EXCLUSIVE: HBO's 'High Maintenance' Elevated by Eclectic Cast of Guest Stars


On Friday, Sept. 16, the popular pot-themed web series High Maintenance makes its debut on HBO
with six brand-new, half-hour episodes.

Offering a glimpse into the eccentric lives of New
Yorkers, High Maintenance connects the narratives of seemingly
unrelated people through their shared weed dealer. In each episode, The Guy, a
fly-on-the-wall deliveryman played by Ben Sinclair, introduces audiences to a
new customer as he makes his routine deliveries. From there, what unfolds are
often funny, sometimes unexpectedly heartfelt stories about strangers in New
York City.

Those strangers are brought to life by an eclectic group of
actors -- from A-listers to an adult film star – that creators (and married
couple) Sinclair and Katja Blichfeld have asked to guest star on the series.

MORE: Creators of HBO's 'High Maintenance' Take Fans Behind the Scenes of Original Web Series

Many of them, such as Broadway star Heléne Yorke, Greta Lee (Sisters and Inside Amy Schumer), Downton Abbey’s Dan Stevens and Orange Is the New Black actress Yael Stone, return for the HBO run after first appearing -- in Stone and Yorke’s cases, multiple times -- on the show when it was a web series streaming on Vimeo. 

“I was like, ‘How can I possibly find a way to be part of this amazing thing?’” Stone tells ET about being a self-proclaimed superfan of the show. “It was a little stalk-y. It was a little Lorna Morello.”

In her HBO episode, “Grandpa,” Stone -- taking time away from her life as Morello inside Litchfield -- plays a dog walker named Beth, who has some serious hipster style and just happens to be what the actress wears off-screen. “Now, I’ve blown my cover on the subway. My kooky grandma glasses that keep me well-disguised are not going to be much a disguise anymore.” 


An Emmy-winning casting director, Blichfeld first worked with Yorke and the actress’s on-screen roommate and gay bestie, Max Jenkins, on 30 Rock before bringing them in for the web series.

“I’m not surprised people love it,” Yorke says of High Maintenance. When the Broadway star first worked on the show, it was very much a low-budget affair (“It was real scrappy,” as Sinclair puts it), with only five people on the crew. Now, it’s a much bigger experience.

MORE: Kelly Ripa Gets Drunk and High in Totally Unexpected, Hilarious 'Broad City' Cameo

But Yorke says that fans of the HBO series should eventually watch the original episodes (streaming on HBO Go and HBO Now). “It’s fun to see the evolution of what this project is,” she says of not only the production values, but the story and recurring characters. “You get that progression. It’s like, ‘Oh sh*t, this is where these people came from.’”

Yorke and Jenkins’ characters, who were collectively known as “A**holes” in the web series, return for the premiere (“Meth(od)”), where their relationship comes to a poignant head, leading Max straight into the arms (and bed) of random hookup played by gay porn star Colby Keller. “I don’t remember who contacted me, but it was like, ‘Yes, sign me up now,’” Keller says, unsure how he came across Blichfeld or Sinclair’s radar. (At the show’s HBO premiere party, Blichfeld had nothing but adoration for Keller in his first major scripted role.)

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A first-timer on the series, Kelly was also a fan -- like many of the new guest stars to join the HBO season. “I was obsessed with that show when it was a web series,” Miriam Shor, the Younger star who makes her debut in episode two (“Museebat”), says. “I think it’s one of the finest shows I’ve ever seen.”

Shor, like many of its guest stars ET spoke to, has nothing but praise for Sinclair and Blichfeld. “I stopped the creators and forced them into having a meeting with me so they would be my friends,” she says, a tactic that eventually landed her a role. “They were like, ‘Fine. We’ll put you in an episode.’”

“I'm always impressed by the beautiful community of people they have around them,” Stone adds.

While Shor couldn’t spoil anything about her appearance, we can assure fans it’s a funny episode that sees the return of Stevens’ women’s couture enthusiast and newcomer Amy Ryan, adding some A-list appeal to the series of friends getting high together.