Portnoy's Complaint is a highly controversial dark comedy set in the transformative 1960s. Written by Philip Roth in 1969, the novel reflects changing views on sexuality, Jewish identity, and personal freedom through its protagonist, Alexander Portnoy, who seeks to discover his own identity and purpose amid these evolving social tides. The novel takes its title from an epigraph that precedes the stream-of-consciousness narrative; the epigraph explains that Portnoy’s Complaint is “a disorder in which strongly-felt ethical and altruistic impulses are perpetually warring with extreme sexual longings, often of a perverse nature.”

The novel takes the form of an extended internal monologue, detailing the life and conflicts of Portnoy, a young Jewish man in his early thirties seeking therapy to address his intense sexual desires—and his immense self-hatred for his taboo tastes. The narrative unravels unconventionally, unfolding through an ongoing session with Portnoy’s therapist, Dr. Otto Spielvogel.

Portnoy recounts his childhood and adolescence in Newark, emphasizing the influence of his family. He describes his mother, Sophie, as a controlling and dominant household figure who often scolds him. His father, Jack, is an honest and diligent salesman who suffers from constipation. His older sister, Hannah, who is described as "overweight," may not be the brightest, but she is hardworking and pushes herself to the limit. The family dynamics are intriguing and humorous.

Portnoy then reflects on his early experiences, noting that so many were filled with humiliation and frustration, He openly discusses his growing obsession with sex, delving into his sexual experiences with different girls using frank, explicit language.

The first girl he discusses is Rita Bubbles Girardi, an Italian girl known for her promiscuity, with whom he shares his first sexual encounter. Then, there is Kay Campbell, known as "The Pumpkin," his college girlfriend from Iowa, whom he likes but eventually loses interest in. Sarah Abbott Maulsby, referred to as “The Pilgrim,” comes from a wealthy New England family, and Portnoy believes they hold anti-Semitic views.

He also encounters Lina, an Italian Catholic prostitute in her twenties, and Mary Jane Reed, an experienced model from West Virginia who fulfills his sexual fantasies and truly loves him for who he is, who he calls “The Monkey.” However, he cannot commit to a serious relationship with her because of their different backgrounds—she is not Jewish, and he is not ready for commitment. After they take a trip to Europe, he decides to break up with her.

Ultimately, Portnoy goes on a pilgrimage to Israel to discover himself and his identity. It is in Israel that he meets Naomi, a tall woman he nicknames “The Jewish Pumpkin” and “The Heroine.” Despite his strong desire, he finds himself unable to be sexual with her, which represents his struggle to merge his identity with his desires. Upon realizing his impotence, he schedules therapy sessions with Dr. Spielvogel.

Portnoy's deep-seated hatred towards his Jewish identity, his parents' overbearing influence, and his feeling of not quite fitting into the free American society he envisions become apparent. The storytelling is scattered, with some stories appearing in pieces, their resolutions arriving only much later. This mirrors Portnoy's confused thoughts, offering a thorough view of his life, which is indelibly marked by intense desires, regret, anger, and fear—and only occasional moments of happiness. The novel concludes as Portnoy screams, signifying his struggle to accept himself, in response to Dr. Spielvogel's question about finally starting the therapy.