In the Class of … series, Nick Rogers takes a monthly look back at films celebrating their 20th or 30th anniversary of initial release this year — six from 1990 and seven from 2000 (the extra in last month’s double-feature column). The self-imposed rules of the column: No films with an Oscar nomination and no films that were among their year’s top-10 box-office grossers.

Is Gus Van Sant embarrassed by Finding Forrester? It’s been a fair question since winter 2000, when the film’s first frame flickered on screens. A clapperboard bearing Van Sant’s name clacks in camera before an incidental character’s freestyle rap. A few months later, Van Sant would deliver an uproarious cameo in Kevin Smith’s Jay and Silent Bob Strike Back, directing the fictitious Good Will Hunting 2: Hunting Season by way of voraciously counting stacks of studio money. And in the ensuing 20 years, Van Sant has seemed to purposefully shy away from anything even remotely similar in its uplift. (The closest he’s come: The ethnic-savior nonsense of 2015’s misbegotten The Sea of Trees, starring Matthew McConaughey.)

Does the clapperboard emphasize the artifice and distance Van Sant brought to something he viewed as pure product? Does his Benjamin-riffling cameo communicate that Forrester was just a way to fund eight years of experimental work that followed in Gerry, Elephant, Last Days and Paranoid Park? Van Sant shepherded an arguable all-time worst remake with 1998’s Psycho. He certainly knows from shame. But it certainly would be odd for him to feel it about Forrester, an imperfect but invigorating inversion of the comforting beats you’d expect from a combination of odd-couple friendship, sports-movie underdog, inspiring-mentor and fish-out-of-water subgenres. Mike Rich’s screenplay is cleaved into three conventional acts. But the film’s patient 136-minute running time allows for crescendos of character and context, most impressively a fearlessness to let racially motivated developments for one of its leads play out with believably latent desperation. Plus, what turned out to be Sean Connery’s penultimate live-action turn expresses compassion and fallibility beneath the codger fury that became the bedrock of Connery’s last active decade.

His character occupies a spacious Bronx apartment overlooking a basketball court, gets fresh air only when cleaning his windows and takes weekly deliveries from a jittery errand boy. Neighborhood teens attach apocryphal tales of a murderous past to “the Window” (as they nickname him), and one night, Jamal (Rob Brown), a basketball-playing bibliophile, takes a dare to break in and retrieve something of value. Startled by “the Window” in the process, Jamal leaves behind a backpack of notebooks with his own poetry and prose. When the backpack falls to the ground days later, Jamal’s work has feedback scribbled all over the margins, with one intriguing note: “Where are you taking me?” 

Meanwhile, Jamal’s state-mandated high school test scores betray his middling grades and he garners the attention of Mailor-Callow, a premier Manhattan private school. They promise a top-flight education … but also apply a full-court press to join their basketball team. After some crotchety face-to-face confrontations, “the Window” agrees to mentor Jamal in his writing as he transitions to Mailor-Callow with some caveats: What they write in the apartment stays in the apartment and there are to be no questions about his past. 

It’s an arrangement complicated by what Jamal learns about his new acquaintance — that he’s actually legendary author William Forrester, who wrote the Great American Novel at age 23 before retreating from public view. Forrester is inspired by the reclusive real-life retirement of The Catcher in the Rye author J.D. Salinger. Thankfully Forrester stays in the realm of ideological respect and literary inspiration rather than renewing the misanthropic author’s interest in the world around him or sensationalizing what Jamal learns about his iconic past. 

Van Sant was also wise to match a relative unknown to Connery’s considerable marquee heft. Brown auditioned as an extra to pay a $300 cell phone bill. But the filmmaker was taken by Brown’s naturalism and wound up choosing him as Jamal. Brown has since enjoyed a steady film and TV career, but his inaugural outing here remains his strongest work. He’s got an appropriately antagonistic chemistry with Connery, and his silent stoicism is a front for Jamal’s unexpected commonality with Forrester — that his secret, too, will be found out and his literary ambitions limited by systems that destroy what they can’t comprehend out of confusion or jealousy. In the meantime, Forrester explains his emigration from everyday life. He became so tired of being defined by one beloved book as though someone’s praise of it could confer comfort upon him in even his darkest days. Both Forrester and Jamal are hemmed in by their responses to respective tragedies in their families and they try to coax each other toward more healthy coping mechanisms. 

Sure, it’s primarily an infusion of Wonder Boys aesthetics into the Good Will Hunting formula. But it’s also one that mulls over the privilege present even in the powerful pathos of that latter film, Van Sant’s most commercially successful work. Had Will not moved past his demons to embrace his mathematical gifts, he would still have made a living in manual labor or trades. It wouldn’t have been sexy or prestigious but he’d still have had plenty of options to make a living. By comparison, Jamal will get only one chance to embrace his prodigious gift and, as is the way of American sports, it’s tethered to Mailow-Callow’s exploitation of his athleticism. Without that, he’ll have nothing to fall back on. And when Jamal lets some of his writing with Forrester leave the apartment, it further jeopardizes his already-tenuous shot. 

That’s because a suspicious instructor named Crawford (F. Murray Abraham) can’t possibly fathom that Jamal is that good and initiates an investigation into academic dishonesty. Abraham is here to serve purely as a jealous and disbelieving dirtbag, and he does it exceedingly well. Rich strains in trying to tether sinister intent from Crawford to both Jamal and Forrester (with whom Crawford has past interactions amid literary circles), but it also illustrates the delusional, and detrimental, vigor with which people cling to their stereotypical viewpoints.

Forrester’s earliest conversations with Jamal are tinged with racial connotations, too. What seems like generational racism on its face becomes a test for how Jamal will respond to all the “bullshit” he’ll face in the world. Case in point: While Mailor-Callow claims to take Crawford’s accusations of academic dishonesty seriously, the school board would really like Jamal to still lead them to a victory in the state championship. Although Van Sant could seem to care less about the onscreen clarity of said climactic game, he and cinematographer Harris Savides key in on body language from Jamal that offers a crucial cue to Forrester, who’s watching at home.

It all builds to a narrative head that feels like the movie’s only misguided choice, albeit a substantial one. Circumstances force Forrester into the halls of Mailor-Callow to defend Jamal against Crawford’s claims, surrounded by sycophants and well outside of his comfort zone. Forrester delivers a reading about loss and family that seems primed to snowball into a signature monologue for Connery … until Van Sant cuts to a montage of mostly anonymous schoolmates’ faces reacting to words we can no longer discern. This sequence spends more time embarrassing Crawford than it does lifting up Jamal or helping us see what he has inspired in Forrester. We fear in the film’s final moments that Jamal might simply wall himself off rather than will himself on, as has been Forrester’s folly, but this decision to delete words of weight for both of them lends it more of an ephemeral feeling than an emotional force. Was it a screenwriter’s miscalculation? Did Connery not want to do it? Was he incapable of delivering it with the full complement of warmth it deserved? Did the studio intervene? Or, again, is this Van Sant thinking this is all just several pounds of pabulum, reminding us that this is, after all, a work of fiction, and asserting that no two such people could forge these connections in real life?

The volume with which this climactic choice clatters speaks to the investment made in the two hours that precede it. Finding Forrester never feels like a cynical work of awards-chasing opportunism; indeed, it was nominated for nothing in an admittedly crowded year of heavy hitters anointed for awards such as Cast Away, Erin Brockovich, Traffic and Crouching Tiger, Hidden Dragon. There is the sense, too, in looking at those titles, that Forrester somehow already felt dated, that whatever chic appeal Van Sant generated just three years earlier with Good Will Hunting had fallen out of favor in a new century. But to paraphrase a line of dialogue tailor-made for early-millennium memes: I’m still a fan now, dog.