Growing up in Scottsdale, Ben Sinclair was active in Temple Kol Ami’s youth group and even served as a counselor at a Jewish summer camp in California. So how did this nice Jewish boy end up selling pot in Brooklyn?

Sinclair is the co-creator and star of the HBO show “High Maintenance,” which explores the lives of the customers of a bike-riding pot dealer called simply the Guy, played by Sinclair. Originally, the show was filmed on the barest of budgets and financed by Sinclair and his then-wife, casting director Katja Blichfeld, the show’s co-creator. In 2014, Vimeo offered to fund and host the series until HBO came calling in 2015.

“The show was made at a time while Katja was working at ‘30 Rock’ and had the summers off between seasons, and I was working in a plant shop in Brooklyn, interacting with Brooklynites and being a plant care consultant,” Sinclair said. “I would go into people’s homes and deliver plants and plant them on their balconies. I spent a lot of time meeting people in their homes and kind of was cultivating the character of the Guy, this dude who would come into your home and be open and welcoming and fun to talk to.”

Though the Guy is the common thread between the other characters, he is not the show’s protagonist. Rather, he is often, though not always, merely a vehicle for viewers to enter into other lives. As critic James Poniewozik wrote in The New York Times in 2016, the show is a “wry, peripatetic series at heart, a vision of urban life as a web of stories connected by wisps of smoke.”

According to Sinclair’s sister, Heather Ross, who is currently running for Arizona’s 6th Congressional District, even from a young age her little brother had a “sense of theatricality and a sense of wanting to be able to capture that theatricality in a fairly permanent way.”

She recalled an incident with Sinclair, who was around 8, and their other brother, Daniel.

“They were filming a music video that included Daniel and one of his friends jumping off of the roof, which was only a one-story house,” Ross said. “Ben was filming them. Daniel jumped off the roof and slipped on the grass and actually broke his wrist, but Ben kept filming the whole time.”

This commitment to capturing reality, however sad or uncomfortable, is something that Sinclair has infused into the series.

“The whole conceit of the show is that you look at a person on the street and you imagine an entire life for them that extends beyond that moment,” Sinclair said. “We were trying to encourage the audience to do that with our main character, him being the centerpiece but the one you know the least about.”

Though he has strayed far from his Valley roots in a geographic sense — he still lives in Brooklyn — Sinclair has continued to explore Judaism, both as a culture and religion, in the series.

“In episode four of this year, ‘Derech,’ we explore a specific former Chasid who has been shunned from his community and is just trying to make his own way in New York, a place that he’s been living his whole life, but now he’s starting over,” Sinclair said. “It’s interesting that so many people can identify with that loneliness and isolation, but I don’t think that’s a mistake. I think our capitalist culture encourages ego, which is to say, the difference between you and the rest of the world. It separates you from the great energy that is time and space.”

The episode features a character named Baruch played by actor Luzer Twersky, who is himself a former Chasid. Another character, a journalist named Anja, pretends to be romantically interested in Baruch in order to gather information for an article.

“Once all of those pieces were in motion, it just started coming together,” Sinclair said. “It was this idea of not other-ising Baruch, not making it be ‘those people.’ I was kind of making fun of myself as a filmmaker as well. In a way, I was both Baruch and Anja in the writing of that.”

Other episodes feature Jewish characters and themes as well, such as the web series episode titled “Elijah,”

which explores the complicated family dynamics of a Seder.

“I recall that I hadn’t ever seen a Seder portrayed on TV before,” Sinclair said. “We just wanted to give you some Seder realness.”

Another web episode was partially filmed in the Valley and features Congregation Beth Israel. Sinclair’s niece, Ross’ daughter Kate, played Sinclair’s on-screen niece. Ross appears in the episode as well, albeit in a brief, uncredited role.

“I have a really interesting link to the Jewish community in Scottsdale and Phoenix and the Southwest in general, because they were some of the largest community feelings that I’ve ever experienced,” Sinclair said.

Ross also remembers the role Judaism played in her brother’s life. She said of all four of the siblings, Ben was the most actively engaged in organized Jewish life.

“Jewish life, that was a big part, for Ben, of how he integrated into society,” Ross said. “I think that really infuses his person and has infused his art. Everything that he does is very much with the Jewish eye. You see it in the show, sometimes very explicitly, but I think that you see it in how he looks around and views the world.” JN

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