There is a cultural fascination with defining the average New Yorker. But is there even such a thing in a city where most people are transplants and can morph into a new person every year, if not overnight? High Maintenance dares to answer this question. While it has the potential to be cheesy, the HBO show is now in its second season and is clearly onto something.
Summarized as “exploring the private lives of dozens of New Yorkers that have one connection, their weed dealer”, season two of High Maintenance is giving way to episodes that are much less about the joys of buying and smoking weed and more focused on the personalities and relationships that color a city where a well-groomed doctor is a drag queen by night and a workout addict tries out alternative sleep cycles and one night stands in tandem.
But in a city as unpredictable as New York, coping often involves a vice. In High Maintenance, weed is it. No matter how diverse the New Yorker, the show relies on “The Guy”, who bikes back and forth across the island, day in and day out, to sell weed. He provides a thread that moves the narrative forward like a game of Connect the Dots played between characters.
In season one, I didn’t mind that I didn’t know much about “The Guy”, played by co-creator, Ben Sinclair. But if I wasn’t laughing or crying to one of the storylines, I constantly found myself looking for clues about him. Does he have parents? A girlfriend? A boyfriend? Did he grow up in the city? By the end of first season, all I knew was that he had a romantic “thing” with Beth, a dog walker played by Yael Stone.
That all changed in the very first episode of season two, when we meet The Guy’s girlfriend, a re-introduced Beth, who now has a steady job as a bartender. We watch them wake up together, banter in their underwear, and end the day together at the bar where Beth works. As this season unfolds, we see more of The Guy’s personality and his reaction to culturally relevant topics, like feminism and all-female political groups. We also meet The Guy’s ex-wife, Jules (played by Kate Lyn Sheil), when he lands in the hospital after a bike accident.
Jules is now in a relationship with a woman, the cause for her and The Guy’s separation, but the two have clearly maintained a friendship. Not only does The Guy feel more comfortable reaching out to Jules than Beth, but also the two still share a vacuum cleaner and live down the hall from one another. Throughout this episode, which takes place predominantly in a dysfunctional ER, Jules and The Guy get high, share secrets, and feed each other chocolate pudding. The storyline of this episode blurs fact and fiction - between season one and season two, Sinclair and his fellow co-producer, Katja Blichfeld, who were previously married to one another, separated when Blichfeld came out as a lesbian.
Knowing this, it makes sense why every episode of season two goes deeper, and gets personal whether tackling how gentrification in Brooklyn is hurting black New Yorkers, the life-altering ex-communication of Hasidic Jews from their devout and at times, abusive, religious community, and the tribulations of a new, female staff writer at Vice who is chasing her first big break despite the media company’s recent sexual harassment allegations.
This shift in the happy go lucky experiences of a NYC weed dealer may be because we live in a crazier world than we did a year ago. But then again, New York has always been wacky. Everyone has an opinion, everyone is trying to be someone, everyone is finding their own way - all set against a backdrop of cockroaches, long lines, and a lack of space. But we would be remiss to say only weed makes it bearable; it’s the people themselves as well. Sinclair and Blichfeld have made High Maintenance a success, instead of a trope, because they believe what everyone needs to believe right now – that at our cores, we are more alike than we are different. The fact that New York City is such a melting pot is what allows each episode’s main character to have an uncanny resemblance to someone you know or used to know, in New York or beyond.
This deeper dive into humanity makes season two of High Maintenance a must-see. We were hooked by the weed, but are sticking around for the show’s offbeat characters that are delicate in their strength, like realizing your bike basket can hold the weight of a person.