Pop Culturing: 'High Maintenance' Returns for a Cozy & Emotional Season 3

Jason St. Amand READ TIME: 3 MIN.

"High Maintenance" returns for its third season on HBO Sunday and it's a reminder that not all TV shows have to be dark and cynical in this overpopulated television landscape.

The half-hour comedy series remains to be one of the most empathetic and humanistic shows today. Even in its most upsetting moments – when it is reacting to the confusing world around us – "High Maintenance" always manages to find hope. Created by Katja Blichfeld and Ben Sinclair as a webseries, their project has lived on HBO now for three seasons now. It's managed to deliver slices of New York City life, shinning the spotlight on a plethora of different people that make the Big Apple one of most exciting places to live in the world.

"High Maintenance" is sometimes seen through the eyes of pot dealer The Guy (Sinclair), who bounces in-and-out of the lives of his clients. Most of the time, the show follows a day in the life of his customers but lately, the show has taken time to explore The Guy's personal life. When episodes center around the folks he meets, it allows "High Maintenance" to tell an array of complex and vibrant stories that feel like you're getting to experience a world you'd never be able to see. That's no different in Season 3 as the show maintains its warm and often hilarious storytelling and its vignette framing device.


Ben Sinclair and Britt Lower in "High Maintenance." Photo credit: David Russell via HBO

Season 3 picks up where Season 2 left off with The Guy taking a break from city life to travel around upstate New York in his R.V. In the first episode, "M.A.S.H." (written and directed by Blichfeld), The Guy's vacation is interrupted when he learns that a friend from his past has died. Nevertheless, The Guy's loss is coupled with meeting a new love interest. The Guy has been shown as a zen dude who doesn't let much bother him. But as of late – since the 2016 presidential election – The Guy seems to be searching for something that he can't seem to find.

"This [season], it's about The Guy's romantic life more so. I have dated three people quite seriously since breaking up, so I had been doing a lot of that kind of soul-searching myself," Sinclair told BuzzFeed of his personal life. Blichfeld and Sinclair created the show together while they were married but went through a divorce during "High Maintenance" Season 2.

"This third season is like, 'Oh, he's got wants and desires outside of selling weed,'" he added. "When I want to separate myself from that character, I also think to myself, 'Dude, you may never have a platform ever again. You could die tomorrow.' I am happy to marry myself to that character, 'cause he's pretty cool. He's like the better side of me."

Meanwhile, the brilliant episode also focuses on Cori (Erin Markey), a friend of the recently deceased. We see things from her perspective as she copes with the passing of her close friend and the important role weed played in their relationship. Weed is celebrated in a beautiful way during the funeral where friends, including The Guy, honor marijuana and how it's brought them closer together.


Ben Sinclair in "High Maintenance." Photo credit: David Russell via HBO

The second episode "Craig," directed by Sinclair, brings the show back into focus and returning to its familiar format. It follows a frequent customer Marty (Gary Richardson) who, after getting his bike stolen, ends up on a path that is a true fever dream. Dealing with a sleeping problem, and later becoming a bit obsessed with getting free stuff from Craigslist, it's one of the show's most fantastical episodes, reaching Lynchian levels of absurdness and horror.

The two episodes are not "High Maintenance" at its best but solid entries into the series. Though they're darker than most episodes of the show, there's always an upbeat silver lining.

"There's a lot of death in this season. And it's like we're saying, 'Life goes on, and we're all gonna die,'" Sinclair told BuzzFeed, later adding that he's most at peace with the world when he's riding his bike around New York City – something The Guy often does on the show.

"All you have to do is just look around and be like, 'Whoa, I live in New York City, what the fuck,'" he explained. "That's incredible. Even that alone."

It's the perfect mantra for a show like "High Maintenance" – one that finds hope and peace in the scariest of times.


by Jason St. Amand

This story is part of our special report: "Pop Culturing". Want to read more? Here's the full list.