There is no American novel with a success story more contentious than that of Philip Roth’s Portnoy’s Complaint. First published in 1969 amid scathing condemnations, it sold over three million copies in its first six years. Even more remarkable is that after four decades, the novel’s commercial and critical success is still picking up speed. Portnoy’s Complaint now outsells The Great Gatsby on Amazon and a Google search yields over 85,000 hits. It was cited in more academic journals in the nineties than it was in the seventies. Greeting the winners of the National Humanities Medal in 2010 (Roth among them), President Obama asked: “How many young people have learned to think by reading the exploits of Portnoy and his complaints?”

With his new book, Promiscuous: Portnoy’s Complaint and Our Doomed Pursuit of Happiness, Bernard Avishai gives considerable thought to why we can’t seem to stop thinking about Portnoy. He draws on an impressive breadth of sources to do so – including experiences with Roth as a colleague and friend, his own relationship to the novel, and a range of literary and cultural touchstones from James Joyce to the New York Intellectuals. While his personal affection shines through, Avishai also shows us just how deft Roth’s novel was (and is) at playing on the cultural ambivalence of the psychoanalytic monologue as a tool of cultural critique.

More specifically, Promiscuous provides incisive commentary on why we find Portnoy’s relentless taboo-breaking so outrageous and yet so reassuring. “The constraints were necessarily gone,” writes Avishai, “not only because satire invited it, but therapy demanded it.” Roth’s situating of a neurotic thirty-something Jewish-American man’s self-struggling within the confines of the therapy couch provided his story with a very particular cultural anchor-point, one which, according to Avishai, the author was banking on his audience identifying with. Yet at the same time this anchor-point, by its very nature, removed all certainty of a social or moral frame of reference. The psychoanalytic session did, and still does, proclaim itself to be a “judgment free” zone, something which Portnoy thoroughly mocks. And yet there is “an enigma that has lodged in the back of our minds along with the caricature, something to do with a voice that cannot mock others without first mocking itself, something enduring because it [is] so disorienting.” Is Roth satirizing therapy or using therapy to satirize that which we otherwise leave unsaid? Is Portnoy the wielder of satire or its ultimate object?

This unsettling paradox at the heart of our cultural relationship to psychoanalysis has become a familiar trope in today’s media culture. Its manifestations are not always the most sophisticated; witness the unending parade of celebrities eager to regain the spotlight by opening up their rehab and counseling sessions to public view. Yet many of the wittiest (or, at least, the most compelling) characters on television – from Gregory House to Tony Soprano – spend some portion of their week on the therapist’s couch. Writers ostensibly employ this scenario to reveal those sides of their characters that are only “allowed” to come out in the confines of therapy. And yet, it is the characters’ complex and ambiguous reactions to this constructed method of self-reflection – one moment condemning it, the next confirming it, at times attempting to wield it as a manipulative tool themselves – that gives us the most disturbing and refreshing images of what our culture champions and condemns.

While most of these popular icons don’t draw directly on Roth’s novel, Avishai’s narrative explicates why Portnoy remains one of the watershed moments for this particular brand of storytelling. His method of grounding the novel within specific contexts is balanced by illustrations of why its themes spring eternal. A good example of this is his smart comment that “If Portnoy’s Complaint could be said to have a fault, it is our hero’s utter lack of morbidity.” Avishai notes that Portnoy’s juvenile recklessness found more receptivity in the post-war sixties than it would have a generation earlier. He cannot quite imagine Roth’s protagonist exclaiming: “You see, I just can’t stop! Or tie myself to any one,” while “standing in a breadline, or sitting by the radio listening to FDR’s reassurances after Pearl Harbor.” Yet he also links Portnoy’s sense of freedom to a fundamental faith in the order of the universe shared by the likes of Voltaire and Locke.

It is moments like these in Avishai’s work that ask us to look beyond our general consensus that Portnoy’s Complaint is indeed, promiscuous, and instead consider how such a label reflects in serious ways on the way we construct fictions about ourselves and others.