Professor Grady Tripp (Michael Douglas) is the author of a very successful novel who is trying to write another, but is struggling with writer's block because of the success of his past and the weight of his future. His wife announces she's leaving him and he also manages to get the chancellor (Frances McDormand) pregnant--and her husband chairs Grady's department. In the meantime, he and his student James Leer (Tobey Maguire) are trying to find a jacket once owned by Marilyn Monroe, and a nubile college girl, Hannah Green (Katie Holmes) boarding with Grady has a crush on him. His literary agent/editor Terry Crabtree (Robert Downey, Jr.) pressures him to finish a novel seven years in the writing. James stirs paternal feelings in Grady and raises homo-erotic urges in Terry, who is accompanied by a transvestite. Terry is the highlight of the cast, stealing many scenes and is funny in a loud role. He spends a night with James and wants to publish his book, too. Grady's most gifted writing student is a pathological liar and also a pot head like himself. His peculiar behavior launches the professor on a odyssey of self-discovery and many misadventures. It all takes place over a long weekend of debauchery of one form or another.
Adapted from Michael Chabon's novel and distilling it to its amusing and melancholy essence, screenwriter Steve Kloves and director Curtis Hanson have created an unsentimental and darkly funny tale. These characters may be down on their luck, but they don't feel sorry for themselves. The cast is exceptional, with Maguire in a great performance and Downey at his manic best. The ending of "Wonder Boys" is a little too trite, but after everything these characters go through, a happy ending seems appropriate. Grady speaks the last lines: "As for me, I lost everything: my wife, my book, my job, everything that I thought was important. But I finally knew where I wanted to go. And now I have someone to help me get there."
