SPOILER WARNING: These book discussion questions are highly detailed and will ruin plot points, if you have not read the book.
Title: The Big Sleep
Author: Raymond Chandler
Page Count: 249
Genre: Mystery, Pulp Fiction
Tone: Witty, Gritty, Fast-paced
1. What did you think of Chandler’s constant barrage of setting details?
2. Do you think General Sternwood had given up on being a parent? What would you have done differently?
3. Vivian visits Marlowe’s office to try and figure out if he is looking for her husband. Why doesn’t she just go to her father?
4. Vivian tells Marlowe, “People don’t talk to me that way.” (p. 19) What does this tell us about Vivian? What does this tell us about Marlowe?
5. Marlow comes in contact with thugs, lowlifes, cops and the rich. Does he speak to everybody the same?
6. Marlowe seems almost unmovable. Almost. What are some examples of Marlowe being human?
-p. 61, Marlowe blushes after Vivian leaves
-p. 190, interaction with Eddie Mars’ wife
7. Do you count The Big Sleep as a classic of American literature? Why or why not?
8. What makes a character classic?
9. What are the charms of Marlowe?
10. Do you think Phillip Marlowe has an equal in crime fiction?
11. Did you see Marlowe as Humphrey Bogart?
12. Who could play Marlowe in this day and age?
13. What did you think of Carmen?
14. Is Carmen not very smart or does she have health issues that can account for her behavior?
15. Rusty Regan, the missing, bootlegging husband, always carried 15 grand on his person. What does that say about him?
16. Why do you think Chandler never lets us see Rusty Regan, alive or dead?
17. What does it say about Phillip Marlowe that he carries a gun and a bottle of rye in his glove compartment?
18. When you read the book, did you see it in black and white in your mind? Color?
19. Why would Vivian “loath masterful men?” (p. 20)
20. Did Carmen getting the drop on Marlowe surprise you? (p. 210)
21. Eddie Mars’ wife says she still loves her husband, even knowing what a criminal he is. (p. 196) Were you bothered by her stance? Why?
22. If you could go back to 1939, would you want Marlowe’s job? What job would you want?
23. What does it say about Marlowe that he is a private investigator instead of a police officer?
24. Did the slang ever bother you?
25. Is everybody (men and women) a smooth talker in The Big Sleep?
26. Any favorite quotes from the book?
27. On page 48, the doctor can’t easily tell Owen Taylor’s time of death. How would this bit of information help establish the novel’s era?
28. There ended up being a good number of characters and quite a few of them dead. Did you ever have trouble following along?
29. One of Chandler’s most famous quotes is, “When in doubt, have a man come through the door with a gun in his hand.” (The quote originates from “The Simple Art of Murder,” found as an introduction essay to his novel of the same name.) Did you see examples of that in The Big Sleep? Is this a good writing practice?
30. Think of characters and their status levels. Is there any social critique within The Big Sleep?
31. Do women have power in this story? If so, what kind?
32. How does Marlowe see women?
33. Does Marlowe have a code of honor?
34. Some of Raymond Chandler’s biggest literary influences were Charles Dickens, Ernest Hemingway and Henry James. Do you see any connections in his work to these authors?
-Ex: Dickens wrote convoluted plots, Hemingway wrote in short, to the point sentences, and James wrote in very dark tones
35. What influence do you think Chandler has had on crime novels?
Raymond Chandler’s website
Extra discussion questions on Spark Notes
Wikipedia page on pulp fiction
Ian Fleming interviews Raymond Chandler
Raymond Chandler’s 1945 essay for The Atlantic about writing in Hollywood
Original 1939 New York Times book review of The Big Sleep
Extra books on Chandler: Raymond Chandler: A Biography and The Raymond Chandler Papers