Now, hold on a minute. If you are a boomer, or if you happen to be engaged to one, there's no need to storm off in an offended tizzy just yet. This isn't some comforting Big Chill we're talking about, nor a whimsical time capsule like Alice's Restaurant. Nay, nay. This is instead a document of contemporary middle-aged complacency, of laziness, of bloated tenure clogging up the machinery. To align one's sensibilities with it is to court futility and whiny emotional detachment. Regardless of one's age or generation, how cool is that?
Douglas throws open the gates of this hell as English professor and erstwhile successful author Grady Tripp. Dryly narrating the derailing of his own life, Tripp explains that it's been seven years since his last novel, Arsonist's Daughter, won awards and put him and his editor, Terry Crabtree (Robert Downey Jr.), on the map. The occasion for Crabtree's arrival in Pittsburgh, where the movie's action begins, is, ostensibly, "Wordfest," the university's annual celebration of scribes. But Tripp knows better, sensing that Crabtree -- himself at loose ends in the publishing world (where he doesn't fit into the new protocol, competence) -- is actually swooping in to peek at the novel Tripp's been promising him for years.
For kicks, Crabs (as he is known) has brought with him a sweet transvestite named Antonia Sloviak (Michael Cavadias), as well as her tuba. This distraction proves nearly adequate to dislodge Tripp from his misery over the departure of his much younger wife, Emily (Elisabeth Granli, in a photo), who bailed on him that morning. The motley threesome swiftly descends upon the opulent home of college chancellor Sara Gaskell (Frances McDormand) and her husband, English department head Walter (Richard Thomas). At the evening's fete, the complexity of these relationships begins to become clear. Tripp and Sara are having an affair beneath the oblivious nose of Walter; student Hannah Green (Katie Holmes) also fancies the old coot; and the celebrated author known simply as "Q" (Rip Torn) is, professionally speaking, a haunting reminder of everything Tripp is not but should be.
Lurking outside in the shrubbery is James Leer (Tobey Maguire, coasting), Tripp's star student, who has already completed his first novel. The thing about Leer, though, is that his creativity is not grounded. Thus the lad can't stop himself from living low and spinning absurd yarns about his own life, which is rich in entertainment trivia, some of it morbid (star suicides, when and how, alphabetically presented), some of it sentimental (he nearly bawls when faced with Marilyn Monroe's lonely jacket, a treasure hidden away by Walter). That jacket leads the professor and his pupil into trouble, as the Gaskells' protective dog tears into Tripp's leg, prompting Leer to shoot the cur.
Thus begins the pensive weekend, wherein Tripp drives around Pennsylvania with Leer and the dead dog, sharing his copious stash of dope, realizing that he never really knew his young wife anyway, and longing to once again be the "wonder boy" that Leer is obviously about to become. Toss in an amusing encounter with an angry bar patron (Richard Knox) who claims Tripp stole his car ("Do you owe him a book, too?" quips Crabs) and some clever asides about Errol Flynn's fetish for condiments, and there you go.
Not everything here is wretchedly, abominably unwatchable. In fact, it's quite nice to see A-list talent eschewing makeup for a more natural appearance. It's also pleasing that this film, for all its bumbling and lack of focus, boasts dramatically low stakes for a major studio release. It's not, for example, The Living But Somewhat Frustrated Novelist's Society, but something far looser. Unfortunately, none of these charms is adequate to stave off the blahs.
The main problem with Wonder Boys isn't a dearth of potentially poignant material or engaging dialogue ("Jesus, James! You make it sound like I'm in a Tennessee Williams play! I don't get spells!"), but rather that it's incredibly difficult to sympathize with Tripp, who only fulfills the first aspect of the movie's tagline, "Undependable, unpredictable, unforgettable." Once again, Douglas gives us a man whose life is crumbling (call it, perhaps, Falling Down 2: Trippin'), only this time, it's all his own fault. When Neil Young starts singing "Old Man," or John Lennon's "Watching the Wheels" is employed to assess the situation, they're both far too apt for comfort. He's not a bad man, Tripp (unless you consider adultery and distributing illegal drugs to minors, you know, bad), but one wishes that Hunter S. Thompson would come leaping in and smack that silly knit cap and those precious spectacles off his hazy noggin.
Late in the film, when Leer's fabrications have finally gotten his elder's goat, Tripp leans across a table and intones, "Don't expect me to feel sorry for you, because I don't know who you are." Back at you, professor. Ultimately, the only memorable sensation one takes away from this movie is a vague sense of Pittsburgh in gray. Wonder Boys is as detached and unfocused as a college pothead. And about as much fun.