Wonder Boys by Michael Chabon

Discussion questions

  1. Grady Tripp was orphaned at age four. He has no memories of his mother and very few of his father. While he was raised by his grandmother, the childhood figure who seems to have most influenced him is Albert Vetch, who wrote short stories under the pseudonym August Van Zorn. How has Vetch influenced Grady’s outlook and life choices?
  1. What is the relationship between Grady and Terry Crabtree? What draws them to each other and how has their friendship evolved over the years?
  1. Grady doesn’t suffer from writer’s block in the traditional sense of not being able to start writing; rather, he cannot seem to stop adding to his long-awaited novel. Why does he struggle to bring his lengthy book to a conclusion? What does the book symbolize to him, and why is he afraid to show it to anyone?
  1. How would you describe Emily, Grady’s wife? What does the way she leaves him (avoiding confrontation by writing a note) say about her?
  1. Hannah Green, Grady’s student and boarder, takes the manuscript for Wonder Boys without his permission, and is the first person to read it. (Before the book starts, Grady had given Emilya short portion to read.) What does her reaction indicate about Grady’s novel and about her attitude towards him?
  1. The Warshaw family has an interesting and somewhat dysfunctional dynamic. Irv and Irene’s only biological child, Sam, drowned as a teenager; their eldest daughter, Deborah, is thrice-divorced; Irene complains of the hardships of living in the remote house to which she and Irv have retired while he spends much of his time in his laboratory to avoid her; and Phil’s wife Marie, a recent convert to Judaism, is the most religiously observant member of the family. What lessons are readers meant to draw from the Warshaws? What are Grady’s feelings towards the various family members?
  1. What is the significance of Grady’s attendance at the Warshaw family Passover Seder? Why does he bring his student James Leer?
  1. Grady often mentions the “midnight disease” that affects writers. What does his physical state tell us about his creative struggles?
  1. Grady often goes places where he is either intruding or not welcome — the memorabilia closet in the Gaskells’ bedroom, the Warshaw home, James Leer’s house — and it turns out the car given to him as repayment of a debt was in fact stolen. How does his frequent trespassing affect his creativity?
  1. Many characters do not think of the consequences of their actions: James Leer when he steals Marilyn Monroe’s jacket, Crabtree when he picks up and then abandons Miss Sloviak, and Grady in manyinstances. Is this lack of forethought tied to their identity as artists or work in a creative realm?
  1. Marilyn Monroe’s jacket figures heavily in the narrative, but other clothing items are mentioned: James’s old beat-up raincoat, the suit Crabtree wears to class when he and Grady meet, the odd purple dress and later the bathrobe that Grady’s sister-in-law Deborah wears to the Seder, Sara Gaskell’s severe wardrobe (“shapeless tweed suits that spanned a brilliant spectrum from oatmeal to dirt”), and the plush bathrobe Grady always wears when writing. How do the garments of the novel tell their own stories?
  1. On several occasions, James lies about his parents and background. Is he a dishonest person or merely a creative storyteller? Why is he so drawn to old movies and particularly to actors who killed themselves?
  1. What purpose does Vernon Hardapple serve in the novel?
  1. Chabon creates memorable visual images in this book, but also describes many smells, sounds, tastes, and textures in detail. Which descriptions stand out? How do these unusual pictures enhance the narrative?
  1. What does the tuba that Grady and Crabtree pick up at the airport symbolize? Why does Grady keep it in his car trunk and lug it from place to place, including his walk through the rain after being attacked by Walter Gaskell with Joe DiMaggio’s baseball bat? Why does he abandon it when Sara picks him up in her car?
  1. Grady claims that he falls in love easily, as if this were a character trait rather than a choice. Is this a believable claim? In many respects he seems to have little moral stamina, but he resists Hannah’s advances. How would you describe his character in ethical terms?
  1. During WordFest the esteemed novelist Q. gives a lecture about the doppelgänger. What is the function of the doppelgänger in this novel? Which characters serve as doppelgangers? Which objects?
  1. What is a “wonder boy”? To which characters in this book could the term apply?

About the author

Michael Chabon was born in Washington, D.C. in 1963 and spent part of his childhood in Columbia, Maryland. When his parents divorced in 1975 his father moved to Pittsburgh and Chabon was raised primarily by his mother. He attended Carnegie Mellon before transferring to the University of Pittsburgh, where he graduated with a BA in English literature in 1984. He earned his MFA in writing at the University of California at Irvine.

In 1988, his master’s thesis, the novel The Mysteries of Pittsburgh, was published to rave reviews and became a bestseller.Chabon struggled to complete his second novel, eventually losing half of his advance to his wife in their divorce and, after five years, giving an unwieldy manuscript, “Fountain City” (unpublished to date, although excerpts can be found on Chabon’s web site), to his publisher, who refused it. His next novel, Wonder Boys (1995), was highly successful andwas adapted into a film starring Michael Douglas, Frances McDormand, Tobey Maguire, Robert Downey Jr., and Katie Holmes in 2000.

His other novels are The Amazing Adventures of Kavalier & Clay (2000), which won the Pulitzer Prize;The Yiddish Policeman’s Union(2007), which won Nebula and Hugo awards; Gentleman of the Road: A Tale of Adventure (2007, previously serialized); and Telegraph Avenue (2012).Other works include the short story collections A Model World (1991) and Werewolves in Their Youth (1999), the young adult novel Summerland (2002), the novella The Final Solution (2004), the essay collection Maps & Legends: Reading and Writing Along the Borderlands (2008), the memoir Manhood for Amateurs: The Pleasures and Regrets of a Husband, Father and Son (2009), and the children’s picture book The Astonishing Secret of Awesome Man (2011).

Chabon was inducted into the American Academy of Arts and Letters in 2011. He has contributed to The New York Review of Books, Details, and The New Yorker, and has written the essay “Secret Skin: An Essay in Unitard Theory” for the Metropolitan Museum of Art exhibition book Super Heroes: Fashion and Fantasy. He's also worked as a screenwriter on Spider-Man 2 and John Carter, the latter film adapted from the work of one of Chabon's literary heroes, Edgar Rice Burroughs.

Hewas married to the poet Lollie Groth from 1987 to 1991. He married writer Ayelet Waldman in 1993; they have four children and live in Berkeley, California.