Parodying Generations X and Y presents filmmakers and writers of all kinds with an admittedly tricky proposition: How does one depict self-consciousness in a fashion that isn't in itself self-conscious? And any work about these generations must somehow address self-consciousness, as privilege and media saturation have allowed self-consciousness to sprout up among younger middle-class Americans like a particularly irritating weed. Every thought, the Internet tells us, is shared by millions of people, which understandably provokes a defensive response from the generations that have grown up taking the availability of the medium for granted. Rather than asserting themselves forcefully, many younger Americans cloak their thoughts in an ironic detachment meant to signal that, yes, they know others have said this before. No one wants to look unintentionally unoriginal.
These sentiments partially contextualize the preponderance of low-budget American films built around white guys who return to their parents' homes in their late 20s or early 30s and essentially spend the entire running time in an emotionally crippled fugue state. These Americans are taught that they, theoretically, could do anything with their lives, so they do nothing out of fear that they might choose incorrectly. Oconomowoc is another such film, as it follows three thirtysomething white guys as they amble about their titular home town, doing little apart from broadcasting their own indifference to the stasis that currently characterizes their lives. In the tradition of Wes Anderson's films (Oconomowoc owes quite a bit in particular to Bottle Rocket), these guys primarily sit around and say hurtful things to one another in a tone of studied affectlessness. They also drink a lot and go about contriving eccentricities that will hopefully set them apart as "unique."
Writer-director Andy Gillies's film is extremely self-conscious, but in a fashion that generally serves the material. It's difficult to parse the intentional effects from the unintentional, as the film has the explicit vibe of a DIY experiment that's more a rehearsal for a movie than a movie in its own right. Oconomowoc is essentially comprised of a dozen or so sketches, some quite funny, that Gillies stages with a slackness that's oddly agreeable for its skepticism. He presents a number of romantic or comedic tropes, such as the very tired device of the cute dream girl who inexplicably "gets" the shiftless, downcast loser, only to discard them with a contemptuous air that effectively embodies the anger of a generation that's tiring of the self-actualizing platitudes their society routinely peddles. The plot, such as it is, involves a scam to steal T-shirt revenues from middle-school children, who effortlessly send the adult con artists scampering away with their tails between their legs. It's tough to tell if Gillies is anything more than a sporadically amusing prankster with a camera, but he does, at least, exhibit some principle in his refusal to sentimentalize privileged moping. Oconomowoc is an engagingly cynical ode to futility.