Every month, we at The Spool select a filmmaker to explore in greater depth — their themes, their deeper concerns, how their works chart the history of cinema and the filmmaker’s own biography. For June, we celebrate the birthday (and the sensitive, insightful eye) of Gus Van Sant. Read the rest of our coverage here.

In a lot of ways, Good Will Hunting is the Rosetta stone for our understanding of modern Hollywood in the late 20th/early 21st century. It skyrocketed fledgling actors and screenwriters Matt Damon and Ben Affleck to superstardom, and landed Robin Williams his long-deserved Academy Award; it was a box office hit, banking over $225 million on a $10 million budget; and it further cemented the campaign-based, Miramax/Weinstein model of securing Oscar gold (for the worse, even before we learned the horrible cost of giving Harvey Weinstein that much power over the film industry). It birthed more than careers — it set the template for independent cinema about moody white boys who can’t self-actualize, which Hollywood would dutifully follow for the next twenty years.

But how is it as a film, especially one in the career of someone as eclectic as Gus Van Sant? Up to this point, he’d made deeply independent movies about queer misfits — even his more heterosexual works, like Drugstore Cowboy, had the air of the outlaw about them. But Good Will Hunting would throw him deep into middlebrow Oscar-bait mode, a schema he’d flit in and out of for the next few decades. As decent as the nuts and bolts are, it’s shocking to see something so…. ordinary from him.

Of course, so much of this is due to Damon and Affleck’s script, which reads both charmingly and obnoxiously as a Young Man’s First Screenplay. You know the story by now: Will Hunting (Matt Damon) is a genius-level intellect growing up in working-class South Boston, spending his time with his deadbeat friends (Affleck, Casey Affleck, Cole Hauser) and pulling janitorial duty at MIT.

One day, he solves the answer to a nearly-impossible math problem on the chalkboard, piquing the interest of stuffy intellectual Professor Lambeau (Stellan Skarsgård), who tries to take him under his wing. But he’s smaht, see? Too smaht fah these MIT jabronies, with their tweed jackets and predictable curricula. To solve the problem of Will Hunting, Lambeau turns to Sean McGuire (Williams), a community college teacher of similarly frustrated genius and background, to counsel him and give him guidance.

Of course, Sean’s not the only one in Will’s corner, however reluctantly Will tries to push them away: there’s Minnie Driver‘s Skylar, Will’s love interest, whose inherited wealth is a logjam for their relationship; and there’s Affleck’s Chuckie, who loves his friend enough to know their lifestyle is poison to him. And for the next two hours and change, these three people (along with Lambeau, who has his own beef to squash with Sean) will try to impress on Will that he’s worth all this attention he tries to push away.

The basics essentially work: Damon, Affleck, and Williams in particular give solid performances, especially for the former two’s inexperience. Damon in the ’90s had this airy, twink-y, mercurial nature, a pretty boy floating through the world hoping not to get caught (see also: The Talented Mr. Ripley). He brings that kind of distance and volatility to Will, making him a kid with deep emotional wounds burdened with enough brooding sadboi self-hatred to keep him from actually acting on his potential. And of course, one can’t forget about Williams, one of the few truly unimpeachable takeaways from the project. His Sean is witty, soulful, relatably coarse to Lambeau, his eyes deep wells of wisdom. The “It’s naht yah fault” scene alone justifies his Oscar.

And yet, it’s so very difficult to watch this movie now in the wake of #MeToo and the revelations of Harvey Weinstein’s gross, systemic assaults on women and destructive power-brokerage for sexual favors. Before this, Weinstein’s aggressive campaigning for Academy recognition was well known, strong-arming and schmoozing voters to see and rep Miramax’s body of work so it could get awards attention. Now we know the dark side of all that dogged entitlement to power and fame (and it was craven even when the movie came out).

That kind of misogyny is baked into the film, too, some remarked and some unremarked: Chuckie propositions women at the college bar they go to, Lambeau implicitly sleeps with one of his female students. Skyler answers a breathy phone call from a lusty professor like it’s just something that happens. Even Sean isn’t immune, putting his late wife on a pedestal in a way that suggests deep fidelity but ends up feeling dehumanizing.

The class politics are almost as confused as Hunting‘s gender politics, even as Good Will Hunting more consciously critiques the hypocrisy of upper-crust academia. Will’s genius-level smarts give us plenty of opportunities to point and laugh at the buttoned-up self-seriousness of Lambeau et al., and the “how you like them apples?” scene is still the classic “snobs vs. slobs” rejoinder. And yet, the script doesn’t see Will’s working-class background as the solution, either; Chuckie’s big scene late in the film has him chastising Will for “sitting on a winning lottery ticket… It would be an insult to us if you’re still around here in twenty years.”

As decent as the nuts and bolts are, it’s shocking to see something so…. ordinary from him.

Ostensibly, Will’s story is of a kid with potential who sees following that potential as class betrayal. But the academic world he’s set to follow offers few answers for him either; what we see of the world of academia is stiff, boring, Van Sant’s camera clearly favoring the free-wheeling camaraderie of Chuckie and his boys. Even the prestigious Lambeau is a man embittered by tunnel vision about what kind of path people should take through life. Everyone’s just as miserable, no matter how many degrees you’ve got.

Looking back on Good Will Hunting, especially in the context of Gus Van Sant’s varied career, one gets the impression that anybody could have directed this, really. A middlebrow feel-good drama about sad white boys, set to the songs of Elliott Smith, doesn’t give one of the pion-queers of the New Queer Cinema that many chances to ply his ambitious cinematic trade. He handles dialogue scenes with a deft, if workmanlike hand, opting for gripping naturalism over the bigger stylistic choices he’d make in stuff like To Die For and My Own Private Idaho.

Here more than ever, Van Sant feels like a journeyman, a capable hand behind the camera serving Damon and Affleck’s script (and performances) first and foremost. Maybe the negative reaction to Even Cowgirls Get the Blues set him, for latter of a better term, straight.

Most frustratingly, Good Will Hunting will probably stand as one of Van Sant’s most successful, well-regarded films. It crystallizes so much about its time, from its young stars who’d leverage their Oscar wins to become two of the biggest stars on the planet, to the way it’d act as a template for every navel-gazing independent movie for the next decade trying to replicate its success. But as an entry in Van Sant’s filmography, it feels disappointingly safe, bereft of the risks that encompass the rest of his work. One can even see parallels between Van Sant and Will himself: a man keeping his nose to the ground, tamping his style and making safe choices so as not to put himself at risk of rejection.

To this, Gus, I say to you: it’s not your fault. It’s not your fault.

Good Will Hunting Trailer: