How to Lose Friends & Alienate People (2008)

(On Cable TV, October 2015)  Comedies about unlikable protagonists are a tricky act to keep up: There’s a limit to the amount of bad behavior that audiences will tolerate before tuning out, and at times it looks as if How to Lose Friends & Alienate People isn’t afraid to test this limit.  Reportedly based on the true story of Englishman Toby Young working for American magazines, this film features Simon Pegg playing one of his most unlikable character: a fame-obsessed smarter-than-thou obnoxious shmuck, gifted with the ability to annoy people almost instantly.  He’s surprised when the fights he picks come back to haunt him, while the audience rolls their eyes.  Much of the film seems aimless, jumping from one set-piece to another without much connective tissue.  When How to Lose Friends & Alienate People does remember that it is a romantic comedy, it’s almost too late to care.  Similarly, the film goes from a prickly but interesting comedy to a far more conventional romantic vehicle as it goes along, although it is far from being the only such movie to suffer that fate.  I suspect that Toby Young’s autobiography is far more interesting, and that the film fell victim to the adaptation-standardization process. There are, fortunately, a few intermittent bright spots here and there, particularly in taking a look at celebrity journalist and the New York magazine scene.  Pre-fame Megan Fox shows up as an object of desire, while Kirsten Dunst shows up for an undemanding role as the hero’s true love.  Still, there’s a sense of missed opportunities, of pointless unpleasantness here that prevent How to Lose Friends & Alienate People from leaving a better impression.  At least Pegg gets to play a real cad for once, and doesn’t screw it up.

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