High Maintenance: the internet’s best web TV series is back

Three new episodes of the fifth season become available today – here’s everything to need to know to get up to speed

Check out nearly any list of top 10 web series and High Maintenance is sure to be on it. Created by husband-and-wife team Ben Sinclair and Katja Blichfeld, the series tracks The Guy, a pot dealer played by Sinclair, as he visits his clients throughout New York City. The series became so popular that Vimeo, a video-hosting site that is sort of like YouTube’s snooty cousin, ponied up money to pay for the production of the fifth season of the show, which makes it Vimeo’s first original series. Three new episodes of the season are available starting today, with the final three for this season available shortly. So, what do you need to know to get started?

Well, not much. In fact, if you haven’t watched all of series so far, you should probably just start at the beginning. Each of the 13 previous episode is between five and 20 minutes long, most of them averaging out in the 12-minute range. You can get through the whole thing in one comfy evening at home. Just a warning: the new episodes carry a $1.99 price tag.

It’s great to watch the whole series at once, noticing how it has changed and evolved from the first episode – which is about The Guy getting stoned with a client who has an awful boss in a hotel room – to something that is much more ambitious and human. We now see the characters in their normal lives away from the weed transaction that put them in touch with The Guy in the first place. They’re more fully realized, moving about the city and interacting with people other than just the drug dealer. In the new episodes the cash injection from Vimeo is especially obvious, with heightened production values, more location shooting, and even snazzier camerawork than this high-caliber show exhibited before.

The show can be funny, but it would be difficult to call it a comedy. Its nuggets of keen observation – about the kids on the subway who say they’re selling candy to keep them off drugs, or the perceived superiority of the guy who works at the wine store talking down to you – aren’t the sort of usual jokes that sitcoms traffic in. Though High Maintenance can be amusing, though its attempts at humor usually tracks a little bit more absurd.

While each episode is free-standing, there is an interlocking structure to the episodes, where you see The Guy either return to repeat customers, or you watch his customers interacting in non-drug-related circumstances (which makes sense, since finding a drug dealer is usually a word-of-mouth phenomenon). This is especially rewarding when you watch them in one big chunk, but something that can be lost on viewers who can be a bit, ahem, forgetful in between episodes.

This structure is especially felt in two of the three new episodes. The first concerns itself with two new characters, an engaged couple where the woman is planning their wedding and the man is planning their escape from New York in case of an apocalyptic event. There is also a sideline about an ASMR – a phenomenon where physical pleasure can be elicited through sound – and I have a feeling that the practitioner will be back in the future.

The other two episodes feature two of the series most popular characters. Episode two is called Ghengis and features an asexual magician named Evan Waxman (Avery Monson) who has been in two previous instalments of the show; first as a customer of The Guy in the season two episode Dinah, and as a member of a Jewish family with the world’s most messed-up Seder in season three’s episode Elijah. This time he plays a man returning to grad school to become a teacher in Brooklyn, and his magic tricks and asexuality don’t go over nearly as well with inner-city youth as he would have hoped. This episode also features Patrick, the obsessive shut-in from season two’s Helen episode.

The third episode reunites us with Ellen (Birgit Huppuch) from season three’s Brad Pitts episode, one of the series finest. The first time we met Ellen she was a cancer patient who has completely lost her appetite and only gets it back after she smokes weed for the first time with her friend Ruth. Ellen is the centerpiece of this new episode, named Ruth after the same friend, when The Guy sets her up with another one of his clients, Victor (Chris McKinney). Victor’s a lonely ex-cop who works as a security guard and longs for human contact so much that he serves as the attacker in women’s self-defense classes where they pummel him under an enormous set of pads.

That’s what continues to make High Maintenance one of the best TV shows today (that’s not even on TV). It’s not really about a weed dealer and his wacky clients, at least not any more. It’s about worrying that the world is going to end, that your dreams of doing something great in the world will be dashed by other people’s selfishness, that you will die alone without anyone to love you or help you. It’s about all the reasons why we smoke pot, especially as New Yorkers, in the first place – and the peace and connections it brings.