Do what you want all the time and, even when you’re not funny, chances are you’ll learn something about how to be funnier. That’s the gist of the advice Jackie Jennings gives and after watching her great series Neighbors, it’s pretty clear that this strategy works. So, learn about the science of comedy by taking some classes and reading some stuff (ummmm, this column much?!) and then, once you’ve got an idea that you believe in, don’t listen to the haters and the blowhards and just make what you want. If you’ve got talent, seeds of your ability will be present in your earliest attempts at originality. If you don’t, well…you can still read this column.
How did you get your start in comedy?
I started doing comedy in college. I was in the improv club when I went to college at John’s Hopkins University. So I did improv and theatre in college and I had heard about UCB as being, “the place.†And it came down to NYC or Chicago and I lived in New Jersey so I felt like New York was the best choice. So I went to New York and started taking UCB classes and that’s kind of how I got into comedy.
And there was no break in between graduating college and moving to New York to do UCB?
It was pretty much right away but I did have a pretty intense day job until about a year ago. My love of comedy was was always there but it wasn’t something I was doing 100% like it is now. I worked very briefly when I first graduated as a video producer/writer/blogger for The Daily Beast and then, after that, worked for a start up called Outbrain for the next four years. It was intense because it’s a start up but it took up all my time and energy because I was fully committed to it. Then last January, I made the decision to just do UCB and do the TourCo so I had enough coming in that I could leave and really do comedy full time.
How did Neighbors come about?
I had been doing some writing stuff, mostly writing with other people, and then finally I was like, “I’ve just got to do something on my own.†The first one of these was actually a piece of something larger and then as I was going through the process of writing I thought to myself “The part at the door is it.†It’s a way to get a ton of funny people in my room in a short period of time. I was going to do something larger but then decided I should just do this. The stuff the neighbors talk about is stuff that I would want to say or have said or have thought. I play the straight man to the crazy people in this series but in real life I am the crazy one. Like the one about the vegan neighbor, I was vegetarian and was vegan for a couple of years and had a neighbor who was cooking meatloaf and I’m the kind of person who was just like, “I really wish they wouldn’t do that.â€
That’s crazy that you recognize that it’s insane to do that and did it anyway.
I first posted the vegan episode on this vegan sub-Reddit and people were like freaking out, talking about how it was vegan-shaming and I just wanted to respond, “I am that person.†And then I decided it wasn’t best to get into a comment war on Reddit.
 Did you write all of these by yourself?
Yes.
Who worked on the project with you?
For the first three, Dave Bluvband shot and directed them. And then I shot a bunch more and Hayley Kosan shot the rest of them. The first three we had someone PA-ing on set, myself, the director, and the actors and I’m editing them myself so it’s a pretty small group of people. Really lean. It’s in my apartment and we have it very scripted but obviously a lot of the people in it are great improvisers so we always do a few takes that are improvised and great stuff can come out of that too.
What’s next for the series and what’s next for you outside of this series?
I’m hoping to do it until I’m tired of it because, really how many crazy people can come through one door. I have an idea in my mind for how I want to button the series. Then for me personally right now I’m working on another series and doing a one person show I’m hoping to put up at UCB in the New Year.
I feel like this would be such a good Above Average series. Have you thought about taking it there?
I actually haven’t talked to anyone about it. I have had a lot of feedback from it but I wasn’t really thinking about that when I made it. I kind of just wanted to make it because I liked it. I thought “Who are the people I wanna work with and who do I think is funny†and then just did that. I would love to do more.
What are some web series that you’re watching right now, besides High Maintenance?
I actually have not seen High Maintenance. I love everything that my friends do. I love John Purcell’s stuff. They did a Serial parody that went super viral and John does Business Work, which I love. And then I’m on a team at UCB with Benjamin Apple and he has a YouTube channel that I love. I don’t know how he makes a new video every day. I’ve talked to him about it and I still don’t know how he does it and how he makes each one so funny.
What advice would you have for people looking to be successful in the digital space?
I would say “Just do it,†which I know is everyone’s advice, but…just do it. It doesn’t matter if it’s good or bad, the more you do it the more you learn. And don’t listen too much to people. People like to give you so much feedback on how long it should be and how it should look, just don’t listen to them and just do it. Those are the two pieces of advice I wish I had when I was starting to do videos two years ago.
Here are your three reasons to watch, my digital neighbors.
1. Jackie Jennings
2. Simplicity
3. Repeatability
“The Veganâ€
There’s an unassuming sweetness to Jennings’s comedy that adds a broad star-quality texture to alt funny bits that might be less accessible if alt funny.
“Good Stuffâ€
Simple is almost always better. Better for budgets, better for crew schedules, better for production, and better for attention to comedic detail.
“Catâ€
When you make a really good web series installment, you want to be able to make more really quickly. This premise lends itself to a near limitless amount of episodes and, for that, we should all be grateful.
Luke is a writer for CollegeHumor and a watcher of many web videos. Send him yours @LKellyClyne.