Where is Grady Tripp, do you think, 25 years later? Obviously Michael Douglas, the actor who plays him in the movie version of Michael Chabon’s Wonder Boys, is still kicking around. For that matter, the even-older Bob Dylan, who sings the movie-opening, Oscar-nominated song “Things Have Changed,” remains with us as well. But Dylan and Douglas are globally famous multimillionaire celebrities who likely have access to the best healthcare American money can buy. Grady Tripp is just a writer, though his dayjob as a college professor, surrounded by ambitious students and faculty, urges him to think in grander terms, or at least phrase it more forcefully. “Q” (Rip Torn), Grady’s unspoken and probably one-sided nemesis for his prolific career, certainly does: “I am a writer,” he announces at a lit-festival speaking engagement, to great reception.

Curtis Hanson’s Wonder Boys, released in theaters back in February of the year 2000, is set over a relatively compressed period of time: A few days during which Grady’s life, naturally, reaches a potential turning point. His younger wife has just left him, an event that does not sound like a first for him. His editor Terry (Robert Downey Jr.) has arrived in town, ostensibly for the festival but mostly to pressure Grady into a peek at his second novel, which has been in progress for seven years and now may be Terry’s last shot at career redemption, not to mention Grady saving face.

The untenable sprawl of Grady’s writing becomes a running gag, funnier because his novel’s subjects are rarely directly discussed: “The genealogy of everyone’s horses, their dental records and so on,” Grady’s prodigious student and tenant Hannah (Katie Holmes) offers an example at one point, referring to the lack of clear choices being made in his writing and, of course, his life. With his wife gone and his married university-chancellor mistress Sara (Frances McDormand) pregnant, it seems as if life is nonetheless nudging Grady in a particular direction; he’s not exactly faced with a monumental moral dilemma. Yet he seems unable to follow the cues – less reluctant to commit than stuck in a haze, trying unsuccessfully to work his way out. It’s easier, in some ways, to busy himself with the lives of his students: Hannah, yes – who, for a young woman in a Michael Douglas movie, remains remarkably clothed, even as she makes her availability clear – but also James (Tobey Maguire), another young talent, far more morose.

Some of James and Grady’s wandering adventures are funny, though in general the harder Wonder Boys pushes toward zany, stoner-adjacent comedy, the cornier it feels. It’s one area where director Curtis Hanson’s old-fashioned craft doesn’t look particularly better a quarter-century later, all that strenuous underlining of supposedly wacky elements like a dead dog or a bunch of weed. The movie is funniest at its most offhand; one of its biggest laughs comes after Grady describes his book’s target length as around 250 pages before we see him add a fourth digit to the page number of what he’s currently typing, taking it from 261 to 2,611.

There’s also the matter of the movie’s creepily cavalier, even cutesy attitude toward Terry’s predatory lusting after James, something the movie seems to brush off and put out of mind more than actually address through characterization. The concerns Wonder Boys does spend more of its time on look unavoidably quaint now, not least because Grady is a tenured professor, rather than an adjunct scraping by. As much as the movie focuses on his advancing age and diminished physical capacity, with Douglas rumpled and limping rather than customarily slick, the whole business of worrying about your eagerly anticipated follow-up novel and how good a twentysomething prodigy might be at writing fiction feels like a younger person’s set of neuroses; the most authentically older-man experience about Wonder Boys is how it ends with Grady quitting pot, settling down, and (from the looks of it) combing his hair again.

The movie itself could not find similarly respectable success. Though it got great reviews upon its February release, it stumbled commercially, and a subsequent awards season rerelease in November 2000 didn’t bring in much more money, either. Fans of the film blamed bad timing, yet the mood of Wonder Boys, with its chilly, slushy Pittsburgh-area environment, is vividly, perfectly February. A year or so later, the movie did receive a respectable three Oscar nominations, for its screenplay, editing, and Dylan song, albeit nothing for Douglas, Hanson, or the picture itself. This seems silly when you see how many nominations Chocolat was afforded that year, but on the other hand, the true nature of this material is not to be feted with endless trophies (even if the movie does somewhat hurry itself into that sort of ending). “I thought it was more literary than cinematic,” an extra in the movie is overheard saying, presumably about a film adaptation, and that remark takes on some extra dimension now, knowing how author Michael Chabon has since published novels with more traditionally, well, cinematic heft: The Amazing Adventures of Kavalier & Clay and The Yiddish Policeman’s Union certainly present their own adaptation challenges (hence the lack of movement on long-discussed movies of both), but they offer decades-spanning scope and a central mystery, respectively, rather than a bunch of writing about writing, writers, and books.

Any lingering uncertainty about Grady’s ultimate fate, then, comes more from what we know about the state of publishing and/or academia this many years later, not the cozy final click of the “save” button that the movie itself ends on. It’s not the fault of Wonder Boys that it couldn’t anticipate how the world would change, but it’s also hard to picture Michael Douglas starring in a more downbeat version of this ultimately affirming story. Even when he’s playing a loser, he can’t help steer back toward the good life.