Ike Zimmerman (Jonathan Pryce), left, takes fellow author Philip Lewis Friedman (Jason Schwartzman) under his wing in “Listen Up Philip.” (Tribeca Film)

Listen Up Philip” plays like an adaptation of a lost Philip Roth novel. Even the film’s title sequence — written in the iconic curlicue typeface familiar from so many of Roth’s early Bantam paperback covers — suggests that it was written somewhere between Roth’s 1959 debut, “Goodbye, Columbus,” and “My Life As a Man” (1974).

The film even has a character inspired by Roth: an older, dyspeptic celebrity author named Ike Zimmerman (Jonathan Pryce), who plays a mentor to the film’s Philip (Jason Schwartzman), a breathtakingly — and, at times, hilariously — self-absorbed young novelist who, as this tragicomic film opens, is preparing for the publication of his second book. “Don’t make yourself any more miserable than you need to be,” Ike tells his morose protégé, who, over the course of the film, ruins two relationships. “Leave that to the women you love. That’s what they’re pretty much there for, in my experience.”

That attitude of offloading emotional investment (and its risks) to others — not just as a form of self-preservation, but in order to generate material for your books — underpins Philip’s very being. To describe him accurately would be to use unprintable epithets (many of which are used in the film), yet Schwartzman manages to inject his character with a modicum of humanity that prevents viewers from checking out early, even as it becomes increasingly obvious that the hero of “Listen Up Philip” is doomed.

Doom may seem like a strong word, but it’s apt. Philip is on an upward trajectory, career-wise, but he’s being eaten alive by his own corrosive self-regard and his inability to protect himself from the world around him. Writer-director Alex Ross Perry follows that trajectory through shaky, 16mm close-ups that, while never affording us much breathing space, gain needed perspective from Eric Bogosian’s omniscient-style narration. Bogosian’s wry voice-over, written by Perry, shapes the film, giving it the heft of a novel.

It’s like watching Philip self-destruct through an “infinitely replenishing prism of regret,” to use one particularly choice phrase.

The film tracks Philip’s slow breakup with his long-suffering live-in girlfriend (Elisabeth Moss, delightful as always). In between scenes with her, we eavesdrop on Philip’s conversations with a groupie (Dree Hemingway) and Ike’s daughter (Krysten Ritter), as well as a somewhat longer affair with a Frenchwoman (Joséphine de La Baume) who teaches at the college where Philip works, briefly, as an adjunct.

But Philip’s most fleshed-out relationship is with Ike, who senses a kindred spirit in the young man. Perry’s acerbic sense of the literary/academic lifestyle — which, oddly enough, involves less actual writing and teaching than drinking and “thinking” — is both exceptionally funny and deeply sad.

At one point, a minor character whom we’ve been introduced to early in the film kills himself. “I’m glad he’s dead,” Philip says. As callous as that sounds, Philip may be expressing a sense of relief, not for himself, but for the deceased.

It isn’t that Philip doesn’t listen, or that he listens only to himself. At times, his character is acutely, almost painfully aware of the world around him. “I feel like my head is a car,” Philip says, “but I can’t drive fast because there’s too much traffic. So instead I’m just moving very, very slowly.”

“Listen Up Philip” makes literary talent seem less like a blessing than a curse.

★ ★ ★

Unrated. At AFI Silver. Contains obscenity and some mature thematic material. 108 minutes.