The greatest compliment I can pay Alex Ross Perry, the writer/director of Listen Up Philip, is his language is noticeably inconspicuous. Like Quentin Tarantino, Perry has the ability to impress with dialogue without it feeling written. And Listen Up Philip is very written. Like its protagonist, the film takes an inner look at what creates art. And, like the novels of Philip Roth (the director's obvious inspiration, both in content and poster font), the language is the star of the show.
The other star is Jason Schwartzman, increasingly one of the most singular actors around, who plays an adult version of Max Fischer, his Rushmore alter-ego. Like Max, Philip is a talented individual, a writer who's about to have his second novel published. And like Max, Philip rubs people the wrong way. He has a beautiful live-in girlfriend, Ashley (Elisabeth Moss), but the film starts with Philip boasting to an ex that he's becoming more than she ever thought he could be and screw you for not believing in me. Like Max, Philip is vindictive.
Philip's character, take it or leave it, is the earplug in Listen Up Philip. He doesn't listen to anyone or anything and it's this not-so-subtle detail that makes Perry's film delicious. Ashley and Philip are on the verge of a breakup and, when Ashley tries to explain herself, her arrogant boyfriend ignores everything and comments on the nature of her words instead. Later, after the two break up and see each other after a long time, Philip hasn't changed. "Stop for a minute while I put my head in this sweater."
Philip learns nothing in Listen Up Philip which is the jumping off point for much of the film's humor. Schwartzman is great at remaining inexplicably likable despite being an certified prick throughout the film. He's the rare actor who can be simultaneously harmful and harmless in the same breath. But make no mistake, the explosions in this film are caused by the dialogue. Perry shows he can be cutting, charming, endearing, and repellant all over the course of 108 minutes.
On the surface, Listen Up Philip is a quiet tale. Philip is a moderate success in the literary world, but is feeling the weight of his successful girlfriend and their hectic lives in the most hectic of places: New York City. He's having trouble writing and seeks out the advice of a successful author he admires, Ike Zimmerman (Jonathan Pryce), who's an even bigger asshole than Philip. The two become fast friends. Zimmerman then invites Philip to stay at his country house upstate. A writer needs a place to write and Philip accepts the invitation. In no time, he's broken up with Ashley and left the city. As he struggles to find himself, the writer takes a job teaching at a local college which introduces him to a new girlfriend and new issues.
The story itself is a triptych of sorts. Perry divides the film into targeted acts that each focus on a character. Philip gets the most time in the first act. Ashley owns the second, and Zimmerman gets some truncated attention in the third act alongside Philip. The technique is novelistic and it stands, practically, to give us a break from the protagonist, who's the biggest cinematic blowhard since Jeff Daniels' Bernard in The Squid and the Whale. And I say that with love. Both Philip and Bernard talk a big game and alienate their loved ones by being pretentious, but they do it attractively. Jerks can be funny if you're not the one they're being a jerk to.
Perry shapes the look of Listen Up Philip similarly to how Noah Baumbach directed Squid, as well. Both films were shot on Super 16mm and both almost exclusively use handheld camera work to enhance the anxiety-riddled lives of their subjects. But Listen Up Philip is buoyed by a very Wes Anderson-like touch: an intellectual narrator (the great Eric Bogosian) who omnisciently updates us on the thoughts in Philip's head he doesn't have time to share. (Another Anderson/New York reference, the zebra wallpaper from Gino's Restaurant and The Royal Tenenbaums, is a nice touch.) In the beginning, we learn Philip "bottles up his emotions to use creatively later." This idea gets to the heart of the matter. Philip only cares about two things: his writing and himself. Everything else comes second and anyone who needs a reminder gets a harsh one.