Picaresque novels are damned difficult to adapt to the screen; such romps are, by nature, episodic and don't follow the emotional arcs people expect from commercial films. What's needed to pull them off is a blazing central performance, a lovable rogue the audience can care about and root for, such as Albert Finney in Tom Jones. Alas, Michael Douglas, getting a chance to stretch in this adaptation of Michael Chabon's novel of the same name, just doesn't have the punch to bring the character of Grady Trippa ganja-loving, ex-"boy wonder" novelist turned college teacherto rollicking life. (Worst offense from an acting standpoint: Douglas tokes and tokes and never seems to get, well, stoned.)
Douglas' morose, lumpish performance is especially ironic given the presence, in a woefully small part, of Rip Torn as a highly successful commercial novelist who's on campus for a weekend literary festival. In a black goatee and dark suits, Torn comes off like Satan's older, more successful brother. Had he been cast as Grady Tripp, Wonder Boys might have had some juice in it, but Torn is, unfortunately, merely a great actor and not a bankable movie star like Douglas.
The problem with the lead role is particularly acute because Grady Tripp's misadventures, over the course of a long lost weekend in Pittsburgh, are mostly undertaken in the company of his anomic, highly talented writing student James Leer (an effectively spooky Tobey Maguire). It's one of those classic setups wherein the student and teacher supposedly teach each other about life, but really it's just two morose guys galumphing around western Pennsylvania in the rain and snow, with the older man often garbed in a frilly pink bathrobe for a touch of endearing eccentricity.
Their weekend is filled with car thefts, dope, liquor, valuable stolen movie-star memorabilia, and other putatively funny goings-on. The bits only serve to obscure and isolate Wonder Boys' one deeply felt performance, that of Frances McDormand as Sara Gaskell, chancellor of the unnamed college, wife of the English-department chairman, and lover of Grady Tripp. McDormand's performance is so sincere and unaffected that she makes you want to scream, "Dump that loser, now!" As McDormand's husband, Richard Thomas is delicious in his few scenes as a baseball-obsessed professor who blathers on about the "mythopoetics" of the DiMaggio-Monroe marriage. Robert Downey Jr., curiously subdued, also gets in some good licks as Grady's book editor, saying he might be on the way out because his publishing company now wants "competent employees."
But the little touches of academic and publishing satire are too few. How director Curtis Hanson, who brilliantly oversaw the adaptation of James Ellroy's L.A. Confidential, could have failed to bring any life to Chabon's novel is Wonder Boys' biggest wonder.