By Lindsey Bahr
Updated October 17, 2014 at 11:05 PM EDT
Credit: Tribeca Film

Director Alex Ross Perry takes a chainsaw to the tweedy highbrow literary scene and the toxic men who inhabit it in Listen Up Philip.

Philip Lewis Friedman (Jason Schwartzman) is one of those fully realized personalities. A successful novelist awaiting the publication of his second book, Philip is at turns cripplingly insecure and a megalomaniac who’s unafraid to alienate and offend. In this exclusive clip, you’ll see Philip meeting up with an ex early in the film.

With the droll, unflinching narration (from Eric Bogosian), and bristly intelligent humor, it’s an indicative sample of the belligerent arrogance Philip displays throughout the film as he leaves his girlfriend (Elisabeth Moss) in the city and retreats to the country house of his literary idol Ike Zimmerman (Jonathan Pryce) for some peace. EW spoke with Perry about his third feature, its cinematic and literary influences, the value in dark humor and why this film transcends the misogyny of the wretched men at its center

ENTERTAINMENT WEEKLY: What are some of the top influences behind Listen Up Philip?

Alex Ross Perry: The DNA of the film is to take the filmmaking and the sort of New York sense of frustrated anxiety that’s on display in Husbands and Wives—not to mention the milieu and the sort of brown, muted, early-90s sense of interior design and wardrobe that that film does so perfectly—and apply that to an experience that is structured like a novel and a script that’s more inspired by fiction and literature than it is by cinema from a narrative arc standpoint. William Gaddis’s The Recognitions was a big influence and the tone and narrative style and prose of Richard Yates’ Young Hearts Crying are all things that are part of the script. Then talking to a cinematographer about Husbands and Wives’ camerawork and eventually showing that film to our production designer and showing the Squid and the Whale to our costume designer to let them look at the soft brown corduroys and tweeds in that film…It’s finding a way to take all these things and let everyone know what I’m thinking, but still let it not just be pastiche and a bunch of stuff that I like and have it be something unique.

People have praised Listen Up Philip for its spot-on depiction of academia and the literary world, but you insist that any insight is purely accidental.

If someone were to say what’s your insight into academia or the world of publishing, I would say nothing. I have this world of filmmaking and cinema and there’s a lot in this film that’s either from that world and I’ve changed it to something else, or it’s just an invention of what I imagine things would be like in the world of publishing and the world of academia. When people say it’s true or insightful I just have to assume that there’s some universal similarities across these professions. People have the same problems, same attitudes, same jealousies, same insecurities.

The male characters in here can be pretty deplorable and there’s the loose connection to Philip Roth, who’s often criticized for misogyny. Is that something you think about?

That’s something people have been saying about his novels for 40 years or more. And he says “of course not, that’s crazy. There’s no male character in any of my books that anybody should think is an admirable character. And the women are subjected to things as a result of these men, but they’re never depicted as being worse than a man.” Showing a bad man doing bad things to a good woman isn’t misogynist if the woman emerges victorious. If it was just a sad movie about women who let themselves be treated that way, then the film would have some serious problems and would also be really miserable to watch. This film does not let its characters be treated that way. In fact the only characters who end the film in a different place and a better place than they begin are the women. That’s relevant. They suffer as a result of these men and overcome what has happened to them by the time the film is over.

Did you enjoy writing any individual character above the others?

I enjoyed writing them all and skipping from character to character. They’re all fun because they all sort of represent different parts of the same person. Philip and Ashley have different parts of me. Philip and Ike have different parts of me. It’s fun to have the two opposing sides of what I’m thinking speak against each other and that’s just fun to watch.

Do you have a favorite sequence? Or is that an impossible thing to answer?

I do have favorite sequence. It my favorite thing I’ve ever done. There’s a sequence a little over halfway through the film where Jonathan Pryce’s character and his buddy bring these two women to his house and from the time where they’re sitting out on the porch talking without doing it to the time when the sequence ends and Phillip’s involved and there and there’s a nice moment with the three men in Ike’s study having a cocktail once the party has broken up. It’s about 8 minutes and to me it’s just the most staggering moment of cinema…and I got out of the way. I’m not praising myself. Jonathan Pryce led that scene. A lot of it was improvised and we just let him find the rhythm. We said, “make sure there’s a little bit of dialogue that has to happen in this scene, but everything else just needs to build to Jason playing the piano somehow.” And Jonathan was really the leader. I was in the other room because the camera was zooming everywhere and there was just nowhere to hide. Watching what that footage turned into and the ballet of the cinematography around the performance was just the most inspiring convergence…what Jonathan Pryce was doing in that scene was just an absurd master class in the most subtle control of performance I’ve ever seen in person, certainly, and in most films.

This film is so dark but also manages to be incredibly funny. How did you settle on the right tone?

I didn’t want the film to be an outright comedy that was just funny. I wanted to do a movie that was fairly cynical and unflinching in its questioning. But in order to do that you don’t want to make some dark, bleak unwatchable misery fest. It’s important to remember why people watch movies and go to the movies and why I started watching and loving movies is to be entertained. Comedy is entertaining and it’s a great way to present something that becomes more than what it is, because you can have something that’s serious and sad and emotional, but if the characters are funny? You know funny people go through bad experiences too and in the middle of a bad experience, a funny person will make a funny joke. That’s the kind of character that I think it’s easier to make an entertaining film about rather than a humorless person going through a bad experience.

Listen Up Philip opens in select theaters Friday and will be available on VOD on Oct. 21.