Many creative people strive for perfection, especially in their first true work. Amongst other things, "Wonderboys" explores what might happen if perfection was actually achieved. Professor Grady Tripp, (Michael Douglas), is a lecturer in Creative Writing whose first novel was a critical success. That was seven years ago and he is still working on his follow-up work. Many of his students admire him, he smokes a lot of dope, is having an affair with his boss's wife and occasionally becomes unconscious for no apparent reason. He is a man without ambition, coasting through life. Mildly jealous of those who still show a passion for life, he becomes entangled in the world of one of his students, James Leer (Toby Maguire), who manages to show even less passion for existence than the professor.
James is recognised by his peers as being both weird, in an introverted semi-postal way, and yet more talented than the rest of them put together. Their half-hearted attempts to pull him down to their level are ignored, leaving James mired in his own depressing view of reality. It's even possible that he has chosen Professor Tripp as his mentor; somehow hoping that someone, almost as disconnected from reality as himself and yet capable of publishing a seminal work, might be able to show James a way through the maze. In a way, this is exactly what happens, but not in any sort of linear fashion. While the film largely follows the professor's point of view, James is often the one our sympathies are drawn to. He lies constantly, in such a creative and self-consistent way, that no one truly knows what is going on in his life. It's as if he is testing plot lines on an unsuspecting audience in an effort to hone his story-telling skills.
Despite concentrating on these two characters, the film is an ensemble piece, chock full of minor but lovingly crafted people that, for the most part, we'd love to get to know better. Tripp's Editor, Terry Crabtree, (Robert Downey Jr.), is an unsuccessful man who has little confidence but an irrepressible energy; seemingly determined to dance until someone shuts off the stage lights. Tripp's student boarder, Hannah Green, (Katie Holmes), is one of the saner characters in the film. She feels a natural admiration for her teacher; a feeling which she tries to promote into a more adult relationship following the off-screen departure of his young wife. How any flesh and blood man could reject Hannah's scantily clad advances is beyond my understanding, nevertheless that's exactly what Grady does.
The dean of the college, Sara Gaskell, (Francis McDormand), who is also Professor Tripp's girl friend, is married to the Dean of English, Walter Gaskell, (Richard Thomas), a clueless boor who obsesses over Marilyn Munroe and Joe DiMaggio. Sara truly loves Tripp and yet sees him for the rudderless ship he is. She is very centered, confident and assertive; firmly placing the emotional ball in Tripp's court. He must decide what he wants or loose the only thing he still seems to enjoy in his post novel depression. As you might imagine, when all of these interesting people are thrown into the mix; along with a murdered dog, stolen memorabilia, an enormous novel that can't find an ending and a determined ex-jockey car thief possibly named Vernon; nobody can predict the result. The only certainty is that it will make for an interesting ride. As Director Chris Hanson says, "All the characters are disparate and yet similar in certain ways. They're all mucking around trying to figure out their lives, just like we are - only they're more amusing along the way."