In a way, I feel for a guy like Simon Pegg, a really funny comedic actor who obviously wants to be taken just a little more seriously as a dramatist, but seems to already be typecast based on his early success (in Shaun of the Dead and Hot Fuzz). How to Lose Friends & Alienate People seems like it might be just what he needs: it begins by asking him to parade about as an obnoxious fool, and then attempts to transition him into a sympathetic romantic. To his credit, Pegg is able to handle this surprisingly well: we are just as apt to believe in him as the object of Kirsten Dunst’s affection late in the film as we are to see him as the source of her disgust in the early goings. It’s just that the script, loosely based on the memoir by Toby Young, doesn’t have enough going for it to hold the transition together, or to maintain the audience’s interest throughout.
Pegg plays a fictionalized version of Young (here named Sidney), who comes to New York when given an opportunity to write for a big-name magazine by its editor (Jeff Bridges). By the time he gets there, we’ve already seen him engage in several ridiculous acts of slapstick, and the trend continues throughout the first act. He has a knack for shamelessly embarrassing himself at parties, which gets him on the bad side of everybody he works with, including a fellow staffer at the magazine (Dunst) who is repulsed by his over-the-top behavior, a beautiful and shallow actress (Megan Fox), and her publicist (Gillian Anderson).
Just when Sidney’s juvenile antics have gone past the point of monotonous repetition, he somewhat inexplicably suddenly achieves massive success with the magazine, through a shady arrangement with the actress and publicist. And although the only reason he’s been writing about Fox’s character in the first place was because he wants to have sex with her, somehow the success this endeavor brings causes him to suddenly become introspective and fall for his coworker instead. The movie then takes a massive left turn, swinging from screwball to romantic comedy. As mentioned, Pegg is surprisingly capable of pulling this off—and Dunst, of course, finds herself right at home—but it’s too big of a shift and too jarring a difference in tone. What we get is the equivalent of a big stomp on the brakes, and suddenly find that whereas at least the redundant humor was what we signed up for, now we are just encountered by a generic romantic love tale. What’s especially disappointing about it is that the movie goes so far out of its way to show us just how despicable a character Sidney Young is during its first two acts, to the point where there’s no way we’re going to all of a sudden buy the sweet girl in his office suddenly seeing him in a new light in its third.
Such unevenness is par for the course here. Making a movie like this is a fine line to walk, of course: too much slapstick comedy gets old pretty quickly, but space the laughs out too much and you run the risk of losing your audience’s attention. To all but abandon the comedy in an attempt to shoehorn a “tried and true” storyline into your movie, though, is a surefire way to ensure that you alienate them as well.