High Maintenance is a show with a very unique structure that's pretty tough to sell. Honestly, I'm surprised I gave it a try at all, as I'm big on serialized character arcs and it was very clear from a simple overview of High Maintenance that this is not what it's all about. I think the reason that I actually wound up taking the recommendation to check it out was that I was a fan of Louie and that show had just one frequently recurring character (if you don't count the one played by Pamela Adlon). So, at least there was some precedent.
There's 19 (I think) webisodes of High Maintenance that run typically between 8 and 15 minutes of length. These were released between 2012 and 2015 and should be watched first. HBO then picked it up as a regular TV series and released 6 episodes (half-hour length) in 2016. High Maintenance follows the adventures of The Guy, a nameless marijuana dealer that travels by bike around New York City and delivers weed to his clients (hence the very clever name for the series). Though he's the closest thing that the show has to a main character, The Guy is not the principal focus of very many episodes. Rather, the show focuses on different clients of his in each installment and how his periodic visits for a sale fits into their lives.
Though the storylines in each installment are mostly are separate from the rest, High Maintenace does a decent job of world-building, as a few of The Guy's clients have cameos during unrelated episodes or get more than one full-length plot over the course of the series to-date. The biggest reason that the show succeeds is that creators Ben Sinclair and Katja Blichfeld have a great eye for talent and they utilized a slate of mostly anonymous character actors (on the other hand: hello, Kether Donohue and Amy Ryan!) that really make The Guy's clients come to life. 15 minutes is not a large amount of screen time, but it's all High Maintenance needs to make viewers feel like they really know these people and get a sense of their stories.
If I have a criticism of the show, it's that when you essentially create your characters and story for each episode from scratch (except The Guy), you can't draw from past episodes to create intrigue and that allows for the potential for individual installments to fall completely flat. I liked all 6 episodes of the official HBO TV series, but a couple of the webisodes didn't do it for me. That made the experience of watching those isolated episodes essentially worthless since the characters and stories don't carry over. Those were a small minority, though; most were very good. Given the non-serialized format, I wouldn't be shocked if the stories that are "duds" differ from viewer to viewer.
For those who have seen the series, my favorite of the webisodes was the one centering on comedian Hannibal Buress and my favorite of the full-length HBO episodes was "Grandpa", which is basically told through the point-of-view of a dog. For those who have not seen the series, I'd recommend giving it a try if for no other reason than that the short length of the webisodes allows you to do so with minimal time commitment. Some of my favorite recent TV experiences (Master of None, Louie) have done a good job of making relatively mundane situations very interesting via great writing and acting. High Maintenace fits pretty neatly into that mold.
Webisodes + Season One Grade: B+
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