The following version of this book was used to create this study guide: Chabon, Michael. Wonder Boys. New York: HarperCollins, 2002.

Grady Tripp is a man in his mid-forties. He lives in Pittsburgh, Pennsylvania and is a relatively acclaimed author. He works as a creative writing teacher at an unnamed college. For the past seven years, he has struggled to finish writing his next novel, entitled Wonder Boys. One day, Grady’s wife Emily leaves him after discovering that he has been having an affair. The same day that Emily leaves, Grady’s friend and editor Terry Crabtree arrives in town. The college is hosting its annual literary festival, WordFest. The first event of the festival is a reception at the home of spouses Walter and Sara Gaskell. Walter is the head of the English department, and Sara is the college’s chancellor. Sara is also the woman with whom Grady has been having an affair.

After Grady and Terry arrive at the Gaskells’ residence, Sara speaks to Grady privately. She informs him that he is pregnant and that Grady is the father. Sara is unsure whether or not she is going to keep the pregnancy. At the reception, Grady sees James Leer, an eccentric undergraduate student of his. Grady recognizes possible symptoms of depression and suicidal ideation in James. Grady soon feels somewhat protective of James, as Grady’s own father died of suicide. James loves old Hollywood movies. After everyone leaves the Gaskells’ house, Grady and James sneak upstairs to see Walter’s memorabilia collection. One item he owns is the jacket that Marilyn Monroe wore when she married Joe DiMaggio. Suddenly, the Gaskells’ pet dog attacks Grady, and James impulsively shoots the dog with a gun. Grady decides to put the dog’s body in the trunk of his car for the time being.

Later, Grady and James go to a local bar with Terry. Terry begins to make sexual advances towards James, and James appears to enjoy this interest. However, James becomes very intoxicated, so Grady lets him sleep on a couch in his house. Grady is surprised to find that James’ bag contains the Marilyn Monroe jacket, which James apparently stole. The next day, Emily’s father, Irving Warshaw, calls Grady and invites him to the family’s Passover Seder. Grady and James drive to the Warshaws’ home. Emily is among the family members in attendance, but she and Grady speak only briefly to each other. James becomes very drunk on wine and beer, so the Warshaws contact James’ parents (or possibly grandparents) to fetch him. James begs to be able to stay, but his request is denied. James accidentally leaves his bag behind, which contains a draft of a novel that James has written. Grady reads it and finds it fairly impressive.

Grady then drives back to his home and feels remorse for abandoning James. Grady enlists Terry’s help in covertly retrieving James. The three of them then return to Grady’s home, and Terry and James spend the night together. In the morning, the police arrive to arrest James for killing the Gaskells’ dog and stealing the Monroe jacket. Terry reads James’ novel and thinks that he should bring it to his publishing company. Terry then talks to Walter and persuades him not to expel James and not to press charges against him. Sara tells Grady that she is going to carry her pregnancy to term. Sara and Grady soon marry and begin a new life together.