My Best Friend's Girl 

We know we’re living in the Web 2.0 world when a star disses his own upcoming movie on MySpace. To be fair, Dane Cook didn’t actually attack My Best Friend’s Girl, only a piece of its marketing — the cheesy poster that appears in print ads and theater lobbies. But that key art is only one symptom of the split-personality disorder that afflicts the whole conception of this R-rated comedy.

Let’s start with the trailer. The Girl preview for “general audiences” sketches the story of a sweet geek (Jason Biggs of American Pie fame) who turns to his loutish best friend for help in wooing the girl of his dreams (Kate Hudson). In other words, a romantic comedy. The “red-band” (R-rated) trailer introduces us to a lout (Cook) who occasionally interrupts his slobby antics and cracks about blow jobs long enough to find himself dangerously attracted to his best friend’s girl. In other words, a young-male-oriented raunch-fest with possible designs on the Judd Apatow audience.

So which is My Best Friend’s Girl? Though Cook’s claims about the movie’s edginess (and funniness) are vastly exaggerated, the second trailer gets it right. The plot revolves around Cook’s character, Sherman “Tank” Turner, who describes himself as a professional asshole. (If the word perturbs you, be warned that the movie sets new records for its use.) Early in the film, he gives us his M.O. when it comes to women: “When I want them to run, I convince them I’m shit. When I want them to come, I make them feel like they are.” Misogynist as he may be, there’s surely a grain of truth here. What besides the attractiveness of assholes could explain Cook’s flourishing frat-boy-comic-cum-movie-leading-man career?

When Tank wants a girl, he acts like a jerk; when he wants to repel one, he acts like a bigger jerk. He performs the latter service at the request of romantically inept men who pay him to show their ex-girlfriends such a bad time that the erring women call them in tears, begging to reconcile. That’s one conceit the film asks us to swallow. Another is that Cook’s roommate and best bud is Dusty (Biggs), whose idea of seduction is bringing a girl a doughnut in the shape of a smiley face. When Alexis (Hudson) tells Dusty she wants to be just friends, he calls on Tank’s services.

In its first hour, the film goes far enough in satirizing rom-com conventions to be briefly interesting. After arranging a chick-flick-style “meet cute” with Alexis, Tank takes her out on his standard nightmare date. But this uptight marathon runner is in a mood to let loose, and she responds to his provocations with such enthusiasm that the two develop genuine chemistry (albeit of the soused hook-up variety). The results are most unpleasing to Biggs, a “nice guy” who never rises above nebbish status. (“A ‘good man’?” says Hudson’s own roommate and devil’s advocate [Lizzy Caplan]. “That sounds like something your parents would date.”)

In its clumsy way, My Best Friend’s Girl explores the female version of the Madonna/whore complex: Women hook up with Cook, it suggests, then marry “good men” who bore them silly (and sometimes secretly cheat on them). Though its misanthropy is entertaining, the film can’t rise above an uneven script and an uncharismatic leading man. A great comic womanizer makes his humiliations and defeats as funny as his triumphs. (Think Vince Vaughn in Swingers.) Cook plays “vulnerable” by mugging like a lost puppy, making his softer moments about as convincing as a heart-shaped box of chocolates re-gifted on V-day.

Alec Baldwin makes an appearance playing a less wittily scripted version of his unreconstructed chauvinist from “30 Rock,” and Hudson is surprisingly funny when she’s being crude instead of cloying. God knows, the world needs a wicked romantic comedy that shows us both men and women behaving badly. But this mashup of dirty jokes and insincere sentiments is as confused as its marketing.