How to Lose Friends and Alienate People is the story of a small time British gossip monger who crashes the right party and inadvertently finds himself in the big time, working for one of the hottest celebrity tracking magazines in New York City. Unfortunately, he’s kind of a horrible jerk. Hilarity ensues.
The comedy is delivered by a large, stellar cast: Simon Pegg (Shaun of the Dead), Kirsten Dunst (Spider-Man), Danny Huston (X-Men Origins: Wolverine), Gillian Anderson (X-Files), Megan Fox (Transformers) and Jeff Bridges (Iron Man). Simon Pegg is brilliant as the horrible miscreant Sidney Young. Megan Fox’s performance as a vacuous starlet is grating, but perfectly appropriate for the character. Kirsten Dunst is annoying, though generally less so than usual, and she and Pegg have very good chemistry, leading to several moments of brilliance between the two. The film was directed by Robert Weide (Curb Your Enthusiasm), who is very effective at selling Sidney’s antisocial behavior as comedy, especially when he is surrounded by the fashionable elite of New York City.
The most successful scenes in the movie are where Sidney behaves somewhere between his initial complete social ineptitude and the scenes where he is portrayed as a totally nice guy, especially when he is trying to be a good guy and failing spectacularly. The scenes with complete social ineptitude are still pretty funny, though it gets kind of frustrating seeing him act so totally inappropriate.
The least successful element of the movie is the romantic subplot, which initiates as a device to humanize Sidney and somehow becomes the main focus of the film by the end. It does provide structure to move the plot forward, but it takes a path that seems ultimately less interesting than the story of Sidney’s burgeoning career in the world of celebrity journalism.
The film does contain some special features, but the selection is pretty slim. Two audio commentary tracks for the film, and a short “Making of” movie that features the cast and crew discussing their experience with the film, including some brief discussion on how the story was changed in adapting the screenplay from the original novel. Overall, while interesting, the special features included won’t extend the value of the DVD by much.
How to Lose Friends and Alienate People provides a fun contrast of an antisocial everyman in the world of the celebrity, though it loses a little bit of its edge late in the film. Definitely worth a try.
ComicsOnline.com gives How to Lose Friends and Alienate People 4 out of 5 vacuous starlets. 
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