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How High Maintenance, a Vimeo Web Series, Got Picked Up By HBO

Motivational quotes don’t work if they’re wrong. The Internet is a breeding ground for half-baked inspirational truisms. One of the most common refrains is to dream big, reach for the stars, and attempt the impossible. This is a powerful guarantee of disappointment and failure. After all, stars are really far away.

Instead, try this one from the makers of High Maintenance, the acclaimed web series out of New York: "Set the bar where you can not only reach it, but where you can go beyond it," says Katja Blichfeld, director and co-creator with her husband Ben Sinclair, who’s also the show’s star. In an interview with She Does the City, Blichfeld explained the approach that propelled High Maintenance from a pet project on Vimeo in 2012 to getting picked up by HBO three years later. "I’m a big proponent of scaling your vision to what your resources are and letting it grow organically," she says.

High Maintenance stars Ben Sinclair as a marijuana deliveryman in New York.

High Maintenance stars Ben Sinclair as a marijuana deliveryman in New York.

If you haven’t seen it, High Maintenance is about a marijuana deliveryman in New York, played by Sinclair and known only as The Guy. Sinclair’s character is the soul of the show: a charming and open-minded stoner who spends his days dropping by people’s apartments with baggies and banter, like the world’s best neighbor. (The couple have called him an idealized version of themselves, the person they both want to be.) But even though much of the appeal comes from Sinclair’s portrayal of the quintessential friendly stranger, the show is most deft in its depiction of The Guy’s customers.

High Maintenance isn’t an ode to weed, or to New York, as some have said, though it does sing sweetly for both. The pot is just background; the core of the show is portraiture. (For a true anthem to cannabis, check out their Tumblr page.) Each episode centers on one or two characters—usually members of the gentrifying generation, though not always—and though the action always builds toward some absurd situation or well-wrought punchline, the focus is how they feel. "What we're coming to realize is that the thing we enjoy doing is capturing these vibes," the couple said in an interview with the art news site Blouin Artinfo. "The cinema of it all, and the story and the plotline — that's just in service to the vibe."

To make the vibe feel real, Blichfeld and Sinclair concentrate on conjuring people’s living spaces. Woven into the dialogue and storyline of each episode is a close meditation on the characters’ apartments. "We're good at tone," Blichfeld told Gawker. "That's the thing we excel at, and that's the thing we feel comfortable continuing to do. And tone is most evocative in an apartment, because a person's style sets their tone."

This attentiveness to the idiosyncrasies of human habitat is a hallmark of the show, and certainly one of the reasons it feels so brilliantly on point, but it’s also a trait born of necessity. Creative endeavors usually start poor, and High Maintenance is no exception. The early episodes were made on anywhere between $500-$1500 per show, a pittance by any standard, and certainly not enough to pay for public location shoots.

Lack of funds is not the same thing as lack of resources, however. In the beginning, the couple relied heavily on their very talented friend pool. One of their greatest assets has been Blichfeld’s experience as a casting director in New York (she worked on 30 Rock). "When I meet someone who has an interesting personality, I immediately default to: How can I showcase that? How can I make good use of their talent?" she told No Effects podcaster Jesse Cohen.

The original aim of the show was to showcase their talents and that of their acting friends—basically, to get more work. Before High Maintenance, for example, Sinclair had been typecast as a creep, a wildman, and an uber-hipster, and Blichfeld wanted to help him break the mold. (These bearded-guy stereotypes are very much in evidence in his acting reel from 2011.) Likewise, most of the episodes are designed to highlight a particular person’s particular gifts, not just their looks. In this sense, the contribution between creators and friends goes both ways: not so much asking favors, but building an ethos of mutual support.

In order to elicit the unique strengths of their actors, Blichfeld and Sinclair leave a lot to chance in the filming, and exert more control in the editing stage. They don’t over-determine the scripts, so that people have space to ad-lib. "We make sure to pull new actors aside in the beginning and say, ‘Listen, you have no control over how you’re portrayed over here’," Sinclair told The Creators Project. "I’m going cut the shit out of this. Your mouth is going to move to lines that you said in another scene. We invited you here because we believe in you. We didn’t even audition you. Just go with it."

Apart from finding talent in their own circles, Sinclair and Blichfeld gather the material for each episode from their own lives. "We're really into low-hanging fruit. We don't like to do anything we can't get our hands on easily, and there's no lower-hanging fruit than our personal experiences," Sinclair says. "We wouldn't try to do something if it didn't feel authentic to something we've experienced." When the driver of an ice cream truck swats the phone out of The Guy’s hand, it’s because the same thing happened to Sinclair in real life. Or when a couple moves to a remote part of Brooklyn and find themselves feeling isolated, it’s because the show’s creators tried the same move, with the same consequences.

Most of all, they rely on instinct. "We make the show by listening to our guts," says Sinclair. The first real test of their intuition came early on, when they decided to eliminate The Guy’s backstory and move him to a supporting role. As it was originally conceived, the character had studied and failed to become a psychopharmacologist, and the first episode, Stevie, shows him dispensing some unwanted pharmaceutical advice. They tinkered with the footage for eight months, according to Resource Magazine, until finally they realized they had to make him as mysterious to the audience as he is to his customers.

Blichfeld and Sinclair’s practical, instinctive, and focused approach has won them many fans, and with fans come backers. Vimeo invested in High Maintenance back in 2014 as its first-ever sponsored video-on-demand web series, which allowed Blichfeld and Sinclair to break out of their budgetary constraints for the last six episodes. The couple used the new cash to do things that they couldn’t otherwise: pay people, tighten their production schedule, shoot outside their friends’ apartments. But the extra money didn’t change what they’re trying to do, and most aspects of the show have remained much the same, including their creative process, which mainly entails smoking weed and talking. (They don’t smoke on set, however.) "Katja and I are together all the time. All. The. Time. It's mostly talking, talking, talking until we sit down and force each other to write," Sinclair told Details.

Much of the talking takes place on walks and bike rides, or at Korean spas. They always start with the climax, and then move backwards. Once they have a strong idea of how the story will work and a deep understanding of the tone they want to evoke, they move to notecards. (They also keep a waterproof pad in the shower, for soggy inspirations.) Everything from overarching concepts to scraps of dialogue gets pinned to a corkboard, which are then arranged according to a rubric they created for the show ("character exposition," "title card," "situation development," "introduction of weed element," "B story," "weed delivery," "climax," and "button."). Sinclair often writes the initial draft and Blichfeld edits, leaving plenty of space for improvising on set.

The creators of High Maintenance know what they’re good at, and that’s what they do. It’s a system that has allowed them to create many beautiful and hilarious moments on screen, always with exquisite timing and restraint. We’ll see what they can do with the resources of HBO behind them. If there are any lessons to be gleaned from the amazing success of the show, they are (a) be real, and (b) be realistic. There are other important takeaways—be generous, trust your gut—but none of them matter much without a sturdy engine of authenticity to carry you to your genuinely attainable goals.

Origin Stories Magazine tells the stories of artists and entrepreneurs before their first break. We publish 2 new stories every month. How High Maintenance, a Vimeo Web Series, Got Picked Up By HBO was published on Apr 22 2016.

Mark circle Mark Mann Mark Mann is a freelance writer based in Toronto and Montreal. He writes about art, technology, business, and urban issues for a wide variety of publications, including Report on Business, The Walrus, and Toronto Life.