How to Lose Friends & Alienate People is a 2008 comedy 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 at Sharps Magazine.

Starring 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.