In the early days of this decade, it was unclear if the DIY web series that populated YouTube and Vimeo could ever make the jump to TV. Now, the sustained success of shows like Insecure, Broad City, and Drunk History has proven to TV execs that the internet is its own talent pool waiting to be noticed, and that a little bit of industry support can go a long way. But High Maintenance, the best web series of the lot, never needed television as a support system.
Created in 2012 by then-husband-and-wife team Ben Sinclair and Katja Blichfeld (a struggling actor and a casting director for 30 Rock, respectively), High Maintenance was built upon a simple premise that allowed for a wide variety of characters and stories. Following a unnamed pot dealer (wonderfully played by Sinclair) who visits a different client every episode, the series relied upon concise storytelling, small apartment settings, and New York’s large talent pool to help bring their lo-fi stories to life. Now, seven years later, the series has just wrapped its third season on HBO, it’s just been renewed for a fourth, and Sinclair and Blichfeld have ended their marriage, but not their creative partnership. A lot has changed since High Maintenance debuted, but its humanist, stoned energy maintains like an old friend.
With 44 episodes under its belt, spanning the internet and television, comprising stories about couples, loners, families, obsessives, and even a dog, it can be helpful for a newbie to know where to start, even though most all of them are worthwhile. It’s time for Vulture’s definitive of High Maintenance episodes, ranked from worst to best.
44. “Selfie†(Season 1, Episode 5)
A strange, high-concept misfire for an otherwise grounded series, “Selfie†features Greta Lee’s return as “Homeless Heidi,†a serial con artist who shacks up with men for free lodging and food. Now married and living comfortably, Heidi sues her ex, Mark (Kyle Harris), after she learns he stole her life story for a TV show. She enlists The Guy’s help after informing him that Mark based a character on his own life, and hired Brett Gelman to play him. The whole thing is a nonsensical, implausible mess, built around an unlikable character that works better in small doses (like, say, a webisode.) A funny Hannibal Buress cameo can’t fix everything.
43. “Olivia†(Web series, Episode 4)
The Guy delivers to two assholes (listed as “Assholes†in his phone). The assholes in question eventually steal from The Guy, who bans them in retaliation. That’s pretty much it for “Olivia,†an exhausting, though accurate depiction of two self-absorbed New Yorkers (Max Jenkins and Heléne Yorke) who look down on everything and everyone but themselves, including our protagonist. Luckily, The Guy gets in a piercing one-liner before he leaves their sight for good.
42. “Jamie†(Web series, Episode 3)
The neurotic activist couple Brenna (Brenna Palughi) and Molly (Molly Knefel) are a comedic highlight of the series, but their first appearance in High Maintenance is more than a little bland. The two find a mouse caught in one of their glue traps, but don’t know how to kill it humanely, so they enlist The Guy’s help. He uses marijuana smoke and a frying pan to send the mouse to the great beyond. It’s nothing special beyond the gag of Brenna and Molly listening to Bon Iver’s “Flume†at deafening volumes to calm anxiety.
41. “Helen†(Web series, Episode 5)
Michael Cyril Creighton stars as the lonely, agoraphobic Patrick, who lives with and cares for his sick mother. He never leaves the apartment, ordering everything to the door, including pot, ostensibly for his mother’s pain, but really just to see The Guy. Though one of the series’ sadder episodes, “Helen†suffers from a clunky, arrhythmic quality that can’t be saved by Ben Sinclair and Creighton’s genial chemistry. Luckily, Patrick returns in better episodes, especially “Ex.â€
40. “Stevie†(Web series, Episode 1)
The one that started it all. We receive a brief glimpse in The Guy’s daily routine, but the episode is mostly a showcase for Bridget Moloney, who plays an overworked assistant suffering from Klonopin withdrawal. Following a brief misunderstanding, The Guy offers her some pot after relaying a brief anecdote about Stevie Nicks’s own withdrawal hell. It’s a nice, lo-fi introduction to the High Maintenance ethos, and it’s a blessing that the show would continue to top itself in the years to come. (Fun fact: Sarah-Violet Bliss, co-creator of Search Party, directed the episode.)
39. “Meth(od)†(Season 1, Episode 1)
“Meth(od)†is High Maintenance’s HBO debut, and, frankly, it’s a strange choice for the series’ big move to television. (Sinclair’s subsequent admission that the first season was influenced by his marriage problems with co-creator Katja Blichfeld sheds some light on the episode’s tone.) The episode marks the return of Max (Max Jenkins) and Lainey (Heléne Yorke), the two Assholes from “Olivia,†but in a more forgiving, yet darker context. Max spins a lie about substance addiction to gain favor with a new group of friends separate from the obnoxious, taxing Lainey. When she eventually blows his secret, Max spirals into a meth bender that eventually lands him back in her arms. An emotionally disturbing episode about the intersection between addiction and toxic relationships, “Meth(od)†is more compelling in theory than in execution, even though Jenkins and Yorke’s performances are standouts.
38. “Esme†(Web Series, Episode 18)
High Maintenance often presents its characters’ most alienating qualities first before breaking them down to reveal the vulnerable core underneath their superficial exterior. Normally, Blichfeld and Sinclair are very good at this, but it never quite materializes with “Esme,†which follows Orly (Tracee Chimo of Orange Is the New Black fame), an obnoxious, Stomp-obsessed dealer for the feminist “Canna-bitches†collective. Orly’s off-putting enthusiasm for Stomp, going so far as to blow off her job to audition for a spot on the team, can be appreciated in the abstract, but her rude personality and irresponsibility does her little favors. When she receives her comeuppance at the end, it feels like a blessing. Meanwhile, “Esme†marks the debut of Yael Stone as Beth, who later becomes The Guy’s love interest.
37. “Proxy†(Season 3, Episode 8)
The strong first half of “Proxy†follows Adriana (Rosie Perez) and Arturo (Guillermo Diaz), a married couple who purchase a silicone baby so they can playact as parents. Though Arturo finds Adriana’s obsession with the doll weird and off-putting, he softens when a public trip with the “baby†turns tense after a white woman accuses the two of being neglectful parents. Later, a final, heartbreaking exchange throws the entire story into sharp relief. In the weaker second half, Erin (Christine Elmo), a multimedia dancer, works as a nanny for a Hollywood director whose wife recently died. Though Erin bonds with the director’s young son (Gabriel Gurevich), who copes with the loss by pretending he’s a dog, she struggles with his older daughter (Rileigh McDonald), who acts out and resents her very presence. As Erin struggles to move on from the job, she learns that her casual hook-up, The Guy, has been seeing other women. From now on, she’ll only call him for weed.
36. “Geiger†(Web series, Episode 15)
Another strange episode, “Geiger†stars William Jackson Harper and Tanisha Long as Andrew and Lucy, a well-to-do couple who embrace survivalist ideology to assuage their existential fears. Andrew’s obsessive paranoia quickly overwhelms Lucy, especially when she realizes that he’s using it to justify his disinterest in children. Blichfeld and Sinclair’s sideways approach to satirizing the hang-ups of the upper-middle class doesn’t offer much in the way of insight, but it’s still funny as hell. Years before his star turn on The Good Place, Harper gives a fantastic performance as a man who descends into madness based on tenuous anxieties about the world’s collapse.
35. “Trixie†(Web series, Episode 6)
“Trixie†introduces Candace (Candace  Thompson) and John (John E. Peery), a thrifty couple who rent out rooms in their apartment on Airbnb to pay the rent. Unfortunately, a host of inconsiderate and weird guests populate their place, stressing them out even more than before. Candace and John are great recurring High Maintenance characters, and Thompson and Peery’s chemistry is a series highlight, but their introduction is a little too muted to be memorable. However, even High Maintenance’s minor episodes feature great scenes, like Candace’s story about Trixie, which is an utter delight.
34. “Grandpa†(Season 1, Episode 3)
The One From the Perspective of a Dog. After moving to the big city from the suburban Midwest, Gatsby the dog (played by the expressive and cute Bowdie) experiences some difficulty adjusting to his new environment, until he develops a crush on his dog walker Beth (Yael Stone). Just when things begin to look up, Gatsby’s owner Chase (Ryan Woodle) fires Beth for smoking pot on the job, prompting Gatsby to plot an escape plan. For many, “Grandpa†was a highlight of the series’ first HBO season, but for me, it felt a little too thin to have much of any impact, even if it falls in line with the season’s overarching theme of people (or dogs) struggling to break free of old identities. At least Gatsby gets a happy ending.
33. “Ghost†(Season 2, Episode 8)
The first half of this episode is a dud: Helicopter Mom (Jessica Hecht) is too involved in her daughter’s life, while Frustrated Dad (Josh Pais) tries to use pot to reignite their sex life. The second half, however, is great, as The Guy helps out an elderly hoarder (Stan Carp) who clearly suffers from either Alzheimer’s or dementia. High Maintenance rarely moves into such despairing territory, but one look in the old man’s cluttered apartment will sink even the strongest hearts. Before The Guy leaves, the man mistakes The Guy for someone from his past and offers some encouraging words. It’s a sad commentary on how the briefest of connections can provoke the strongest of memories.
32. “Blondie†(Season 3, Episode 3)
A relatively minor episode, “Blondie†splits its time between two characters, one young and one old. Raymond (Ethan Hutchinson), a young boy with the day off from school, desperately tries to help his barista mother at her upscale café, but mostly just gets in the way. Meanwhile, veteran New Yorker and ’70s culture casualty Barbie (Annie Golden of Hair and Orange Is the New Black fame) moves in with the nudist Arthur (Arthur Meyer), who doesn’t yet know the full extent of her unpleasant personality. After a few weeks of conspiracy theories and unfriendly living habits, Arthur begins to doubt the durability of their living arrangement. Fortunately, Barbie’s accidental weed consumption brings them closer together, even if it’s only for a little while.
31. “Pay Day†(Season 3, Episode 5)
The two couples at the center of “Pay Day†both have money problems, just not in the way you might think. When Ayasha (Hye Yun Park) and her older partner, Doc (Margaret Cho), add kinky financial bartering into their sex life, it reveals fissures in their relationship regarding age and financial security. Meanwhile, two bored summer school teachers (Jenn Harris and Micah Sherman) start an affair only to miss out on a major financial opportunity while in bed together. Though ultimately too bland to make an enormous impression, “Pay Day†is still a good example of High Maintenance’s it-takes-all-kinds worldview, sensitively embracing queer identity and offbeat sexual dynamics. Plus, the teachers’ comeuppance at the end of the episode is a series highlight.
30. “#goalz†(Season 2, Episode 9)
High Maintenance frequently pokes fun at or examines the cultural Zeitgeist, but any time a show tackles the internet or social media, it can devolve into hectoring even under the best of circumstances. Fortunately, “#goalz†never becomes an annoying treatise on The Way We Live Now, although two out of the three stories — a guy quitting the internet cold turkey, and a comedian facing harassment and death threats after a controversial tweet — are fairly bland despite their relevancy. The last story, about a middle-aged woman (Alexandra Auder) who attempts to match the record for longest individual dance competition, is inspired, especially when it moves from a kooky celebration to body horror in just ten minutes.
29. “Dongle†(Season 3, Episode 7)
The primary stories in “Dongle†involve a recently emigrated Puerto Rican construction worker (Cedric Leiba Jr.) who crushes on a bodega worker (Juan Torres-Falcon), and a young girl (Thandi Inès) who saves her family’s fireworks display, but the episode comes alive in the B-plot starring The Guy and Lee (Britt Lower). They attend a “Holidazzle†boat party thrown by Lee’s friends together only for her to feel judged by the crowd, including The Guy’s ex-wife Jules (Kate Lyn Sheil). We finally learn why: Lee publicly defended her actor ex-husband’s abusive behavior before he was #MeToo’d, and even though she left him, she still has to live with that choice. The Guy stands up for Lee to Jules, but also discovers the ways in which he and Lee are simply not simpatico. High Maintenance excels at depicting the weight of casual disappointments, such as the moment when Lee can’t even fake enthusiasm for the fireworks display that The Guy so clearly wanted to share with her. Sometimes the best chemistry takes a backseat to very messy baggage.
28. “Museebat†(Season 1, Episode 2)
Muslim college student Eesha (Shazi Raja) longs to get high while living at her aunt and uncle’s place in Brooklyn, and a married couple, Leo (Lee Tergesen) and Gigi (Amy Ryan), who frequently engage in group sex must disclose a STD to their playmates. These two premises might be tenuously connected on face, but they’re linked by Blichfeld and Sinclair’s bone-deep interest in exploring cultural difference. Eesha, a Westernized first-generation immigrant, struggles with her dual identity while living at home, trying to break free of her family’s confines even though she loves them. Meanwhile, Colin (Dan Stevens) and Becky (Katja Blichfeld) are outsiders invited to an orgy under false pretenses, struggling to understand the group sex culture when a problem arises among the members. Both stories take place in the same apartment building and eventually collide in an off-handed way.
27. “Jonathan†(Web series, Episode 8)
Comedian Hannibal Buress stars as himself as he struggles with PTSD after a stranger opens fire at a comedy club during his set. Though Buress excels when he’s more verbose and dynamic, he conveys restrained depression well, especially in a pivotal scene when he and The Guy play Gears of War 3 together. Plus, “Jonathan†makes a convincing argument that the best way to ease back in a normal routine is to rediscover your passions. Features Carlen Altman (The Color Wheel) as Hannibal’s girlfriend Olivia, and a brief cameo by Homeless Heidi.
26. “Heidi†(Web series, Episode 2)
An early High Maintenance highlight that showcases the series’ impressive use of montage, “Heidi†introduces the title vagabond as she moves in with Mark for a couple weeks, mooching off his income and apartment. After The Guy makes a visit, he tells Mark that he’s dating Homeless Heidi, who has previously ensnared various men under similar circumstances. It’s a very funny reveal, and The Guy offers a free edible to Mark as a token of his sympathy, but offers some crucial parting words: “You better hide that because homegirl will snatch a baked good.â€
25. “Craig†(Season 3, Episode 2)
Sometimes High Maintenance breaks from its slice-of-life routine and moves in a more fantastical direction. Take “Craig,†which features two Craigslist-related stories that foreground mood over narrative. In the first half, The Guy tells the narcoleptic Marty (Gary Richardson) to check Craigslist for his stolen bike (“It’s not just sublets and cum,†he says. “It’s also bike pirates.â€), which sends him down a rabbit hole of buying cheap items from sketchy sources. The second half follows Darby (Catherine Cohen), a performance artist with a proclivity for flashing strangers, who goes on a Missed Connections date and meets her provocateur match. With the former using dream logic as a device and the latter assuming the playfully reckless energy of its subjects, “Craig†wonderfully illustrates the flexibility of High Maintenance’s storytelling.
24. “Tick†(Season 1, Episode 4)
Generational differences are some of the lowest-hanging fruit for comedy writers. They can be easily exploited for cheap jokes that do little else but flatter the audience’s preconceived notions about “olds†or “the youth.†Blichfeld and Sinclair take on the more difficult task of examining the melancholic plight of Baby Boomer Jim (Peter Friedman), who spends his days exploring his younger side by getting high and keeping up with millennial slang. Meanwhile, his uptight daughter Quinn (Bridget Moloney, making a return following her web series appearance) and her husband (Paul Thureen) live in his house and struggle to balance parenting their young daughter with Jim’s hectic lifestyle. For an episode featuring a day rave and a backyard “preschool for adults,†it is remarkably free of condescension. Instead, “Tick†is content taking an observational tone, preaching tolerance and empathy toward those who try to bridge the gap between themselves and their parents.
23. “Fingerbutt†(Season 3, Episode 6)
The first half of “Fingerbutt,†which follows a chic septuagenarian (Kathleen Chalfant) whose first experience modeling makes her feel insecure about her age, might be a little sleight, but the episode’s second half more than makes up for it. Gene (Ken Leung), a depressed veterinarian, decides to microdose psilocybin instead of taking antidepressants and subsequently becomes a blissful, awkward space cadet. High Maintenance rarely indulges in standard “stoner comedy,†but it runs wild with Gene’s foray into the world of psychedelics. His guileless demeanor befuddles his patients, but he becomes accustomed to the drug’s mood-improving effects, even if that means he sometimes tries to communicate with turtles. Gene’s experiment comes to a hilarious end when he purposefully takes a higher dose of psilocybin and has a bad trip at work. Right as his paranoia spikes, he’s forced to remove a pet cat that has gotten stuck in a tuba. It does not go well.
22. “HBD†(Season 2, Episode 7)
Eliza Hittman (Beach Rats) directs this coming-of-age episode about Emily (Gina Piersanti), a teenager whose sexuality blossoms when her bohemian mother’s friend Claudia (Cécile Delepière) comes to stay at their home on her birthday. The episode is a little slight, but the scenes when Emily starts to “notice†Claudia are appropriately charged, and Emily’s debauched birthday party is a lot of fun. Hittman brings a subdued, yet eerie energy to the episode as Emily struggles to be seen in crowded rooms, even when the spotlight is squarely on her. Blichfeld’s script features a few notable grace notes, especially a brief, hidden romantic gesture at the episode’s end.
21. “Derech†(Season 2, Episode 4)
An ex-Hasid invites a Vice journalist on a date to a Shabbat dinner filled with friends who are “off the path.†The Guy loses access to his bike and relies on a chance encounter with an old client to make his deliveries. A drag artist gets thrust into an emergency situation after a long night out. Though patchy at times, especially when crosscutting between its three story lines, “Derech†features plenty of insightful material about what it means to be free, especially in a world that likes to box people into identities. It also features the introduction of the improvised, eminently catchy song, “What Are You Up To, Elisabeth Shue?†which New York Times film critic A.O. Scott believes should be sweeping the nation.
20. “Steve†(Season 2, Episode 10)
A sweet epilogue to High Maintenance’s second season, “Steve†follows two couples (Alexandra Fiber and John Gallagher Jr., and Anna Suzuki and Omar Shaukat) on the day of the solar eclipse as they work together to pull of the perfect proposal. The romantic element, coupled with the unifying nature of the eclipse, makes for a sweet episode, but it’s the subplot involving The Guy that has more weight. He signs his divorce papers with Julia (Kate Lyn Sheil), celebrated with a picture and a long hug, and eventually meets up with Beth (Yael Stone), who explains why she ghosted him and reveals she’s returning to Australia. The season ends with The Guy taking Beth’s RV (named Steve RV) to go on a road trip, only to be stalled before leaving Brooklyn, a fitting conclusion to a curious, adventurous season.
19. “Cruise†(Season 3, Episode 9)
A loving tribute to New York narrated by legendary tour guide and philosopher Timothy “Speed†Levitch, “Cruise†would easily function as a touching series finale, sending The Guy and High Maintenance off on a good note. The episode splits the difference between a broad first half following an acting teacher’s (Reed Birney) inebriated night on the town, and a grounded second half that follows The Guy as he reunites with two high-school friends. While Sarah (Cassie Beck) and Bryan (John McKeever) are in town to see a cancer specialist for their infant son, The Guy does his best to help take their mind off things by tripping down memory lane. The episode ends with The Guy back on his bike (the RV’s engine failed for the last time) and free of a relationship (it’s absolutely perfect that High Maintenance mentions The Guy’s amicable breakup with Lee in passing via text). As he cycles to his next delivery, he breathes in the New York air and takes a minute for himself. God’s Popular Man lives to ride another day.
18. “Ex†(Season 1, Episode 6)
The season-one finale features two stories: the first considers the return of Patrick (Creighton), who struggles to break out of his depressed, reclusive rut, and the second focuses on The Guy, who’s a victim of a robbery and returns to his ex-wife’s apartment looking for emotional support and his spare keys, only to find her new partner Gwen (Rebecca Naomi Jones) alone instead. Patrick’s story is a fitting end to the character’s journey, as he learns that the world outside his small apartment isn’t so frightening after all, and ultimately “breaks up†with The Guy, whom he relied upon for human connection. Meanwhile, The Guy’s story is one of a handful of times High Maintenance peeks into the character’s personal life. We learn that he lives across the hall from his ex-wife and that her new girlfriend isn’t the biggest fan of his continued presence. After a crossed text message, the two part on amicable terms, while The Guy endeavors to sort out his life.
17. “Namaste†(Season 2, Episode 3)
“Namaste†features the return of John (John Peery) and Candace (Candace Thompson) as they win the affordable-housing lottery and move out of their hippie co-op and into a low-income housing unit in a fancy Greenpoint building. They quickly learn the numerous ways in which the community has been stratified by class, and things come to a head when Candace, John, and The Guy deign to use the building’s sauna. The episode’s other story involves a black realtor (Danielle Brooks) who longs to move into a brownstone in Brooklyn, only for the elderly owner to put it on the market before telling her. Both stories examine New York real-estate struggles, but from a grounded perspective involving a universal desire for a stable home.
16. “Genghis†(Web series, Episode 16)
Avery Monsen reprises his role as Evan Waxman, an asexual amateur magician who gives up his well-paying job to become a Brooklyn public-school teacher so he can “make a difference.†This goes about as well as can be expected, as Evan encounters a hostile group of summer school students and otherwise indifferent teachers who have been worn down by a broken system. Blichfeld and Sinclair chronicle Evan’s summer as his enthusiasm curdles into despair, especially when the students mock his sexual orientation. The final scene, in which Evan admits to his students that he’s more selfish than he initially believed, is one of the most startlingly honest moments in the series.
15. “Dinah†(Web series, Episode 7)
“Dinah†introduces a couple of characters that will continue to recur: Chad (Chris Roberti), a free spirit who travels the world attracting women and fun in equal measure, and Kabir (Azhar Khan), a kind doctor who occasionally sleep-eats. When Chad comes to town for a wedding and sleeps on Kabir’s floor, he overstays his welcome, putting a strain on Kabir’s relationship with Annie (Kether Donohue, now of You’re the Worst fame). It’s later revealed that Chad and Annie slept together sophomore year of college, sending Kabir into a fit of rage the night before he’s on call. The trio of performances enhance Blichfeld and Sinclair’s excellent script, and their chemistry suggests a layered, complicated history between the three friends that gets called into question after staying in close quarters with each other for too long.
14. “Globo†(Season 2, Episode 1)
High Maintenance begins its tour de force second season with an episode about Our Current Political Moment, a recipe for disaster that lends itself to speechifying and overcooked diagnoses about the current era. Yet, Blichfeld and Sinclair bring a gentle, humanist edge to life in 2018 by centering it on an unnamed tragedy — mass shooting, Trump’s election, discriminatory legislation, take your pick — and following people who aren’t wrapped up in the news cycle. The result is an episode that’s empathetic towards those affected by ever-fucked global politics and those who just want to go about their day, trying to find some light in a dark world. A scene of a busboy and his son playing with a balloon on the train takes on extra emotional weight not because it courts the Zeitgeist, but because it’s informed by it.
13. “Sufjan†(Web series, Episode 17)
One of the show’s more Brooklyn-centric episodes, “Sufjan†impresses because of how it mines a universal tale about moving struggles out of a quintessentially New York story. Ezra and Reagan (Micah Sherman and Hannah Bos) move to Ditmas Park after being priced out of Williamsburg, but struggle with the geographic isolation from their work and friends. When they find out their regular dealer won’t deliver to their new neighborhood, they rely on The Guy, who decides to make the trip but then gets waylaid saving a kid from diabetic shock. “Sufjan†examines the practical realities of adulthood and financial spending, as well as the habit-forming nature of marijuana. Can you really complain about the money you’re spending on cars to Bushwick when you’re spending the same amount on drugs? The answer is more complicated than you might think.
12. “Breathwork (Season 3, Episode 4)
One of the series’ funniest episodes, “Breathwork†follows a film set during a day of chaotic reshoots from the perspective of the cast — i.e., Jemima Kirke and Tom Lipinski, who play exaggerated versions of themselves — and crew — which features old faces like Gigi (Amy Ryan) and Kabir (Azhar Khan). The day starts with an on-the-fly location change following a death in the building of the original shooting space and only gets worse from than there. After The Guy delivers to set, the crew tries to find time to get high while the actors cause even more delays by adding in their own creative input. When the shoot finally begins, a potential murder and a swarm of bees have entered the picture. Meanwhile, Lee struggles to put her life back together in New York after a public humiliation that’s connected to why the film needed reshoots in the first place. Luckily, The Guy helps her relax with good vibes and a joint.
11. “Fagin†(Season 2, Episode 2)
Sometimes, the strangest things connect the most different experiences. “Fagin†features one story about a middle-aged couple slumming it in a loft while visiting their daughter, and another about a feminist activist group meeting that initially goes awry out of liberal insecurity. Both stories are connected, or interrupted, by the presence of a pet snake named Fagin that affects both worlds just by moving through them. Blichfeld, Sinclair, and co-writers Rebecca Drysdale and Isaac Oliver showcase High Maintenance’s satirical and humanist sides here. The series can poke fun at the messy infighting of activist groups, and also depict a middle-aged couple’s heartwarming pot-fueled night in a new city.
10. “Qasim†(Web series, Episode 11)
Arguably the weirdest episode in High Maintenance’s run, “Qasim†follows Scott (Jordan Dean), a fitness-obsessed man who’s on the “Uberman schedule,†which means he only sleeps two hours every day. When Kellie (Anna Rose Hopkins), a girl in Scott’s cycling class, goes out with him one night, her initial enthusiasm quickly wanes after learning about Scott’s spiritual mentor and cultlike tendencies. The episode features one of the series’ best montages: a three-minute look at Scott’s daily life — working out, creating collage art, working out some more, taking 20-minute naps, eating, working out again, masturbating — set to the anxious pulse of “IO†by Dawn of Midi. Plus, The Guy dresses like a pot dealer (picture trench coat with cooking pots inside) and visits a couple (Henry Zebrowski and Katie Hartman) that like to scare trick-or-treaters as an anniversary present to themselves.
9. “Brad Pitts†(Web series, Episode 10)
For a series about marijuana, High Maintenance rarely goes to the typical stoner well, rightfully choosing to portray the pot-smoking community as a diverse, varied one. Although every episode features pot, very few are actually about pot, simply because Blichfeld and Sinclair treat it as an integrated part in their subjects’ lives. A notable exception is “Brad Pitts,†one of the series’ best episodes, which follows Ellen (Birgit Huppuch), a woman who tries marijuana to help with the symptoms from her stomach cancer treatment. Immediately after The Guy rolls a joint for Ellen and her friend Ruth (Jennifer Smith), Ruth freaks out and calls The Guy back into the house to make sure she’s not having a stroke. While Ruth panics like a teenager, Ellen stuffs her face full of food for the first time in a while. “Brad Pitts†is like the best version of that laughable Maureen Dowd column about trying pot for the first time, only with a much better ending.
8. “Elijah†(Web series, Episode 9)
How quickly can you craft a believable portrait of a dysfunctional family? The answer is about ten minutes. Blichfeld and Sinclair follow the Waxman family at Passover dinner, catered by an obnoxious Top Chef reject (Theo Stockman) who puts bacon in the matzah balls because the family is Reform. The matriarch (Dawn Luebbe) criticizes everything, the youngest daughter Rachel (Jessica Rothe) gets drunk and flirts with the chef, the host couple Joel and Shira (Fred Berman and Bettina Bilger) do their best to entertain their young son, while the asexual Evan (Monsen) desperately tries to lighten the mood. The episode ends with a surprise visit from The Guy and a young boy sneaking in on a double hand job. A perfect Seder.
7. “Matilda†(Web series, Episode 12)
The first Guy-centric episode of the series, “Matilda†follows The Guy as he tries to scramble enough money together to take his middle-school-aged niece Kate (Kate Ross) to the Matilda musical. His travails take him all over New York, including the apartment of Wicked star Kyle Dean Massey, who has Max the Asshole hiding in his bathroom. Despite a valiant effort, The Guy fails and ends up taking Kate to an off-brand feminist TED Talk event, run by Molly and Brenna, where they have fun anyway. A sweet episode that features a stellar, natural performance by the young Ross, “Matilda†shows a sensitive, mature side to The Guy for the first time, and how an unexpected night out can become an adventure.
6. “Googie†(Season 2, Episode 6)
With The Guy recovering from arm surgery following a bike accident, he enlists the help of friend and former client Abdullah (Abdullah Saeed) to make his deliveries. As Abdullah drives around Brooklyn, The Guy takes a forced vacation and has a mild existential crisis about his place in life. He stays inside, constantly smokes, binges on The Wire, and assuages his parents’ worries, but after a day of being inside, he decides to take mushrooms and explore the city. By the end of it, he realizes his relationship with Beth has come to an abrupt end, and that he doesn’t want a partner in his pot business. Abdullah preaches efficiency, better product, and more customers, but The Guy firmly admits, “I know, but I just kind of like doing it on my own.†It’s a moving statement of purpose, and an admission that his job will always be a little unfulfilling, but an open pathway to human connection. Plus, Kabir returns as a Juggalo who preaches the beauty of David Lynch, and who doesn’t want that?
5. “M.A.S.H.†(Season 3, Episode 1)
A wonderful meditation on death and regeneration, “M.A.S.H.†finds The Guy living out of an RV in upstate New York when he learns his old friend Berg (Chuck Montgomery), or Baba as he’s called by friends, has suddenly passed away. The Guy attends his wake, which brings together a vast hippie community to pay tribute to a man who had so much love (and drugs) to give. Written by Blichfeld and Sinclair, “M.A.S.H.†pulls off the momentous feat of depicting hippies with dignity while still poking fun at their spacey sing-alongs and aging traditions. They save special sympathy for Cori (Erin Markey), Berg’s roommate who takes his death very hard because he offered her compassion instead of judgment. However, when one life ends, a new relationship begins. The Guy meets cute with Lee (Britt Lower), a soon-to-be divorced woman looking for a friendly face following a trying period. Their gentle connection and instant chemistry will put a smile on the face of any longtime viewer of the series.
4. “Rachel†(Web series, Episode 13)
High Maintenance often relies on clever, short-film plotting, rooted in upending expectations. “Rachel,†starring Dan Stevens as Colin, a writer and stay-at-home dad who cross-dresses in the privacy of his home, arguably features the best “reveal†in the series’ history. When Colin’s wife, Becky (Blichfeld), returns home with their sick son and finds her husband at home getting high in a dress, she isn’t phased by the cross-dressing, but is upset that she had to leave a sales meeting because of Colin’s irresponsibility. A great example of the series’ observational bent and concise storytelling, “Rachel†conveys Colin’s crisis of masculinity in hushed tones, with the emotional climax pivoting off of Colin feeling comfortable to wear a Rachel Comey dress in front of The Guy.
3. “Ruth†(Web series, Episode 14)
In a series that features plenty of couples, “Ruth†presents the best of them all: Ellen (Huppuch), introduced in “Brad Pitts,†and Victor (Chris McKinney), a lonely doorman and part-time self-defense instructor. The Guy sets the two of them up and they embark on a fun date, complete with food, weed, and karaoke. Things threaten to go south once Victor learns about Ellen’s stomach cancer (now in remission), but the two get back on track after Victor accidentally places pepper on his eyes and genitals. Sweet without being sentimental, romantic without being schlocky, “Ruth†embraces late-period romance with all of the complicated baggage that comes with combining two enormous lives. Sometimes caution must be thrown to the wind, even if that caution amounts to taking a new beau out bird-watching.
2. “Sabrina†(Web series, Episode 19)
The web series’ best episode was also its last on Vimeo. “Sabrina†follows The Guy as he travels with Chad to a house upstate for a mushroom-taking weekend with Chad’s friend group. The Guy is an outsider, but he, like us, slowly learns the group’s unique dynamics, which are built upon a complex web of secrets and strained relationships. The tense conversations and passive-aggressive back talk will be familiar to anyone who has ever been a part of a tight-knit group of friends, and Blichfeld and Sinclair take great care in highlighting the natural chemistry between the actors, which include John Early (Search Party) and Tonya Glanz (Timeless). A pitch-perfect depiction of taking psychedelics in a large group, “Sabrina†captures the hazy insights and stark realizations that arise from a trip, as well as the uncomfortable feeling of looking in on a storied history that doesn’t involve you.
1. “Scromple†(Season 2, Episode 5)
High Maintenance is nothing without The Guy, a beacon of kindness and generosity in a cruel world, so the episodes that focus on him are necessarily special. But the series’ best episode follows his ex-wife, Julia (Kate Lyn Sheil), a brand specialist currently doing pro bono work for a LGBT church. Blocked at work, she starts jonesing for some pot, which she has given up at the request of her girlfriend Gwen. After a long, desperate search in both her and her ex’s apartment leads nowhere, she learns that The Guy is in the hospital after a bike accident and the two reconnect while he’s whacked out on pain meds. “Scromple†is a melancholic look at an expired relationship that produced good times (and possibly some bad habits) and how people can remain family even after they’ve left each other’s lives. Sheil and Sinclair’s performances are phenomenal, and their bittersweet scenes together are an easy highlight. Sinclair and Blichfeld’s real-life breakup inspired “Scromple,†and there are times when it’s as if we’re getting a mediated peek into the co-creators’ emotional history. The final shot of Julia ripping a bong alone in The Guy’s apartment, while her girlfriend sleeps across the hall, speaks volumes without so much as a word.