Wonder Boys is a 2000 comedy-drama film directed by Curtis Hanson and written by Steve Kloves. An international co-production between the United States, the United Kingdom, Germany, and Japan, it is based on the 1995 novel of the same name by Michael Chabon. Michael Douglas stars as professor Grady Tripp, a novelist who teaches creative writing at a university but has been unable to finish his second novel.
The film was shot in Pittsburgh, Pennsylvania, including locations at Carnegie Mellon University, Chatham University, University of Pittsburgh, and Shady Side Academy. Other Pennsylvania locations included Beaver, Rochester and Rostraver Township. After the film failed at the box office, there was a second attempt to find an audience with a new marketing campaign and a November 8, 2000, re-release, which was also a financial disappointment. Despite this, the film received three Academy Award nominations at the 73rd Academy Awards, including Best Adapted Screenplay, winning Best Original Song for Bob Dylan's "Things Have Changed".
Plot
Professor Grady Tripp is a novelist who teaches creative writing at an unnamed Pennsylvania university. He is having an affair with the university chancellor, Sara Gaskell, whose husband, Walter, is the chairman of the English department in which Grady is a professor. Grady's third wife, Emily, has just left him, and he has failed to repeat the grand success of his first novel, published years earlier. He continues to labor on a second novel, but the more he tries to finish it the less able he finds himself to invent a satisfactory ending. The book runs to over 2500 pages and is still far from finished. He spends his free time smoking cannabis.
Grady's students include James Leer and Hannah Green. Hannah and James are friends and both very good writers. Hannah, who rents a room in Grady's large house, is attracted to Grady, but he does not reciprocate. James is enigmatic, quiet, dark and enjoys writing fiction more than he first lets on.
During a party at the Gaskells' house, Sara reveals to Grady that she is pregnant with his child. Grady finds James standing outside holding what he claims to be a replica gun, won by his mother at a fairground during her schooldays. However, the gun turns out to be very real, as James shoots the Gaskells' dog when he finds it attacking Grady. James also steals a very valuable piece of Marilyn Monroe memorabilia from the house. Grady is unable to tell Sara of this incident as she is pressuring him to choose between her and Emily. As a result, Grady is forced to keep the dead dog in the trunk of his car for most of the weekend. He also allows James to follow him around, fearing that he may be depressed or even suicidal. Gradually, he realizes that much of what James tells him about himself and his life is untrue, seemingly designed to elicit Grady's sympathy.
Meanwhile, Grady's editor, Terry Crabtree, has flown into town on the pretense of attending the university's annual WordFest, a literary event for aspiring authors. In reality, Terry is there to see if Grady has written anything worth publishing, as both men's careers depend on Grady's upcoming book. Terry arrives with a date whom he met on the flight, a trans woman named Antonia Sloviak. The pair become intimate in a bedroom at the Gaskells' party, but immediately afterward, Terry meets James and becomes infatuated with him, and Antonia is unceremoniously sent home. After a night on the town, Terry and James semi-consciously flirt throughout the night, which eventually leads up to the two spending an intimate night together in one of Grady's spare rooms.
Tired and confused, Grady phones Walter and reveals to him that he is in love with Sara. Meanwhile, Walter has also made the connection between the disappearance of the Marilyn Monroe memorabilia and James. The following morning the police arrive with Sara to escort James to the Chancellor's office to discuss the ramifications of his actions. The memorabilia is still in Grady's car, which has conspicuously gone missing. The car had been given to him by a friend as payment for a loan, and, over the weekend, Grady has come to suspect that the car was stolen. Throughout his travel around town, a man claiming to be the car's real owner repeatedly accosted Grady. He eventually tracks the car down, but in a dispute over its ownership, the majority of his manuscript blows out of the car and is lost. The car's owner gives him a ride to the university with his wife Oola in the passenger seat, along with the stolen memorabilia.