As an avid fan of the of the Comedy Vault in Batavia, I was thrilled to finally attend my first Comedy Vault open mic, held every Wednesday. Before the open mic, I sat down with Kyle Alan, prolific Chicago comic and frequent Comedy Vault open mic host. We delved into topics such as open mic strategies, the perils of comparing yourself to comedy peers, the art of being an exceptional host, and the best open mic spot in Chicago.

Kyle does comedy all around Chicago in just about any venue you can think of, including comedy clubs, breweries, pubs, and outdoor events. He has loads of hosting experience and has performed with the best comedians in Chicago. Kyle is extremely high energy, talks fast, and has a Lewis Black-style anger to him. He understands the mechanics of how to write a joke and he is absolutely the best open mic buddy you can find. I had the pleasure of sitting with him throughout the open mic (he wasn’t hosting on that particular night) and he knew all the comics and gave me the inside scoop. After his set, he told me what he learned, what went well, and what he will change about future sets based on the night’s performance. It was a wonderful education and if you can sit with Kyle at an open mic, I recommend it. He is the open mic sherpa!

Beyond his performances, Kyle is a generous supporter of live Chicago comedy, frequently showing up to support comedians even when he isn’t on the lineup. For instance, when Jack Baker headlined the Comedy Vault on July 6th, Kyle showed up to watch the show. His presence is always felt, often marked by his distinctive, booming laugh that resonates from the back of the room. After sets, he makes it a point to commend each comic. Comics like Kyle are the people who make a comedy scene a community.

Now, let’s dive into our conversation.

KB: Tell me how you first became interested in comedy and doing comedy.

KA: I can’t say what the first comedy album was, but I will say the first comedian I got into was George Carlin around the time I was in college. A few years later, I started getting into guys like Louis CK. Yeah, I know the controversy surrounding Louis, but at the time, he was a great comedian. He still is. It’s just he has a lot of baggage. Then I started getting into guys like Burris, Daniel Tosh, so on and so forth, and then that got me interested in stand up in general. And then over time I became more and more curious, and I just decided to pull the trigger and go to my first open mic. That was at Riddles Comedy Club in Alsip, Illinois on September 29, 2015.

KB: Did you do well your first time?

KA: I didn’t completely bomb. I tried listening to a recording of my first set, and I really couldn’t understand what the fuck I was saying because I was going a million miles a minute.

KB: You were nervous.

KA: And also, too, you just get that adrenaline rush. Yeah, which is why it’s pretty common to do well your first time. Most people won’t really kill their first time, but people might do good enough, and that’s because of the adrenaline energy that they’re giving off.

KB: So that’s why people do well their first time and their second time they bomb because the adrenaline rush isn’t there?

KA: Yeah, they kind of have like a bit of a slump when it gets to the second set because they don’t have that same adrenaline. Because it’s not the first time. So that’s why you’ll see, like, people who do really good the first time. They’re all jacked up and they’re all, like, running with adrenaline and energy. Then the second time they do it, not as much adrenaline, because they’ve already done it. There is a fight or flight response that first time you go up.

KB: I have tried it and it certainly isn’t for me. My second time, people weren’t listening to any of the comics on stage. They are just staring at their phones.

KA: Yeah, but that just goes with the territory. You have to earn people’s attention. You have to love it. You have to feel like you have some type of calling for it, whether it be wise or not. If you’re half-assing it, you’re only going to get so much from it. The more you put into it, the more you get back. At least that’s the way I look at it.

KB: After your first open mic, where did you go from there?

KA: I kept doing Riddles a lot and kept doing lots of open mics and getting stage time. And that transpired throughout the next eight years or so. I just kind of kept going. Aside from the pandemic in 2020, I’ve been pretty consistent with trying to work on my craft as much as I can.

KB: What did you do during 2020?

KA: Alcoholism.

KB: Same. I was riding that negroni train pretty frequently throughout the pandemic.

KA: The 2020 pandemic gave me a break from comedy and time to reevaluate a couple of things, and that’s where it kind of led to me sort of like reinventing my style to a degree. That’s why I started wearing the leather jacket and the bandana..because I was always a metal head That was always a part of me that when I started doing comedy, I kind of, like, held back. I tried to be a little bit more clean cut. I tried to be like a club comic and then I just got tired of it. So fuck it. That’s not me. I’m not having fun with that. Even though people, like, give me shit wearing bandanas. That’s because I want to wear it. And yes, I’ve heard too many times that people compare me to The Amazing Jonathan.

KB: I just did a whole David Foster Wallace deep dive last year, so I’m as pro bandana as someone can be right now.

KA: I’ll take David Foster Wallace over the Amazing Jonathan.

KB: So you work a day job, right?

KA: Yes. I have a flexible job that let’s me do stand-up.

KB: Fantastic. How do you develop new material?

KA: When I originally started out, I tried to write close to an hour every day. And, of course, there were certain days where I was a little bit more relaxed on it than others. But then with the pandemic, I realized that as much as I was pretty good with my writing, I was also pretty scripted with my delivery, so that’s why I kind of changed it up where I stopped writing physically as much. Instead, what I’ll do is I’ll just talk out a premise out loud because it makes it harder to overthink or overanalyze the premise if I’m just saying it out loud. And two, it makes it a more conversational cadence, which is much preferred in terms of stand up because we’re trying to craft an illusion that we are talking to the people. We’re all trying to make it seem like it’s an organic conversation, and when you have material that’s too scripted, it kind of shatters the illusion that you’re saying this for the first time. Of course, there are people who can get away with finely tuned material and have a good delivery and so on and so forth. Personally, me, I think I benefit from having more of a conversational cadence.

You can learn how to write jokes and all that. But it’s another thing to learn how to tell jokes because everyone has their own particular way. There’s always a different way of going about doing it.

KB: How many open mics do you do a week?

KA: I try to keep at least a minimum of four mics per week.

KB: Beyond the Comedy Vault, do you have open mics you like to frequent? Do you try new places all of the time or have the same open mics you like to routinely do?

KA: There’s always going to be, like, a certain amount of places that I rely upon to try out new material or to get a reaction. But it’s also important to try out different places, too. You can’t really get too comfortable in one place. If you do that, you’re actually doing yourself more of a disservice. Yeah, because then you get used to that environment, to that club or to that audience, and then you branch out and go to a different room where people there aren’t really your crowd and then you just eat a dick. And the thing is, you want to diversify where you perform to become a more well-rounded performer. If you’re trying to be a better stand up comic, then you have to work for it.

KB: What do you think is the best open mic in the Chicago area?

KA: Probably the Comedy Vault. It is the most consistent one.

KB: That’s really surprising to me that with the vibrant Chicago comedy scene, you’d pinpoint a suburban open mic as the best. Why is the Comedy Vault open mic the best one?

KA: They have a crowd. And other mics don’t have a crowd. Let’s put it like this…they’re a comedy club so when they have an open mic, people come out to the open mic to watch because the context for comedy is there. It’s not like you’re performing at a bar open mic where they just set up the speaker and then they say, hey, we’re about to start a comedy show, meanwhile, they are driving people out of the bar, or maybe like, people in the bar are drunk and want to heckle. In terms of that, I feel like a great open mic is one that has an audience. But often times, you’re not going to find an audience.

KB: How is the comedy hang at the Comedy Vault open mic? I was really intrigued by Mike Bridenstine’s book on the Chicago comedy scene and he talked about how good the open mic hangs were in the 2000s and how that was essential to everyone getting better. He lamented that the hang has sort of dissipated from the Chicago comedy scene. Is the Comedy Vault bringing that back a bit you think?

KA: Yeah, we all get drunk afterwards. Every open mic that I try to go to, I try to cultivate that type of hang and it’s not because of just frivolously having fun. But I think also being amongst your peers in a fun setting is actually beneficial because you get the opportunity to talk about stand up with other seasoned comics, people who might be veterans, and that is a good way of knowing about it. I feel like a lot of my education was just by being around people who are better than me.

KB: As far as doing open mics, do you do as many as possible. Do you have a strategy?

KA: Doings tons of open mics in one night isn’t necessarily going to guarantee you to be a better comic. It may help in terms of becoming more comfortable on stage and all that. But I feel like every time you go up on stage, there needs to be a plan. There needs to be a goal. You have to work on something. If you’re going to be doing the same shitty jokes at four open mics, you haven’t really improved much. Besides that, you just did the same joke four different times. And it didn’t work.

KB: How many times do you do a joke before you know that it doesn’t work?

KA: That depends. Some jokes take a while. Sometimes you need to personalize it. Sometimes you need to figure out the delivery a little bit or you need to trim it down. You have to mind the word economy. Maybe say this a little bit differently. And then some, you just have to put on the back- burner if they are not getting laughs whatsoever. And if it doesn’t feel natural, then put in on the back-burner. Get rid of it. Hold on to it and see if there’s a moment where you can make it work. That’s really the best way to go about doing it.

KB: So at tonight’s open mic, do you try all new material? What’s the plan?

KA: I always try to do jokes for shows I got coming up. If I am bored, I will put a new joke in the middle.

KB: And you regularly host the Comedy Vault open mic. How did you get plugged into that?

KA: They just asked me. And, I mean, it sounds like a cop out to say that but I’ve known them for a while. I’ve been coming through their club. I’ve worked with them several times, so they know what I could do. And I guess the thing is, you just have to put yourself out there, put the work in, and build those connections, and then people can start noticing you. Or maybe you start reaching out to them.

KB: So you did the Comedy Vault open mic a few times and got plugged into the system if you will?

KA: I mean, it’s a little bit more involved than that. It involves meeting the staff and all that. Talking to the manager, building relations with the club, and working with them. And it’s not just like that for the Comedy Vault. It is like that for most clubs. It’s about building relationships and establishing connections.

KB: Hosting looks like an important and hard job. How do you think about hosting?

KA: . I feel like every comic at some point should get an opportunity to host. And the reality is that hosting is not like what people think it is. A lot of people, they think that hosting is you’re just the guy who does a set up front and you get to do jokes between comics. No, that’s not what it’s about. When you’re a host, you are the MC for the show. People overlook that aspect a lot. You have to think in terms of the show. You have to put the show over you. And that’s a difficult thing for some people, because some people are selfish, narcissistic assholes.

You also need to learn how to host because it’s a good way to get yourself loosened up. You can’t always just expect to do your act upfront. You’re going in cold. So you have to go up there, you have to try to pry open the crowd a little bit and sometimes some gentle little crowd work works and maybe, like, MC stuff, maybe. You have to make announcements as well. When you’re like MCing for the club, you’re an ambassador for the club. Also like, the one thing that hosting has benefited for me is that it gave me an opportunity to be on stage multiple times, but I don’t really do material between jokes. What I do is if someone did really good, I’ll just bring up the next person. It’s all about maintaining the momentum of the show.

KB: Everyone says Liz is doing everything right at the Comedy Vault. What does that mean?

KA: Liz is willing to go out and try to improve the club in any way possible. So she’ll go out to LA or Austin to network with people at different clubs and bookers and all that, and she’s willing to do all that work. She builds relationships with headliners who come through. She’ll book a comic at her club to headline, and then when they’re, like, filming a special, she’ll go out there and be part of the taping.

KB: How can any club owner not do that? It seems like an obvious best practice.

KA: Not many bookers will do that. I don’t want to be presumptuous in that, but in my experience, not many of them will go out and do that because they’re busy usually, and it costs money to get out there. But Liz is willing to go out there and actually see a comic who’s doing some cool filming or a festival. So she builds a rapport with people she books and because of that, that’s how she’s able to get other, bigger name comics. Like she’s getting Brian Posehn next week.

KB: Recently, you did a gig at a brewery in Naperville. How do you get gigs like that?

KA: You build a rapport and you get to a point where you’re like several years in and you have built up enough connections, and networked with enough people that when there is a spot, they may reach out. And that’s really what it boils down to. There is no real secret to it. You could reach out to promoters or whatever and try to get a spot but then there’s also just simply if you work at it and then people know you and then you’ve shown that you’re consistent, people will ask you.

KB: What is your advice for comics who are starting out?

KA: Don’t overthink it or try to rush it because you’ll burn yourself out. And then you’re going to be miserable, and you’re not going to have fun with it. And that’s the point. You want to have fun with this because if you’re not having fun with this, there’s no point in doing any of this because the reality is pursuing stand up comedy is such a fruitless labor. You are going out of your way, disrupting your social life, compromising your finances, putting miles on your car to go out to open mics with a bunch of strangers just to go up on stage for three to five minutes. And then a lot of these places, at least for me, aren’t close so that mean driving an hour to get like four minutes of stage time.

KB: How do you cope with bombing?

KA: You have to have the proper mindset that failure is a regular occurrence on the route to success. So you cannot succeed if you don’t fail. And you got to get in the mentality of that. Anything that doesn’t work, you have to learn from it. So it doesn’t feel great, but bombing on stage is like a shot from a doctor… Doesn’t feel nice, but it’s healthy. There are people who are just bombing day in day out, but they don’t learn from it.

KB: How long does it take to be able to listen to the audience? I heard somewhere that it takes like 40 open mics to have the brain presence to be able to even listen to the audience?

KA: Everyone develops at a different rate. And here’s another thing we can add to it. One thing you have to make peace with when you’re starting out doing stand up comedy is that there are going to be peers. Some will just develop at a faster rate than you will, of course, and that’s just how it is, and that’s not necessarily your fault. Now, you can use that as motivation to work harder. You can’t throw in the towel and give up hope because so and so has gotten better within a span of six months and just booked their first hosting spot. You have to go about it at your own rate. And you have to keep working at it.

KB: What is something about the Chicago comedy scene that you think most people don’t know but they should know?

KA: Chicago is a great place to start doing comedy and to learn the basics but the reality is that a lot of the great Chicago comics didn’t become great comics by staying in Chicago. They all left Chicago at some point. The unfortunate thing in Chicago is there is a very limited industry in terms of stand up and where you can go from there. Now you can get to a point where you could get booked regularly and start headlining like clubs or shows across the state. But the reality is that it’s beneficial to leave, to go to an area that does have an industry.

KB: Who is your favorite local Chicago comedian?

KA: Vince Carone. If you want to talk about a man who has, like, a solid work ethic, it’s Vince Corone. This is a guy who tours all over the Midwest, across the country. He has five hour-long specials. The man just knows how to pump out material. He found this style, and he knows how to make it work. I’d be remiss if I didn’t mention some of my friends. Tom Feeback, who I’ve seen grow up… I met Tom before he started doing comedy and then I told him to come out to an open mic, and he just blossomed from there. Luca Ferro, Brando Harris, there are so many people I think are really good.

KB: What do you think about stand-up as an art form? Do you think it is fair to call it that or are comedians closer to glorified drink salesmen?

KA: Sand-up comedy is an art form that is very much undermined and underappreciated. A lot of people don’t really value stand-up comedy like we do. A lot of people just simply view us as we’re just going up there and just talking and there’s no craft or there’s no artistry to what we’re doing because we make it look easy, right? So in their mind, what we’re doing is easy. But no, it’s not.