1. When the SS Eastland capsized in 1915, 844 passengers and 4 crew members lost their lives. What did you think about the author’s decision to begin the novel with this event?
2. Did you find Benny’s attempts to save passengers admirable or foolish?
3. Why doesn’t Benny tell his father about the Eastland when he returns to the factory? What does it say about their relationship?
4. Hannah and Leo Lehrman have lofty ambitions for their son, Benny, and they are unable to accept his passion for jazz. Do you think they would have been more open to Benny’s love of jazz had they not already lost one son?
5. Is Benny rejecting his family and his faith with is music? Or is he “coming closer to God” as his music teacher Mr. Marcopolis tells him?
6. Chicago is the author’s hometown. The sights, smells, and sounds of the city are beautifully described in detail. Did reading the novel inspire you to visit? If you live there or if you’ve already visited, does the novel enable to see the city with fresh eyes?
7. The author breathes new life into historical figures such as Al Capone, Louis Armstrong and Rudolph Valentino. How do these celebrities contribute to narrative of the novel?
8. Napoleon’s grandmother tells him “Everyone needs a trickster in this world.” Do you agree?
9. Discuss the significance of Pearl’s discovery of the “absence of sound” beneath the waters of Lake Michigan.
10. Do you think that Pearl is the wise, quiet strength of the novel?
11. Benny and Napoleon experience anti-Semitism and racism at different points in the novel. Do these injustices provide a bond between them that is even stronger than their love of music?
12. Did the scene in which Benny rushes Napoleon to Marta’s surprise you? Discuss the author’s skill in setting up this fictive moment, and how that scene made you feel.
13. Discuss Opal and how she embodies the novel’s central them of the freedom to pursue one’s passion in a very powerful and poignant way.
14. Does Benny’s return to a more traditional way of life—work, family, and marriage—seem like a failure or a new beginning?
15. What do you think the future holds for Benny and Pearl as we leave them bathed in the glow of “The Century of Progress”?