The Long Goodbye Discussion Questions

  1. What are Philip Marlowe’s reasons for rescuing the drunken Terry Lennox, calling him “My friend” (p. 10) after barely meeting him, and taking him home? Why does he tell the homicide detectives, “I’ve got a reasonable amount of sentiment invested in him”? (p. 42)
  2. After Marlowe gets beaten up and tortured in the police station, the lawyer Endicott accuses him of wanting “to play the big scene” (p. 56). Does Endicott accurately perceive Marlowe’s character?
  3. Why does Marlowe not feel the same kind of instinctive sympathy for writer Roger Wade that he feels for Terry Lennox, both of whom are down on their luck and troubled by alcohol?
  4. How are we to interpret the typed manuscript (p. 203-207) that Wade wrote while drunk, and which he instructs Marlowe to remove from the typewriter? Why does Marlowe save the scraps of this manuscript and then, later, put them down the kitchen garbage disposal at the Wades’ house?
  5. After Marlowe hears the wealthy mogul Harlan Potter denounce the media and American middle class consumerism (p. 233-235), he observes judgmentally of the old patriarch: “He hated everything.” (p. 235) Given Marlowe’s outlook on lawyers, cops, physicians and the upper class, does he show affinities with Potter’s view or is he someone very different from Potter?
  6. Is Marlowe serious when, later on, he describes himself as a “romantic”? (p. 280) Do you think he is? Describe from relevant passages in the text what Marlowe’s attitudes are toward individuals from different minority groups, including blacks, the Japanese and Mexicans. How does Marlowe view homosexuals? What attitudes does he have about women generally, and particularly blondes? Do these attitudes affect the way he conducts his investigation, and if so, how? Do these particular passages in the novel affect the work’s literary value?
  7. What does Marlowe mean by the phrase, “Crime isn’t a disease, it’s a symptom”? (p. 352) Does his preceding monologue about how “cops are all the same” (p. 351) accurately sum up the attitudes of most law enforcement officers?
  8. Does Marlowe care about the rule of law, or does he act primarily to enforce his own personal sense of justice? Is there merit in policeman Ohls’ criticism that Marlowe has knowingly allowed deaths to occur that he could have prevented?
  9. Does Marlowe offer contemporary readers a code of conduct for living that we should admire and try to imitate?
  10. What does the conclusion of The Long Goodbye offer in the way of wisdom about marriage? About friendship?

The Chicago Public Library would like to thank the Great Books Foundation, a nonprofit educational organization based in Chicago, for contributing these questions. For more information about Great Books anthologies and Shared Inquiry™, a Socratic, text-based method of learning, visit the website at

Content last updated: April 30, 2008

Print this page