Good Will Hunting is one of the great fairy tales of the 1990s, and one of the great films about mentorship. In fact, watching it made me realise how rare it is to see screenplays that are so focused on mentorship, which is the most important human relationship as the film presents it, exceeding even friendship, family and romantic love. In essence, the story revolves around the three mentors who allow Will Hunting (Matt Damon), a prodigy, to come to terms with his considerable gifts. First, we have Gerald Lambeau, a professor played by Stellan Skarsgard, who discovers Will solving an apparently impossible mathematical problem on a chalkboard at Harvard, where he works as a janitor. Second, we have Chuckie Sullivan, played by Ben Affleck, Will’s best friend, who provides him with the final impetus he needs to leave his blue-collar life behind. Finally, and most importantly, we have Dr. Sean Maguire, a therapist played by Robin Williams, who is hired by Gerald to help Will make the most of his incredible talents. Virtually the entire film revolves around these three relationships, in a plangent testament to male camaraderie, friendship and, above all, mentorship that has rarely been rivalled since. 

All of this takes place against a rich Boston backdrop that was still relatively novel in mainstream American cinema at the time Good Will Hunting was released. The thick Boston accent here becomes a kind of indie cred, making it quite difficult, at times, to discern exactly what people are saying, especially when Will gets together with his group of buddies, which includes Casey Affleck luxuriating in the deepest Boston brogue of his career. Screenwriters Damon and Affleck both grew up in Boston, and structure the city around the class divide between Masshole blue-collar workers, and imported Ivy League elites. Will straddles both worlds, since he can easily hold his own with the best Harvard academics, but despises everything they stand for, and so aligns himself with the working-class substrate of the college, in his employment with grounds and maintenance. When he falls in love with Skylar, an English student played by Minnie Driver, it only enhances this tension. As an English heiress, Skylar is born to the manor of Ivy League, and yet her English accent also comes very close to the Boston dialect at its most working-class. In either case, it’s notable that Skylar is the only main character without a surname, since in a film that’s so driven by male mentorship, she exists mainly as a plot device, and as an emblem of the city’s class divisions.

Against that backdrop, director Gus Van Sant unfolds a prodigy drama that quickly distinguishes itself from other films of its kind by the sheer extremity and implausibility of Will’s genius. The way the film presents it, he’s the smartest person who ever lived, way beyond the prodigies of any film before or since. There’s no fact he doesn’t know, no book he can’t cite, and no speciality he hasn’t mastered, to the point where he effectively displaces Harvard, becoming a one-man university in and of himself. In both the most literal and profound sense, he knows everything – at least intellectually – meaning he’s not really tenable even as a once-in-a-century phenomenon, as Gerald tries to claim by comparing him to a famed nineteenth-century Indian guru. Yet the sheer hyperbole of Will’s prodigy, which is perhaps better described as omniscience than mere genius, is one of the most interesting parts of Damon and Affleck’s drama, and serves at least three conceptual and artistic roles.

First, by presenting us with a character who literally knows everything, Damon and Affleck uniquely evoke one of the most common experiences of young manhood – thinking you know everything. It’s at this point that Van Sant’s input really comes into play, since as a director peculiarly attuned to the plight of defensive male youth, he’s able to draw out the film’s vision in a remarkably resonant way. The first act is all Will’s bluster and braggadocio, along with its corollary, in the mid-90s – paranoia about being mistaken for gay, or labelled effeminate. This is Will’s great fear about entering therapy in the first place, which he brattishly expresses by outing his first therapist, and performing a campy musical routine for his second therapist. The same fear percolates, on and off, throughout the film, and eventually becomes a part of its fabric, whether in an incidental shot of Skylar reading a manual on “Sexual Dysfunction in Neurological Disorders” (her Harvard specialty, apparently) or one of Will’s quips about Michelangelo’s sexual orientation. Sean’s first gesture with Will, then, is to forsake therapy for a more inclusive model of mentorship, which he starts by sharing his own experiences, before proceeding to tease out the contradictions of Will’s persona, such as his reason for taking a janitorial job at Harvard if he was really so indifferent about Ivy League recognition. Key to Sean’s mentorship here is a certain spikiness, a willingness to be callous or even rude at the right moment, that adds a real edge to Williams’ performance, and prevents it from devolving into the sentimental rehash of Dead Poets’ Society that it could so easily have been.

If Will’s extreme prodigy captures the young male feeling that you know everything, then it dovetails with a second and more historically specific phenomenon – the emergence of an information economy. Blessed with encyclopedic knowledge, inexhaustible insight and photographic memory, Will is basically a personification of the internet, and the “information superhighway” of the mid 90s. The film is full of scenes in which Will hyperactively “downloads” streams of data, in the form of long monologues that are almost impossible to follow, since they play as great slabs of written language rather than naturalistic spoken language. Will speaks in hypertext here, and the screenplay mirrors it in the fast-paced banter with his friends, which is “knowing” in the same way that Will is “knowledgeable,” and feels drawn from the cursory style of early internet chat services. I was part of the last high school generation before the internet became truly omniscient, and I remember our jokes and quips segueing into an abbreviated style that in retrospect now feels proto-digital. Something of the same quality suffuses Good Will Hunting, which raises the question of how to preserve machismo in the face of unprecedented data waves, and finds its answer in Will himself, as an embodiment of a new kind of muscular data, information that is still embedded in virility.

Of course, these two aspects of Will’s prodigy overlap, since the feeling of knowing everything, for young men in the late 90s, was only enhanced by the confidence of having an internet at the tip of your fingers. Towards the end of my high school years, I remember students increasingly having the temerity to challenge teachers on the basis of what they had seen online, and in many cases being right. That ability to challenge previously unassailable authority figures leads into the third dimension of Will’s genius – namely, the way it encapsulates the prodigious dreams of indie cinema at this point in time, when it was as improbable for an indie auteur to cross over into the mainstream as it was for a janitor to cross over into the Harvard teaching stream. The sheer implausibility – even impossibility – of Will’s genius thus allegorises the film’s own conditions of production. Against all odds, Damon and Affleck made it with their first indie effort, and against all odds Will does indeed know everything, and still finds some kind of tentative peace. And the way those two miracles fuse and converge makes Good Will Hunting a unique testament to its filmic time and place, strangely and paradoxically timeless in the dexterity with which it crystallises its own mileu.