heated exchange, he steals back the ring from Sophie, and inadvertently (because of anger) reveals that he killed Cuba. An enraged Sophie attacks him and a huge fight ensues then after the fight, Sidney leaves, quitting his job atSharpsand heading to New York.
He meets Alison in the park, where they were showing her favourite movie; La Dolce Vita . She has finished her book and the two finally get together, with him giving her his mother's ring. The movie ends with him accidentally throwing the book onto a candle and jumping for it to stop it from going into flames.