7 Questions with Jena Kingsley |

by Ryan Meehan

Jena Kingsley was born and raised in New York City. She attributes everything she knows about comedy to a loving yet dysfunctional family. Her name is pronounced Jena, like Jameson, but only one N. Her parents spelled it wrong. Most recently Jena has made her mark internationally with her pranks on unsuspecting New Yorkers. The media has called her pranks “Genius” and “Brilliant.” Perez Hilton called her “one bold and funny lady.” She released three viral prank videos in a row (“Are You On The List”, a Starbucks Prank where she posed as a Starbucks Bouncer, and “No Selfie Zone”, where she set up no selfie zones in NYC subject to fine, and “Social Media in Real Life” where she tries out the things we do on social media on unsuspecting New Yorkers) both garnering major international media attention landing her on CNN, TIME, MTV, ABC, The Today Show, USA Today, AdWeek, Perez Hilton and more. In sixth grade she won an award for writing excellence, which of course means nothing now. She is the writer/creator of the popular blog “Darcy Dates” and she also blogs for the Huffington Post. She is a regular guest of “Huffington Post Live” and Sirius XM. She has written for The New York Observer, New York Post, XOJane, HowAboutWe, BeautyBlitz.com and others. She made her television debut appearance doing stand up in 2015 on “Live From Gotham” on AXS-TV. Her stand up appearances include The Stand, Gotham Comedy Club, Levity Live, Caroline’s Comedy Club, Governors, Stand Up New York and others. She also recently appeared at The New York Comedy Festival, and she’s my guest today in 7 questions.

RM: Who was the first comedic performer that absolutely blew you away and drew you into the world of comedy? What was so special about that performance that made you want to dig a little bit deeper into the art form as opposed to being just a casual fan?

JK: It’s hard to say. There isn’t one comic who inspired me to go into comedy. Comedy was just always part of my life. My biggest comedic inspirations growing up were Carol Burnett and Lucile Ball. As for stand up, I remember Rita Rudner and Ellen Degernes being the first two female stand up comics I watched on television. I remember Ellen doing a bit about traveling on an airplane and befriending the people next to you and in their air you are best friends, and then they became total strangers by the time you got to baggage claim. I thought it was one of the most hilarious accurate observations I had ever heard. I think that’s when I realized why I loved comedy so much. It was just incredibly hilarious observations of the world. Things you do every day all day but never stop to think about. If I had to pick one favorite it’s probably Louis C.K. His “Shameless” set is hands down one of my all times favorites. I’m not even sure I answered this question properly.

RM: What can you tell us about your background in improv? Who did you study with; and how have you been able to apply that training to your stand-up?

JK: I started improv as a kid. Growing up I would constantly take dares and I loved being challenged to make the biggest ass of myself possible. It was one of my favorite past times. When The Jerky Boys came around, I was like, “I can do that!” My friends would make me prank call tons of businesses. This was obviously before caller ID. I grew up in New York City and in high school my friends would challenge me to get us all free taxi rides by improvising these crazy scenarios with the driver. And it often worked. I then went on to study at UCB back when they had their show on Comedy Central. I used to go out to Nutley, New Jersey to do random background characters on their show. It was really fun to watch Amy Poehler and Matt Walsh and that whole crew do their thing. Improv is always a good thing to understand when you do stand up because you can’t always predict how the audience will take your material so you have to be able to switch gears quickly, or talk on a tangent if something is working.

RM: For those who aren’t familiar with “Darcy Dates“, what is the primary subject matter of that blog?

JK: I wrote Darcy Dates under a pen name, Darcy. It was a blog I wrote for myself and a few friends about dating after divorce in New York City. I couldn’t believe how crazy that whole thing was so I found began writing my stories, almost like a diary to share with my friends. I found writing these comedic pieces on the things I encountered to be pretty cathartic. I had never anticipated that it would become so popular and how many people wanted to turn it into a television show. Stay tuned.

RM: What are the three most important functional elements necessary for the execution of a successful prank?

JK: To pull off a successful prank you first need to have a great idea. I like to do things that are socially relevant (No Selfie Zone, Starbucks Bouncer, Social Media in Real Life, Terms & Conditions), things we encounter on a regular basis, but turn them on their side just enough to confuse people. Secondly, you need to commit completely. People always ask me how I keep such a straight face and my only answer is, in the moment I have to fully believe I am bouncer, or a park ranger, whatever I am at that moment. It never even occurs to me to laugh. That probably means I’m crazy on some level. Lastly, be prepared! I am more prepared when I go into these pranks than people think. You can never anticipate how people are going to react, which is where improv skills are so important, but I prepare for almost every scenario. The only thing I wasn’t prepared for is how many people actually took the pit bull in my latest social experiment, Terms & Conditions.

RM: Which of the New York City clubs would you say is the best room for your particular brand of comedy?

JK: I always love doing ladies’ nights. I think it’s a hard business for women so I love when women support other women and I love when a full crowd shows up to support women in comedy. My favorite ladies night is thrown by my good friend Robyn Schall at Caroline’s. Always a good time. My favorite club in the city is The Stand. No matter what night you go the lineups are always amazing. Anyone can walk in and just start performing at any moment, everyone from Louis CK to Bill Burr, and they have always been super supportive of me so for that I am forever grateful.

RM: If you had to classify comedy as more of an art or a science, which of those two things would you say that it is more of than the other and why?

JK: Comedy is an art, not a science. If it were a science, it would be easier. Well not easier for me, because I am terrible at science. It’s a creative field, which in itself means it’s artistic. There is also an art to timing. Knowing how your jokes are going to land…timing the delivery. It’s an art.

RM: Which portion of the comedic writing process would you say is your specialty; and why do you think that you excel at that particular facet of your craft? Can you foresee the answer to that question being different ten years from now?

JK: This is too difficult to answer because I’m great at all of it. Just kidding. It’s too hard for me to answer that. I’ll leave that one to my fans or critics.

RM: What’s up next for you in the remainder of 2015 and beyond? Anything big in the works that we should know about?

JK: I think when you are a creator you are constantly trying to “come up with your next great idea.” It’s the execution that can be difficult but you have to keep pushing. I am always in talks with brands, my videos tend to be good content for brands. I have some televisions shows I am pitching, so stay tuned!