Adapted from the memoir of the same named written by Toby Young, How to Lose Friends & Alienate People is a satirical movie about celebrity journalism and “making it” in the business. It stars Simon Pegg as an aspiring journalist named Sidney Young — names have been changed for the purpose of the film — who comes to New York in order to work for Sharps Magazine under Clayton Harding (Jeff Bridges) who was once in his very position. Now, he has to work his way through celebrities, their publicists, and his own work colleagues in order to have his unique personality shine through.
Much of the film consists of Young embarrassing himself and getting into disagreements with the other people at his work. He refuses to write puff pieces. He tells famous people, including a pretentious director (Max Mingella), that the best movie of all time is Con Air. He lusts for an up-and-coming celebrity, Sophie Miles (Megan Fox), even though it’s clear that his real love interest is Alison (Kirsten Dunst), a woman who works with him and is the only one who appreciates his personality.
There are a few funny moments scattered throughout this film. There are, sadly, not enough of them. How to Lose Friends & Alienate People runs for almost two hours in length and doesn’t contain nearly enough laughs or bite to justify that running time. Comedies almost wholly work best at 90 minutes and this one probably would have been a touch more successful had it trimmed 20 minutes of fat off its bones.
It still, however, would not have been a complete winner. For all of its desires to be a biting satire of this industry, it never really spews as much vitriol as it likely should have. It picks easy targets and makes the most shallow of observations. There isn’t enough to it that makes it worth seeing. It’s The Devil Wears Prada but somehow less enjoyable even though it was given an R rating — which is something it didn’t need; apart from one topless scene and a scattering of F-bombs, none of which was needed, it could have been a PG-13.
None of the romance works. By the time the film ends, we’ve seen Young go through more than a couple of romantic partners and he seems to care so little about all of them that I couldn’t get involved in any of the relationships. Granted, only one actually makes the attempt to be anything more than superficial, but the climax hinges on that — the film transitions into a poor rom-com near its finale — and it just doesn’t work. The two actors share little chemistry and there’s almost no reason for us to care if they work out.
What How to Lose Friends & Alienate People is destined to become is background noise while you do more important work. It’s not memorable or sharp enough to be worth dedicating your whole attention toward, but it’s got a couple of decent chuckles that will make you laugh when you catch them while paying attention to something else. Its satire just isn’t biting enough, especially given both the potential and the real-life story, to justify spending the time watching it.
Simon Pegg is a funny person and it’s entirely possible that the movie, if given a better script, could have been hilarious with him in the leading role. He has good comic timing and the type of expressions that work well for making fun of others. He is underused here. The film is too safe to really play to his strengths and while he makes some things funnier than they are on paper, he can’t carry the film on his back. Kirsten Dunst barely leaves an impression as his work colleague, and Megan Fox is terrible — perhaps intentionally, perhaps not — as the object of desire. Perhaps the funniest moment in the film comes from her winning an acting award for a performance in a fake film as Mother Teresa.
How to Lose Friends & Alienate People is a moderately funny movie but it played it too safe to be worth seeing. There’s no bite to the satire and much more slapstick than you might think. It’s based on real events that were somehow more crazy than the antics that happen here. It works best as background noise while you do more important things with your life.