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High Maintenance – The Top 10 Episodes Ranked

High Maintenance Cover

High Maintenance is a brilliant series to binge-watch on HBO. It is based on the web series of the same name, created and directed by Katja Blichfeld and Ben Sinclair. Sinclair stars as ‘The Guy’, a bike-riding weed delivery service and his unconventional adventures in New York City. Each episode follows the various adventures of The Guy as he interacts with a variety of eccentric Brooklyn characters. The show has received critical acclaim for its portrayals of boredom, loneliness and the human condition. High Maintenance premiered on HBO in 2016, the episodes were released on YouTube and Vimeo before that. Sadly, in January 2021 it was confirmed that the creative pair would not be returning to HBO for a fifth season. 


Top 10 High Maintenance Episodes Vimeo

High Maintenance started out as a DIY web series that became popular on YouTube and Vimeo. The then-married couple started creating content in 2012, with their Vimeo premiere airing on November 11, 2012. They created a total of 19 episodes over six seasons, with the episodes having a runtime of between five and 20 minutes. At the time, Sinclair was a struggling actor and his wife was an Emmy-Award winning Casting Director for 30 Rock. They created episodes that relied on concise storytelling, small apartment settings and the very best talent New York had to offer; to bring the low-fi stories to life with a humanist, stoner-energy. 


Top 10 High Maintenance Season 2 Premiere

High Maintenance was scooped up by HBO, with the first season premiering on September 16, 2016. Sinclair and Blichfeld had since been divorced but still maintained their progressive partnership in creation. With HBO they created a total of 34 episodes over four seasons, with an average running time of 30 minutes. Indiewire described the series as “TV’s most human show.”

“This series has always understood and celebrated New York’s singular weirdness, and often surprising and beautiful communities that spring up therein.” – VOX

Each of the episodes is unique, with its own storylines played out by its own characters. Celebrating diversity and the beautiful communities it creates. Here is our countdown of the Top 10 High Maintenance episodes ranked!


#10 M.A.S.H – S3 E1
Top 10 High Maintenance Season 3 Episode 1

In the Season three premiere of High Maintenance, The Guy is spending some time away from the bustling city life in his RV, called ‘Steve RV’. He receives some upsetting news of the passing of his good friend; Baba. The Guy makes some new connections at Baba’s wake, where Cori is trying to adjust to her new reality without Baba. The episode manages to poke fun at the spacey sing-along hippies, yet still portraying them with absolute dignity.

#9 Steve – S2 E10
Top 10 High Maintenance Season 3 Episode 10

The final episode of season two sure leaves a lasting impression, which carries die-hard fans through to the premiere of the next season. The episode covers the beginning of one marriage and the ending of another as we experience a newly engaged couple playing along with the finalization of the divorce between The Guy and his ex-wife. The opposing narratives allow for lots of quirky interactions and the audience is reminded to choose love when the going gets tough.

#8 Googie – S2 E6
Top 10 High Maintenance Season 2 Episodes 6

The Guy has to undergo arm surgery after a bike accident. Abdullah temporarily partners with the Guy, allowing him to take a break from the life of a bike-riding weed delivery man. The new guy wants to streamline the delivery process by making deliveries in his car, allowing him to avoid the human interaction that the Guy so cherishes. The pair discuss a possible longterm partnership which The Guy later turns down, as he likes his business as it is. The distinction between the two delivery men showcases why The Guy is the heart and soul of the show.

#7 Cruise – S3 E9
Top 10 High Maintenance Season 3 Episodes 9

The season three finale sees Leonard considering moving back to New York. The Guy connects with old highschool friends who are in the city seeking treatment for their child, who is battling cancer. Even though the visit is under difficult circumstances, the episode demonstrates the affectionate spirit that can still be found in New York City.

#6 Derech – S2 E4
Top 10 High Maintenance Season 2 Episodes 4

An ex-Hasidic man explores life in New York City, outside of his sect. He experienced a typical night out in the Big City where he meets and connects with a writer, who seems to have ulterior motives. The Guy eventually crosses paths with the newbie, while driving around the City going about his deliveries. The episode features insightful material about what it means to be free and experience life to the fullest, especially in a world full of stereotypical boxes.

#5 Scromple – S2 E5
Top 10 High Maintenance Season 2 Episodes 5

The Guy’s ex-wife, who is a freelance brand strategist, is struggling with her latest assignment and is in desperate need of some weed! On her quest, she finds out The Guy is in the hospital. She rushes over, and the two end up connecting while he is high on pain medication. The episode gives the viewer a glimpse into the life of the co-creators emotional history.

#4 Trick – S4 E2
Top 10 High Maintenance Season 4 Episodes 2

The Guy has a new friend by his side, a dog named Fomo. Viewers are introduced to Matthew, who is on a date with a first-time male escort named Travis, unfortunately, the evening ends with both men feeling disappointed. The second part of the episode follows Kym, an intimacy coordinator, who connects with a familiar face, named Evan, on a movie set. Kym is forced to navigate her romantic feelings when she finds out Evan is asexual. The episode is a great example of the unique intricacies in modern relationships, where the partners define what works for them, regardless of what is perceived as “normal”.

#3. Globo – S2 E1
Top 10 High Maintenance Season 2 Episodes 1

In the season two premiere, The Guy is awoken with news of an unnamed tragedy that has overcome the nation. He ends up being busier than normal, as New Yorkers reacts to the news that is going to change the world forever. The episode follows a bunch of people who are not typically wrapped up in the news cycle. The viewer is left feeling empathetic towards those affected by the catastrophe, going about their day trying to find the light in a dark world. All the while, three individuals spent all night and day in a hotel room ignoring the world and enjoying the bliss of ignorance, even if it was just for a moment.

#2 Cycle – S4 E1
Top 10 High Maintenance Season 4 Episodes 1

The season four premiere is an adventure that ensues as The Guy tries to reunite a lost one-eyed canine with their owner. A workaholic journalist named Yara records a fight she has with her boyfriend, all for career gain! Meanwhile, Arnold, a frustrated singing telegram employee, is looking for some relief while crisscrossing New York City on a crazier-than-normal workday!

#1. Grandpa – S1 E3
Top 10 High Maintenance Season 1 Episodes 3

The episode revolves around the adventures of a dog, named Gatsby, in New York City. Gatsby recently relocated to the city, from the suburban Midwest, and seems to have a hard time fitting in. His owner eventually employees the services of a local dog walker, with who Gatsby falls in love. Things can not be going better for this canine when his owner fires Beth, the dog walker, for smoking pot and drinking beers while on the job. Gatsby is not happy and ends up hatching a plan to escape and be with his love.

Do you agree with our list of the Top 10 High Maintenance Episodes? What is your favourite High Maintenance episode? Hit us up on social media and let us know!



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