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.