‘High Maintenance’ Season 3 Preview: Plot Details and January Episodes Guide

High Maintenance Star Ben Sinclair
Yael Stone and Ben Sinclair in ‘High Maintenance’ season 2 (Photo: David Russell / HBO)

High Maintenance returns to HBO’s primetime lineup on Sunday, January 20, 2019 at 10:30pm ET/PT. (Seasons one and two aired on Fridays.) The third season consists of nine half-hour episodes and stars series co-creator and executive producer Ben Sinclair. Co-creator Katja Blichfeld also executive produces along with Russell Gregory.

Amy Ryan, Gary Richardson, Arthur Meyer, Jen Harris, Micah Sherman and Abdullah Saeed return as guest stars. Joining the series in guest starring roles for season three are Jemima Kirke, Margaret Cho, Guillermo Diaz, Rosie Perez, Kathleen Chalfant, Ken Leung, and Annie Golden.

The Season 3 Plot: The critically acclaimed show uses The Guy, a marijuana dealer (played by Sinclair), to tell a variety of stories about New York lives, including his own. 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.

High Maintenance January 2019 Episode Details

  • Season 3, episode 1: “M.A.S.H.”
    Debut date: SUNDAY, JAN. 20 (10:30-11:05 p.m.)
    While spending time away from the city in his RV, The Guy (Ben Sinclair) gets upsetting news, but makes an intriguing new connection. Cori (Erin Markey), meanwhile, tries to adjust to a new reality without her friend.
    Written by Katja Blichfeld & Ben Sinclair; directed by Katja Blichfeld.
  • Season 3, episode 2: “Craig”
    Debut date: SUNDAY, JAN. 27 (10:40-11:10 p.m.)
    After his bike is stolen, regular customer Marty (Gary Richardson) consults The Guy (Ben Sinclair), whose suggestion sends him down a surprising path. Bored with her mundane life, Darby (Catherine Cohen) finds ways to unnerve and bewilder strangers.
    Written by Isaac Oliver & Zack Schamberg; directed by Ben Sinclair.