In the new season of High Maintenance, an impressionable, young Brooklynite’s life becomes ruled by the anxiety of disaster preparedness and carcinogenic food avoidance, an asexual magician tries to make a difference and crumbles under the abject cruelty of teenage summer school students, and a middle-aged doorman wades through the routine of his solitary life, from his side job as a self-defense instructor to phone calls with his mother and nightly solo karaoke performances.
These are the kinds of uncomfortable and sometimes upsetting scenarios that make the two-year-old web series so enticing. (The show is produced by Vimeo, which is owned by IAC, the company that owns The Daily Beast.) High Maintenance is about the daily encounters of a New York City pot dealer, making his way across the city by bicycle to deliver his product to a wide-ranging cadre of clients. But don’t be fooled by that synopsis, High Maintenance is not your average stoner comedy. In fact, marijuana is a supporting character at best, treated no less innocuously than wine or Thai takeout, and taking a back seat to far more compelling and crippling vices. Sure, there are the occasional stoned giggle fests and pig-outs, but High Maintenance is a character study; each episode a 5-to-12-minute vignette that offers glimpses, almost as if through a peephole, inside New York City's coexisting worlds and tying them together through the common thread of weed and the charming, nameless guy who delivers it.
“The Guy,” played by Ben Sinclair (who created the show with his wife, casting agent Katja Blichfeld), is our ticket into the apartments and personal lives of people we all know but don’t really know. People we pass on the street, sit next to on the subway, say hi to at work every day. Through The Guy we learn that the lives of those we might never talk to, like the doorman or the street performer or the famous comedian, are no more interesting or less depressing than our own. We discover that those who we perceive as "normal" have some of the most fascinating secrets: the hot guy you've been eyeing at the gym is in a bizarre cult; the gorgeous girl you've spent the entire weekend in bed with is actually homeless; the brooding author and stay at home dad wears a dress around the house. With Sinclair as our non-judgmental guide, we see that these revelations are not meant to shock us but, perhaps, enlighten us.
In last season’s episode “Rachel,” Colin, the cross-dressing stay at home dad played by Downton Abbey’s Dan Stevens, keeps his dress on after placing an order with The Guy. When he arrives, The Guy returns a copy of Colin’s first novel and the two chat about the book for a few minutes before The Guy says, “Ok. Look, man. You’re wearing a dress right now. I can’t pretend that you’re not wearing a dress, you don’t usually wear dresses. But you look good, man.”
Colin mutters a thank you and The Guy continues to tell him about another cross-dressing customer who doesn’t pull off ladies’ clothing quite so well.
“His taste fucking sucks,” The Guy says. “Your taste, it works, man. I’m like, ‘where’s my dress?’”
“Yeah,” Colin says, smiling. “It’s Rachel Comey.”
The two proceed to get high and talk about Colin’s struggles with writing his second novel. Later, when Colin’s wife, played by Blichfeld, returns home from her high-pressure fashion job, she is elated to discover that her husband let the weed guy see him in a dress.
“I’m so proud of you,” she tells him. As the camera pans to a crayon drawing by the couples’ son of both his parents in dresses, she says, “You are going to fucking die when you see this collection.”
High Maintenance nails some of the humans of New York’s more familiar plights, from dietary concerns that border on obsession, a desperation for money that leads to renting one’s apartment on AirBnB while living there, that awkward conversation where you are the only person who thinks Vice News is bullshit, the panic induced by realizing you have less than $50 in your bank account that makes it hard to resist just a little sympathy for the financial troubles of the self-absorbed—and broke—scenesters identified in our even-keeled protagonist's cellphone only as "Assholes."
High Maintenance, like a good high, is funny and sometimes unsettling, the characters’ lonely lives brightened and enlightened by a bearded bike messenger bearing bud.