Harlem Shuffle

Content Warning: This section of the guide contains discussion of racism and illness or death.

Gather initial thoughts and broad opinions about the book.

1. Did you find Whitehead’s portrayal of Harlem as both a community and a setting for criminal activity compelling or surprising? How does it compare with your previous knowledge about this part of New York City?

2. This novel marks a departure from Whitehead’s previous Pulitzer Prize-winning historical fiction works The Underground Railroad and The Nickel Boys. If you’ve read either of those works, how does this novel’s exploration of race or history differ?

3. In what ways does Ray’s character compare to and contrast with other crime fiction protagonists like those in Walter Mosley’s Easy Rawlins series?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Ray justifies his involvement in criminal activities by compartmentalizing his life. When have you found yourself separating different aspects of your identity or life? Were the results positive or negative?

2. The furniture store represents Ray’s attempt to build a respectable legacy different from his father’s.