Even This Late It Happens: 20 Years of Wonder Boys

Michael Douglas in Wonder Boys (2000) | Paramount
Paramount Pictures

Wonder Boys is a story told in earth tones and academic textures: Cashmere turtlenecks, warm russet bookshelves, dirty snow lining campus sidewalks, a faded pink chenille robe. Dante Spinotti’s cinematography is a late-winter mood board without bright colors, depicting spring semester in Pittsburgh as scattered flurries and driving around in a 1966 Ford Galaxie with the heat on, passing chimneys of factory smoke and lights reflected on a polluted river. 

Slick neo-noir L.A. Confidential made Curtis Hanson into a household name in his early 50s and gets most of the glory; but the late filmmaker’s Wonder Boys, released three years after that, is musty and lived in. It’s a movie that keeps on growing—not taller, but deeper, like tree roots—long after you’ve first seen it. The narrative is one of writers writing, some of the most self-important work there is, done by people who believe their imaginations worthy of a paycheck and who’ll suffer eternally on account of all that time spent in their own heads. 

It’s simultaneously a tale dealing in second chances and second-act epiphanies—most of the players here are either midlife, already knee-deep in careers, habits, and marriages, or at the very least schlepping around the emotional gravitas of someone twice their age. The film’s themes are also reminiscent of a Mark Strand poem I read aloud at my mother’s wedding to my stepfather (who got married in their 60s). “Even this late it happens: the coming of love, the coming of light,” the verse begins.

It’s difficult to make a movie about people who sit and write because it’s not terribly entertaining business. Hanson navigates around this by focusing on the details of campus life, the delicate ecological balance between teachers and colleagues and students, February weather and the pathetic fallacy. The New York Times’ A.O. Scott wrote in his review that Hanson’s film was “like a George Cukor movie with a bad head cold—slow, muffled and vague.” In other words, a screwball comedy without any of the screwiness; one “slowed down,” as Roger Ebert phrased it in his four-star review, to real life speed.

Despite favorable critical consensus, it comes as small surprise that a movie bent upon a meandering, aimless plot (so described by Hanson himself) was a flop at the box office when it dropped in February of 2000. Paramount admitted they mishandled the initial rollout, and in a surprising move the studio gave the box office failure a second shot, rereleasing it that November with a new marketing campaign emphasizing the ensemble cast. Sadly, it was a financial disappointment once again. 

In an interview with Amy Taubin for the Village Voice, Hanson explained of his film’s advertising, “The very things that made Michael [Douglas] and I want to do the movie so badly were the reasons it was so tricky to market. Since films go out on so many screens at once, there’s a need for instant appeal. But Wonder Boys isn’t easily reducible to a single image or a catchy ad line.” 

A “wonder boy,” by definition, is a popular or successful person—a term Hanson likely identified with on the heels of L.A. Confidential. But in some sense, Wonder Boys feels like a natural next step following that kind of late-in-life hit: a picture about an artist who’s terrified of not living up to his first success, tormenting himself into perpetual writer’s block.


Wonder Boys was adapted for the screen by Steve Kloves while remaining faithful to Michael Chabon’s somewhat grittier 1995 novel of the same name. Three men cling to the story’s corners: Grady Tripp, James Leer, and Terry Crabtree; an old writer, a young one, and an editor. (Father, son, holy ghost.) Grady is Michael Douglas at his gentlest and most gentlemanly, habitually stoned and observing the things that happen to him through a woozy protective layer and little brown glasses that sneak down his nose. He’s a creative writing professor at an unnamed Pennsylvania university, and James studies under him because he read Grady’s The Arsonist’s Daughter, a literary triumph published seven years earlier. It made James want to become a writer himself. 

James is young-20s Tobey Maguire, delicate and effete with pale skin and a clerical collar, described alliteratively by Grady as the “sole inhabitant of his own gloomy gulag.” He can list off every old movie star who’s committed suicide alphabetically and remembers precisely how they did it. He’s a lot of fun at parties. “Most young actors have a nervousness or a need to do something when they’re on camera,” Douglas said of his co-star. “Tobey has the ability to exist—to truly exist, at a truthfulness that you don’t see except in actors like Humphrey Bogart.”

Professor Tripp hasn’t published a follow-up to the breakout book that secured him tenure. Not yet. His dogged editor Crabtree is played by Robert Downey Jr., oozing flamboyant moxie in a Yankees cap and putting the dour writer types to shame. “Crabs” comes to Pittsburgh under the guise of WordFest, a college-sponsored publishers’ weekend; but really, he’s hungry for news of Grady’s second novel. It’s about done, but still requires “some tinkering,” Grady claims. We all lie to our editors. Grady has been lying to his for a very long time. 


Just as Grady isn’t your typical leading man—more shlubby than studly, likeable but lackadaisical—the relationships between the people in this story aren’t traditionally cinematic; more like you’ve stumbled into the room and surprised them. When we first meet Grady, we hear about Emily, the beautiful young wife who walked out on him that morning, yet she turns out to be a red herring, a person we never actually meet. Grady’s pretty student Hannah Green (Katie Holmes, the last person you’d expect to find here) rents a room in his house and flirts recklessly—but although she wants to sleep with her teacher, she’s a red herring too. He doesn’t want Hannah. He doesn’t even consider her. 

Grady’s romance is with the age-appropriate Sara Gaskell, played by a formidable Frances McDormand. She’s the university chancellor and married to Walter, chair of the English department—technically Grady’s boss. Grady and Sara’s affair isn’t salacious, just two people who’ve accidentally fallen in love with each other. When they get upstairs alone at a party—one to celebrate WordFest’s kickoff, held annually at the Gaskell’s house—they fall onto a bed and collapse immediately in each other’s arms, an intimacy years in the making. He lays on top of her and she reveals she’s pregnant. 

“Don’t you think there’s no way?” she asks him of having their baby, and before he can answer fully she adds, “Fuck you for saying that there’s no way. ’Cause there could be a way, Grady.”

Although she pleads his name like a little girl, Sara is Grady’s equal. 

“With Wonder Boys, the thing that hooked me with that was that she was a 43-year-old woman married to one person and pregnant with someone else’s child,” McDormand told Moviemaker Magazine of a role she assumed somewhat skeptically. “And the film wasn’t about her character, it was about the male protagonist, but that was enough of a conundrum to keep it interesting for me. And to Curtis Hanson’s credit, he shaped a performance out of me.”

Sara forgives Grady for not knowing what he wants, letting him off the hook again and again—not because she’s weak, but because she can tell he needs the weekend to decide about the baby. It’s not often you see someone as forgiving as Sara on-screen, at least a character who isn’t also a cuck or a victim or the heroine who will later find someone who truly appreciates her and dump this loser. She doesn’t want to dump Grady. 

Grady is too busy with James to reckon properly with Sara because James has shot and killed Poe, Sara and Walter’s dog, with his little cap gun. The dog murder happens at the WordFest party after James steals the jacket Marilyn Monroe wore on her wedding day to Joe DiMaggio. It’s Walter’s prized possession, kept in a locked safe, but James liberates it because it looks “lonely.” 

Describing this plot feels somewhat like outlining the chaotic darts and dashes of a Kandinsky painting, but watching the film is soothing, more like rain pattering on a brittle windowpane. Poe was shot because he was attacking Grady, you see: he sensed Grady was having an affair with his owner’s wife and took a bite out of his ankle for good measure. James was trying to defend his teacher from a pup well-versed in sexual tension. No one’s motivations are cruel, just human. 


I remember my own early 20s, when marijuana still held a transformative power. My friends and I would get stoned and sit around and talk or watch Planet Earth and the iTunes Visualizer for hours. What Wonder Boys presumes is that these kinds of hangouts can linger on into adulthood. This interpretation is not strictly realistic, of course, because Grady mostly sucks on joints all day to dodge life’s drudgery. But it feels cozy, alongside the romantic notion of intellectual vigor that’s rewarded with a job allowing a person both freedom and steady pay—a job that can be done easily under the influence, no less. I’m not sure that happens anymore, for teachers or writers or even most Americans. Twenty years ago when Wonder Boys hit theaters, the internet was but a fledgling concern, no streaming services or Twitter to distract from creative pursuits. Imagine how much writing they must’ve gotten done. 

Writing speed is a comical point of pride in Wonder Boys. The bearded, pompous “Q”—another teacher in the school’s English department, so self-assured he requires but a single letter—finishes a book every 18 months. And James is a prodigy, churning out stories in an afternoon. He’s just finished a book over Christmas break. While Grady’s first book won him the PEN Award, he can no longer keep up; this is an age of high demand, where prolific is what matters. If you don’t write it, someone else will, and if you write it, they’ll ask you what’s next. 

Grady’s been working on his follow-up novel for years, a book that is now over 2,000 pages single-spaced. He keeps them locked in a drawer because he knows they’re bullshit. He certainly doesn’t want Crabtree getting hold of them; that incorrigible editor, prowling lustily about town for not just men, but new talent. 

(I sometimes wonder how my peers find the time to tweet clever observations all day, maintain the relationships they so often post about, and write thousands of words worth publishing. Grady certainly could never.)

Michael Chabon was an expert on the literary sophomore slump. After publishing his first novel, The Mysteries of Pittsburgh, he started on a follow-up called Fountain City and spent 5 ½ years writing it before giving up amidst claims he felt the unfinished tome “erasing me, breaking me down, burying me alive, drowning me, kicking me down the stairs.” When Chabon finally got the courage to abandon the thing, he began Wonder Boys and was done a zippy seven months later. Grady is blatantly based on Chabon himself.

The film’s characters speak like they’re in a novel, and much of the script is lifted straight from Chabon’s verbiage. Grady narrates in voiceover, referring to everyone by their first and last name and saying things like “you could stand him up in the garage next to the snow shovels and he’d be all right” when James gets too drunk. Grady and Crabtree—like a pair of naughty boys long past their expiry dates still pulling pranks—even play a game wherein they invent novelistic backstories for random passersby, which is how they come to meet “Vernon Hardapple” (more on him later). 

James is likewise constantly inventing, a pathological liar who gives Grady phony information about where he lives and what his parents do. No one knows his real story until Grady reads the book he finished over Christmas, The Love Parade, a novel he describes to Crabtree as “true.” The highest compliment. After that, the teacher goes from seeing James as a problem to seeing him as a student worth rescuing, a talent worth fostering. 

In turn, James shows Grady the truth about himself. “‘It was a shock to see him shuffling into the room like an aging prize-fighter. Limping. Beaten,’” Crabtree reads aloud from a freshly-scribed page on James’ typewriter when they visit his house. “Sound like anyone we know?” 

The teacher has given up, having what he calls “episodes” wherein he gets so dizzy he passes out, usually after imbibing on weed or pills. Grady was James’ hero, and now? “His heart,” Crabtree continues reading, a tad ashamedly, “once capable of inspiring others so completely, could no longer inspire so much as itself. It beat now only out of habit. It beat now only because it could.” Grady’s expression is vague, but you can tell he’s considering it. 


The ensuing evening is one of small but essential revelations, set to Bob Dylan’s centerpiece track off 1997’s Time Out of Mind: “Not Dark Yet,” a song about when life grows exhausting. “Behind every beautiful thing, there’s been some kind of pain,” Dylan whines world-wearily. Once the song begins, three things occur: James joins Crabtree to spend the night at Grady’s house, and five years before Brokeback Mountain we watch two men go to bed together without fanfare; Grady finds his renter/student Hannah asleep with his book, which she’s taken from his room and read illicitly, but the point is that she couldn’t stay awake to finish it; and Grady calls Walter at 3 a.m., stoned, to tell him he’s in love with his wife Sara. 

The film’s soundtrack has several Dylan songs on it, one written specifically for Wonder Boys: “Things Have Changed” was released as a single in 2000 and won both the Academy Award and the Golden Globe for Best Original Song. In his Oscar acceptance speech, the singer thanked “the members of the Academy who were bold enough to give me this award for this song, which obviously is a song that doesn’t pussyfoot around nor turn a blind eye to human nature.” 

Dylan reportedly agreed to contribute to the score after seeing just 90 minutes of early footage. Perhaps he saw himself in Grady, a middle-aged writer facing the twilight of his life, unsure if he’d make great art again.


Back to the aforementioned Vernon Hardapple, a gadabout local and one of the nuttiest deus ex machinas ever put to screen. Grady’s gurgling Ford Galaxie was loaned to him by a friend, but he comes to learn this friend had stolen it from Vernon—so when Grady discovers his car missing following the Dylan-scored night of revelations, he and Crabtree rightfully suspect Vernon stole it back and realize they need to track the guy down; James’ backpack with Marilyn Monroe’s priceless jacket is still inside the vehicle. 

Before they set off, Grady grabs his hefty stack of book pages out of Hannah’s bedroom. First he asks her what she thought of them. 

She tells Grady that as a writer, he didn’t really make any choices at all. His book is full of “genealogies of everyone’s horses, and the dental records, and so on,” but despite beautiful prose it is apparently not a novel even his most ardent admirer can get through. She suggests it might be better if he were not always writing “under the influence.” Grady bristles, objects, and walks out. You can tell he knows she’s right. He’s been avoiding making more decisions than just amorous ones. 

Hannah’s critique makes us understand that Grady was writing something interminable—perhaps fearing an ending too big of a commitment. With the book’s conclusion would have come the inevitable editing process, eventual publication and reviews and opinions about whether his second book lived up to the glory of the first. By avoiding an endpoint, Grady remains in comforting stasis. The same goes for the marriage he no longer cares about but doesn’t end and the substance abuse slowly wearing down his body. 

The following series of mishaps, once Grady locates Vernon, results in the latter brandishing a gun and Crabtree fleeing in fear, crashing the stolen car into the side of a building and causing the pages of Grady’s book to fly out the gaping doors and windows. They flutter in the wind alongside the Monongahela River, gathering in piles like purest snow. When the Crabtree comforts the writer—“naturally, you have copies?”—Grady reveals he has but an alternate version of the first chapter. 

The book is gone and surprisingly, Grady is relieved. Like Chabon giving up the tome that was “erasing” him, he’s been freed. It’s better than when Amy March burned Jo’s manuscript in Little Women, because Crabtree has only done what any good editor should: release the author from his mortal coils. Vernon’s pregnant girlfriend Oola (who is wearing Monroe’s jacket) asks Grady, sweetly, what his book was about—and he says he doesn’t know. Vernon asks why he was writing it, if he didn’t know what it was about. “I couldn’t stop,” Grady admits.


After losing his book, Grady begins to figure things out. He has long since confused his identity as a writer with his worth as a lover, assuming Sara only wants him because she is “a junkie for the printed word” and he “manufactured her drug of choice.” But he hasn’t written a book in seven years. That’s not what she loves him for. 

The weekend isn’t without its casualties. Grady loses his job, in addition to his novel and his unseen wife. And yet he finally figures out where he wants to go. He might be a better teacher than he is a writer—guiding his students is what made the last seven years of his life worth it, he tells Crabtree. He donates his remaining weed to another student, throws away the pink bathrobe he wore to pen his second book, and realizes his first one still matters to people after Q offhandedly praises a passage. 

“Take a bow, James!” Grady hollers at the conclusion ceremony of WordFest, where it’s announced that Crabtree will be publishing James’ first novel. James holds forth his arm and dips his body with absurd formality to riotous applause. “Wonder boy,” Grady murmurs under his breath. But the story’s title, of course, is plural.

It’s never too late, I suppose, is what this movie is about. To change career tracks, to fall in middle-aged love, to quit doing something you hate, to start becoming someone you like. Wonder Boys’ failure at the box office feels apt, now, for the story of a man who cannot live up to past successes and so adjusts to a new breed of triumph in order to stay sane.


There’s a throwaway line Grady says when he’s visiting his wife Emily’s parents’ house. “It’s the kind of house you’d like to wake up in on Christmas morning,” he tells James, who is tagging along and makes himself comfortable on the couch with a joint and a bourbon after informing the professor of his in-laws’ home: “it feels really good in here.”

Wonder Boys, too, feels like waking up on Christmas morning. I need it to be Christmas morning, in my head and on my screen because it’s impossible anywhere else.

In my head I am in Pittsburgh with these writers, to whom nothing wholly devastating ever happens; who deserve and are always offered a second chance. And thank god for that. As James would say, it feels really good in here.