Michael Chabon's outrageous novel Wonder Boys is about the weird and absurd world of writers. Professor and author Grady Tripp is a spaced out pothead blundering his way through life, like a fast moving powerboat motoring into port casting a wake that disturbs everyone and everything it passes. His link to two men in particular is the background for the lost weekend that changes his life forever.
Terry Crabtree, Tripp's long-time editor and friend, link up with a young, aspiring student writer named James Leer. Crabtree, about to be fired from his job as an editor has flown to Pittsburgh to attend WordFest, a writer's conference at Coxley College and on his flight has struck up an acquaintance with Miss Antonia Sloviak, a poorly disguised transvestite. Tripp is currently wrapping up an epic novel titled “Wonder Boys” and he teaches literary and writing skills at Coxley, where he has been having a five-year long affair with the Chancellor, Mrs. Sara Gaskell. Today his wife Emily has given up on their marriage, his third, and has walked out on him.
Disregarding the personal dramas unfolding in their lives, Tripp and Crabtree soldier on to a reception party with Miss Sloviak at the Gaskell's home before the WordFest lecture that evening. Tripp proceeds to get high smoking a joint in the yard when he spies Leer, his student and a talented but unrefined writer, about to commit suicide with a small caliber pistol.
The two return inside to the party where Tripp shows Leer the Yankee memorabilia collected by Sara's husband Walter, which includes the wedding coat Marilyn Monroe wore when she wed Joe DiMaggio. Walter is Tripp's department head and boss. After the two stay behind in the house as everyone moves on to the lecture on campus, Tripp is attacked by the Gaskell's blind dog, Doctor Dee, when the dog is shot and killed by Leer.
Going on a drug and alcohol spree and attending the lecture in a narcotic blur, both men soon pass out. Tripp manages to drive Miss Sloviak home and during the ride she transforms into Tony, a woman-to-be cross dressing guy. Later at the Hi-Hat, a funky, decrepit bar Tripp dances with Hannah Green, the pretty blonde co-ed renting out the spare bedroom of his house with a not so well disguised crush on him.
Everyone gets home safely, but Tripp discovers the Monroe matrimonial jacket is now in the knapsack of Leer, his Galaxie 500 has a dent in the hood shaped like a butt, and he has a wicked hangover. Tripp takes Leer for a ride to Sara's where Grady neglects to mention to her he has her dead dog in his trunk or Monroe's coat in the knapsack.
They move on to celebrate Passover at his in-laws the Warshaw's in Kinship, PA. Emily won't talk to him, her sister Deborah is cynical, quirky, and bitter, Philly is a bit of a goof and a loose screw, and all the while the parents are kind but in denial of the impending break up. The three siblings are of Korean descent having been adopted as children. Tripp errs when confiding in Deborah about his mistress expecting his child. He finds Leer to be unreliable regarding the truth about his past life. Leer's parents come to pick him up when he becomes ill from Passover Wine, smoking pot, and playing beer pong. Tripp leaves when Emily confronts him after she has learned of his secret from her sister. As he leaves he runs over Mr. Grossman, a nine-foot long boa that has escaped from the Warshaw home and puts the remains in the trunk.
When Tripp returns home he finds the house is a mess and an ex-student of his named Jeff viewing the television without sound. Hannah is reading his unfinished opus of a novel. She critiques his novel and lifestyle. He rouses Crabtree in an effort to retrieve Leer from his uncertain situation. Leer willingly returns to Tripp's house, as Doctor Dee is put in his bed as a decoy. Leer spends the night with Crabtree. In the morning a police officer comes to bring Leer before the Gaskell's to explain his role in the missing dog and coat. Tripp assures the officer that as soon as he gets his car out of the shop the coat will be returned, but in reality, the car has disappeared, taken away by the original owner, an ex-boxer named Pea Walker. Tripp and Crabtree borrow Hannah's car to track down the Galaxie 500 and the coat taking Tripp's manuscript with them. They find the car as Tripp hurls Mr. Grossman's corpse at Walker and a tuba case at another tough guy, then lose all but a few pages of the text of Tripp's novel, and then return to the school for the closing ceremonies.
Leer is outside the chancellor's office while a conference with his parents is occurring. Crabtree tells those assembled he will publish Leer's first novel The Love Parade. All is forgiven of him when the coat is returned while Tripp is now the scapegoat for all that has transpired. Tripp falls over a balcony rail and is hospitalized. His novel and car are gone, his marriage ruined, his affair and unborn child exposed, his job is in jeopardy, and his friends are distancing themselves from him. Even Hannah has taken up with Jeff. After checking himself out of the hospital, he decides that it is now or never to get his life straightened out.
This report prepared by David Fletcher