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‘High Maintenance’ Trailer: The Guy Invites You to See New York from Behind the Wheel in Season 3

HBO's unclassifiable weed delivery show packs up the bike and heads to a new night of the week.

High Maintenance Season 3 Trailer HBO


For a show set in one of the world’s most iconic cities, “High Maintenance” has managed to brew up a trademark visual image of its own: The Guy (Ben Sinclair), purveyor of weed to the most wide-ranging of New York clientele, riding his bike down a busy street.

“High Maintenance” Season 3 is switching things up a bit, putting the show’s main dealer inside a moving vehicle for once. Judging by the looks of HBO’s trailer for the upcoming episodes, that also includes some pretty revelatory experiences at a car wash and some rainbow-tinged offerings for some of New York’s most stressed out residents.

Series creators Katja Blichfeld and Sinclair return to the series as executive producers, and the show’s traditional assemblage of one-off guest stars returns with an impressive new collection. Amy Ryan will return to the show after appearing in the early Season 1 episode “Museebat.” Among those making their “High Maintenance” debut this season are Rosie Perez, Jemima Kirke, Margaret Cho, Ken Leung, Guillermo Diaz, Kathleen Chalfant, and Annie Golden. Season 3 will run for a total of nine episodes.

“High Maintenance” was one of the first massive web-to-TV success stories, hopping to HBO after being originally distributed through Vimeo. Now, it’s making a second big jump, moving to the network’s Sunday night lineup after airing its first two seasons on Friday nights. That shift is building on an already solid critical standing; the blistering Season 2 premiere “Globo” made our Best TV Episodes list during the heart of the summer.

Watch the full trailer for the new season (including some close-call car accidents and some shots of RVs winding through the upstate New York roads) below:


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

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