In He's Way More Famous Than You, six years after an uncomfortable bout with fame during The Squid and the Whale's press tour, Halley Feiffer leads the pathetic life of a cartoonish Hollywood has-been. She has a severe drinking problem, obsessively checks her dropping IMDB ranking, and is pathologically invested in rooting for Dancing with the Stars contestants, especially Ralph Macchio. Since nobody will hire her and her agent wants to dump her, she decides to catapult herself back to the stardom she never really had by writing an Oscar-winning script, which is a direct transcription of incidents from her real life (including the one that prompts her husband to leave her, in which she asks him if he's fully erect mid-intercourse). Halley then tries to convince her brother's boyfriend (Michael Urie, who also wrote and directed the film), otherwise known as "the gay guy from Ugly Betty," to play her romantic interest. They settle for casting the brother himself as her lover because, since he's gay, it isn't incest.
Everyone in He's Way More Famous Than You is playing some version of their real selves, and while its meta elements can be amusing, the film is much funnier and weirder in theory than in practice. There are several scenes in which Urie so shamelessly lingers on the off-the-wall ethos of the script that Bruce LaBruce's The Raspberry Reich, even early John Waters, come to mind, but the film mostly suffers from not allowing its style to be contaminated by the weirdness of its spirit. It follows the arc and aesthetics of a traditional narrative for too long, sometimes giving the audience the sense that its humor is also traditional in nature (and as such, its humor fails), only outing itself as strange, and strangely conceptual, in brief moments—as when Halley's confrontation of her producer in the middle of the street about having extorted Ben Stiller to make their film project possible turns into a sort of uncomfortably public display of horniness.
The film seems to be inhabited by an entire generation brainwashed by TMZ, for whom fame is the only compass available in the world. Everyone speaks like Paris Hilton, everything is "for a part" or "for a project," and everyone's credentials seem to be mostly delusional. And they aren't even in L.A.! He's Way More Famous Than You doesn't have the conceptual gravitas to evoke a critical look into this culture of celebrity yearning and affectation. It's as though the filmmakers themselves were too close to the material and thus more symptoms of the culture than critics of it. It would have been nice, then, if the film had surrendered to its lunacy more blatantly, more carelessly. It instead lost itself in the balancing act between flirting with the nonsensical and refusing to give up the safety of the literal.