Based on the memoir by Toby Young, a British journalist who's made a career out of what he calls "negative charisma," How to Lose Friends and Alienate People lampoons the self-importance of Hollywood, the publishing world, and well, Toby Young (known in this roman à clef as Sidney Young). It pulls off this satirizing brand of comedy in some wildly amusing ways -- it's when the film abandons the satire that things start to drag. Simon Pegg plays the beguilingly obnoxious writer, who's running a soon to be defunct humor magazine out of his London apartment when he gets a call from Clayton Harding, the editor in chief of a Vanity Fair pseudonym called Sharps Magazine, offering him a job in New York. Convinced that he was hired for his caustic wit and biting disdain for celebrity culture, Sidney subsequently embarks on a series of tactless misadventures that make awesomely merciless fun of every vapid aspect of the stargazing glitter-mag industry. The bits themselves are alright on paper, but they're ten times funnier onscreen because Pegg sells them with such blind exuberance (he could take home the Oscar for manic silly dancing). Of course, the most brilliantly mocked character is usually Sidney himself, with his transparent hunger to get behind the velvet ropes, but Kirsten Dunst plays a good straight man to his antics, and there's a great turn by Danny Huston, who once again employs his training in Creepy Grin Acting as a slimy section editor. There's also a fantastic appearance by Gillian Anderson, who positively kills it as an impeccably shrewd, string-pulling publicist with the keys to just about any star worth writing about, and the sway to keep a magazine like Sharps from ever using its teeth. Jeff Bridges plays the powerful but bored Clayton Harding, who would be in the middle of a midlife crisis if his disillusionment weren't tempered with scotch-soaked apathy. Hit with pangs of nostalgia for his irreverent youth and compunction for his insipid empire, it turns out that he hired Sidney to come in as a bottom-rung contributing editor in the celeb-gossip section more or less on a whim. Bridges utilizes an odd combination of hamming it up and phoning it in, which somehow ends up stealing the whole movie. Even in a perfectly cut suit and with his silver mane slicked back, he still calls to mind "The Dude" from the Big Lebowski every time he speaks, partly because he seems to be playing every scene drunk, even when his character isn't drinking (but is, we can assume, spaced out on ennui. And maybe an offscreen highball). It's possible that this effect was intended by the director, as the film includes what appear to be a smattering of Dude references, including a character who drinks White Russians (a theme that did not, for the record, appear in the book), but maybe Bridges' effortless charm (effortless to the point of detachment, in this case) is just so damn bewitching that you can't help making the rest of the movie about him in your own head. The fact that Bridges steals the show by barely trying is telling, but it could be a lot worse. The movie is consistently funny; the problem is that it could have been a lot funnier, and probably more interesting. There's a scene about halfway in where we learn some unexpected stuff about Sidney's past -- a fairly unique twist that provides a lot of potential for the direction of the story. But instead of running with it, the script completely drops the revelation in favor of a prototypical romcom plot, which isn't executed too badly but also doesn't quite seem right. This is basically the weakness of the whole movie: there was clearly more room to explore Sidney's jerky behavior and general piggishness to hilarious ends, and there was apparently even the potential to pursue a little aw-shucks-maybe-he's-not-so-bad character development, but the shoehorned romance, while fairly sweet and rarely saccharine, just doesn't fit. They toned down the main character's extremely entertaining nastiness so that it could make any kind of sense for him to get the girl, but you can't help feeling like they cheated you out of more laughs -- especially when most people would go see a conventional romantic comedy if they wanted to see a guy get the girl, lose the girl, and get the girl back. Maybe it's a little naïve to complain about Hollywood watering down and standardizing a story this way, but considering the subject matter, it's also a little ironic.