How to Lose Friends and Alienate People is an uneasy marriage of satire and romantic comedy. The film's inability to decide whether it wants to be sweet and life-affirming or vicious and nasty creates not only a disconnect on the story level but results in tonal shifts that are dizzying. By trying to obey two masters, How to Lose Friends ends up serving neither with enough faithfulness to earn it a recommendation as either a parody or a lighthearted love story.
The film is loosely based on Toby Young's autobiographical account of five years spent writing for Vanity Fair. Not only have the names been changed to protect the guilty but a lot of the rough edges have been smoothed out for mass market consumption. The film tries to do what The Devil Wears Prada accomplished in the fashion industry, but there's no Meryl Streep here and Jeff Bridges isn't given the opportunity to step into a similarly spotlighted role. How to Lose Friends is at its best when eviscerating celebrity culture and exposing the collaboration between "journalists" and publicists, but that material is never given its due because the filmmakers feel the need to shoehorn in a romance. It's ironic that a movie about the superficiality of Hollywood ends up falling victim to the characteristic it is lampooning.
Sidney Young (Simon Pegg) is moving up in the world. When he gets a call from mega-publisher Clayton Harding (Jeff Bridges) to board a plane and come to America, Sidney jumps at the chance to join the Sharps magazine staff. He soon discovers that his wit and penchant for practical jokes are not welcome in the prim and proper office environment, where kissing ass and buffing celebrities' images are more important than generating good prose. Clayton tolerates Sidney, but the Brit falls afoul of his immediate boss, Lawrence Maddox (Danny Huston), and one of Hollywood's most powerful publicists, Eleanor Johnson (Gillian Anderson). This is unfortunate for Sidney, because Eleanor represents up-and-coming starlet Sophie Maes (Megan Fox), who is the object of Sidney's wet dreams. Meanwhile, the only one to show patience with him is co-worker Alison Olsen (Kirsten Dunst), but she's so hung up on Lawrence that she doesn't recognize what's in front of her.
How to Lose Friends contains an element of near-greatness: a parody trailer for a Mother Theresa biopic in which Fox's Sophie has the lead role. Brilliantly devised, this faux trailer indicates what the movie could have been had it ditched the romantic subplot and torn into the material with fangs bared. Seeing the Mother Theresa stuff does not require spending two hours in a movie theater, however - MGM is using it as part of the marketing campaign and the entire trailer can be found (legally) on-line. (Giving away for free the best part of a movie doesn't seem like savvy marketing, but who knows?) There are some other cuttingly amusing moments as Sidney stumbles from one misstep to the next on his way up the Hollywood ladder, but the climax, which has been liberated from a sack of clichés, feels flabby and unsatisfying.
This is Simon Pegg's second consecutive romantic comedy and, although one would not consider him leading man material, How to Lose Friends provides him with an opportunity to lock lips with Kirsten Dunst and Megan Fox - not bad for a guy who's still probably best-known for dueling zombies in Shaun of the Dead. The quality Pegg brings to the project is the ability not to appear embarrassed by the most embarrassing of situations. Considering that his character is constantly making an ass of himself, that's a valuable characteristic. Kirsten Dunst has shown that, when freed from the expectations that accompany playing Mary Jane Watson, she can generate screen appeal. Her previous forays into romantic comedy territory, including Wimbledon and Elizabethtown, have been largely successful, and this is in the same vein. Meanwhile, in a part that emphasizes her sex appeal, Megan Fox shows an aptitude for comic timing. Jeff Bridges and Gillian Anderson are solid when called upon, but they spend a little too much time on the sidelines.
This is the feature debut of Robert B. Weide, who is probably best known for his behind-the-scenes involvement in Curb Your Enthusiasm. How to Lose Friends represents a near miss: a movie that ends up disappointing because it can't decide what it wants to be. Romantic comedy fans will be dismayed by the long detours taken between romantic interludes and by the not altogether satisfying resolution. (In particular, what happens to the ring.) Those searching for satire will find aspects of the movie too neutered and fearful of offending. (Names may have been changed, but that doesn't mean certain people won't see themselves in the characters.) The end result is that How to Lose Friends and Alienate People feels jumbled and disorganized. It's not altogether unpalatable, but that doesn't present it from being a mess.