Gather initial thoughts and broad opinions about the book.

1. The guide compares Cricket’s story to the picaresque tradition of novels like Henry Fielding’s The History of Tom Jones, a Foundling or Paul Auster’s Moon Palace. How did the novel’s sprawling, decades-long structure feel to you as a reader? Did Cricket’s journey feel like a grand adventure, a series of random chances, or something else entirely?

2. What was your main takeaway from the lifelong bond between Cricket and Olympia? Did you find their connection to be a source of strength and inspiration, a pattern of mutual destruction, or something more complicated?

3. Think about the book’s emotional impact. Which part of Cricket’s life story resonated most with you: his challenging childhood, his artistic struggles as a young adult, or his final years seeking contentment? What made that particular period so memorable?

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

1. Cricket’s life is shaped by several key mentors, including his grandfather Silas, the artist Oana, and the professor Marcus Carpenter. Think about a mentor or teacher who had a significant impact on your own path. What lessons from them have stayed with you, and how do they compare to the guidance Cricket received?

2. Cricket ultimately chooses a life of quiet, skillful labor over the pursuit of fame and fortune, a decision the novel frames as a form of rebellion. Have you ever made a choice that prioritized personal contentment over a more conventional definition of success? How did that decision shape your perspective?

3. The relationship between Cricket and Olympia is a powerful, defining force throughout their lives. Do you have a formative friendship from your youth that has endured or continued to influence you over time? What do you think makes those early connections so powerful?

4. For Cricket, drawing is a refuge and a way to create order out of chaos, especially in his childhood. What role do creative or skilled pursuits play in your own life? Do you have a practice, hobby, or craft that is a sanctuary or a way to make sense of the world?

5. Jed develops his own unique philosophy of creativity, viewing his seduction of neglected women as a form of art or a “happening.” Have you ever redefined a conventional activity as a personal art form or a creative practice in your own life? What does this suggest about the boundaries of what we consider art?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The university critique scene dramatizes the conflict between traditional skill and conceptual art. How does this clash mirror real-world debates about artistic value, such as the appropriation art of Richard Prince mentioned in the guide? Where do your own sympathies lie in this debate between craft and concept?

2. Jed’s deployment and death are set against the First Gulf War. What impact did grounding the story in this specific historical conflict have on your reading experience? How does the novel use this backdrop to explore the random, often senseless ways that large-scale events can shape individual destinies?

3. Kyle Heaney’s studio operates like a factory, with a team of skilled artisans executing his ideas for a global brand. In what other fields or industries today do you see a similar tension between individual craftsmanship and large-scale, brand-driven production?

Dive into the book’s structure, characters, themes, and symbolism.

1. Olympia is a force of nature who is both a loyal friend and a destructive influence in Cricket’s life. How do you interpret her motivations throughout the novel? Is she ultimately a product of the corrupt art world she navigates, or is she one of its primary architects?

2. How do the diverse reactions to the nude figure reflect changing social attitudes and their impact on art? Do you think Cricket’s arguments for nude models are justified? Why or why not?

3. The theme of Contentment as an Act of Rebellion is central to Cricket’s journey. At what point in the story did you first notice him actively choosing this path over the ambition that Olympia represents? What key events seem to push him toward this philosophy?

4. Does Eggers’ critique of the sterile gallery extend to museums? Why do you think he left the comparison between these two art venues out of the novel?

5. Does Cricket betray his younger self by choosing to abandon his ambition to become a world-renowned artist? How does this shift reflect a universal experience towards personal ambition?

6. Cricket moves from Indiana to Chicago, Turkey, and finally Paris. How does each of these settings reflect or influence his internal state and artistic development at different stages of his life?

Encourage imaginative and creative connections to the book.

1. The novel ends with Cricket and Olympia reunited, looking at drawings of themselves. What do you imagine their future looks like after this moment? Describe what you think might happen in the next chapter of their relationship.

2. If you were to curate a gallery exhibition based on the art described in the novel, which three pieces would you choose to feature and why? What would be the prevailing idea you would choose to link these pieces together?

3. Imagine Contrapposto is being adapted into a film. Who would you cast in the lead roles of Cricket and Olympia, both as young adults and in their seventies? What qualities would these actors need to capture the essence of the characters across their long lives?