First season episodes 'Meth(od)' and 'Grandpa' both placed on numerous year-end lists in 2016, while second season episode 'Globo' was ranked as one of the best episodes of 2018 by sources such as Time and Variety. High Maintenance has received critical acclaim for its portrayals of boredom, loneliness, and the human condition. On January 14, 2021, it was confirmed that the series would not return for a fifth season. HBO renewed the series for a fourth season, which premiered on February 7, 2020. The show's second HBO season premiered on January 19, 2018, and its third on January 20, 2019. High Maintenance originally premiered as a web series on Vimeo on November 11, 2012, and began airing as a television series on HBO on September 16, 2016. The full series consists of six web series followed by four television seasons, released from November 2012 to April 2020.

Each episode focuses on different characters as their lives intersect with The Guy. The show follows The Guy, a cannabis courier (played by Sinclair), as he delivers his product to clients in the New York City borough of Brooklyn. High Maintenance is an American anthology comedy-drama television and web series created by ex-husband and wife team Ben Sinclair and Katja Blichfeld.