How to Lose Friends & Alienate People is a 2008 British comedy film based upon Toby Young's 2001 memoir How to Lose Friends & Alienate People. The film follows a similar storyline, about his five-year struggle to make it in the United States after employment at Sharps 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.
Directed by Robert B. Weide, it stars Simon Pegg, Kirsten Dunst, Danny Huston, Gillian Anderson, Megan Fox and Jeff Bridges, alongside Max Minghella and Margo Stilley. How to Lose Friends & Alienate People was released in the UK by Paramount Pictures and in the United States by Metro-Goldwyn-Mayer on 3 October 2008.
Plot
Sidney Young, an aspiring British journalist who runs a failing polemical magazine, attempts to infiltrate a party organized by Clayton Harding (Jeff Bridges), the CEO of Sharps, one of the most prestigious magazines in the world. In doing so, he momentarily gains Clayton's sympathy, as the latter began his own career through polemics.
Sidney is offered a job at Sharps, and moves to New York City, but he quickly earns the scorn of his colleagues, including Alison Olsen (Kirsten Dunst) and the manager Lawrence Maddox (Danny Huston), as a result of his rudeness, vulgarity, and general unattractiveness. Interviews with famous performers must be arranged by publicist Eleanor Johnson (Gillian Anderson), who imposes restrictions on published content.
On one occasion, Sidney accidentally kills the dog of rising actress Sophie Maes (Megan Fox), to whom he is intensely attracted. Alison, although despising him, agrees to help conceal the mistake. Sidney gains Alison’s respect by explaining his disapproval of Eleanor's practices, and Alison reveals that she also despises her job, and has been working sporadically on a novel for years, which she hopes to publish. At a bar Sidney meets a girl (Charlotte Devaney) and brings her home, but she turns out to be transgender. He later brings her to strip for Lawrence at work (to get incriminating photos).
At a party, Sidney discovers that Alison was having an affair with Lawrence, but has chosen to end it. He is approached by Sophie, who has become drunk, but forfeits the chance to sleep with her, upon discovering that Alison is also drunk and needs to be driven. At his apartment, Alison meets Sidney's father, who turns out to be a well known philosophy professor, and a member of the nobility.
Later, Sidney attempts to ask Alison on a date, but learns that she is reuniting with Lawrence, who has just divorced his wife, Clayton's daughter. Being heavily depressed, Sidney compromises his journalistic principles and begs to work with Eleanor. Not only does Eleanor agree, but Lawrence and Alison are pressured to leave the magazine by Clayton, as a result of Lawrence's divorce, leading to Sidney's promotion.
Sidney works hard, writing to please others rather than criticize, and earns several more promotions within a short time, as well as gaining access to the highest celebrities and most exclusive social gatherings. On the night before a prestigious film-awards ceremony, Sidney attends an informal party led by Sophie, and is pressured into surrendering his gold ring, which was a gift from his late mother.
He regains his contempt for high society, and the next evening, as Sophie is approaching the stage to claim her award, he seizes her to take back the ring, cursing, and confessing that he killed her dog. In response, Sophie attacks Sidney, attracting negative attention on camera; nonetheless, Sidney, no longer with Sharps, rushes back to Alison in NYC, who by now has separated with Lawrence, and they begin a relationship.