Paranoia in ‘High Maintenance’s Second Season

The new season of High Maintenance starts in the same spot HBO’s first season started: with the semi-protagonist weed dealer, The Guy, getting a haircut. In the HBO pilot (the series is a continuation of a web series that ran on Vimeo for 19 episodes), a haircut is a metaphor for the series’s transition to a cable. The Guy didn’t want a radically different style, just a bit off the top. This time, his appearance in the salon is a nightmare – the stylists are different figures from his life, and The Guy (played by series co-creator Ben Sinclair) loses his iconic beard. It’s unsettling and foreboding, a fitting start to the new and very different season of this semi-anthology show about a Brooklyn weed dealer who introduces audiences to new characters all over the borough, and accidentally trips the wires tenuously connecting these characters in ways they don’t always recognize themselves. Though this new season represents a tonal shift for High Maintenance, it is still the funny and sweetly empathic show it’s been since it was an independent Vimeo production in 2014. Co-creators Sinclair and Katja Blichfeld (broken up since late 2016) also open up their collaboration this season to more directors and writers, letting the show breathe a little bit and expand the series’s occasionally insular world of white gentrified Brooklyn.

In the first episode of this new season, something tragic but vague has happened in New York City. Characters check their phones and react with shock and misery, and The Guy finds himself particularly busy helping New Yorkers medicate away their responses to the news. Though it’s never made explicit, one hint toward the end of the episode suggests a theme: an unnamed-in-a-bar man insists that going forward, comedy and television writing will be great, inspired by this tragedy. At the end of last season, The Guy mentions in passing, “If Trump wins we’re all moving.” This season definitively takes place in a world where Trump has won, and the show has lost a bit of its ethereal pleasure. These episodes include elements of foreboding violence, with one character getting an emergency tracheotomy in a deli, another landing in the hospital after crashing into a parked car, and a friendly gathering interrupted by a new gun owner trying to solve a pest problem with a bullet (she assumes she knows how to shoot because, “How hard could it be? I have a Master’s.”). The violence Americans feel under Trump and the paranoia pot users feel under Jeff Sessions are palpable throughout. Familiar characters now gather to make protest signs and discuss the racial politics of their social circle. There are still plenty of characters who just like getting baked in the middle of the day, but High Maintenance in Trump’s America is a different series, and stoners have somewhat different priorities.

One returning focus of High Maintenance is New York real estate. It would be impossible to make a TV show about a weed bicycle messenger in Brooklyn without addressing white gentrification, and High Maintenance hits some of its highs and lows when it tackles this topic. Candace and John are back, as a young couple who first appeared on the Vimeo episodes attempting to make rent by AirBnBing their spare bedroom. These two are swiftly becoming a bellwether for what High Maintenance wants to say about the changing face of rent. Their episode of this season (about qualifying for low-income housing in a fancy apartment building whose amenities are available only to those paying full rent), directed by Shaka King, is also balanced against another real estate story: Danielle Brooks makes her High Maintenance debut as a real estate agent who transitions from a local Black dealer over to The Guy (who, unlike her usual dealer, sells vape pens) while struggling to make sure an apartment she’s selling goes to a Black couple. High Maintenance must honestly address the racial politics of gentrification and marijuana use, and producing episodes not written by Blichfeld & Sinclair is hopefully a step – or a pedal – in the right direction.

Part of what made High Maintenance perfect for the web series format was a fact about the nature of weed: in New York City, the main place to get high is at home. Every episode, The Guy delivered to someone else’s private space and shared a unique moment with them. As the show’s budget rose, its scope did too, making possible episodes like ”Matilda,” which took The Guy all over Manhattan, or Genghis,” a story set in the New York public school system to which weed was mostly incidental. In this, the second season of the show’s run on HBO, private spaces have also changed dramatically. A post-Trump New York City transforms private spaces to shared meeting and organizing areas. John and Candace, formerly living semi-independently and AirBnBing, are now living communally in a gorgeous loft coöp; Molly and Brenna’s apartment (which hosted an unauthorized “TEDx event” in the web series) is a meeting place for consciousness-raising and sign-painting for the next rally; a subway car in the season premiere becomes a pressure-release valve for New Yorkers whose only connection is riding the subway way too late at night after a long day. High Maintenance has always used marijuana to explore diverse spaces across Brooklyn (with varying levels of success), but this season the creators appear to be focusing more on the ways that weed brings people together. The result is characteristically touching and challenging stories, occasionally with some truly great sitcom chaos.

High Maintenance’s format allows it to tell these kinds of variegated stories. The series operates as a sort of semi-anthology, but unlike, say, Philip K. Dick’s Electric Dreams or even The Guest Book, individual episodes of High Maintenance can be entirely distinct genres. The Guy himself is almost a cipher (though the show’s been pulling back the curtain little by little), appearing in people’s homes sometimes only for a few moments an episode to deliver a story catalyst. The show’s closest analogue may be Room 104, another HBO series, on which the motel room is a platform for all different kinds of stories. Over its years in production, High Maintenance has also expanded its world to follow its fascination with people whose work takes them all over New York – The Guy, of course, but also dog walkers and people who collect cans for recycling and, in the case of the second season premiere, Luiz, a busboy and restaurant delivery courier. The city is tense around him, and Luis, as a Latino immigrant, is particularly vulnerable in Trump’s America, but he must focus on his own day-to-day, making deliveries and picking his son up, and in the process allowing the audience a peek into a series of different environments that The Guy would have little reason to appear in.

The title High Maintenance began as a little bit of a pun but has become a question: What does it take to maintain? For many of the characters on the series, getting through the day requires weed. For Blichfeld and Sinclair, this has been the case, as for many people with widely varying levels of productivity. As more episodes have been produced that follow characters more unlike The Guy, the show has explored more of what it can take to maintain. This season features characters using religion, anonymous hookups, and activism to stay sane in a world that feels out of control. The paranoia that allegedly comes with being high has rarely been a plot point on the show (perhaps because stoners know it stems not from pharmacology but from the stigma of prohibition); this season paranoia permeates everything. The 2016 election has created a new urgency for High Maintenance. For its characters who dwell in white, gentrified bubbles, marijuana may no longer be enough to maintain. This nuance has kept High Maintenance from making the easy pot jokes that Disjointed depends on, or even holding onto the frivolity of the unfortunately short-lived Mary + Jane. High Maintenance’s characters are much more than just goofy stoners. Eventually they must head over to Molly and Brenna’s, make some signs, and let the world know what else matters to them.

Season 2 of High Maintenance premieres on HBO tonight at 11:00pm.

Photo by David Giesbrecht/HBO.

Harry Waksberg is a writer and lazeabout based in Riverside, CA. He is the creator and writer of the web series Doing Good.

Paranoia in ‘High Maintenance’s Second Season