Portnoy's Complaint
One long howl from a psychoanalyst's couch. Alexander Portnoy, a guilt-strangled New Jersey son, confesses everything to his silent analyst: the smothering mother, the martyred father, and an adolescence of compulsive masturbation pursued with a desperation that is somehow both filthy and holy. Roth's 1969 monologue made him famous and infamous in the same week — it blew open what American fiction could say out loud about sex, shame, and the Jewish family, and it is still the funniest thing he wrote. The whole confession turns out to be the setup for the analyst's one-line punchline.
It is one uninterrupted aria of complaint, and a hundred pages in, the joke's shape is fixed: Portnoy is appalling, knows it, and narrates his appalling-ness at the top of his lungs. The women exist mostly to be wanted, used, and then filed as grievances — 'The Monkey' worst of all — so the book's candor about his selfishness never quite frees it from sharing his blind spots. Hilarious in bursts, wearying at length, and dated wherever the shock was the whole point.
The case for it and the rest of the canon open with Pro.