This chapter addresses the significant place of psychoanalysis in Roth’s life and work, his changing notions of its value, and the way his work contributes significantly to “confessional” literature. Roth himself has admitted the ways that placing his characters in analysis created a kind of stylistic freedom; in Portnoy, the confessional setting allowed him to create “completely unbuttoned” scenarios. While Portnoy’s Complaint is perhaps the most famous example of this, Roth engaged with the “talking cure” as early as 1963 in the short story “The Psychoanalytic Special,” and psychoanalysis figures significantly into novels such as Letting Go, My Life as a Man, Deception, Patrimony, and Sabbath’s Theater. These novels not only illuminate Roth’s fraught relationship with Freudian analysis, but also highlight the connections between Roth’s representations of psychoanalysis and gender, as his protagonists’ anxieties are expressed through an engagement with psychoanalysis.

This chapter traces the crtical reception of Roth's Portnoy’s Complaint, released to significant controversy. While many deemed the novel to be brilliant and hilarious, others found it offensive. Many readers were taken aback by its unabashed engagement with sex: protagonist Alex Portnoy speaks frankly about many aspects of his sexual life, particularly his propensity for masturbation. As is the case with many of Roth’s works, readers interpreted the protagonist to be almost wholly autobiographical. Moreover, many Jewish critics and rabbis, specifically, felt that the book’s material further revealed Roth to be a “self-hating Jew."Yet for many of the same reasons that it was criticized, Portnoy’s Complaint has also been hailed as one of Roth’s signature works, which exemplifies a coming into his unique voice and trademark sense of humor.

Many times over the course of his career, Roth was accused of antisemitism, even though he explored and criticized antisemitism in his own works. This chapter will explore this conundrum, examining how and why Roth faced such accusations, and pointing to where they are misguided.