If you've never read Roth, places to start. (I get asked this pretty often.)
  1. Goodbye, Columbus (1959).
    His first. If you're under 26, it's an impressive first book of stories, sharp, poignant, well-structured. If you're over 26 it's like "How could someone that young write so goddamned well."
  2. Portnoy's Complaint (1969).
    Obviously. Brilliant verbal performance that seems like it must've been produced in one sitting; actually the product of ten years of meticulous drafting. Masturbation and incest fantasies as the key to modern Jewish men.
  3. The Ghostwriter (1979).
    One of his shortest and best. Where Roth's debts to Henry James and Bernard Malamud meet his fantasies about Anne Frank surviving.
  4. Operation: Shylock (1993).
    Postmodernism! Two characters named Philip Roth. History and absurdity, overlapping. Israel as broken, mythical fantasy. Plus the most devastating description of chronic back pain in literature.
  5. American Pastoral (1997).
    A masterpiece from Roth's late stage, and one of the best novels about the American '60s and its legacies. Which is saying something. (Also glove-making.)