High Maintenance is an American drama and comedy series that is the creation of the duo Katja Blichfeld and Ben Sinclair. The series revolves around a nameless character, The Guy (essayed by Ben Sinclair), who travels across New York City and couriers’ pots to the customers and learns more about his client’s personal life.
The series gives a deeper perspective on the loneliness and boredom of an individual and how it affects human conditions. High Maintenance comprises six web series and four television seasons to its credit, which spanned from 2012 to 2020. The show’s episodes, initially streamed on YouTube and Vimeo, later made their way to HBO.
The show was in itself a success when it was airing on the internet alone, and after it entered HBO in 2016, it became even a bigger name indicating that the web series has a lot of potentials when given the support. However, the show has now stopped airing, as in January last year, it was confirmed that the show would not be returning with its fifth season.
The list of the twenty best High Maintenance episodes we are going to share here is from both the web series as well as the television series. The episodes make for an interesting watch, and you must read the list until the end to find the best ones!
20. Dinah
- Season: 2
- Episode: 4
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 2/20/2013
In the episode, we see an old friend arriving to stay with his couple of friends in the town. He arrived to attend his wedding to Dinah. But now that the guest has stayed a bit longer than usual, the couple is tense about his presence.
On the other hand, we see The Guy witness them in an unpleasant situation after he delivers to an asexual magician.
19. Stevie
- Season: 1
- Episode: 1
- Directors: Sarah-Violet Bliss
- Release Date: 11/9/2012
In the opening episode of the first season, we see The Guy head towards a hotel for his delivery. There he goes to a hotel room with Stevie. The woman struggles with clinical anxiety issues and has a very impatient boss. And then a regular delivery trip turns into an unexpectedly long adventure.
18. Geiger
- Season: 5
- Episode: 2
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 11/11/2014
The episode sees a woman trying her best to deal with her fiance’s existential anxiety, basically with compromised survival tendencies. The couple strives to deal with the situation to the best of their capacity. Meanwhile, The Guy tries to relate to an ASMR YouTuber.
17. Trixie
- Season: 2
- Episode: 3
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 1/17/2013
The episode sees a couple trying to earn some extra cash by renting their spare room for guests. But The Guy hears a tale about Trixie when he goes out to deliver to that couple, who seems upset due to the unthoughtful behavior of their incoming AirBnB guests.
16. Qasim
- Season: 4
- Episode: 1
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 11/28/2013
In the following episode of High Maintenance, we see one of the clients of The Guy named Kitty, an attractive girl from the spin class who begins dating a fitness freak with strict lifestyle enthusiast Scott.
The Guy’s customers start dating, but Kitty learns about his very different alternate schedule and the motivation behind it and Qasim. On the other hand, The Guy dresses for Halloween.
15. Helen
- Season: 2
- Episode: 2
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 1/17/2013
The episode follows as The Guy delivers to a man with agoraphobia. He happens to be living with his mother and has a weird obsession with Helen Hunt.
14. Jamie
- Season: 1
- Episode: 3
- Director: Thomas DeNapoli
- Release Date: 11/9/2012
In this episode of High Maintenance, The Guy meets Jamie and her lesbian partner when he goes out to deliver them the stuff. The couple was stressed because of the presence of a mouse in their apartment.
13. Genghis
- Season: 5
- Episode: 3
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 11/11/2014
In this particular episode of High Maintenance, we see a man already frustrated with his corporate job, trying to find purpose in life and strive for a change in the world. He consequently quits his job and decides to become a teacher.
But his attempt does not turn out to be fruitful as, in the process, his positive outlook on things gets challenged by his experiences in life.
12. Sufjan
- Season: 6
- Episode: 1
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 2/5/2015
The story in the episode revolves around a couple, Erza and Reagan, finding themselves unable to invest in Williamsburg. Consequently, they look out for a more affordable neighborhood to live in. But soon, it dawns upon them that it is tough to put money into real estate in New York as they won’t be able to have everything.
On the other hand, we see The Guy helps in saving a young child from a diabetic shock.
11. Heidi
- Season: 1
- Episode: 2
- Director: Ben Sinclair, Katja Blichfeld
- Release Date: 11/9/2012
In the episode of High Maintenance, we see Mark and Heidi see each other after the former’s breakup. They soon end up becoming a cute new couple, and everything seems perfect in their life until one day, when they call The Guy for the delivery of marijuana.
10. Olivia
- Season: 2
- Episode: 1
- Director: Ben Sinclair, Katja Blichfeld
- Release Date: 1/17/2013
In the episode, The Guy reluctantly delivers to a man and a woman who is saved in his phonebook by inappropriate names and has an artist friend named Olivia. On delivering to the ill woman and his son, he finds himself in an inappropriate situation with the man and bashes out some epic one-liners before leaving them for good.
9. Jonathan
- Season: 3
- Episode: 1
- Director: Ben Sinclair, Katja Blichfeld
- Release Date: 4/20/2013
We see stand-up comic Hannibal Buress starring himself in the episode. He happens to suffer from post-traumatic stress disorder after the incident where a stranger fired him in the club where he was performing. Thus, The Guy tries to cheer him up.
To add to it, Jonathan states that the best possible way to get back into the routine is by finding the passion once again, and it appeared convincing. We see the cameo of Homeless Heidi, and Carlen Altman portrays the character of Hannibal’s artist girlfriend named, Olivia.
8. Elijah
- Season: 3
- Episode: 2
- Director: Ben Sinclair, Katja Blichfeld
- Release Date: 4/20/2013
In this episode, we see the Waxman family at Passover dinner, with the top chef catering for them. You can easily make out that the family is a dysfunctional one, where the head happens to criticize each and everything, and the daughter Rachel gets drunk and then flirts with the chef. At the same time, the hosts, Joel and Shira, try their best to keep their young son entertained, and one of the family members turns out to be an asexual magician.
Thus, the chef calls The Guy for the delivery, and he arrives just in time.
7. M.A.S.H.
- Season: 3
- Episode: 1
- Director: Katja Blichfeld
- Release Date: 1/20/2019
In this episode of High Maintenance, we see The Guy discovering the sudden demise of his old friend Berg or popularly known as Baba, which makes the episode a good one in terms of both deaths as well as the birth of new connections. In his wake, The Guy meets the rest of the hippie community who had gathered to pay homage to a man who had so much love to give.
The group seemed to have deep sympathy for Berg’s roommate Cori who was deeply affected by his demise as he happened to offer her compassion rather than judgment. In the episode, we also see new bonds being made. The Guy meets Lee, who happens to get divorced soon and is on the lookout for someone new. They both share a great vibe and chemistry and hit it off well.
6. Sabrina
- Season: 6
- Episode: 3
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 2/5/2015
This one was the final episode of High Maintenance before it collaborated with the streaming platform HBO. In this particular one, we see The Guy for the first time away from the streets of Brooklyn on vacation with a few of his customers and their mates. But soon, the supposedly amazing vacation gets transformed into a nightmare when long-buried frustrations begin to surface.
To save the trip on the last day, they all decide to consume large quantities of mushrooms, accompanied by it some hilarious moments.
5. Brad Pitts
- Season: 3
- Episode: 3
- Director: Ben Sinclair, Katja Blichfeld
- Release Date: 4/20/2013
In the episode, we see an apprehensive woman discussing with her bird-watching friend Brad Pitts. But soon, she discovers that her friend is unwell and thereby suggests that they should smoke marijuana together so that her friend’s low appetite gets cured. We see The Guy delivering them the stuff and getting all the way high with the professional druggies.
4. Matilda
- Season: 4
- Episode: 2
- Directors: Katja Blichfeld, Ben Sinclair
- Release date: 2/4/2014
In every other episode of High Maintenance, we have seen The Guy play a secondary character, helping others in their lives. But in this particular episode of High Maintenance, we see The Guy as the main focus.
This episode sees the cameos from the “Jamie” episode of the show. We see The Guy trying his best to entertain his niece, who happens to have come to meet him from out of town. Thus, he decides that he will not be carrying on his business in her presence. But when their plan to see Matilda gets messed up, one of The Guy’s clients offers to help them out.
3. Scramble
- Season: 2
- Episode: 5
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 2/16/2018
The list would be incomplete if we did not talk much about the episodes primarily focused on the generous-hearted Guy, who happens to give hope in this world. In this particular episode of High Maintenance, we see Guy’s ex-wife named, Julia, learning about his former husband being in the hospital after meeting with a bike accident.
The two then happen to share a moment and connect, despite their different realities now. Thus, this episode gives a good picture of the fact that even if the equation between two individuals changes with time, they tend to remain a family even after parting ways and exiting each other’s life.
There is no doubt that the real-life separation of Sinclair and Blichfeld led to the creation of this episode, and the actors have phenomenally done their part. One can feel glimpses of the creator’s troubled history in the story.
2. Rachel
- Season: 4
- Episode: 3
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 3/28/2014
In the current episode of High Maintenance, we see the appearances of characters from previous episodes of the show, namely Olivia and Trixie. The story is about a man who gets obsessively attached to his previous success and secretly dresses up in his wife’s clothes.
During this time, writer’s block sets in, and he becomes filled with procrastination and a desire for fashion. This puts a strain on his marriage. Then the Guy makes a delivery to him and gets introduced to Rachel, the man when dressed, and helps him by giving motivation.
1. Ruth
- Season: 5
- Episode: 1
- Director: Katja Blichfeld, Ben Sinclair
- Release Date: 11/11/2014
In this top-listed episode in our list of the first season, we see The Guy plays matchmaker here. He chooses to send his two middle-aged customers who have a liking for marijuana on a blind date.
I hope you enjoyed the list of some of the top High Maintenance episodes as much as I did while writing about them. The series is filled with diverse characters and stories that do not let one get bored easily. The four seasons to have made the television presence can be viewed on HBO Max, HBO Now, Spectrum On-Demand, DIRECTV, Hulu and Max Go. The episodes can also be purchased from VOD platforms like Amazon Video, Google Play Movies, Vudu, and Apple iTunes.
The one-hour-long episodes were available on Vimeo, while the rest half had a reduced duration of half an hour. The episodes have simple stories to tell about individuals in New York and how everyone deals with their own sets of challenges that the outer world is unaware of. Be it a couple, family, loner, or even a dog, the show has it all and is, all in all, a good watch.
