The Story Behind the Web's Buzziest Weed Series 'High Maintenance'

How two married writers turned an online series about a New York pot dealer into a Vimeo-sponsored must-see hit

Scene from Ben Sinclair's 'High Maintenance.' Credit: High Maintenance

When Ben Sinclair and Katja Blichfeld set out to make High Maintenance, their Web series about a weed delivery guy in New York City, they had one important goal.

"We didn't want to become some 'stoner' show," says Blichfeld, a former casting director on 30 Rock. "We don't really know that [particular] brand of stoner portrayed in movies. The people we know who identify as stoners are actually some of the most productive, successful, creative people we know. High Maintenance looks like the world we live in."

Having debuted in 2012, the show plays like finely drawn vignettes of urban life in among the not-always upwardly mobile. Each installment follows a largely new set of characters that all have one thing in common with folks from the previous episodes: the same scraggly, warm-hearted weed deliveryman, known only as "the Guy," and played by Sinclair. 

The pair first began conceptualizing High Maintenance a few months after they got married in 2010. They originally figured each episode shouldn't run longer than five minutes because, as Sinclair puts it, "The assumption with the Internet is that people don't want to give you their time because they've got other stuff to do." But after the first few episodes, fans were craving more. "They were saying, 'The show is addictive.' The biggest critique [we got] is that it's not enough." Gradually, the episodes have gotten longer — one stretches to nearly 19 minutes — and more emotionally complex, introducing characters struggling with cancer, PTSD, loneliness and sexual identity.

"Once we figured out that the reason these people were smoking pot was more interesting than the fact that they were smoking pot, that's really when the episodes started to germinate," says Sinclair. The result is a heady blend of offbeat comedy, quiet tragedy and grainy realism that feels like a spiritual cousin to Louie or Girls.

"I never set out to make a comedy," says Blichfeld. "Ben was definitely geared more towards hard comedy and felt more of a facility for that kind of stuff than I did. But in the beginning, our expectations for viewers were that they would only want to watch something five minutes long or less — and if you watch something of that length, it's going to be funny and leave you with a good feeling. It really wasn't until we got some feedback that we felt comfortable enough to make episodes that had more heart or sadness in them."

"These are short stories that are meant to live online. There will never be High Maintenance: Fire Walk With Me."

The couple self-financed the first 13 episodes, and gradually garnered a loyal fan base that included comedian Hannibal Burress and Downton Abbey star Dan Stevens, both of whom appear in episodes of the show. FX flirted with the idea of turning the series into a more traditional 30-minute sitcom, but when that fell through, Vimeo stepped in to fund six more episodes, as part of the Web video platform's first foray into original programming. The first three of those installments were released on November 11th, and the next three will follow by early 2015. For the first time, viewers will have to pay to watch — $1.99 per show or $7.99 for the whole six-episode run —but the modest budget allowed Sinclair and Blichfeld to pay their actors, upgrade their cameras, rent locations and hire extras.

"It's an experiment for everybody," says Blichfeld. "It feels uncharted in some ways, and I can't speak for Vimeo, but we don't eye this as something that is going to make us some huge fortune."

Sinclair says that the company’s involvement pretty much began and ended with providing money — the couple will get to keep 90 cents out of every dollar the show makes after Vimeo recoups their investment. But it also feels like there's a big picture shift at stake with this experiment as well. "This is an opportunity to try to prove that you can make something, sell it directly to your audience and get most of the profits from it," he says. "If we prove that an artist can release their work and not have to sell most of it away or sell out — and that attracts other artists to release their work on this type of platform — then it's going to be a huge, huge thing for how we watch media."

Sinclair and Blichfeld certainly have aspirations to make full-length TV shows or films at some point, but they've permanently shelved any ambitions to follow in the footsteps of shows like Broad City and Children's Hospital and turn High Maintenance from a web series into a TV show, or into anything else for that matter. "These are short stories that are meant to live online," says Sinclair. "There will never be High Maintenance: Fire Walk With Me. This is an art project."