'High Maintenance' Season 3 Trailer: When New York Burns You Out, Stoners Just Roll With It

Based on the web series from Katja Blichfeld and Ben Sinclair, “High Maintenance” might be one of the best shows on television you’re not watching, though clearly someone is since HBO has renewed it for a third season. Remember that critically-acclaimed episode of Aziz Ansari’s “Master Of None,” where Aziz and all the characters on the show took a backseat and the episode centered on a series of random New Yorkers instead? That’s a little what “High Maintenance” is like, but to be fair, it came first as a web series in 2012.

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Regardless, the show, also stars Sinclair as “The Guy,” a bike-riding, weed-delivery salesman with an eclectic variety of Brooklyn clients and it was a terrific glimpse into the lives of New Yorkers who often aren’t given center stage. Over what is now becoming four seasons if you consider the Vimeo web series a season (we do, it’s essentially watching), “High Maintenance” introduced you to a number of kooky clients that bought weed from the Guy and occasionally, you would see them featured again down the line.

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Here’s the official synopsis:

This season, HIGH MAINTENANCE profiles everyday people whose stories of success, failure, love, and loss intersect across New York, while delving deeper into personal life of The Guy, who is spending less time on his iconic bicycle and more time in “Steve RV,” a set of wheels gifted to him last season. Featuring an intricate web of memorable returning characters and unforgettable new faces, the new episodes find New Yorkers exploring their relationship with the city, touching on such themes as death, parenthood, sexuality, fantasy, aging and more.

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However, season two of the HBO line was a bit of a game changer. Katja Blichfeld and Ben Sinclair famously divorced and left him for another woman (strangely enough the very premise of The Guy’s storyline, written before it actually happened in real life). So, season two, tried to spend more time with The Guy, getting to know him and his experience, his ex-wife, her girlfriend and that kind of personal struggle for the weed man.

And we have to say, season two—outside of the opening episode, set the day after the November, 2016 election when Trump was won the Presidency, which might’ve been one of the funniest episodes of television that aired in 2018—it was a bumpy, uneven season “High Maintenance” didn’t make our cut of the 20 Best TV Shows of 2018 this year).

But we’re hoping season three has some major redemption and sticks to its roots. Notable guest stars who have appeared in the past, return including Amy Ryan, Chris Roberti, Yael Stone and more.

“High Maintenance” usually features some pretty good indie directors too like Eliza Hittman (“Beach Rats”), Shaka King and of course, Blichfeld and Sinclair, who continue to write and direct the show despite their romantic split. The directors of season three haven’t been revealed yet, but we’re hoping for an equally exciting list.

“High Maintenance” returns for an all-new season on January 20, 2019, on HBO.