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Portnoy's Complaint (1969) is American writer Philip Roth's most popular novel, with many of its characteristics (comedic prose; themes of sexual desire and sexual frustration; a self-conscious literariness) having gone on to become Roth trademarks.

Structurally, Portnoy's Complaint is a continuous monologue as narrated by its eponymous speaker, Alexander Portnoy, to his psychoanalyst, Dr. Spielvogel. This narration weaves effortlessly through time and describes scenes from each stage in Portnoy's life, with every recollection in some way touching upon Portnoy's 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. Roth is not subtle about defining this as the main theme of his book. On the first page of the novel one finds this clinical definition of "Portnoy's Complaint", as if ripped from the pages of a manual on sexual dysfunction:

Portnoy's Complaint: A disorder in which strongly-felt ethical and altruistic impulses are perpetually warring with extreme sexual longings, often of a perverse nature...

Other topics touched on in the book include the assimilation experiences of American Jews, their relationship to the Jews of Israel, and the pleasures and perils the narrator sees as inherent in being the son of a Jewish family.

Portnoy's Complaint is also emblematic of the times during which it was published. Most obviously, the book's sexual frankness was both a product of and an inspiration for the sexual revolution that was in full swing during the late 1960s. And the book's narrative style, a huge departure from the stately, semi-Jamesian prose of Roth's earlier novels, has often been likened to the stand-up performances of '60s comedian Lenny Bruce.

Ever since its publication, speculation has abounded as to how much of Portnoy's Complaint is fiction and how much is thinly-veiled autobiography. Roth himself pokes fun at these parlor games in his 1985 novel Zuckerman Unbound, where alter-ego Nathan Zuckerman is continually accosted by clueless strangers who cannot believe he was exercising the creative faculties of a writer when he wrote the sex scenes in Carnovsky (the alter-novel to Portnoy's Complaint).

Still, by cross-referencing data from interviews, the autobiography of ex-wife Claire Bloom, Roth's own pseudo-autobiography The Facts, and his more biographically mimetic Zuckerman novels, the following can be established about Portnoy's Complaint with a high degree of certainty:

• The novel began as a dinner-table comedy routine delivered by Roth to New Republic drama critic Robert Brustein and their circle of mutual New York City friends (The Facts)
• Like Portnoy, Roth was heavily influenced as an adolescent by the World War II radio dramas of playwright Norman Corwin. Both teenage Portnoy and teenage Nathan Zuckerman (cf. I Married a Communist) produce politically-didactic radio plays as their first forays into literature, and so it is highly likely Roth began his career with a similar work of juvenilia (I Married A Communist Interview)
• Portnoy's career as a civil rights attorney reflects Roth's own Popular front-inspired civic idealism; when he was visited by lawyers from the Anti-Defamation League to discuss the controversy over a story in Goodbye, Columbus, Roth recollects that: "as a high school senior thinking about studying law, I had sometimes imagined working on their staff, defending the civil and legal rights of Jews" (The Facts)
• The central female character of Portnoy's Complaint, Mary Jane Reed (aka "The Monkey") is a caricature of Roth's first wife, Margaret Martinson. Specifically, the women share the same neurotic need to submerge themselves in Portnoy's/Roth's Jewish identity so as to co-opt some of the same family love that was missing from their own lives (Claire Bloom's Leaving a Doll's House, The Facts).
• Roth and Portnoy share the same birth-year (1933) and birth-place (Newark, New Jersey)
• The various high literary references made by Alexander Portnoy (to Tolstoy, Dostoevsky, Yeats) reflect Roth's own tastes, as they recur in novels narrated by different characters, including ones (for example, Mickey Sabbath of Sabbath's Theater) who are not sufficiently educated to realistically be able to toss off such references

• Gore Vidal, author of Myra Breckinridge (1968), quipped to Roth's second wife, Claire Bloom: "You have already had Portnoy's complaint [her previous husband]. Do not involve yourself with Portnoy."

• Dick Cavett reported in his autobiography that on one occasion, a male guest was unable to appear on Cavett's talk show. Cavett jokingly told the studio audience that the guest could not be there because he was "suffering from Portnoy's Complaint". It being a less liberal time on television, the network censors cut that comment from the broadcast tape.

• Following in the footsteps of Goodbye, Columbus, Portnoy's Complaint was in 1972 made into a film starring Richard Benjamin and Karen Black. The results were decidedly less successful than the first movie, with Leonard Maltin calling it a "cinematic massacre".

• In 1969 the book was declared a "prohibited import" in Australia, though the Australian publisher, Penguin Books, resisted and had copies printed up in secret and stored in fleets of moving trucks. Several attempts to prosecute Penguin Books and any bookseller carrying the book failed.[1]

• A Complaint is a genre of the early modern literature period in England in the late sixteenth and early seventeenth centuries. Typically a Complaint is told by a female as a rebuttal at the end of a sonnet sequence, commenting on being a spurned (rather than jilted) lover.

• Portnoy's Complaint #52 on the Modern Library's 100 Best Novels of the 20th Century
• Portnoy's Complaint (Internet Movie Database entry) A 1972 filming of the book.