Before the Comedy Vault’s open mic on a Wednesday, I had the privilege of sitting down with the wonderful Jack Baker. We talked about how he got started in comedy, how he got good, filming his special, free speech and comedy (we fundamentally disagreed and that was fun), The Comedy Vault, and our favorite comics.

If you don’t know Jack Baker, you aren’t going to enough comedy shows in Chicagoland. Baker has been doing comedy in the Chicago area for over 14 years. He filmed his first special, Jack Baker’s Disease, last year at the Comedy Vault, which he released on YouTube. He regularly performs in the Chicago suburbs and he will be headlining the Comedy Vault on July 6th. If you’re reading this after July 6th, you can see Jack’s upcoming shows here.

Baker is a razor sharp joke writer, who tells stories about his life experiences, ranging from living with ulcerative colitis and shitting himself in an Aldi to getting beaten up by his short, hot wife. In our interview, he shared that he constantly thinks about crafting jokes, a dedication evident in his life performance. There is no filler in Baker’s comedy. Baker’s sets are streamlined and impactful, delivering punchlines without unnecessary setup. Additionally, Baker’s delivery adds an intellectual flair to his humor; seeing him live feels like being on a tour with the docent of a comedy museum. In fact, his articulate voice is eerily similar to an eloquent law school colleague of mine who is now a federal judge—a stark and amusing contrast when you picture a federal judge discussing such candid, everyday human experiences.

This unique style and commitment to comedy have not gone unnoticed by other comics. Jack recently received a shout-out in the May edition of the Comedy Gazelle, where a fellow comic praised his ubiquity in clubs and the quality of his special, noting, “Jack is a comic you see at clubs everywhere and has a great special, but has never really broken through in Chicago the way he deserves to. Whip-smart jokes mixed with a laid-back attitude, Jack is such a natural and always makes any show he is on better.” This endorsement captures the essence of Jack’s presence on stage. Watching him perform is always a pleasure; he exudes the same confidence trying out new material as I feel relaxing on my couch at home. A particularly delightful experience is catching Jack try out new material at the Comedy Vault’s Wednesday open mic—an opportunity to see the comedy gears turning in his brain.

My biggest insight from talking to Jack is that a successful stand-up career is entirely feasible even if primarily based in the Chicago suburbs. Once established in the city, a comedian can enjoy a strong following, frequent performances, and even film a special—all without ever needing to use the Park Chicago app. Jack exemplifies this pathway. He stands as a testament to a comedian who balances a healthy, fulfilling life with a robust comedy career.

I encourage anyone reading this to prioritize seeing Baker live. Now on to my conversation with Jack:

How Jack Got Into Stand-Up

KB: So how about we talk about how you got started in comedy?

JB: I started listening to Mitch Hedberg in 7th grade. When I was in college, I started writing parody songs. Bo Burnham was really getting popular at the time. I joined a sketch comedy group called Premium Bananas. It was as bad as you think it would be. And then we did that for like, a year and a half. I was with a student group. At NIU. We went to a show at second city, and then it was like I wanted to do stand up, and I’d like written these songs and sketches and stuff. And going to the show at Second City was the thing that made me think: Alright, I need to find a place to sign up and do this. When I was 20, I did my first open mic set at Comedy Under the Tap in Oswego, a sold out crowd of 85 people.

KB: What made you pull the trigger and decide this is actually the first night to do stand-up?

JB: I just sent them a message, and they had one spot open three weeks from then. So it’s like time to get jokes together.

KB: And so you go and you perform for like, 85 people and it went well?

JB: Yeah. Most open mikers do well their first time because they have crazy, anxious energy.

KB: Do you remember what you talked about?

JB: I’m trying to remember. My first joke was about breast milk. “I saw a study that humans can actually live their whole lives on nothing but breast milk, even into adulthood. It just gets really uncomfortable for your mom.” So that was my first joke that I ever told. My comedy’s gotten better since then.

KB: Hey, there’s a lot of worse jokes than that. And so how long did it take you to get back up on stage?

JB: I was in school. It was probably a couple of months. And then when I came home for the summer. I started going up more regularly. And then kind of like summer break, winter break, through the end of college trying to do as many open mics as I can, and then once I graduated, it was really all I was trying to do.

KB: Did you mostly do poorly for months or did some sets go well and some sets go bad? How does it play out in those early days?

JB: Early on, I feel like when you’re starting in comedy. You have to be delusional enough to think that it’s going well, but not so delusional that you don’t recognize that you’re terrible. Yeah. So you have to find the little victories when you can. You’ll have one joke that gets a big laugh like, all right, that was good. And then as you do it more and more, the bar for what constitutes a good show keeps getting raised. At the beginning, it is one good laugh. Now, it is if I don’t kill with every joke, I could have done better. It’s kind of like what I strive for now, but if that’s your goal when you’re six months in, you’re going to be miserable and depressed and you’re going to quit.

How Jack Got Good at Stand-Up

KB: When you start doing comedy, how long does it take for you to be able to actually hear the audience and not be so nervous in your own head that you can’t listen to what they like and edit based on that feedback?

JB: It takes a long time. Early on, you’re trying your best to say funny things…you almost do anything for a laugh.

KB: How did you get tons of stage time?

JB: There was a club that used to be in Aurora, the Comedy Shrine. And so I was like the house MC for years. Going up in front of cold crowds. And the club was.. a lot of the shows were sparsely attended, so just the reps of going up and doing like 10 to 15 minutes every Friday and Saturday in front of between, like, 10 and 50 people. It was just doing that over and over and over again. You just kind of get thick skin and realize that some will go good and some will go bad but if you don’t give it your best and do it confidently, it’s never going to be very good. Yeah. I feel like most of stand up is just tricking the audience into thinking that you know what you’re doing.

KB: Isn’t that most of life too?

JB: Yeah. The comedian who stands up there confidently and tells their jokes will always do better. It takes a very long time to truly get to that point where you can do that and understand what that means. Both for like you and from the audience’s perspective.

KB: How many years before you felt like a competent comic?

JB: Ten. I felt really good before Covid. I took, like, a year off. And then when I came back, I was like, oh, no, I wasn’t very good before. But then getting back into it after Covid and then working really hard at it, that was when I started to feel like… I really progressed a lot in that first year coming back. And then, from there on, it was kind of like, all right—I think I’m ready to record a special. And so it’s time to get my material together and really write it down to each individual syllable.

KB: I apologize for my naive and basic question but I just don’t understand how anyone can go up and do an hour. How do you memorize it? How do you remember all the words?

JB: I’ve always just kind of had a good memory, so I’ve always been like, lucky in that way. With my 48 minute special, I talked about three things. I talked about marriage, I talked about health, and I talked about my family. There were basically like three kind of 14-15 minutes acts in the special. When you can group material together thematically, it makes it so much easier.

KB: How do you create 48 minutes of material?

JB: I just think about jokes all the time. Literally. As I’m walking around, I walk my dog thinking about jokes. I’m driving, I’m thinking about jokes, I’m doing the dishes, taking a shower, everything. I am always thinking: how can I get this tighter? How can I simplify this idea? Am I talking too broadly? How can I get more specific? I am constantly trying to figure out different ways to tell the jokes. And there are so many open mics. The Comedy Vault’s is a great one. You just go to open mics like all the time. I try to go to at least one or two every week. It’s not nearly as much as when I was 23. Of course, now I’m old. I’ve got a job and a life. I can’t be out until midnight every day. And so I try to use my time as effectively as I can. And so every time I go to an open mic, I always want to have a very clear idea of what it is that I’m working on. And I’m also at a point, too, where I have lots of opportunities to do longer sets, which is great. And I’m always really appreciative of that because that gives you a time to stretch out. When the audience is on my side, it’s a good place to try this newer joke. If it’s not working, you can always just get out of that and go into something else.

KB: So how does it work at an open mic in terms of trying new material every time or doing a joke that you know works?

JB: Just reps, making sure you know the right wording. I also have a lot of clean shows coming up, where I have to do longer, cleaner sets. I am trying to bring back things I haven’t done in a while and it is better to do it at the Comedy Vault open mic than in front of the crowd that paid $25 a ticket.

KB: Asking out of total ignorance, why do comics do jokes that work already at an open mic?

JB: There’s always lots of different reasons. Sometimes you’ll be like, I want to try this joke with changing this one word. Even the mic stand taking it out versus holding it changes the way you perform. There are little things that change the way you tell your jokes and you don’t think about it, but they do. A joke will come off differently to the audience if you’re standing still versus if you’re walking around. The joke will come off differently in the audience based on where you’re looking in the room, how far you are from the front of the stage…like all those things will factor in. You were talking about how when you’re starting out, you don’t think about that stuff. You’re just up there trying to do whatever you can to get laughs, but once you do it enough times, you start to see like, oh, you know what? Okay, this show we are not at a comedy club; we’re in a bar. It’s kind of loud. These people aren’t necessarily comedy fans. They just came because there was, like, a thing to do. So the way that you perform…you can’t go in, like at a club. In a club, you have the expectation that everyone knows how the show works. At a bar, you can have the expectation that they don’t necessarily know how the show works, and so you sometimes have to teach them.

KB: How do you teach them?

JB: I always just like to start doing my smartest, quickest jokes as quickly as I can just to get them into the rhythm of stand up comedy and understand, like I say, a thing then you laugh at that thing. Then I say another thing and you laugh at this. The audience is not talking. You want to just do that confidently to show them how it’s supposed to go. So then the rest of your set, then you can start to have fun and get more loose and play with them. But if you start getting loose and playing around with them, they think that that’s how the rest of the show is supposed to go, and so that can lead to all kinds of heckling.

KB: So you regularly do the Comedy Vault open mic. What other open mics do you like to do?

JB: There’s lots of good ones. There’s Moe Joe’s in Plainfield on Tuesdays. There’s Josephine’s in Villa Park on Tuesdays. The Laughing Academy. And then, I mean, in Chicago, there’s like four or five every single day. but I’m not going to drive into the city to do open mics.

KB: A huge insight for me is that you can become a good comic by not even going into the city.

JB: I think it’s important to when you’re first starting out, because you should go to as many different places as you possibly can to see how your jokes fly with as many different kinds of people. And you also want to see what everyone else in the scene is doing so you can see better comedians and go, okay, that’s what I’m striving, for. But I’ve been doing it so long. I’m not comparing myself to other comedians.

KB: That was literally physically obvious when I was at this open mic a few weeks ago. You were back in the corner focused on your jokes and there was like a cabal of 22-year old comics from the city at one table and you didn’t feel the need to be at that table.

JB: I don’t need to be there. Yeah. That’s also just like a social thing, comedy, especially when you’re young. It’s all fun, and that’s kind of like a hangout, and that’s like make friends. You’re going to war with them and get really bonded by all the terrible comedy shows, trips that don’t pay a lot of money and that whole experience. You become friends forever.

The Comedy Vault & Favorite Comics

KB: Everyone raves about what a great club the Comedy Vault is and how Liz does everything right. What makes Liz and the Comedy Vault stand out?

JB: It’s the little things. They don’t do the check drop until after the headliner is done. That makes a big difference when you go to other clubs. About 10 to 15 minutes before the headliner is done, they do the check drop. And it just fucks up the end of the show. At most clubs, they’re prioritizing their wait staff, being able to turn over the tables faster by doing the check drop while the show is still going on. It’s at the expense of the last 15 minutes of the headliner set. When clubs do that, they’re putting their own money making over the experience of the people watching the show.

KB: I’m trying to think of clubs I have been to that wait until the end of the show. I was at another show in the Midwest that definitely did it 15 minutes before the end like you said. I can’t believe I never noticed that.

JB: Who did you see?

KB: Ian Carmel. He has a joke I think about every week. It’s something like “They way I feel about sex is like Now that’s what I call sex volume one.” I love comics who do have jokes I think about every week. Mitch Hedburg has one for me too. When someone hands you a flyer on the street, “Here, you throw this away.”

JB: For me, the one I think about every time I go grocery shopping is Rory Scovel has this great joke about how, when you’re not sure where an item is in the grocery store, you look down the aisle to try and see if the thing you want would live next to the other food. It’s like “What’s that down there? Jams and jellies? I don’t see rice living next to jams and jellies…not after what happened.”

KB: Yes! He is unbelievable. I couldn’t believe that special where he was like I don’t have anything… I am just going to go out there and talk to people with no material. It was unbelievable.

JB: He is my favorite comedian. Mitch Hedberg has that one from when he was a metal band, “They either loved us or they hated us or they thought we were okay. I say that joke. All the time.”

KB. Mitch is the best.

JB: Yeah. He was the comedian who made me want to do stand up. In 7th grade I watched his Comedy Central half hour for the first time, and that was like, when it clicked and I was like, that’s what I want to do.

Comedy is Free Speech/Jack Thinks I’m Out of My Mind

KB: Switching gears, I think comedy is the most honest form of speech and communicates complex ideas in the most compelling way. Do you see comedy in this romantic way that I do?

JB:I think that people just like in general, audiences just like to laugh. And most people aren’t there to think too hard. And that’s why it is impressive to find someone who can do the kind of comedy that can make you think while still being funny.

KB: Yeah. That’s when it’s really great. I just think it’s the highest art form.

JB: Comedy is a weird thing because it is like this great art form that we spend so much time pursuing, but then, on the other hand, we’re also just like glorified drink salesmen. That’s why we’re here: so they can sell drinks and food. And so that’s why I feel like it’s always good to keep balance. You don’t want to. Get so far up your own ass artistically that you lose sight of the fact that we’re just saying silly things to entertain people who have a two drink minimum.

KB: It’s a good attitude and I’m not a comedian. But I think the honest speech we get from stand-up seeps into the culture. I think the Overton window for what you can talk about is the largest in comedy and that trickles down to speech in all of society. Jack isn’t buying this at all.

JB: I think it’s interesting the things that people choose to talk about and why they choose to talk about them. And so when you say, like, free speech…I feel like a lot of times so-called free thinkers… I don’t really think that you can’t say anything dangerous in a club that has a two drink minimum. If you were actually saying something that was truly outrageous, it couldn’t exist within the capitalist society that we live in. Look at Lenny Bruce in the 50s. He was actually doing things that were like…je was getting arrested. He was saying outrageous things for the time. It wasn’t for the purpose of saying outrageous things. He was trying to make a larger point. And I think that what you see a lot of the times now is comedians saying outrageous things, thinking that they’re making some larger point. But they’re just talking to suburban white people who are paying $60 to be there.

KB: I think the aggressive honesty that is appropriate in stand-up is moving us toward more like this, less repressed communication. Like, you know, the whole idea that, you should never bring up politics, sex, money, or religion in polite conversation… I think comedy moves the needle on what constitutes appropriate conversation in other contexts and I think that is good.

JB: I think it does, but only in a way that benefits what is still within the mainstream viewpoint. You can’t bring up actually divisive hot button political issues that really make audiences mad. Talking about, like, making jokes about pronouns, you’re not gonna actually face consequences for that. My question when comics bring up certain topics is “why is that the thing that you want to talk about?” Because you could talk about literally…that’s the great thing about stand-up…you can talk about any possible topic that you want to. And what does it say about you that that’s the thing that you want to talk about.

KB: I just feel like writing any joke that’s funny is so hard. Isn’t that what people are trying to do? Or do you feel like comics craft material by first thinking: “What topics do I want to talk about?”

JB: I talk about the things that are interesting to me and that happened to me and that I think about because I don’t really think that my thoughts about the world are that interesting or unique. I know myself better than anyone else in the world. So that is a subject that I can talk about with100% confidence and I know that. Everything I say is right about that topic. Whereas when you start talking about politics or whatever, people automatically bring in all of their own shit into it. And so now when you, like, you set up a joke, you create an expectation, and then the punchline subverts that expectation. And that’s all jokes are. But when you start talking about things that other people have their own opinions on already now, your job is so much harder because the setup for your joke not only has to accommodate what you think about it; it has to accommodate what every single other person in the room thinks about it.

KB: So you’re saying you haven’t come across any ulcerative colitis (Jack’s online special has a large chunk of material on his ulcerative colitis) truthers out there?

JB: No, people did give me a lot of like, you got to stop 5G comments on my special. Yeah, it’s like a conspiracy thing.

KB: I thought you mean 5G like a list of five things that start with “g” (gluten, etc)

JB: I did get the gluten comment too. It’s weird when you talk about having ulcerative colitis or something like that, people will come up to you and give you medical advice. Strangers will share. And it’s always like, my cousin knows a guy who has this thing. It’s never like I’m a doctor, right? And then the best, though, is people after shows will come up to me and tell me about all the times that they shit their pants, and that is my favorite.

KB: Yes! So that’s what I mean by free speech. Comedy enables that aggressively honest conversation. Like, you can’t have that in most places. But if I had that experience of shitting my pants, I would definitely want to talk about it with other people. So it’s the comedy and that speech and you talking about your shitting your pants in an Aldi that facilitates that truly honest conversation.

JB: I guess. You should never be ashamed about talking about shitting your pants.

KB: I agree! Of course I agree. I think you shouldn’t be ashamed about talking about anything and I think comedy moves us closer toward a world where that can be true. I pushed two people out of my vagina and definitely pooped when I did it. Why are we not talking about these experiences? Why does it have to all be like the weather? And traffic. That’s what I mean by aggressively honest free speech. It’s hardly political. It’s like political comedy is like a niche comedy, in my view. There’s only a few people who really specialize in that.

JB: I like to express some of my viewpoints in jokes, but it’s never the main focus of the joke. There were a lot of political jokes in that special, but they’re not overtly political. I say that God’s not real. And make fun of church. I make fun of cops and how racist they are. It’s like subtly, trying to get my viewpoints across.

Filming His First Special

KB: So I think the Comedy Vault is, like, magical and amazing, obviously. I wrote a whole review talking about how much I love it here. How did it come together with you doing your special here at this club?

JB: Well. I have known Liz and then the original general manager since before they opened the club here. They were running an open mic at EvenFlow and so I met them prior to that, and I actually had meetings with their original manager to kind of just talk about some of the things that go into running a comedy club and things to look out for. It’s been a really good relationship. And then the original manager, we were kind of friends and because of my experience working at the Comedy Shrine, producing shows, and managing the club, You just learn a lot of things.

KB: What little things make a comedy club great?

JB: The little lights on the table, like the laminated menus, like how to do all this stuff to make the show go well. We just kind of talked about a lot of that stuff. So we’ve just had a very good relationship since the beginning. They’ve had a lot of opportunities for me. And so when I was thinking about wanting to record, they were the first people I talked to. They were really excited and did everything to help make it happen.

KB: How did you film it?

JB: I had five cameras. So there is a company called the the Mind Faucet. They originally rigged up a camera upstairs mounted on the ceiling in the back and they record all the shows. Maddie rigged that up. He’s the director and he did the audio. And so they’ve done some filming here. Adam Ray and another comic were trying to pitch their specials to networks and so they taped their sets here to send them off to get evaluated for the special. I was really excited they want to do my project and they brought out four cameras. There were four filming the stage and one walking around filming the crowd and getting reaction shots.

KB: What day did you film?

JB: The Sunday before President’s Day weekend so it’s a three day weekend for some. My wife’s a teacher, and they all have the holiday off and so it was easy for her and others to come.

KB: By the way, who was in the crowd? It was a great crowd.

JB: My fans! It was a great show…the best crowd I have ever performed in front of.

KB: I am excited to see you headline the Vault on July 6th. Are you filming there too?

JB: No, I mean, there’s the camera up there, so I’ll have the tape. So maybe some clips or something.

KB: Is it all new material?

JB: Probably 40 minutes new material.

KB: Why not film?

JB: I need to do it somewhere so it looks visually different.

KB: Oh, that’s true. That’s very true. Duh. Why didn’t you have the Comedy Vault little logo in the back when you filmed your special?

JB: That’s a good question. It was one of the things that I first thought about. I wanted it removed because it’s visually distracting. So if you see something behind you. It draws the attention away from me.

KB: You were very specific about the cities you were in for all of your stories in your special.

JB: Yeah. I feel like specificity is funnier than being general. 100 people is not as funny as 92 people.

KB: What are you goals with comedy? You seem really happy with where you are at and I love that.

JB: Yeah. I just like to do my shows. And write my jokes. I have a lot of health problems. So I have to prioritize my health and my family. I filmed my special. Now I’m coming up with a new one. I am probably never going to move to New York to try to make it. This life is much better.

KB: I think Chicago should be a place where people can get famous doing comedy. No one should have to move.

JB: I would agree. Yeah, I mean, Pat McGann did it. I don’t know anyone else who’s done it without moving.

KB: Worst show you ever did?

JB: I’ll give you two different answers. One, I performed in Milwaukee, Wisconsin at the Potawatomi casino during a Packers/Vikings playoff game¹. There were twelve people in the crowd. Two of them got kicked out for heckling me.

KB: That’s fantastically terrible.

JB: Yeah, that was just like. It was just awful. I’d do a half hour. I was like four or five years into comedy. It was one of the worst experiences in my life. The second one it’s just like any show where you feel like you’re going through the motions. Before Covid I was kind of like stuck in comedy. I wasn’t happy with the new jokes I was writing. I wasn’t coming up with anything new so I was just going through the motions. You’d drive an hour and a half to do a show, and you do 25 minutes of jokes that you don’t care about. Yeah, and it goes fine, and then you drive home and it’s like, well, why did you do that? Why aren’t you out there doing the things that you really want to do? Push yourself to come up with new things. And push yourself to try new things. And anytime you don’t do that, it’s just a waste of time. And so those shows bother me the most in retrospect. Getting heckled and stuff? That’s a fun story.

KB: When you were feeling that way, did you ever consider during Covid not returning?

JB: Briefly. Yeah. And then when I first came back, I didn’t immediately start doing great again. And so it’s like, man, is this really something that I wanted to do but then you start doing it again and coming up with new jokes. And kind of that excitement…the spark for it. I will say that not one of the jokes that I wrote during Covid worked.

KB: Really? Why didn’t they work?

JB: Yeah, I don’t know. It just didn’t connect with audiences One of them, I kind of re-wrote using a completely different context and it works now.

KB: It’s so fascinating that you can’t know if it’s going to work until you try it in front of an audience. No other art form is like that.

JB: Yes but sometimes you also just know. Sometimes when you write a joke, at least for me, I’m like, no, I think that one’s just good. That one’s just going to work. And so I’ve had lots of times where I’ve written a joke I feel really confident about and I am just going to do it tonight on the Saturday show.

KB: Not to brag but I had that last week when I was playing quiplash with my friends on Zoom. The prompt was to come up with a novel that had “taint” in the title and I came up with “Great Textpectations.”

JB: I would have gone with “A Tail of Two Taints” or “Jane Taint.”

KB: I’d actually really love to see you play quiplash because you’re a good joke writer comic. You don’t tell long meandering stories. You like get right to the jokes.

JB: Thank you. Yeah, I feel like I like both, but I feel like when you tell a story, it’s also not telling a story. You’re telling a bunch of short jokes. That story about shitting my pants at Aldi, it’s like a five minute story, but it’s also just a lot of little jokes that are put together with that kind of arc to them.

KB: True. It’s also the only joke I can think of that was, like, foreshadowed at the very beginning of the special. I don’t think ever seen that happen before.

JB: I like doing that. It’s just silly.

1. Baker hilariously details this experience in a blog post: https://fancyboysclub.com/2019/09/18/my-worst-time-onstage/ ↩︎