Interview: ‘The Guy’ on Lemon Haze, Nostalgia, and Season 2 of ‘High Maintenance’

Published on January 18, 2018 · Last updated July 28, 2020
"The Guy" Interview on High Maintenance's Season 2 Premiere | Leafly

What an auspicious moment for the return of High Maintenance. Following the story of a New York City weed delivery guy—“The Guy”—peddling his illicit wares via bicycle, the show’s second season on HBO premieres January 19, 2018, arriving at a best-of-times, worst-of-times crossroads for cannabis culture. On New Year’s Day, California’s adult-use (read “recreational”) stores opened their doors for the first time, instantly creating the world’s largest legal retail cannabis market. Then, just three days later, US Attorney General Jeff Sessions struck back by rescinding the Cole Memo, which protected state-legal cannabis from interference by federal law enforcement.

Rather than strike fear into the resistance, however, the Attorney General’s aggressive action has bred resolve. On January 10, Vermont stepped up to pass legalization through its legislature, and New Jersey has since announced a 100-day plan to do likewise—despite the ominous smoke signals that continue to emerge from Washington DC.

So what’s all that got to do with a TV show?

Well, perhaps in a few years I’ll be writing a think piece called Whither The Guy, because earlier this week, New York governor Andrew Cuomo jumped on the legalization bandwagon, announcing plans to begin studying cannabis legalization statewide. And if that leads to cannabis stores suddenly cropping up in the Big Apple like Starbucks, it’s hard to see how High Maintenance’s main character could ever hope to keep his delivery business afloat.

Legalization, of course, is a many-splendored thing, and a black market in anything fosters injustice, corruption, and abuse. But all that said, as a transplanted New Yorker living in legal California, I do have to admit that one of the many reasons I love watching High Maintenance is for a warm and hazy feeling of how things used to be.

I called Manhattan home for close to ten years before moving to the West Coast, and during that time I ordered cannabis from any number of different delivery services. Not all the time—too expensive. But certainly whenever I wanted some herb right away and my regular guy wasn’t coming through. It was like the gig economy before that was a thing, only with a major difference: Order something via Postmates or GrubHub and you make the exchange at your apartment door, quickly and impersonally. But the weed guy (or gal) is someone you let inside. You two are in a benign conspiracy together from the jump—and therein lies the narrative brilliance of High Maintenance. The Guy is constantly intersecting with his customers in their most intimate spaces, often in unguarded, vulnerable moments.

The show debuted as an independently produced web series back in 2013, a labor of love co-created by Ben Sinclair (who plays The Guy) and Katja Blichfeld shortly after they married. They’ve since split romantically, but remain partners in writing and directing the series. They’re also both people who genuinely appreciate cannabis and credit it with serving as a creative inspiration. Of course, they’re always quick to point out that the show’s not about pot, it’s about people, and they’re not selling cannabis, they’re selling characters. But they get the cannabis stuff right, and with some new cannabis TV shows out there rushing into the new space with no cannabis cred whatsoever, that’s pretty commendable.

In anticipation of the new season’s premiere, I spoke with Sinclair about cannabis as a jet lag cure, dealer nostalgia, side hustles, and Lemon Haze.

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Leafly: Hey Ben, how’s it going?

Ben Sinclair: Good man, but I just got back from a trip to Asia and I’ve never experienced jet lag like this before. So feeling a little strange. 

Have you tried weed? I hear it works wonders for that.

You know, not surprisingly, I did try that. But I didn’t smoke for three weeks while I was on this trip, because in the Indonesian airport over the loudspeaker you frequently hear a voice just causally reminding you that traveling with marijuana is punishable by death. So the first time I smoked after I got back I got really stoned.

It felt good. It was almost worth taking that break just to get that stoned again. But it didn’t make me sleepy. It made me wide awake.

Cannabis culture has changed a lot since you started making High Maintenance five years ago. How is that reflected in the new season?

I think the changes in weed culture have really expanded the kinds of people my character can visit. Not because it’s legal in other states, but because it’s increasingly socially accepted everywhere. Legalization has also gotten me thinking more about the The Guy’s precarious position. If we’re lucky enough to keep making the show, at some point we’re going to have to address the way legalization affects his business.

We haven’t gotten into that up till now, because we like to keep the focus on the people who buy from him, their lives and stories, and not get caught up in the wheelings and dealings aspect. But this season we began to give some context for The Guy as a weed vendor and there’s a lot of room to keep playing with that down the line.

I feel a certain nostalgia has built up around The Guy, particularly for those of us watching while smoking weed we bought at a store. For all its criminality and imperfections, The Guy’s operation actually hearkens back to something kind of innocent.

It’s interesting you say that, because this season, for the first time, we go into The Guy’s apartment, and a lot of the things we put in there were chosen to evoke nostalgia. He’s got an old Nintendo system in there, a vinyl record player with big speakers, and like a papasan chair.

We designed his apartment to create a kind of throwback feeling and give the impression of someone who is resisting change. Or who is more comfortable doing things the old way. I think that’s reflective of a little personal story arc that we’ve been slowly depicting over the years, but also it is definitely related to what you just said. Part of the appeal of this character is a nostalgia for the way people have been buying and selling weed for a long time.

Do you share that nostalgia?

Now that I can patronize the stores while I’m in California, I do feel more in control as a customer there. But I still happily overpay for my weed service in New York, as a kind of donation back into the community from which I grabbed stories. I feel like it’s my duty and karmic imperative to keep supporting overpriced-mashed-baggie-of-weed culture.

People come up to me all the time and say, I used to sell weed, or I still sell weed, on the side, in a word-of-mouth way. It’s a side hustle that supports a lot of artists and other people trying to make ends meet. And all of the dealers and delivery services operate differently. There’s never an easy clear way to sign up and start ordering. In my opinion, that’s pretty cool. I like having to work to get something.

But if you look carefully at the Guy’s case of weed this season, it does appear more professional, with vacuum sealed, labeled buds ready for sale. So there is an acknowledgement that he’s trying to keep up. He’s even started offering vape pens as part of his inventory. There’s a whole episode about gentrification where vape pens serve as a symbol of that divide.

What’s your favorite strain right now and what does it cost via New York City delivery? Leafly has a huge strain database so I’ll link it up.

I actually use the Leafly app, so that’s very cool. Lemon Haze is what I’m liking right now. Good terps [laughs]. It costs $60 for an eighth that’s actually probably 2.8 grams. Sometimes you can buy two of those for $100.

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David Bienenstock
David Bienenstock
Veteran cannabis journalist David Bienenstock is the author of "How to Smoke Pot (Properly): A Highbrow Guide to Getting High" (2016 - Penguin/Random House), and the co-host and co-creator of the podcast "Great Moments in Weed History with Abdullah and Bean." Follow him on Twitter @pot_handbook.
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