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High Maintenance and the Aspirational Kindness of The Guy

Photo: HBO

The Guy has always been a benevolent spirit. In the first episode of the High Maintenance web series, long before co-creators Katja Blichfeld and Ben Sinclair landed an HBO deal or even Vimeo funding, The Guy pays a visit to Quinn (Bridget Moloney), an overworked assistant who’s ordered weed for her impatient, demanding boss. He quickly deduces that Quinn — who has been hysterically babbling from the moment he walks in the door, all while her phone incessantly buzzes from an onslaught of texts — suffers from anxiety brought upon by stress and pharmaceutical withdrawal. On his way out the door, The Guy offers Quinn a sample for herself, and though she profusely declines, he finally gets through to her. “I feel obligated to tell you this,” he says. “Stevie Nicks described Klonopin withdrawal like being pushed into hell, and this is a woman who used to have cocaine blown up her ass with a straw.” Minutes later, The Guy and Quinn are getting baked in the bathroom and Quinn’s work phone is in the toilet.

An anthology series about the trials and tribulations of New Yorkers who procure marijuana, High Maintenance initially employed The Guy as a structural linchpin. He walked in and out of his clients’ lives, providing a service as well as fleeting good vibes or measured advice. He was, necessarily, an enigmatic figure (hence the anonymity), someone whose gentle visage made you want to know more about him, even though the transient nature of his profession guaranteed a certain distance. The show was never about him, but, to steal a phrase from another famous stoner, his presence tied the room together.

The Guy has always been a conduit for other people’s stories. His access into his customers’ apartments mirrored our access to their lives. But The Guy’s innate charisma and friendly disposition quickly became too captivating to ignore. The series has never indulged in a hackneyed origin story, preferring to mete out personal details about him in dribs and drabs. In the web series episode “Matilda,” The Guy’s teenage niece comes to town for a Broadway show and it’s revealed that he hides his profession from his family. In “Rachel,” he explains that he wears a wedding ring to communicate that he’s trustworthy to strangers even though he’s not really married. When the series moved to HBO, we learn that The Guy was married, but his ex-wife (Kate Lyn Sheil) left him for a woman, mirroring the real-life story of Blichfeld and Sinclair’s divorce. By the series’ third premium-cable season, which just wrapped up this past Sunday, The Guy’s own struggles with love and work frequently take center stage. After all, his plight is classic High Maintenance: a man in his mid-30s wondering how long the independent life he’s built for himself can truly be sustained.

The Guy’s evolution from organizing principle to three-dimensional character is somewhat predictable given the very nature of television. Writers eventually shade in backstories and fine-tune personalities to escape static characterizations. The Guy’s internal mystery could only be preserved for so long before it became either a liability or a coy pose. Inevitability aside, The Guy’s position would have been elevated anyway simply because he’s played by Ben Sinclair. For over seven years, Sinclair has given one of the best performances on television, one that’s as casual and understated as High Maintenance itself, which all but guarantees it will be criminally overlooked. Watching Sinclair develop his character onscreen, not to mention mature as an actor, over the course of the decade has been a genuine delight. Though it would be rank hyperbole to describe The Guy as iconic considering the limited reach of High Maintenance, his overall appearance — lanky frame, low-cut shirt, bike helmet, semi-scraggly beard — has come to represent the archetypal urban millennial drug dealer. Prestige TV, with all of its myriad options across multiple platforms, would be a much colder place without Sinclair’s tender energy to remind us that the Everyman can still be a potent symbol of goodness in the world.

If High Maintenance is predicated on the strong belief that everyone — of all shapes and sizes, across every sociopolitical line, no matter how marginalized or ignored by society — not only has inherent worth but a story worth telling, then The Guy is the walking embodiment of that worldview. His curious, nonjudgmental perspective allows him access to all walks of life and affords him the potential for intimate connections with a diverse array of people. After a rising comic (Hannibal Buress) suffers PTSD following a mass shooting during one of his sets, The Guy becomes the only person he can stand to be around longer than a few minutes. When Colin (Dan Stevens), a cross-dressing author, wears a dress in front of The Guy for the first time, he’s treated to unreserved validation. (“Your taste — it works, man. I’m like, Where’s my dress?” he says enthusiastically.) Later, he plays Cupid to two lonely, middle-aged customers, helps an old man suffering from dementia, and acts a citywide source of relief when the world falls apart. His selfless, altruistic personality makes him a modern version of the Good Samaritan who lends a helping hand, and some bud, to those in need.

Still, The Guy is defined more acutely by his relaxed form of allyship, which mostly amounts to treating everyone that he comes across with the utmost respect. This past season follows The Guy’s summer romance with Lee (Britt Lower), a woman he meets upstate who’s reeling from a messy divorce with an actor embroiled in a #MeToo scandal. High Maintenance refuses to dive into any of the nasty details, but instead chooses to follow Lee as she struggles with returning to public life. Strangers constantly stare while she’s walking the streets, projecting false sympathy or undue judgment onto her. She worries that her friends disapprove of her because she previously made excuses for her husband’s behavior. In the midst of this chaos lies The Guy, who offers a shoulder to lay her head and a joint to take the edge off of life. Though the relationship ultimately doesn’t work out, The Guy’s generosity toward her while she’s building a new life from a troubled place is the best illustration of his character. His strength derives from his bottomless well of compassion.

Unfettered kindness, the type that never calls itself out for external recognition, has always been in short supply. It’s much easier to default to a defensive position, to close oneself off as a means of self-preservation for the sake of health, time, or safety. Worse, it’s tempting to do the right thing solely for the sake of a reward. Being vulnerable enough to engage with the larger world, especially in such a cloistered, high-pressure city as New York, is no easy feat. The Guy has become a testament to thoughtful living through the sheer act of treating strangers with basic decency. High Maintenance covers a wide spectrum of lives, featuring people who face unique troubles stemming from different or complicated backgrounds, but at its center lies a man whose modest character is downright aspirational. The point is that he’s not some mythical being who has come down from on high to teach us how to be nicer to each other. He’s just like everybody else, prone to weakness, harboring his own share of failures and regrets. But by being The Guy to so many people, he burns a little brighter than the average soul.

High Maintenance and the Aspirational Kindness of The Guy