One out and proud comedian Jessica Kirson, whose act has racked up over a billion views online, is coming to Northalsted Market Days on Aug. 9.
Born in New Jersey, Kirson graduated from the University of Maryland and earned a master’s in social work from New York University—she initially wanted to be a therapist like her mother, whose work provided much inspiration for Kirson’s ultimate decision to be a comedian. She has been the host of several podcasts, and her popular YouTube channel showcases her stand-up, especially her crowd-work.
A mother of four, Kirson acted in Robert De Niro’s feature film The Comedian and created the FX documentary Hysterical. Her most recent documentary appearance was in Are We Good? about comedian Marc Maron.
Her comedy specials include Talking to Myself and I’m the Man.
Windy City Times: Hi, Jessica. Where are you calling in from?
Jessica Kirson: I am in New York. I was stuck in an airport for 10 hours in North Carolina last night just trying to get home.
WCT: Are you always touring?
JK: I have been touring for so many years; it is insane. The title is the Never Ending Tour and that describes it perfectly.
I am finally taking a vacation in August.
WCT: Do you like all of the traveling?
JK: No, but when I started in 1999 I was having a blast. Yesterday, I was stuck in Greensboro after four shows. I wanted to die and I was exhausted. My body was hurting from traveling and sleeping in a hotel.
These days, I treat myself nicer now and stay in better hotels. I had to work on that because I am so used to being a down-and-dirty comedian in horrible situations.
WCT: The stand-up comedy culture is rooted in liquor and late nights. How do you navigate that?
JK: I don’t drink and the hours are hard. Sometimes people mean well, but they are so wasted that they will yell out things. This one lesbian yelled out, “You are amazing,” and I couldn’t go off on her because she was being nice.
Recently two gay guys were on mushrooms at my show and I thought, “This is new. People used to drink or smoke a little pot, but now they are on psychedelics. Do they think I am a goat?”
WCT: In that situation, how would you predict what they were going to do?
JK: I just yelled in their faces and it was hilarious.
WCT: Chicago’s Pride parade was not a drinking event like it used to be. The new generation was there with their families and, in general, aren’t big drinkers.
JK: I know. My mom used to come to Pride with me.
WCT: When did you come out of the closet?
JK: I came out in 1994.
WCT: So did I.
JK: I had a hard time with it. As you know, it was very different then. I was so worried about what people thought of me. I was always popular for being funny and I wanted people to like me. I realized the power of humor at a very young age. I knew if I made people laugh, they would be happy and I could make friends.
I felt down as a child with a hard family life. I met my first partner in my Jewish sorority at the University of Maryland. I was a senior and 21 years old. She was 18. We truly just fell in love. It was a secret for three years that was really hard to hide.
I told my mother and she knew what was going on. She said every time we said goodbye that I was sobbing about her, even though I was going to see Melissa the next day.
My mother thought that I would never be able to hold hands with someone of the same gender in the street and that I would never have children, although she was a therapist and accepting.
It was hard for me to come to terms with it. I didn’t think I was a lesbian at the time and I thought Melissa was an exception. I was a tomboy my whole life and it seems obvious now.
WCT: Do you feel coming out helped you in your career?
JK: Here’s the deal, I never wanted to be labeled a lesbian comic. I wanted it to be just a part of who I am, not my whole identity as a comedian.
A lot of straight people come to see me perform. I have done a lot of TV where I was a comedian who happened to be a lesbian.
Unfortunately, some of my friends who are seen as lesbian comedians don’t work a lot in the mainstream.
WCT: I know it was tough for Judy Gold at times to be out and find work.
JK: That’s a good example. She’s a friend of mine. It is hard out there and I don’t give myself enough credit. When I get a standing ovation, I have to force myself to stand up there and accept it.
I have worked hard and it is very rare for a female comedian to get to where I am. The best compliment is when someone doesn’t see me as a female or male comedian and they just see me as a comic.
WCT: Have you performed at a street festival like Market Days before?
JK: Yes, I have done sets outside for Pride events many times.
WCT: They are trying to integrate comedy into the programming at Market Days. Matteo Lane was in 2022 and Joe Dombrowski in 2025.
JK: How did those two go?
WCT: It went well. Joe brought people up onstage to play games. Your crowd work is strong, so this gig might be easy for you.
JK: What people see online is my crowd work, but I have hours of material. I always feel it out to see if it is an opportunity to do crowd work.
If there are many people outside, then it can go either way.
WCT: Some of the crowd will be drinking.
JK: I am used to that, but it can be weird to perform outside. I just did an outdoor show in Edmonton, Canada and it went great. I did a little crowd work at that gig, but they loved the material.
WCT: Your material was hilarious on your stand-up special, I’m the Man. I read that Carol Burnett influenced you.
JK: Yes. I love her, Lucille Ball and Gilda Radner. I grew up at the exact same time as Laraine Newman. She was an original cast member from Saturday Night Live and Hannah Einbinder is her daughter. She sent me a message recently that she thought my podcast was funny, and she is one of my idols.
WCT: I really gravitate towards female comedians.
JK: I made a documentary all about that called Hysterical. I am in it, but I also created it and executive produced it. It features Nikki Glaser, Kathy Griffin, Sherri Shepherd and Margaret Cho. The movie is all about our careers.
WCT: Talk about a whole other career—you have a wide range of character voices on your podcast.
JK: That is my passion from watching Saturday Night Live. I love playing characters.
WCT: What’s the best gift a fan has brought you?
JK: People bring me special gifts a lot. They make art and bracelets a lot. Gay men are very thoughtful. Last week one of them wore a hat with an electronic sign that said “I love you, Jessica” on it.
WCT: Do you have a rider for your dressing room at venues?
JK: I am always changing it depending on what I am eating. It’s either bagels and cream cheese or a vegetable/fruit plate. It depends on how depressed I am.
WCT: I will let the Market Days organizers know.
JK: You are so sweet. I always like a coffee or espresso before I perform. I love gummy candies, just not with pot in them.
WCT: Have you visited Chicago often?
JK: A lot and I have to tell you I might record my next special there. I love Chicago audiences and the shows are always crazy when I perform there.
WCT: Well, I think Market Days will be one for the books. What are you working on next?
JK: I have been filming a gay dating show on my YouTube channel. I did four of them in New York and I want to travel with it. I hook people up onstage and I would love to do that in Chicago.
Kirson brings her stand-up act to the Addison Stage on Sunday, August 9 at 6:30 p.m.