To be young and reckless, allowing yourself to be engulfed by the restless feelings of youthful abandon to the point where it seems like you have not truly lived unless you’ve flirted with death, either physically or psychologically, is one of life’s most interesting gifts, a blessing and a curse depending on who you ask. Gus Van Sant has often been fascinated by the idea, since many of his films tend to have recurring themes throughout them, often relating to the challenges of youth and the obstacles that exist when navigating that ambiguous space between adolescence and adulthood. We see this portrayed brilliantly in Drugstore Cowboy, his incredible sophomore directorial outing, and the film that brought him to international attention, establishing him as one of the key voices that emerged in the early stages of this budding independent film movement that was about to change the industry forever. Based on a novel by James Fogle (which would only go on to be published after the film’s release), the film follows Bobby Hughes and the motley crew of eccentrics that surround him. Their days are spent robbing pharmacies all along the Pacific Northwest, setting out to find any kind of drug that will feed their ongoing addictions, which none of them is willing to recognise as beyond dangerous. Set over the course of a few months, the story follows Bobby as he navigates several changes, including efforts to set himself on the right path after a tragedy nearly lands him another extended stay in prison, and in the process, realising that going straight is not nearly as easy a process as he may have imagined. A complex, engaging character-driven film that deftly blends dark comedy and philosophical drama, Drugstore Cowboy is one of the great examples of the kind of independent filmmaking emerging towards the end of the 1980s, where harrowing stories were combined with a range of artistic eccentricities that made these such deeply compelling, captivating works that challenge the narrative confines and present a version of the world that is heartbreakingly resonant and profoundly moving, simultaneously being unsettling and nuanced in equal measure.

Some subjects are inherently more cinematic than others, even when they can address certain topics in a more critical way. In the case of Drugstore Cowboy, it is established relatively early on that this is going to be a film about the perils of drug addiction, both in terms of the poor choices made while actively pursuing these narcotics and the challenges that come when trying to get off them, which can sometimes be equally as dangerous. Van Sant has very little issue building a film around a controversial topic. In fact, he’s intrigued by the idea of presenting a story that challenges the confines of particular narrative conventions – when we look at films about addiction of any form, they’re either harrowing morality tales, or instances where the addiction is glamourised, or at least not viewed as critically as perhaps it should. In the case of this film, the director is trying to find the perfect balance between the two, showing the realities of addiction through an honest and uncomplainingly bleak lens, while also not trying to come across as too heavy-handed in terms of its thematic content. However, this is actually not a film that builds itself from an exploration of addiction so much as it is a quietly poetic coming-of-age story about youth and how it can lead people to make impulsive decisions that can change the course of their lives forever. When you’re young, you truly feel invincible, and there is a genuine belief that the drugs and alcohol can’t do any lasting harm, and that the world is essentially just a large playground in which these people can play – after all, all one needs to be able to do to survive is to outrun the authorities. Naturally, this is not the case in reality, which is where Van Sant finds so much of the film’s nuances, since it explores how these young people realise that they are not immune to both physical harm and legal proceedings, and that their decision to live fast through dodging the consequences wherever possible is bound to have negative effects on them, much more than the narcotics that fuel their desires. It’s a harrowing look at the challenges that come with growing up in a hostile world, using a common theme such as addiction as the starting point for a daring and provocative piece of cinema.

In much the same way that Drugstore Cowboy proved to be Van Sant’s breakthrough as a filmmaker, it also has a similar effect on Matt Dillon, who immediately skyrocketed to worldwide acclaim as a result of his performance here. He was not a newcomer, having already worked under the direction of auteurs like Francis Ford Coppola and Arthur Penn (and had a decent career with roles across multiple genres), but it was Van Sant who truly understood how to take his raw, unfiltered energy and harness it into something not only interesting but entirely unforgettable. The part of Bobby Hughes is a challenging one – he’s a young man who demonstrates such enormous bravado, but in a way that does not feel blindly masculine, but instead quietly sensitive, which requires an actor who can handle a more introspective approach, which is certainly the case for Dillon, who embraces the character as more than just a one-dimensional archetype, and instead as a character with multiple different layers, each one intriguing and complex. It’s not surprising that this proved to be his breakthrough moment, and he makes the most of every aspect of the film, which is designed to be a showcase for any actor fortunate enough to get the role. Dillon is so brilliant that we don’t even notice the wonderful work being done by the supporting cast, who are also excellent, but pale in comparison. Kelly Lynch, James LeGros and Heather Graham are solid as the other members of Bobby’s gang, each one being a distinct personality more than just peripheral goons, adding layers to an already very complex film. Similarly, we find scene-stealing work from some of the smaller players, particularly William S. Burroughs, whose casting as the drug-addicted priest who becomes Bobby’s spiritual advisor in the last portions of the film is absolutely genius. He’s not a particularly good actor, and his line readings are certainly stilted – but his presence alone is staggering, and knowing that someone who lived the kind of perilous life depicted in this film only makes Drugstore Cowboy all the more impressive. This is a phenomenal film, and the actors are a large part of why it succeeds, bringing nuance and complexity to roles that would have likely been one-dimensional archetypes in the hands of most other performers.

Van Sant has never been one to attempt to educate audiences, despite many of his films being about complex social issues. He views himself as a storyteller and artist rather than a teacher, and this film makes this very clear. Considering the subject matter, he was walking a very narrow tonal and conceptual tightrope, one that needed an approach that didn’t trivialise the core themes, but also not present them as overly heavy-handed, unbearable kitsch morality tales. Drugstore Cowboy is not attempting to be some fable about the pitfalls of addiction, but rather presents a more diverse and complex portrait of what it means to be young and driven by impulse more than logic. We don’t always know exactly what the film is trying to convey, since it bounces between a vaguely absurdist, stream-of-consciousness narrative (reflecting Bobby’s ongoing existential crisis, which we soon come to understand is taking place in his head as he undergoes the process of recovering from his addiction), and social realist drama. Van Sant is equally adept at both, and works closely with his actors and the other creatives working behind the scenes to craft a film that is beautifully poetic in not only message, but execution as well. The darkly comedic tone that occupies the first two acts gradually shifts into something more sombre and pensive as the story progresses, giving the illusion that we are drifting through the protagonist’s mind, observing the world in the same way he does: frenzied and maniacal in some parts, deeply haunting and slow in others. It’s a masterpiece of tonal control, and the aesthetic of the film (particularly the cinematography by Robert Yeoman, another master of his craft who was still finding his artistic voice at the time) only contributes to this, becoming a fascinating piece of storytelling that knows how to handle certain themes that are not usually easy to convey on screen. Van Sant does not normally get credit for how he is able to blend emotional resonance with some unique artistic flair that ties everything together beautifully and with a sensitivity that only emphasises his unique set of skills.

While he may not be viewed as the radical, exciting young voice he was when he first emerged as a filmmaker, Van Sant has never lost his incredible ability to tell meaningful stories. Drugstore Cowboy was his first breakthrough and will likely be viewed as one of his crowning achievements, particularly since this would serve as the springboard for future works, particularly his next film, My Own Private Idaho, which will forever be viewed as his defining masterpiece for multiple reasons. It may not be explicitly queer in terms of its narrative (but there is some subtext, enough to lend itself to a relatively strong reading), but it does find the director working with some themes that would come to be indicative of his style and narrative approach. Youthful rebellion, incredulity towards authority and the desire to break free from socially-mandated shackles that only further consolidate the dominance of the status quo are all in focus here, and we find that he is very much developing them into defining traits that would inform many future films. However, even as a work all on its own, Drugstore Cowboy is a brilliant piece – it is challenging, unconventional and deeply moving. It manages to be both bitingly funny and profoundly harrowing, and the director’s refusal to shift his focus in moments where a lesser director would choose to look away only strengthens the nuances that guide this film forward. It’s a masterful work, a daring and provocative dark comedy that is never afraid to be different, knowing that its complexities are not without merit, especially in those quieter and more intricately-woven moments. As a whole, Drugstore Cowboy is a very impressive piece of filmmaking. It has many layers to it, some of them more bold than others – but it gradually dismantles our expectations and rebuilds them into something far deeper and more profound, taking a relatively simple premise and reworking it into an impressive example of the genuinely mastery that went into this pioneering era of independent cinema, which would not exist without directors intrepid enough to take such bold, unflinching risks.