Prospero's Pit Episode 18: Caleb Hearon

whatever, or like it on Instagram if I'm bored. and people say: how do I start comedy? and I'll say, moving to Chicago, it's the best scene in the country, um, but I was involved a little bit with Second City. I liked it, I liked it a fi, I refused, it was something like that. I kind of had a not a bad attitude, but I had a certain attitude toward some of the institutions in Chicago like Second City. I really thought he was just thinking about Bor because they chain people up for years and you put on the suit and tie and go on the tour.

Co and then the next thing you know you're 32 years old and you're still waiting to be given the main stage so you can be seen on SNL and my feeling was that if I want SNL to see me, I can do it like this. in the next year, yeah, and I don't want to wait for these older people in this theater to tell me I can do it and I did, but I did a fellowship there which was great, there are some really great directors at Second City and a lot of great comedians who They work there so I wasn't a fan of the process, but I like the awesome people who made IO.

I did IO in Chicago, I did a couple things out of annoyance, but yeah, so what was it? I missed the question, I was, well, I asked you a second question in the middle, but I was wondering when you decided to move to Los Angeles, to La, yeah, classic. Hmm, I had auditioned for SNL, they had taken me to New York. They had given me a screen test. and I didn't understand it and um at that moment I was uh you know, I was just like what am I doing? I should have understood. I'm very grateful I didn't get it, but at the time I didn't. agents or managers or whatever and I started doing internet videos because I was basically like Steve Higgins, who's amazing, he's like one of the greats from SNL, um, he told me I should do internet videos and I was like okay during the um audition process for SNL and I was like, well, I'm not going to need it because you guys are going to hire me and he was like, oh, you know, and then when they didn't hire me, I was a little mad and then I started making videos on my own. to say, well, if you want videos, here are their videos, then I got managers and, um, I had agents in Chicago at the time, but I got bigger agents, um, and I thought, I think I'm ready to get out of Chicago this is like 20 at the beginning of 2020, okay, so I have managers, I had interested agents, but I hadn't signed with them yet and I was like, I'm going to quit my day job, I'm going to stop being an administrative assistant, I'm going to be a part-time comedian.

Complete, it's time, baby, I'm getting attention. I have a lot of followers online from time to time. It happened and I drove for Uber for about five months. There is. I left my job with benefits, but I had told myself I was moving to Los Angeles that year and then my lease was up in May 2020 and I thought I was still going to be gone, so I moved to Los Angeles. during the heyday of Co wow because I said I was going to do it so I guess I gotta go yeah no I feel like that's what happened to me.

I moved straight to LA at the beginning of Covid as it was, I mean we were completely shut down and it was over, I mean, I felt like it was over and especially if you were trying to get into the industry at that time, it was like it was the worst moment you could. possibly like trying to do that, yeah, but I feel like it's funny because I'm not from Kansas City. I wasn't born or raised in Kansas City, but I feel like I've talked enough about Kansas City. Yeah, and it's funny seeing people who are from Los Angeles is like their reaction to why we're talking about Kansas City right now.

Have you had any funny encounters like what's it like when you're like people ask? Where are you from? I'm telling everyone about Kansas City. I mean, I wasn't born or raised in the city. I was born and raised about an hour and a half north of here in small towns like boy Cy Brookfield Missouri. Mom, but I always talk about Kansas City because it's really cool and people don't realize it and it's so easy and fun and nice here, the people are cool, the food is amazing, you know, Prince, uh, once. in an interview with Oprah Prince was like Minneapolis, uh, because you know he was Minneapolis, it was her Kansas City, it was her place and she was like Minneapolis, like oh, you know, yeah, right, and she and he were like, oh yeah , I always live in Minneapolis and I think she said something about the weather or something and he said yeah, the cold keeps all the bad people away and I think it's like Kansas City.

Winters in Kansas City are the saving grace that will hopefully keep it from being like Austin. Yes, I love it here, I think it's great. I tell everyone and I once had a conversation with this guy on a plane. I think I was flying from here to Los Angeles to go back to work or something and he was like, it was a push a TV producer was into reality TV or something, but he was like there used to be a group of us, it was like Yes, there used to be a group of us who lived in Kansas City as a couple as agents for the big agencies and the producers lived in the city and they flew every Friday night, I think, they flew from Los Angeles to Kansas City, they spent the weekend of the week here with their families and then every Monday morning they would fly early to LA, work all week and then come back when they were on a show or something and then when they're not on a show they were just here and I think Which, as an entertainment person, makes a lot of sense because I always have to go to New York.

I always have to go to Los Angeles and then here and there you have to go to Chicago and Atlanta and Ken City right in the middle of all of them and real estate is cheap, so I always make the proposal to my friends. Like buying a house, what's it going to hurt? buy a house in Kansas City, come on, yeah, no, I'm in the exact same boat. Umm, that's fascinating. I had no idea that this little bubble of producers existed. I did not do it. NE, there's a serious film and TV scene, as you know, here, where ASAP Rocky just filmed her music video here, which is one of the newer things, but we know I've been on several commercial sets here. working as a personal assistant and stuff like that and yeah, it was cool to come from LA and find out what was going on and find a thriving film and business scene here, um, but yeah, what I've had. have you been noticing the increase in likes it feels almost like a mediocre increase from um KC right now I feel like it's a buzz is a buzz word right now yeah I'm I'm I'm I'm I'm freaking out for a By the way, I felt like for a couple of years I was being like the amazing you guys from Ken City, if you'd told me when it was like I lived in Ken City right after high school before college.

I was working for a senator here in Westport and um again in law school, yeah, and if you had told me when I was 18 that I was 28 choosing to live in Kansas City with the option to live pretty much anywhere I chose to live in Kansas City, I would have said, Okay, it was cool then, but I would have never thought. I don't know, you get a little older and your priorities are a little different and you think about it and then you see that it changes too and it's changed so much that for years I feel like I've been in the "no guys, kitty is really cool.

I'm trying to convince people and now there's a lot of things happening where I'm like, oh wait, no, it sucks, it sucks, don't come, no. I come because I'm legitimately concerned about um I'm very involved with KY renters and I'm very grateful for the work they're doing to keep people housed and not kicked out but even Beyond just likes to keep people in their homes and They are not neighborhoods that are Ginger, like the underserved investors who buy up the West Bottoms and buy cool places in Kansas City. I know they're going to turn it into a cautious Parker Jinny's ice cream, yes, and I love the cups and the ice cream, but I do it.

I don't want Kansas City to be ruined by that kind of rampant commercialism with those ugly Square apartment buildings above and a Capital One Cafe below, that's coming and if Kin City continues to become as cool as it has been doing, it will happen in certain places in which I wonder how we can mitigate keeping as much as possible out, that worries me, yes, and I would almost say that it is already here. I mean those those apartments along the river along the Berkeley Riverfront are horrible, it's just disgusting to see there's a Chase Bank on Tru, yeah that's crazy, Chase Bank on truce, yeah I mean no I can believe it, yes, and that's great.

I had no idea you were as involved with Casey's tenants as I would love to be. talk more about that, yeah, what's your, what's your involvement, oh God, I mean, when I say I'm involved, I mean, I keep up and share things, I'm nowhere near what I expect, when I do say. It seems like I'm just a fan because I don't want to seem like I'm doing the kind of work they do. I try to raise money for them. I do a benefit show for them, once a year. We have done it in our second annual edition that will be held in November.

Oh, incredible. And I want to do it every year. Tara, who runs Casy Tenants and created it. She is a friend of mine. She is a genius. She's a really badass activist. and she would hate this um if she sees this she will um but yeah, I share her stuff, I keep up, I donate money when I can, I really think that, like I try, my activism has gone from when I was younger to I was a I was a teenager and I was in my twenties, it was all about candidates and I thought if we can elect Bernie, you know that will change everything and there is partial truth to that, but then I see what happened with Bernie and so many other great candidates.

I've really moved to a place where I'm fine now, the parties, the candidates, I'm moving towards the causes, I'm just going straight for the causes and tenant organizing to me is like the crux of leftism and how we can win in the problems because if you listen to any of Casey's tenants' stories or look at what they're doing, they're organizing as rural white conservatives, yeah, and like downtown, like you know young queer people, people of color who don't you would expect these two things to come together, yes, but if you have a Trump flag in your yard, you have a Black Lives Matter sign in your yard, eventually gentrification comes for all of us, yes, and it's like that kind of unity.

I have not seen it anywhere else in the political organization. Casey's Tenant is doing it in a way that other places in the country do, but I just haven't seen the level of success, ferocity and power that Casey's Tenant has. wielding I'm so inspired and impressed by them and honestly I should do more I want to do more I really should have one of them on the show I've been following it's similar to you I just like from afar sharing their stuff when I can and um yeah I'm Speaking of that Chase Bank on truce, there are a couple of companies that I found on truce that are actively working to better support the community, but also to keep it local and keep it, one of them is Like Minded Café, uh, davius ​​​​young, who's been on this podcast, just started a non-profit organization and that works like empowering youth and entrepreneurship in the community and then of course Ruby jeans with Chris well there and, you know , empower only people.

I'm talking about gut health and just your overall well-being. It's interesting to see that kind of cause coming from local businesses. Don't know. It's like, that was you you were talking about, like leadership and politics. And then you look at the ones that are actually on the street that are actually there every day um and I like people like that, I find that the ones that I meet are really encouraging to see um it feels like there's some kind of activism tied to local businesses and how we like it can balance that and see what that looks like.

I definitely want to explore more of that, yeah, but it was amazing. I'm so glad we could talk about that. It's great that you're involved and I'm going to do it. I'm going to find Casey's tenants here. I'm involved as a fan, yeah, I mean, that's really what it comes down to. I'm a big fan of theirs and I think I like the work they're doing in Kansas City. It's the most crucial job in the city and I actually have a little bit of um. I don't think I've ever talked about this in public, but I talk about it a lot in private. um I have a little bit of a problem with some of the casual celebrities like some Kansas City celebrities and I don't need to name them, some of them are my friends, but there's kind of a representation of your city that has become a part of, You know, celebrities are brands and like there's some kind of representation of your city, whether it's Casey or not, this is something that happens everywhere, but it's about dressing like you, when you go out to Los Angeles, you know that They are going to photograph you in the cafeteria, so you put on. like a jersey from your hometown sports team, yeah, and that's great, but there's a lack of real activism and a lack of access to the city and telling the real truth about what's happening in the city. city, um, that happens sometimes with these people who get lifted up like you already know who the guy in Cleveland is, like you're sure there are famous people fromCleveland and everyone's like, oh my God, he's from here and it's like I don't know.

Hopefully, I hope that as Kin City continues to change the people who are from here and have some kind of influence, my influence is very small. People who have a lot of influence, especially, will like to participate and pay attention to what is happening here and not just to them. You know, do a pitch at the Royals game, which is great too, but it's like Kansas City's 30% blackness and the displacement of people. Through greedy capitalists like commercial real estate, Enterprise will mostly affect to that 30% of the city, yeah, or to the Hispanics on the Kansas side, like, I don't know, there's a lack of talking about these things in depth by people who I affirm that I love the city I go to, it's a little annoying, you know, yeah, but Casey's tennis is great, uh, um, I want to turn left, real quick, uh, make a video for us again, be funny, don't be like that. annoying make me laugh uh you're just making me sad now no no no um um uh I don't want to talk more about your career uh so you're also a writer for um oh uh uh um a or the big boca spin-off yeah Human Resources re Human Resources thank you um um and I mean, we just got out of this, but there was a massive writers' strike, what was that like?

How were you involved in that? Were you involved in that? How was that? you know, how to navigate your career, as well as the writers' strike and all that stuff that happens, yeah, the writers' strike. I was in a writer's room when we started the strike, so I was at my job when we found out we were on strike and then I left my job. that day and I didn't come back, yeah, um, and then we were going to restart it after the strike, but the show got canceled and, unfortunately, I'm not going back to that job, mhm, the strike was, you know, you know, you said It was a tough turn. on the left, but, interestingly, it's like everything is in the same vein: the strike was about greedy billionaires telling the working class what is possible and what is realistic, which is always my favorite love when mega Rich people tell us what is realistic. like it was actually a day, yeah, but that's what it was about and I was very proud of the union for going on strike and I was very proud of all of our leaders on the bargaining committee and people like Adam Conover, who is a Very funny comedian, but I also think he has a brilliant political mind.

Yes, we made a lot of gains that we wouldn't have made if we hadn't gone on strike. It's horrible that we had to do it. The strikes are brutal. Support staff and people that I'm lucky with because I went on tour and I have other things to do thank God, yeah, but not everyone has that and it was really, really hard, but now we're out of it, yeah, um. I hope that, like us, we continue to enjoy the strike when we need to and get the protections we need. Yeah, it's a pretty tough entertainment industry in general, but yeah, the strike was like I was really proud of it. and I'm super professional, I'm always going to tell the truth and I'm always going to say what I really feel and if that means I can't work with someone, then they, um, and yeah, I was very vocal about it. the fact that I think studios and networks are greedy M and there are a lot of creative executives that I like, there are a lot of people that, you know, make creative decisions that agree with us and are also getting squeezed by these guys, yeah , but the guys at the top, the CEOs, the big guys, those guys just suck, you know, they just suck, they ruin everything, they take the fun out of everything we could be doing.

It's so cool there's no reason. that anyone needs to be fighting in this part of town, yeah, but these losers really are just losers, yeah, but I mean, yeah, that's what the strike was about, a group of people who, you know, barely make enough money in a year. to get their health insurance coverage, if they do, a lot of people don't say, "Hey, can we please not be replaced by Ai?" and the boss says, "We'll be a real kid, come on, so yeah, but I'm glad I did it." Now that it's over, I hope everyone can get back to work.

Yeah, you were talking about that before, but you said you were pushing to do this show that takes place in Kansas City and all that. Do you believe? I like to tell myself more about that idea, I love it, it excites me so much. I've had a lot of ideas about a TV show set in Kansas City or some kind of story that takes place solely in Kansas City, so I'd love that. Listen to that, you know, we'll see how it develops and changes when you develop with um a network and things that sometimes turn out to be a little bit different than what you thought it was originally, for better or worse, as you know.

You never know, but I really like the direction that my friend Holmes and I are taking, who are also a comedian who also lives in Kansas City, we met in Chicago and we started writing this show about our kind of friendship, um, I I would. describe it as an intergenerational comedy like queer about roommates it's us that we live with like some older lesbians um and yeah, the show is pretty much what living looks like, trying to live an interesting life in the middle of the country, yeah, and I think That plays a lot into a feeling that Holmes and I had growing up, we spent a lot of time in Omaha as a kid and teenager and I was exclusively in Missouri, but I think there's this feeling when you grow up in a place that is It's not okay to be a place that It's not like New York, Chicago or Los Angeles, where you go.

I have to get out of here if I want my life to mean anything. I need to get out of here. I can't wait to get out of here. and it's not true, but then you leave here and you go to other places and you say: oh, I'm still gay or I'm still fat or I'm still depressed or, you know, I don't really even like it Here you go I or you and you have a great time okay, but you also realize that there are so many wonderful things about home, and you know it's different for different people, obviously, if you're like a trans woman of color, that's a different story, but Our characters are taking a look to this question: can you lead an interesting young, artistic, gay life between the coasts?

Yes, our answer is yes, but you know that's a question when you're a teenager and you don't have enough facts. So you go, man, I just gotta get out of here, yeah, and I partly think it's true, yeah, but partly I think it's not true either, yeah, and I think it's a great story because of how complex it is. is and how there's a middle ground of yes, no, kind of blurry, that's what makes stories great, um, I think it's interesting that on the one hand, I'm an active believer that it's not true that you have to leave your At home, to find yourself, you have to completely abandon your roots before you can do something new, but at the same time I like to look around me, especially in the suburbs of Missouri and the suburbs of Kansas, the environment makes It's very difficult to find me. like going out, I like it, I really like being creative and also being unique as an individual.

I was just talking about how you know we light up the parking lots a lot more than the roads themselves, like getting around, there's a lot of emptiness. The space is a lot like big parking lots and gas stations and U, yeah, it's interesting, you know, it's kind of a concept that I've been juggling back and forth, like this, like a very concrete reality in which to people like to live here, especially young people who, like you, know that they are trying to figure it out, they don't know what's out there, but then, living in this reality that is so bleak and flat and concrete, it feels difficult, you know, to go out. times. and it's hard to find yourself in that and be unique, but then you have people here in Kansas City who are so bright and vibrant and so artistic and cool and stuff, and they just light up these similar spaces.

I almost could, I almost could. I'm moved to tears every time I see a weird teenager, yeah, in a Walmart in Missouri, like I'm, you know, at home with my family or something and I'm in the middle of nowhere and I see you. I know this emo teenager who wore an animal skirt because I was like listening to Paramore secretly, you know, I mean, I was being like, you know, I think I wanted to be different and expressive and weird, but I was too cowardly and I was also in the closet. And I thought I can't give any hint, you know, and I think so, the audacity of truly being an individual and particularly in suburban or rural settings in Missouri and Kansas is like I was very impressed, especially as a young person. like 13 year old kids, yeah, come on buddy, you're so brave and brave and I hope you keep whatever it is, but yeah, I couldn't do it if I was in the city, if I was in Kansas City, if I was in Westport, maybe time. but yeah, where I was, I definitely wasn't pushing, it was like pushing buttons, even thinking maybe we should have gun control when I was 17, you know what I mean, people are like that, you know. like I'm an anarchist B, you know what I mean, I can't imagine being a real individualist like a weirdo, yeah, which is cool, but those people like those kids, those 13 year old kids like in Lee Summit or wherever they listen to emo and Everybody's got neon clothes and whatever's going on they're some of the cool ones like they're some of the biggest rebels in the country because I feel like you know in Los Angeles, at least my experience in Los Angeles is like a lot of people are dressed up. up like these kids or like these Rebels or these like the cool punk like the cool kids, you know, it's in L.A., they're all trying to unite with each other with coolness and stuff, but it's actually these kids here that they're like walking around a quick trip to the parking lot listening to Paramore, whatever they're listening to, let it be real, I feel like it's real, those are the kids, it's like, oh, get out of their way, yeah, they're cool , since I really think like the I think that being punk in Los Angeles and New York is over.

I really believe it. I think there are so many great things. I love the. I will always live in Los Angeles part of the year as if I was always going to be in Los Angeles. sometimes I'll always be in New York sometimes I love those places I just think we've really heard it, we've heard about it, we've heard about being young and a little lost in New York and the like. We've heard that story millions and millions and millions of times at this point. I think the real thing about Punk now is to go somewhere else and make your own path and I think you know even Chicago, to a certain extent, is losing a little bit of that, but I think Chicago still has it, I think and I'm also interested in the artist in I'm interested in artists in Kentucky who make leftist poetry for no one.

I'm interested in ceramic artists in rural Wyoming. I'm interested in Kansas City videographers. I'm interested in. To me, the most interesting art comes from people who are not at NYU and who are not going to study film. You know, and that's okay, there's nothing wrong with that. I love a lot of people who studied film at NYU, they're like my friends, you know? But now, what interests me is, in addition to all those stories, that we are undoubtedly going to hear, of which we are going to hear. the kids who got into NYU guaranteed that they're going to be stories that we'll have the same with UCLA USC Northwestern, that whole kind of pedigree, like people who move to L.A. and do pretty well in an improv theater that we go to to listen. from them you know, now I'm interested in hearing from people we wouldn't normally hear from.

I think that's what's fascinating and the kind of punk rock thing for me now, yeah, and it's not even me. I'm like I live in Los Angeles. I write. for TV shows like, I'm on the super cool alt, doing it just because you want to do it so you like the Spectrum corporate type sold out. I'm more on this extreme, you know, but I just think that what's going on there is more interesting, yeah, you know that well, so what would you recommend to some young kids that are here or to young creatives that feel like they want to be storytellers?

And whatever medium it is, what would you recommend they like? You know, some advice from Caleb Baron, tell the truth, like tell the truth, I think that's what I come back to all the time, it's like telling the truth to yourself about what you really want because I had to make an adjustment of count on myself. like when I was in Chicago, you know, I would sit around with my artist friends and think I just wanted to do cool things with my friends, which is partially true, but the other truth is that I grew up poor and I never want to do that.

Being poor again and that's why I need to earn money and that's it. I can't, I can't be a starving artist all my life. That won't be my trip. I need to earn enough money to pay my bills and those of the people around me. The bills get paid, that's how it is for me, that's part of my truth, right, and it's not a very nice thing to say, that's how I feel, so you have to tell the truth to yourself and you also have to tell the truth. truth with your material and I think you also have to be prepared to tell the truth to the people you work with, like if you're going to work, if you work in the arts, you're going to work withsome shady characters you know and I think I'm not telling the truth. that's how we get so many, well it's sure how many of these billionaires continue to do their thing as they like to politely go to similar dinners even though they are like trying to steal from healthcare workers but it's also the It's like you feel like the comics bring 15 year old girls into The Green Room and it's like telling the truth isn't just an artistic endeavor, it's also a moral endeavor, uh, and vice versa, and I think what I come back to At most when I'm trying to write, create, or make a big business decision about whether I say yes to this or say no to this, you're going to have these kinds of moral dilemmas in a career of mine.

It's been short and I've had several of them and what I come back to is that You have to tell the truth, that to me feels like the ultimate and you know someone else would say something different and maybe in a month I'll say something different, but I think what I've been thinking about most lately is telling the truth, wow, yeah, no, I don't have much to say about it, I think you're like that, lie, lie. kid cash those checks tell those lies baby lie all the way to the B no but that's awesome I love it thank you so much for sharing that uh what's going on where what could people find you doing where can they tune in People, um, when is this coming?

I have no idea who to say who can say probably in the uh probably closer than New Year's okay, cool, well, yeah, I don't know what I'll do then, but I think I'll travel, so if You, if you see me in the world, come say hello, um, but yeah, always, uh, always online at Kaleb. He says things mostly on Instagram these days. You can follow my Tik Tok if you want. I'm not posting. You can follow my Twitter if you want. a I'm not going to post um, but I'm committed to at least updating people on Insta um, yeah, and come see a show like you know.

I'll do shows in Kansas City from time to time, um, but if you see that I'm on tour, please come out and yes, if you're in Kansas City and you see me out, please say, hello, yeah, that's cool, thank you very much for being on the program. I appreciate it, thank you for having me, yeah.