[3] The novel tells the humorous monologue of "a lust-ridden, mother-addicted young Jewish bachelor," who confesses to his psychoanalyst in "intimate, shameful detail, and coarse, abusive language.

"[6] Structurally, Portnoy's Complaint is a continuous monologue by narrator Alexander Portnoy to Dr. Spielvogel, his psychoanalyst; Roth later explained that the artistic choice to frame the story as a psychoanalytic session was motivated by "the permissive conventions of the patient-analyst situation," which would "permit me to bring into my fiction the sort of intimate, shameful detail, and coarse, abusive language that [...] in another fictional environment would have struck me as pornographic, exhibitionistic, and nothing but obscene.

Portnoy is "a lust-ridden, mother-addicted young Jewish bachelor",[4] and the narration weaves through time describing scenes from each stage of his life; every recollection in some way touches upon his central dilemma: his inability to enjoy the fruits of his sexual adventures even as his extreme libidinal urges force him to seek release in ever more creative (and, in his mind, degrading and shameful) acts of eroticism;[citation needed] also, much of his dilemma is that "his sense of himself, his past, and his ridiculous destiny is so fixed.

And the book's narrative style, a huge departure from the stately, semi-Jamesian prose of Roth's earlier novels, has been likened to the stand-up performances of 1960s comedian Lenny Bruce.

The two aspects that evoked such outrage were its explicit and candid treatment of sexuality and obscenities, including detailed depictions of masturbation, which was revolutionary in the late 1960s, and the irreverent portrait of Jewish identity.

Penguin Books, the Australian publisher, circumvented the importation ban by having copies printed in Sydney in secret and stored in fleets of moving trucks to avoid seizure under state obscenity laws.

[11] Attempts to prosecute Penguin and any bookseller carrying the book were successful in Victoria and Queensland, but failed in Western Australia (where "works of recognised artistic, scientific or literary merit" were immune under the local statute, notwithstanding that they may have been obscene) and New South Wales, where prosecutors gave up after two trials resulted in hung juries.