High & Low Maintenance (w/ Ben Sinclair)
Great Moments in Weed History
David Bienenstock
4.8 • 669 Ratings
🗓️ 8 April 2026
⏱️ 51 minutes
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| 0:00.0 | I'm looking on everything. |
| 0:05.0 | I'm going to, welcome to an-new great moments in weed history. |
| 0:25.8 | This is going to be a wholly unique episode in the long run of this podcast, and honestly, one that feels long overdue. |
| 0:35.9 | My guest has been on the show before. |
| 0:39.6 | Writer, actor, and director Ben Sinclair is best known as co-creator and star of the HBO series High Maintenance. Way back in |
| 0:46.3 | 2020, he was our honored guest for a live taping of great moments in weed history as part |
| 0:52.9 | of the Brooklyn Podcast Festival. |
| 0:55.4 | That episode, which you can find in the archives, told the story of New York City's legendary |
| 1:00.8 | Prince of Pot, Mickey Caesar, who started a pre-legalization weed delivery service in the 1990s |
| 1:07.6 | that surreptitiously advertised the phone number 1, 800 want pot, and then serviced those |
| 1:14.0 | calls via bicycle messenger. The Prince of Pot story was a great fit for Ben because his character |
| 1:20.3 | on high maintenance was a bicycle delivery guy selling weed in New York City. I first saw |
| 1:27.0 | high maintenance when it debuted as a self-funded web series on YouTube in 2012, |
| 1:34.1 | a true labor of love co-created by Ben and his then-wife, Kacha Blitchfeld. |
| 1:40.3 | Immediately, I became an early champion of the show, |
| 1:43.7 | sharing that YouTube link with every stoner I knew, which was a lot. |
| 1:49.8 | Eventually, the series grew from humble beginnings to four critically acclaimed seasons on HBO. |
| 1:56.8 | Along the way, I had the pleasure of hanging out with Ben on a few occasions. |
| 2:00.5 | He came to the |
| 2:01.4 | High Times 40th anniversary party, the launch party for my book, How to Smoke Pot properly, and |
| 2:08.0 | we've shared some fun hangs off and on since, but it's been a minute. Then I clicked on a recent |
| 2:15.3 | New York Times headline. |
... |
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