Talking About the End of Chicago’s Upstairs Gallery

The Upstairs Gallery started in September of 2010 as a small performance space in Chicago’s Andersonville neighborhood. It is now one of the city’s best known comedy theaters. After four years of putting up some of the most exciting and experimental theater in Chicago, it is closing at the end of this month. The Gallery is operated by Alex Honnet, Caitlin Stephan and Walt Delaney. I spoke with Alex and Caitlin about the Gallery’s shift from “performance space” to “comedy theater”, as well as the upcoming second installment of their independent comedy festival, A Jangleheart Circus.

Could you talk about the place that Upstairs Gallery is now versus when you first started?

Alex Honnet: Yeah. We have a weird sense of legitimacy. A lot of people who see Gallery shows and get it and really like it here. Like, get that there’s actually some really good improv here. And some people think its just all these dudes fucking around. So, I think both are true. We are both those things at the same time.

Caitlin Stephan: It’s come full circle. In the beginning I was just going to support a friend, I had no idea what I was getting myself into and was just coming to see a bunch of students come to fuck around. And it grew to this giant thing that I am happily involved in. I only started taking classes [last] October. I have done a set here and there, but only in the last year and a half. I was always just behind the scenes. My entire improv experience happened backwards. I was just being a supportive friend and Alex was like “Oh, this is what I’m doing right now. A bunch of us are putting up shows at this space.” And then I started falling into the scene, but only as a spectator.

AH: It was a very natural process. It’s really weird to hear you talk about the Gallery as a fixed thing. Especially with it ending. There is like this weird feeling of, not giving up, but acknowledging that it was an experiment, an experience, and representative of a set time when people were this and when these groups played here. It’s weird to see that perception, I don’t think he had a sense of what people thought about it until recently. Our experience of it as a place where we work and we are putting up this stuff, that could always potentially end if we didn’t want to do it any more. Versus the perception of the community that this is like the Playground or iO or the Annoyance. Like, “Where do you go to see improv in the city? Oh, you go to Annoyance or iO or Upstairs Gallery.” It’s so strange to look at it that way.

SC: In my mind it was always like “this is what we’re doing now, but what are the next steps?” In almost every meeting one of the bullet points was: what are the next steps?

AH: What’s the next thing, how’re we gonna grow, how is it gonna change?

How did Jangleheart come about?

AH: Jangleheart was something that had been in the back of our heads, that we might try something like that, and I think the productions we were putting up here kept on getting more and more insane, kind of culminating in something called Ribfest, which is an idea that Caitlin had of an improv festival that’s going in multiple rooms of the Gallery at the same time. From that we got a lot of confidence and we were like “why don’t we just try this thing?”

CS: I was talking to someone today about Ribfest. That was the baby of Jangleheart. Just like everything we’ve always done, it was a “are we capable of doing this?” thing. And then we were.

AH: Like this is a crazy idea, let’s see if it works. I think everything’s worked reasonably well. There’s never been anything that failed miserably, like as long as everyone’s having a good time I think that’s a success. So we have a pretty low barrier. Jangleheart was the first thing that if this goes poorly then we’ll be in some serious financial trouble. But we weren’t. It turned out okay.

Did you feel at all that you were making an entry to a different level, a professional level?

AH: I think there was a lot of pressure to try to make it good. It is very interesting to do it this year versus last year. Last year we were super concerned with all sorts of small tiny details and all these things, and when the festival happened none of them really mattered. Capacity was a huge thing. We were really obsessed with capacity last year. Making sure we didn’t oversell tickets. And calculating the math of how many performers we had versus how many audience members at any given hour, and how many tickets we could sell every day. Stuff like that. For me, it was a huge energy and head drain. It stopped me from focusing on some of the things that really do matter in terms of just making sure everything is running well. So, I don’t think we were necessarily entering a new level, but we really wanted this thing to go well because it was so much a bigger production than anything we had ever done before.

CS: I think, for me, certainly a year ago I was so much more stressed out about things in my personal life, and I’ve learned to just let that stuff go. There were so much little tiny stuff I was worried about, like making sure everything was ordered on time, and everything looks perfect, and then that sort of stuff I don’t think matters. I think that we know now what we have to stress about and what we don’t. We will personally have a better time at the festival.

AH: To answer your larger question, I don’t think anything we’ve ever done has been an attempt, a play at relevance or a bigger level. It’s much more a place of “this would be really cool if we could do this. Okay let’s try it!”

CS: For me I think it was tring to invite other people to have the good time that we have, and not be like…I don’t want to diss other places, but I wanted it to be a looser thing. Like, “Why do these kids have such a crazy good time, and why are people obsessed with improv and comedy in Chicago?” I think it was a chance to show a greater mass of people, “This is why. This is the fun time that we have. Come do it with us.”

You mention on the About page of your site that you are making an effort to make a better festival with higher quality shows. What is the difference between last year to this year?

CS: I think this year, we have another year under our belt of seeing the people performing. So I think we were trying to think of the most enjoyable experience for the viewer.

AH: Yeah. I think this year, pound for pound, there’s maybe two sets that I don’t know if the team or group will put on a great show. And that was because we got caught up in wanting to be inclusive in some way. But everything else is fucking lights out, or a very cool idea that we are proud to have in the festival. Like, different and strange.

Is there a different balance of the cool conceptual stuff versus just a great improv group?

AH: There is definitely a lot more written material this year. There is a lot more written material, a lot more sketch. That standup community in Chicago that does a lot of solo sketch all the time, there’s a lot more of that this year. We spent a whole year working with Matt Byrne (editor of the Steamroller) and he did a good job of bridging the gap with those folks for us. There’s a lot more of that this year. And the nice thing about having the Upstairs Gallery house teams in the festival is, they all get two shows in the festival and it is basically a bankable, really good improv show. Those teams will put on a really great improv set. So we have a nice core of good improv automatically.

CS: I think this year versus last there is a whole lot more Chicago representation. Of course that’s always been the goal, but like we were saying before, we were also trying to be polite and outreaching and trying to get other teams from other cities involved. And this year we only have a couple of New York and LA teams coming.

You mentioned that you have less out-of-town teams coming, more Chicago people who you know can do a good job. As someone who lives in Chicago, why do I want to see these shows at Jangleheart when I can see them all of the time?

AH: Two reasons I think. First, if you don’t operate in the Gallery’s circle as a performer you probably haven’t seen a lot of the groups we’re putting together, if you are in the general public you have probably never even heard of them. So while you can see them all the time you probably haven’t, or have been meaning to and now you can see a ton back to back. Find your new favorite thing. Second, almost all the written material being performed is either from out of town or has been created new for Jangleheart. Third, I know I only said two things, I think the vibe is going to play into it a lot, people are going to be surrounded by so much cool comedy the whole time and you can just bounce around checking out all kinds of stuff. It’s great.

CS: One of the main things we really focused on last year and again this year, is not just your average, one-off improv show. It’s about the whole experience. Just like when you go to Bonnaroo, Lolla, or Pitchfork, you are going not just for a concert you could see as a one-off, you are going to be a part of this greater thing. It’s about being with your fellow festival goers and experiencing it all together. The idea, which I think was pretty successful last year, was to have all of these people in the same place at the same time creating a certain buzz all around the Den. The energy was palpable. This energy then translates into the improv itself. Everyone is so high off of the whole thing that they put on a really great show. And, because it’s a special thing and not just a one-off show, people tend to go all out and make things a little extra special for their audience.  When it’s all said and done, everyone has this shared experience and it’s amazing.

Are tickets still available?

AH: Yes, very!

Will Jangleheart go on beyond this year?

CS: I feel like we’ve been answering that question with, “No this is not the last Jangleheart”. I suppose we’ll see what our post-Upstairs Gallery lives are like.

AH: Caitlin and I are still going to produce stuff in the city, after the Gallery closes, as “the Upstairs Gallery”. The brand will live on.

Why are you guys ending the Gallery?

AH: That’s a big one. It feels like we’ve reached this point where it has started to become more work than fun. In order for it to be something, in terms of where we grow next, it would have to become work. So we sat down and looked at what that would be or what shape that might take, the idea of trying to do it and run the Gallery at the same time is really overwhelming and daunting. So it becomes a question of “are we going to start to resent it for not being something it was never even meant to be? For not being able to change past a certain point. Do we want to be doing this for another five years? Is this where I see myself at that time?” And we asked ourselves that question and the answer was no. There is so much change in the community, there might not need to be a place like Upstairs Gallery with all the stages at iO, and the extra stage at the Annoyance, there’s so many spots opening up. So, it made sense for us to bow out.

CS: I’ve had to answer this question in so many facets of my life because people at work know what I do and they don’t fully understand it, so to answer that question is always weird. Just depending on who I am talking to sometimes I feel like a failure, but then I have to go back to the root of it all and say “wait, what were we setting out to do?” We were not by any means setting out to run a theater at the level of iO, or the Annoyance, or the Playground. We were just people fucking around to see what the fun thing would be. So by no means did we fail because there was no greater goal.

How or why do you think you ended  up on that level?

AH: I dunno man. You have to tell us. There was this wonderful thing where these really talented people didn’t feel like they were getting opportunities at theaters, they started working with us, and we caught them as they were starting to put out really good stuff, and that propelled us into the stratosphere where young people could play. I think a lot of veterans started to take notice of that, and we just got a reputation as a place to do cool stuff, and the rest is history. Other than that, I have no clue.

CS: We very rarely said “no” to people’s ideas and we certainly didn’t put constraints on what you could or couldn’t do. I think part of the reason of stopping now is to not become this big problematic club house of exclusivity. I mean, you can’t put every single thing up, but I think because we did support most of these insane ideas that came along, that’s why people gravitated towards it. Because they couldn’t have that chance elsewhere.

Griffin Wenzler performs stand-up, sketch, and improv in Chicago.

Talking About the End of Chicago’s Upstairs Gallery