Kendra Cunningham is juggling more projects than you can fit into a tweet: two award winning web series’, a television pilot, and a killer blog. Plus, she’s producing and co-starring in a feature film and working on a screenplay. I haven’t even mentioned her ever-growing list of stand-up credits that helped land her a prestigious invite to the Edinburgh Comedy Festival. We met up with this Boston transplant to talk about her ongoing to-do list and to find out if we’re ever going to meet her fabled mom.
Do you think differently in terms of stand up and your web series? Is it one or the other or can you use ideas the same in both?
Well, I feel like I have a lot of the same themes. There are definitely some things I would like to do as a joke but don’t translate into stand-up. The first [web series] that we did was Lonelygirl48. I wanted to do that as a joke but there was just no way for me to do it. It was too wordy and long and weird. That was the first time I did something that was visual comedy. So even though I think it’s the same themes and psychological stuff, it’s definitely a different communication, a different medium.
Do you think it’s been a smooth transition from stand-up to web series?
I would like to be doing more sketches but it takes so much more. I love the collaboration of it and everything. But for stand-up if you want to do jokes you can find an open mic and you don’t have to plan with anyone else. You just work out the jokes and that’s it. But if you want to get a good video up you need to have at least ten people on board.
Take me through your writing process; do you have a set schedule?
No, I’ve tried that. I’ve written out things for me to be like, “this day I’m going to work on this, I’m going to work on a script.” I meant right now I’m getting myself to wake up on Thursdays to work on a script because I hired life coach to help me. I had this script sitting there and I really wanted to get it done, so now I have accountability to someone. For the most part, in terms of my writing, I definitely write something everyday but sometimes it may be just a couple of tweets and other days it may be a premise for a blog or whatever. I wish I had a routine I’d probably get a lot more done.
How do you decide what’s a sketch and what’s blog or stand-up?
I feel like it sort of depends on what its all about. A lot of times I’ve used a joke that I’ll tweet. I’ll use that as a premise for a blog then expand on it. Then sometimes I take the blogs and think, “Oh that would be a really funny sketch.” Like one funny thing can turn into seven funny things. Then I’m like, “Oh that can work as a sketch.” Not too many times am I somewhere and I think this will be a great sketch, rather than this sketch would be great joke or blog.
“Why’s Everybody Always Hitting on Me?” is more heightened character than your stand-up. Do you use sketch to explore more avenues?
I think definitely that’s what I’ve been doing. It wasn’t really a conscious decision but it’s kind of the way that came out to be funny. Really just on the day we started to shoot, I would like to do stuff that are more reality-based characters – but I have a lot of fun playing the ridiculous people that are completely off the leash.
Both “Loneygirl48” and “Why’s Everybody Always Hitting on Me” are relatable. Is that something you set out to do?
I think that I like relatable. I think it’s on my list for everything I do. I don’t really think about it when I write it.
It’s not really a goal?
Well I want it to be. I don’t want to be the weirdo comic like, “I don’t know what she’s doing but its funny.” I love the fact that people find it relatable because it means they understand what I’m trying to communicate. I’m conscious in that I hope people will find it relatable.
This is the second time you’ve won best web series at the Boston Comedy Festival; the first time was for “Lonleygirl48.” Do you have any more goals for “Why’s Everybody Always Hitting On Me?” Maybe just the character or are you looking to do other things?
We started to think about doing some more. Vicki (Kuperman) and I –we’re going to shoot some scenes for the feature film – It’s a buddy comedy. That’s what’s on the burner right now. After that, I don’t know what were going to do. I would love to spend time and do more of that character but at the same time I’d love to do other things. I mean, if I had the time and the money to just do this stuff all the time, I’d do ton of them. But with the limited amount of time I have to dedicate to it, I don’t know what’s going to happen.
Do you find that when you get an idea in your head that once it’s out you don’t want to do it anymore?
Sometimes yeah… I’m at the point where I just want to do the thing that’s the easiest to produce [laughs]. Like in my living room, with people who live in my neighborhood. I’m not lazy but I just want to get more done!
You also set up a FundAnything for your pilot Swagger. What can you tell us about that?
It’s done. I just literally today finished emailing with [the editor]– I’m re-editing it. I have the 22-minute pilot and I have the trailer. The trailer has the tone I want for the pilot but the pilot doesn’t have that tone yet … I’m really thinking I might put it in festivals for pilots unless someone comes along and scoops it up.
Your mom is very present in your blog and also in your stand-up. When are we going to see her?
[Laughs] I got her on a podcast.
Yeah – that was going to be her entry. I got her in the podcast and two days later she was like “I don’t think you should post that because (she told a story about work, she works at the statehouse in Boston.) What if someone hears it from work and I’ll get in trouble.” Anyway, every time she comes she promises me she’ll do a sketch with me then she’s like, “No I don’t feel like it.” I don’t think she’s someone who would be a natural in front of the camera.
I think the character you’ve created is just so great – she might not live up to the dream.
[Laughs] I don’t want anyone to be disappointed in her.
Your blog is great and you write, perform, and produce. Do you think that a comic has to have their hands in everything to make waves?
I mean – it seems that way. I think for me personally that if I hadn’t done all of that I don’t think I’d be as confident in my stand-up as I am. Then there are some other people who barely do anything and suddenly they’re doing something huge. I don’t know. I actually enjoy all those different mediums, so for me it’s good to get them out of my system and work on it. Sometimes I wish I didn’t like all that so I could not do it and I could be complaining about how I just spent 4 hours at the gym [laughs].
In an ideal world are you doing it all: writing and producing or just performing?
I would definitely like to write and produce. My ideal world I would love to be able to do – I like doing the Beauty Bar show every Wednesday – its fun… it’s not high stakes. If I could do once a week, a work out type of thing, then pick like 2 weekends a month to perform and figure out in the other time how to write and produce stuff.
So just performing more?
I would like to perform on my terms. I don’t want to be a road comic. I don’t want to be doing every weekend. If I can do one or two fun weekends a month – maybe one would be enough. I really like performing but there are so many shitty shows that it’s a spirit killer. I think it would be awesome if I could call the shots on everything I did.
What are you most proud of?
Honestly, I’m just proud that I tried to do anything at all. I really wasn’t creative until my adult life. I think it’s pretty cool to have the web series because it’s a very tangible thing. It takes 3 minutes and you get a really good sense of who I am.
Where do you see your career going?
I would love to do all things I mentioned or I think I’d be really happy being a talk show host… I feel like the reason most people get into comedy is because they want to express themselves. I don’t want to get into a position where I am no longer allowed to do that. For instance, if I were to be cast in a sitcom that I didn’t write, I’m no longer doing what I set out to do because I’m acting basically. To me, I feel like a sitcom-actor job – if you’re not writing producing – it’s sort of like a corporate job because you still answer to someone else. I just want to have some sort of connection to what I’m doing instead of just “this is what I do to make money.”