‘High Maintenance’ Season 3 Review: The Transition from Vimeo to HBO Finally Pays Off

The new season maintains the show's essence in a prime Sunday time slot, although its storytelling risks don't always pay off.
High Maintenance Season 2 Ben Sinclair
"High Maintenance"

Time slots still hold some currency in the streaming era, and never more so than on HBO. The network takes chances on experimental content, but tends to premiere its more out-there offerings on non-Sunday nights. Now, we’re seeing the once-risky “High Maintenance” receive the Season 3 coronation of a Sunday-night premiere, right after the Judd Apatow-produced “Crashing.” This approbation only confirms what fans have known since its Vimeo days: “High Maintenance” is a brilliant show, even when its risks don’t highlight the show’s strengths.

Watching Ben Sinclair and Katja Blichfeld’s creation shift from its origins as a web series to a grown-up half-hour comedy has been fascinating. (This critic humbly admits writing that any sort of transfer from the web to television felt like a bad idea.) The only character in every episode is a pot dealer (Sinclair), known as The Guy; he serves as the entry point to a quasi-anthology series that concentrates on his customers, highlighting a diverse range of lifestyles and cultures.

What helped the show adapt from its web series origins to a more standardized length is it held on to its vignette structure for most episodes. It also found ways to blend stories to feature multiple characters who perhaps connected by the most tenuous relationships, but never felt out of sync with the show’s sense of self.

High Maintenance Season 2 Ben Sinclair
“High Maintenance.”HBO

“High Maintenance” has always loved the mess of life, the sagging flesh of its characters, their cluttered domiciles. Befitting a premise rooted in drug use, there are touches of surreality. However, this isn’t David Lynch territory; the emotional core is direct and true, often delivered as a gut punch.

The Season 3 premiere begins with a bit of a departure. Previously tethered to his bike, The Guy acquired an RV at the end of Season 2 and is now on the road, roaming the wilds of upstate New York. This takes the show out of its comfort zone of New York City, where there’s never a shortage of humanity on display. However, this breather also allows for some exploration of who The Guy might be, a welcome choice given that the show’s structure often leaves him in the margins. The revelation that comes is the Guy himself isn’t quite sure what he’s looking for; he just knows he’s looking.

Episode 2, “Craig,” returns to the pre-established format, with a focus on clients. It’s a bit slight due to the somewhat superficial treatment of its new characters, but full of fun, and delivers on the show’s knack for surfacing nuances of city life (in this case, Craigslist ads).

High Maintenance Season 2 Ben Sinclair Sefareki Wainigolo.Sefareki Wainigolo.
“High Maintenance.”HBO

These two episodes aren’t the series’ strongest; “High Maintenance” might not have put its best foot forward for viewers who watch whatever HBO presents on Sunday nights. For them, there’s still two brilliant prior seasons to watch. It’s a show that functions well on a standalone basis, but also once you dive in, consume everything (including the pre-HBO episodes, which HBO GO/NOW packages as “High Maintenance Web Series”). Sinclair and Blichfeld’s world feels real and lived in — a real show, about a real city.

Grade: A-

“High Maintenance” Season 3 premieres Sunday, January 20, at 10:30 p.m. on HBO.

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