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Ben Sinclair: High Maintenance And The Battle Of The Podcast Stars

Ben Sinclair at the Bell House in Brooklyn, New York.
Mike Katzif
Ben Sinclair at the Bell House in Brooklyn, New York.

Before playing a weed delivery man in the HBO comedy series High Maintenance, actor and writer Ben Sinclair worked as an actual delivery man. Sinclair worked at a Brooklyn floral shop for three summers, where he delivered flowers directly to the shop's clients. This experience directly influenced High Maintenance, which Sinclair co-created with his then-wife, Katja Blichfeld. The series follows an enigmatic weed delivery man known as "The Guy" as he meets new clients and explores the intricacies of life in New York City. Every episode introduces a new character and a unique story, with Sinclair's character serving as the show's connective thread.

Ben Sinclair appears on <em>Ask Me Another</em> at the Bell House in Brooklyn, New York.
Mike Katzif / NPR
Ben Sinclair appears on Ask Me Another at the Bell House in Brooklyn, New York.

In a conversation with NPR's Ask Me Another host Ophira Eisenberg at the Bell House in Brooklyn, New York, Sinclair talks about the personal experiences that inspired High Maintenance, his love of Chekhov, and writing fan letters to Steven Spielberg.

Later, Sinclair, a self-described "pod-head," guesses the names of popular podcasts based on bizarro-world versions of their titles.


On Chekhov"I'm cuckoo for Chekhov. I thought it was so fun to be in a Chekhov play... So I went to Russia to study it and I don't know what happened. I was at Chekhov's grave and I did a grave-rubbing of his grave with a crayon. I was expecting to feel something and I felt nothing. It was the most Chekhovian moment of my life."

On Working As A Flower Delivery Man in Brooklyn"I would go from apartment to apartment in Williamsburg, just hanging out in people's places. ...People would be like, 'You're the help!' and I'd be like, 'No, I'm in your house! Let's talk!' I think The Guy came out of that time of [my] life."

On The Role Of Weed in High Maintenance"[Weed is] a portal topic to talk about any other story and really, at the end of the day... [High Maintenance] is about human suffering and people looking for a way to put a pause on human suffering just so they can collect themselves a little bit."

Heard on Ben Sinclair: High Maintenance And The Battle Of The Podcast Stars.

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