ACMI’s season of Alex Ross Perry’s films makes for disparate viewing. There’s Impolex, loosely based on elements of Thomas Pynchon’s “un-filmable” novel Gravity’s Rainbow, a hallucinogenic wilderness ramble with an amnesiac World War II soldier. And there’s the sarky, lo-fi The Colour Wheel, in which a misfit brother and sister embark on a quip-laden odd-couple road trip. Then there’s Perry's most recent work – the critically acclaimed Listen Up Philip, with Jason Schwartzman as a bitter, cruel New York novelist, and a star turn from Elizabeth Moss.

They’re all sharp, funny and weird. But they are also connected by Perry’s interest in characters, literature and the intersection of humour and emotion.

Broadsheet: Hi Alex! Do you consider your films to be comedies?

Alex Ross Perry: I think comedy is an element that is important in couching some of the more dramatic things I am mostly interested in exploring. These movies, with the same themes, characters and ideas, but minus any sense of laughs or fun, would be much more difficult to embrace. I like to say they are very straightforward dramas about people who happen to be somewhat amusing. But also I am certainly not above a silly gag here and there if the mood on set points us in that direction.

BS: How does Impolex relate to Gravity’s Rainbow, and what made you decide to develop something that by all accounts was un-filmable for your first feature?

ARP: It is really a response to the book. When I put down Gravity’s Rainbow after months of reading it, I felt like I wasn’t yet finished. I had to express something about the world of emotions and ideas it had planted in me. I always said that the film is more of an adaptation of a book report of Gravity’s Rainbow, like a treatise on the themes, images and general ideas that the book suggests. It really sent me down a rabbit hole of research about this aspect of World War II that I had never known about, and that research, which was monographs published by the Smithsonian about rockets and such, informed the film as much as Pynchon’s fiction. I think the film moves and breathes in the manner of his writing, and that was the greatest takeaway and influence he had on me.

BS: Your work is inspired by 20th-century literature. Where does Listen Up Philip come from? Any author in particular, or is it just inspired by the whole angry-old-writer scene in general?

ARP: I definitely fetishise a huge cross section of writers from the post-war American tradition. To me, guys like Mailer, Yates, DeLillo, Pynchon of course, Salter, are all incredibly fascinating and brilliant writers. But by far the largest and most prominent influence on the film, and on Colour Wheel as well in a way, is Philip Roth, who has taught me not just ways to incorporate humor and emotion into storytelling, where you would be forgiven for eschewing it, but also a strong sense of identification with east-coast-specific fiction. He is a north star for me, no question.

BS: All your films are very different, and it’s a strange experience watching them all together. Do you look back and see a consistent thread through them all?

ARP: To me they are all about very lonely people going through what is clearly the worst period in their lives. By the end of the film, the terrible period has not ended, but there may be light at the end of the tunnel for the first time. That is the time of a character's life that I am most interested in chronicling. So films as different and Impolex and Listen Up Philip feel to me very connected when I consider that they come from the same place of difficulty and sadness for their characters.

Alex Ross Perry’s films Impolex, The Colour Wheel and Listen Up Philip from April 2–26.