Right around the point horn-dog magazine writer Sidney Young (Simon Pegg) is frantically scouring a fancy garden party for cocaine so he can take advantage of the dim-bulb starlet (Megan Fox) he's been fervently stalking, the putrid showbiz comedy "How to Lose Friends & Alienate People" appears to hit DEFCON 5 in mistaking its brand of moral laxity for cutesy irreverence.
When Sidney's scheme is thwarted by the screenplay's need to have him do the right thing and safely drive home his drunk, depressed and lovelorn co-worker Alison (Kirsten Dunst), you then worry for her safety in such loutish hands. And she's the one we're supposed to root for him to win over.
Ostensibly a rom-com reorganizing of British author Toby Young's 2001 satiric memoir about the self-sabotaging, cheeky swath he cut through his brief celebrity journalism career at Vanity Fair, the movie version, scripted by Peter Straughan, drops its surrogate into a soul-imperiling scenario at the fictional rich-rag Sharp's: Will Sidney cozy up to celebs or be allowed to take them down in print? (And can he do both?)
But when it's not turning the real Young's escapades -- ordering a stripper to a colleague's office on Take Our Daughters to Work Day or asking a musical comedy star upfront if he's Jewish and gay -- into lifeless comic bits, it appropriates everything else like "The Devil Wears Prada," "The Apartment" and anything by the Farrelly brothers. It leaves the whole affair derivative, tone-deaf and garishly unfunny. Pig urine and transsexual genitalia gags jostle for position alongside forced slapstick, dumb one-liners and the film's only (unintentionally) humorous material: the disingenuous sentimentalizing of "glossy posse" outsiders who deplore what they've become after they work to acquire their every desired perk.
Director Robert Weide, whose stewardship of the TV series "Curb Your Enthusiasm" indicated an understanding of hostile laughs, can't make up his mind whether the fame-grubbing Sidney is a principled jerk, an immature closet romantic or Jerry Lewis. He's impossible to follow as a protagonist, much less care for, and the rubber-faced Pegg -- normally good at wiry slacker charm -- throws everything at the wall to little effect.
Dunst's frustrated novelist, meanwhile, is more believable when she calls Sidney "loathsome" in the first half than when affixing a moony stare at him in the second. And Danny Huston and Gillian Anderson, as a sleazy editor and icy power publicist, respectively, hit their marks with expected professionalism. But only a curtain-haired, cigarette-smoking Jeff Bridges as Sharp's impresario Graydon Carter -- I mean, Clayton Harding -- intriguingly connects institutional bitterness with A-list gatekeeping. His dismissive tossing of a T-shirt of Sidney's emblazoned with a crude slogan out of a top-story window is the movie's funniest gag and somehow acts as its perfect critique too.
"How to Lose Friends & Alienate People." MPAA rating: R for language, some graphic nudity and brief drug material. Running time: 1 hour, 49 minutes. In general release.