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.

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 and the manager Lawrence Maddox, as a result of his rudeness, vulgarity, and general unattractiveness.

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.

[5] In 2006, Simon Pegg was announced as the lead,[6] Kirsten Dunst was revealed to appear in the film in late April 2007,[7] and in May 2007, Jeff Bridges and Gillian Anderson were added.

[8] Toby Young, who wrote the memoir, was banned from the set at the request of Kirsten Dunst after she overheard him providing feedback to a producer on her performance in a particular scene.

How to Lose Friends & Alienate People opened as one of the United Kingdom's number one films at the box office, taking the equivalent of US$7,055,425 during its run there.

"[14] In the United States, Roger Ebert of the Chicago Sun-Times gave it 3½ out of 4 stars, calling it "possibly the best movie that could be made about Toby Young that isn't rated NC-17.