Wonder Boys is a 2000 feature film based on the 1995 novel of the same title by Michael Chabon. Directed by Curtis Hanson, it stars Michael Douglas as professor Grady Tripp, a novelist who teaches creative writing at an unnamed Pittsburgh university. He has been unable to finish his second novel, his young wife has left him, and he is sleeping with his boss’ wife (Frances McDormand), who is also the Chancellor of the university. Grady's editor (Robert Downey Jr.) is in town to take a look at the book and becomes interested in a book that a student (Tobey Maguire) from Grady's creative writing class has just completed.

Wonder Boys was filmed in Pittsburgh, Pennsylvania, including locations at Carnegie Mellon University, Chatham College, and Shady Side Academy. Other Pennsylvania locations included Beaver, Rochester and Rostraver Township. The film reunited Katie Holmes and Maguire, who had appeared together three years earlier in The Ice Storm.

After Wonder Boys 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.