Is Wonder Boys the Best-Ever Onscreen Depiction of a Writer?

Pete Townshend of The Who once praised Bob Dylan’s “Like a Rolling Stone” because each verse means something different to the listener as they age. “It’s quantum,” he said. I feel similarly about the 2000 film adaptation of Michael Chabon’s Wonder Boys. On my first viewing, I (over)identified with James Leer, a moody, precocious undergraduate played by a wan Tobey Maguire. Now I see myself in Grady Tripp (Michael Douglas), the addled professor wrestling with a novel manuscript, beset by problems of his own creation, and in need of a good haircut. A recent re-watch also cemented my belief it’s the best depiction of a novelist ever put to film.

A quick summary of the plot. Set on a university in or near Pittsburgh, the film opens with our shaggy prof teaching a student workshop ahead of the campus’s weekend-long literary festival. Grady’s wife has recently left him, and his mistress Sara Gaskell (Frances McDormand) informs him she’s pregnant with their baby. Complicating things further, she’s the university chancellor, and her husband chairs the English department. He’s also juggling the romantic overtures of his student Hannah Green (Katie Holmes), who rents his spare bedroom; the obsequious James Leer, an emo agent of chaos; and a visit by his hard-partying agent Terry Crabtree (Robert Downey Jr.), whose own floundering career could be saved by Grady’s long-awaited follow-up to his breakthrough The Arsonist’s Daughter. Said follow-up has metastasized past 2600 pages, with no end in sight. Oh, and a Little Richard lookalike keeps trying to steal Grady’s car.

If some of this sounds very 90s, the film premiered amid a run of novels on the sex lives of college professors: Francine Prose’s Blue Angel, David Lodge’s Thinks…, and Chip Lambert’s sections in Franzen’s The Corrections. Wonder Boys avoids the predictable teacher-student liaison in favor of Grady and Sara’s relationship, making it one of the few Hollywood films to center middle-aged romance. The director Curtis Hanson also wisely invoked the Frances McDormand Rule of Filmmaking: If you want to improve your film, cast Frances McDormand.

Hanson was a protean talent with a knack for literary adaptations. He elevated genre fare like L.A. Confidential (James “I Love Dogs” Ellroy), In Her Shoes (Jennifer “I Hate Franzen” Weiner), and The Bedroom Window (Anne “No Nickname” Holden). That last film, a generic potboiler, is buoyed by the reliably excellent Isabelle Huppert and Elizabeth McGovern.

For Wonder Boys, Hanson and screenwriter Steve Kloves adhered closely to the source material, lifting dialogue and preserving the structure. They wisely cut the Passover Seder scene, which the author admitted was torturous to write, and slimmed down Grady’s proud corpulence. (Hollywood.) Where Chabon’s exuberant prose is stuffed with asides, digressions, and flashbacks, Hanson’s direction is restrained: No zooms, establishing shots, slow motion, or Dutch angles. The $55 million production, shot almost entirely at eye level, has a cozy realism.

As for the look of the film, it’s pissing rain, icy sidewalks, and what Denis Johnson called “clouds like great grey brains.” The horizon’s full of industrial smokestacks and cement overpasses. In other words, an ideal setting for staying in. And Hanson puts care into his interiors. Classrooms of dark wood. Hallways of marmoreal grandeur. A greenhouse one character likens to heaven. And Tripp’s two-story craftsman—Jesus Christ. It’s an AD Open Door for English majors.

What makes Wonder Boys so good on writing? Take the opening. After a credits sequence set to Dylan’s “Things Have Changed,” for which the future Nobelist won an Oscar, we find Grady reading James Leer’s story aloud to those workshop students. Then Tripp’s voiceover jumps in to provide commentary about the story. That is, he interrupts his reading of another writer’s work to talk to us, the audience. Brazen, egocentric, and unabashedly writerly.

The film is chock full of moments just for writers. When Crabtree asks about James Leer’s novel manuscript, Tripp says, “It’s good. It’s very good. It’s… true.” This may sound slight, but in our age of hyperbolic blurbing its simplicity is practically zen. Who wouldn’t want that reaction to their work? And did I mention that Grady looks into the middle distance when he says it?

Or take the references to Edgar Allan Poe and “The Cask of Amontillado.” Why cite a tale of one man’s murderous revenge over an unspecified insult in a movie of comparably low stakes? It’s not like novelists are more prone to envy and insult than others… (I’m fucking with you. Of course they are.)

Hanson also understands how boring the act of writing is 99 percent of the time, and acknowledges this when Grady first sits at his typewriter. Five minutes into his session he and the camera both pass out.

And the climax! Due to a madcap confluence of events, Tripp loses the sole copy of his epic novel to the Monongahela River. I’ve watched the scene a dozen times and it still gives me acid reflux.

The film is not without problems. It’s very white and very male. Hannah’s published two stories in The Paris Review, but Crabtree ignores her? And the James Leer character shouldn’t work at all. He’s a pathological liar hellbent on alienating his fellow students, who (surprise!) hides that he comes from money, and who shoots a dog. There’s also the lazy correlation between Grady’s weed consumption, his hypergraphia, and his inability to fix his life. While I can’t write with even a G&T in my system, I’m pretty sure Pynchon wrote Gravity’s Rainbow stoned.

There’s also the film’s tepid reception. It bombed at the box office. Producers blamed the studio’s marketing, but what should they have done? A roadshow tour of MFA programs? It’s tough to imagine a film with Tennessee Williams and Jean Genet jokes cracking $100 million domestic. The producers probably hoped for a bigger awards boost, but in this century only two actors have won Oscars for playing writers, and real ones at that: Nicole Kidman (The Hours) and Philip Seymour Hoffman (Capote).

But Wonder Boys succeeds. It succeeds because it failed, and because at heart it’s about failure. And writers are connoisseurs of failure.

Consider the ending. Grady Tripp loses his manuscript and is ultimately liberated. His grand project, the bedrock of his identity, had been an albatross all along. Without the anchor around his neck, Tripp can finally change, and he ends up happy with Sara Gaskell.

This always struck me as darkly funny. In the last shots, we see the voiceover become the novel Grady has just finished writing—one of those metatextual winks screenwriters love and audiences cringe at. But there’s no indication the book is any good, or that he’ll try to publish it. Grady’s partner and infant child are the true source of his happiness, not writing. Wonder Boys, in its litany of failure, knows it’s foolish to think otherwise, even though it’s a lesson most writers never learn (or wish to). That’s quantum.