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Learn more@WhatsApp.com she just like grabs the back of my shirt and tugs on it and goes, I love this. And I turn around, I was like, hey, Meryl Streep.
A
This is good one. I am Jesse David Fox, senior writer at Vulture and author of comedy Book. My guest today is Caleb Herron. We talk about his new HBO special, model, comedian, and how not getting Saturday Night Live was the best thing that ever happened to him. Find out why he is or is not one of the 25 most influential creators working today. So here is Caleb Heron. I'm here with Caleb Heron. Thank you for joining me.
B
Thank you for having me.
A
What's the funniest thing that happened to you this week?
B
Okay, so I was visiting home and this is maybe like two weeks ago, but this is the most recent thing I can think of that really cracked.
A
Not running this week. So.
B
So there you go. My, my little cousins are kind of obsessed lately with the idea of me being famous. They love talking about it. They're very interested in it. And I'm always trying to, like, redirect them. I'm like, you know, there was a couple months ago that I was home that they brought it up and I was like, you know, that's not a very interesting thing to be. I'm a lot more interesting things than that. I'm nice, I'm, I'm funny, you know, whatever, whatever. And I'm trying to, like, get them off this obsession with fame because I think it sucks, you know, but they're kids and they were over visiting my house in Kansas City. And one of them, he's very sweet, he's on the spectrum, so very literal, you know, and he comes over to me and he goes, cousin Cal, can I ask you a question? And I go, yeah. And he goes, does it bother you that we call you the F word? And for a second, I mean, we hadn't talked about the famous thing for a second, so I was like, pardon? I was like, what do you mean? And then I. I sat with it for a second. I was like, oh, no, I'm not mad at you when you do that. But I had to really parse through him not calling me a But. Yeah. And then I. We had. We had to talk about that. But it really made me laugh.
A
Funny.
B
I. And then I walked around the whole day telling everyone in the family who would listen. I was like, listen to what your kid just said to me.
A
So our is a new segment. Our first segment. Wait, I'm gonna do it. Okay. This is the first time ever doing this segment. It's very exciting for me. All right, so we have a new segment. This is our first segment of the show. It's called who are your guys? In the grand tradition of WTF with Marc maron, I ask who are your guys?
B
Oh, God. Well, mine are so complicated. Monique, always. Monique, always one of my guys, Monique, her specifically, her queens of comedy set. Have you seen where she comes out in that pyram? Like, it's like a rotating pyramid. I think they filmed it in Memphis or something. And she comes down in, like, this, like, cut up, sexy leather outfit. And she was fat back then. Like, she. She hadn't lost the weight and she looks so good. And she comes out and immediately she's like, every skinny in here should be standing up and applauding me right now. Or every fat. And then she starts going in on skinny women. And just the whole set is like a master class to me. And like, I had watched my dad. I grew up watching, like, Carlin and prior and like, very, very, very, like, kind of offensive, you know, like edgy comics. And Monique had an element of that, but it was just to see a woman do it in a way that a woman or a gay person would do. It was in many ways similar but just different enough that I was like, ooh, something else is going on. And a fat woman up there owning the room like that. I really felt like I didn't know at the time that I was like, oh, I could do that. But it felt so good and affirming. So Monique, always. And then I do always have to just be honest. Roseanne, like the original Roseanne before she bec. New Roseanne. New Roseanne. We are not Tight. I'm not loving your ideas, girly, but yeah, the original Roseanne was like everything to me. And that show was like, she was so godamn funny on that show. Like DNA, can't deny it funny. And the show was so great and they cast it so perfectly and John Goodman in it. Roseanne's definitely one of my guys. My other guys. There was this, this period of time in like high school and college where me and my friends were just watching everything. We were watching everything. Like anybody who put out a new special, we just loved it. Zach Galifianakis is. His Live at the Purple Onion special is one of my all time, like, North Star favorite comedy specials. And I actually, I think Zach might hate me because we've. He did. I had a birthday show at Largo a couple years ago. I don't think I've ever talked about this on a podcast. Had a birthday show at Largo and I love Largo. I love Flanny. I love, like Largo is my favorite room in la. The tickets are more premium because they do one show a night. And so it's harder for me to convince myself to do a headlining show there very often because my fans are broke and baristas and. But I'm. Every once in a while I go to a Largo show and just have the night of my life. And I had one for my birthday a couple years ago and Zach was in town. He doesn't know me from Adam, but Flanny was like, hey, do you want to have Zach Galifianakis on the show? He's looking for stage time. And I said, of course. That'd be a dream. Well, Zach's comedy was so pivotal to me. When I was like, figuring out comedy, comedy that I, before I brought him up, I was like, hey, you're not gonna like this, but I have to. I have to really glaze you, you know? And he was like, please don't. And I was like, I know, but I have to. And I really, I brought him up and I was like, this guy is like on the Mount Rushmore of comedy. As far as I'm concerned, he's a legend. I can't believe he's doing this show. And he just squirmed. He hated it so much. And I get it. I know you don't want to go up to that kind of thing on a lineup because then it's like the expectations are up here and. But I just think he's so brilliant and I love the way he does his life as well. He's just like, on a farm in North Carolina with his family, pops out and does, like, a movie. And then comes. I'm just like, I really think he figured it out.
A
Yeah, I think so. You are literally Shooting Devil Wears Prada 2 Currently you have a popular podcast that has allowed you to play some of the large, the great American theaters. Yeah. Why film a stand up special?
B
Well, stand up was kind of my. My. My first, like, foray into being solo act at all. I was doing improv, and I was doing sketch, and I was doing all these group things, and stand up was where I really found, like, my solo, like, singular voice. And I just had been trying for years, I mean, to be 100 honest. The. The hour was ready long before it sold and kind. I don't want to say no one wanted it, but, like, no one was beating down the door to make it. And then I was at this point in my career a couple years ago, I guess, had been a year and a where I was just like, I'm tired of waiting around. I'm frustrated that in my estimation, there are people who are not as practiced or as good at the thing I do that are getting things that I would like to have an opportunity to participate in, and I need to make some things happen for myself. And so I started the podcast hoping that it would, over time, help out a little bit. And then it randomly kind of did do very well right out of the gate, which feels like, you know, weird to say, but it did. And. And then. Yeah, then. Then all of a sudden, you know, two, three people want to buy it and make it. And so then I have to, like, get it back together. But I had been working on that material for so long before that. Yeah. That the opportunity to make it with HBO was just like, well, duh.
A
Yeah. You know, the special is introductory in both, and, like, it shows sort of these types of comedy you can do. There's lots of different styles that are sort of mixed in, and also just sort of a lot of just who you are. It's not just like, here's literally my life story, but you get glimpses of it. How did you approach this being your first special and knowing you'd be introducing to sort of a new audience?
B
Yeah. Well, the most important thing for me was I sat down. My managers, Tova and Olivia, who I've been with for, like, almost six years, I. We. We sat down and we're like, okay, we have this big hour of material. I knew I wanted to cut some stuff. There was some Personal stuff about grieving my dad that I was like, I don't think that makes it into hbo. I think that's for the live audience only. And so we knew there's some cuts. There had to be some additions of some other stuff, whatever, whatever. But when we sat down and kind of talked about this, like, what is the point? Why are we doing this? I'm not doing a tour right afterwards, so it's not to sell tickets necessarily. We really landed on, like, oh, we. This will be hopefully, like, a nice expansion for people who already know me on what they think about me. Some people just think I'm like, gay guy from their phone who, like, does podcasting, and that's cool. But then, yeah, a whole bunch of people maybe don't know who I am. And so we wanted it to be introductory, and we wanted it to be kind of, you know, when we were picking jokes or leaving jokes out, it was kind of like the, the question of whether or not it goes in or stays out was, does it say something about me and my view of the world and why I should be up here with a microphone or maybe, maybe I shouldn't, but that are we making the case for, like, this is a guy that should be up here telling jokes and why and how? So, yeah, I wanted it to be introductory and wanted it to be first and foremost funny. And so I cut some of the more saccharine. In the actual tour hour, I had some more sappy saccharine, kind of sweet stuff about grieving the loss of my dad.
A
Yeah.
B
And then for the HBO special, we cut some of that because I was like, I just don't want to do one of those comedy specials. Not for my first one and not right now. Maybe never. That feels like the lights lower. And I said, I sit down on the stool and I start to get real. You know, I just, I have no problem with that kind of stuff, but I just was like, I would like to be funny more.
A
Yeah, I, I, I'd heard that you cut that stuff. And it was interesting because I've been thinking a lot about how grief, how grief and trauma has become commodified. There's an interview that I've been talking about a lot recently with this academic named Catherine Lu. Luau. With this academic name, Catherine Liu. And she was essentially talking about how trauma has been essentially. What's the exact word? Trauma has become depoliticized by the middle class and upper middle class and especially with the Internet. And today has been used as a way of, like, propping up one's personal brand. And I think it's really interesting because clearly it has been shown as a way of getting attention. And I was curious if you wrestled with like yes, there's benefits of sharing complicated things that happen in your life and especially if you have processed already. But there is also, I think a weird market pressure to do so. Did you feel that and did you feel like you wanted to push back upon it?
B
Look, I felt and feel like the, the very self serious, dramatic, one man show version of this hour is there. If I want it, I just want to be funny and I want to make people laugh. And I feel like, you know, I think sometimes with that thing that you're talking about the people kind of, I would refer to it as like pimping out their trauma for like a content totally fine. I really don't have any judgment for it because if that's what you need as an artist in that moment and it feels good to you, then go nuts. But to me it feels like it's a way to prove depth. And I don't feel like I need to prove depth. I feel like I have. I talk for an hour plus every week on microphone to my, you know, my fans and I think they know. I think they know that I'm more than just like a singing, dancing clown. Although I am also that. And so, yeah, I didn't feel like the HBO special needed to be a place where I proved that I was some serious artist. I am a serious artist. And the serious artistry that I wanted to do in this special was the serious artistry of trying to make people laugh.
A
Yeah, yeah. And display craft of doing so like you can be serious about it without being like, now there's a time to be serious. Specifically as you talk about so how purposeful this, this special is. I really was struck by you sort of come out and with a mission statement, but the mission statement is I'm randomly so happy right now. Yeah.
B
Okay, good one, Caleb.
A
Yeah, but it is. But it did feel like what you were saying is like you were pushing back on these sort of like the. What you're. The irony, I guess you're pushing back is the assumption that everyone has to be negative because things are bad. And you're just going like I'm happy. And that sort of sets the tone. Was like that how you thought about what happiness means to you?
B
Yeah, I mean, like, I don't know. I do feel. I've been saying this a lot on the, on the show and on stage, but I'M like, I do feel optimistic. I feel like pessimism is a privilege. I feel like the most pessimistic people I know right now are people who are doing pretty good. And so I feel like, I don't know, there's this part of me, I'm very aware of all of the different types of people who will like anytime I say something like on a show like this, this or my show or on stage, I go, I can think of the 20 different ways that people will take it. And I could talk about each of them at any given moment. I go, these people are going to say this. And so when I say, oh, I'm happy right now, I just in my head go, oh, yeah, well, you're like a CIS white guy who makes good money doing a pretty easy job. So of course, like. And I say to that, totally. But I also think it would be even more annoying to be a CIS white guy who makes pretty good money at an easy job who's like, we're all. You know, I'm like, that is disingenuous because that's not. I. I don't think that my, my joy is from organizing and, and my joy is from belief in joy is from necessity. Because if I. My raw feeling in the morning when I wake up and read everything that has occurred while I was asleep or is set to occur today is I feel devastated, I feel sick, I feel confused, I feel all of the things that people are talking about, but then I feel nothing productive from those emotions. And so I feel like choosing joy and being like, okay, I'm going to donate here. I'm going to post about this. I'm going to try and do this. But then also I am gonna go get dinner with my friends tonight and have a good time and try to talk about something else sometimes. And sometimes you just talk about the bad stuff for four days straight, you know.
A
But also the special is like, it's. You have a choice of being like, this is what I'm offering you. And it's like, I always think about like, if you're gonna have people pay for something, you might as well like try to make their lives better, not worse, right? Like, there's obviously a value in reflecting exactly how the audience is feeling and that they see, feel, seen and heard. But you do that in other spaces. But like you're creating a product like can I can make a person see the world slightly better and is that probably is positive for them because there is no value, I imagine to just sort of like, if you don't want to be so negative that you essentially are supporting hopelessness and, like, one might as well just give up.
B
Yeah. And also, like, it's a big media landscape. Some would say it's oversaturated. I am one of those people. There are many, many, many options. And so I think, like, when people get, you know, people get upset that I'm flipping about the X, Y, or Z, or that I shouldn't be joking about this or that I'm, you know, too catty about this thing that I should be sincere about or whatever I to that I'm like, rock on. That's a totally valid criticism. Go somewhere else. There are options. Like, you don't have to. Yeah, there's many bad things about the kind of niche vacation and fracturing of our media landscape and the, like, the death of the monoculture. There are many bad things about it. But one of the good things is you don't have to with me at all.
A
Yeah, yeah.
B
My bills will be paid even if you leave. So, like, go away. Go, go. Go listen to someone who will be sincere or who will do the. The, you know, the drama hour special about their dad dying. Or go if you don't like the way that I'm approaching all this or if you think it's annoying that I'm talking about being happy right now when things are so bad, if that feels tone deaf to you, rock on. Totally heard. Go do something else.
A
Yeah, it.
B
It's the. It's the singular benefit of the time that we're in.
A
Literally, the one benefit is, the only.
B
Thing is that if you don't like the way I'm doing it, I'm not the one guy with an HBO special this year. So go do something else. Yeah, that's fine.
A
Can you talk about developing. So the first joke is the idea of being a Midwestern aunt pilled. Can you talk about developing that joke? Well, actually, can you explain. For those who haven't seen the special, can you just explain the basic arc of the bit?
B
Yeah, the joke is just like, I feel like it's kind of talking about this thing of, like, I do feel randomly happy. And I do. I am. I've been referring to it lately as climbing cringe mountain. I'm just like, I'm enjoying the little things. I'm being cringy. I'm having fun. I'm like, I'm seeing, you know, when you see a picture that, like, your aunt would share on Facebook or my aunt would share on Facebook, I guess that's Like, I got my coffee and the weather's nice. Happy Wednesday. Like, I see things like that, and it works. Like, it works on me. I'm like, oh, that's so true. So the joke is kind of talking about this thing of, like, I feel like as I've gotten a little bit older, I have started to become like, an older Midwestern woman who, like, can find joy in the simplest things. Part of that's practice that I'm, like, trying to do that. But, yeah, crafting the joke was just kind of talking about. I think it's a funny. It's. It's kind of a funny juxtaposition between what people think of me, which is. I think a lot of people see me and know me correctly as, like, you know, a kind of irreverent, leftist, like, younger gay comic, you know, and that's. That's a lot of the stuff I do that falls into many of the buckets or many of the things I do fall into that bucket. But then there is this part of me that is like, you know, texting my friends, like, a picture of flowers from my walk and being like, let's have a great day, guys. Love you. And it feels so like I'm becoming the women who raised me in a beautiful way. But, yeah, that's what the. The joke was originally about.
A
Yeah, there is something really. It's a. It's a really. It's like a really gradual way of entering a special that, like. And they're all like these little sketches, and I think it's the one about seeing the dog, and you sort of act out the dog is so sensitive to see when playing your dog. And you're just like, that's nice. That's basically all you. It is. There is this. It's almost like it's borderline an anti joke in so much as the audience is expecting. Then you doing a twist and you're like, no, I just thought it was.
B
No, that was nice. Yeah. Well, I have. There were so many things that. The first time I watched the special, back after the cut, I was like, I hate this. And I had to text friends that have done this before and be like, please, God, tell me you hated it the first time. And there were so many things about it that I'm like, oh, I could have done this better. I have a very conversational style. So there's plenty of parts where, like. Like, look, we did. We did the show twice that night. If we had done it seven more times, we would have gotten seven different hours. Like, I changed so much on the fly. Even in the recording, which I love about my style. But also in a recording, then you go, there's 20 seconds there where you. Where instead of taking the straight path to the next point, you. You went around the bushes and like, I watched that and I'm like, God damn it. That wasn't efficient. But all that is to say one of the things that I struggled with was like, is the opening of the special to Meandery. Did we take too long to get to a laugh? Are people are. Is. Because now everything you're thinking about the attention span.
A
Yeah.
B
And people are going to shut off the app and go to. They're going to leave HBO and go to another platform to watch, you know, whatever unscripted show they're loving right now, which makes me want to die. But yeah, you're thinking about like, how did I get to a laugh quick enough? And even though it works in the room, and it worked in the room for a year and a half, you start to watch it on screen and go like, oh, it's a different thing for the screen. So that was a real consideration that I had.
A
Yeah. I think it's really interesting because in some ways the whole purpose of it is this is a. I'm creating a thing so you do not have to treat it like content that where you need to keep your attention. That's like, that's the fundamental premise of the joke. But at the same time you're watching and you're like, yes, but now it is. Did I do it too well? Did I give people too much of a space?
B
Yeah.
A
To be like. I mean, you're. We all are living it. You know, the feeling of itching, being like. But I can right now.
B
I could choice or. Yeah.
A
Or like, even I'll watch it. But like, while this is. While I'm waiting for the punchline, I'll just like look at Instagram for like three seconds. And I mean, as you said, there's like 20 million ways in which people are going to watch it. And some people are going to be like, well, I trust Caleb, so I'll watch it. Or some people will be older and don't have their phones when they watch stand up specials. And I think you just sort of have to. That's the whole premise of stand up. But just like, you have to trust the fact that you tore it and now is the pace that works.
B
Yeah. And you also have to. My musician friends talk about this a lot and I'm really inspired by them in Many ways, but that you make the work, you make the work you believe in and then once it's out there, it's, it doesn't belong to you anymore. And so I go, look, this, I, I. My solace about the hour now, it's a, you know, it's. We're recording on the day that it's coming out. And so by the time this comes out, it'll be out in the world and a bunch of people will have had opinions about it that I hope I haven't seen good or bad. I would like to kind of stay away from all of that. But it's. There's now and it's like a different thing. And it's like once it's out in the world, it belongs to everyone else. And the solace that I have to take is exactly what you said, which is like, I toured this in 40 cities and it worked in the room. And so I, the thing I have to focus on, I think if I want to be healthy about it, is like, it worked in the room. You liked it in the room. The recording is its own thing. People are going to experience it in a different way. I actually, for the first couple years of my career was pretty anti recording stand up. I said no to every opportunity to record a standup set for years because I feel that standups is meant to be in the room. It's supposed to be an in the room art form. But then you build a piece that you like enough and you go, I'll give a shot at recording this. And I feel really good about it. But in the room is the point.
A
Yeah.
B
You know.
A
Yeah, yeah, it's interesting. I'm just like debate. I'm thinking about it and we won't know. We'll see what people say. I mean, it will be a thing where it'll be some people's favorite thing. How this sort of. There's like, because you'll do an example and then you sort of have a poetic way in which you describe their life. And I think, like, I always say that, like, I love when comedians have those moments that are partly for them and partly where they get to indulge a little bit because, like, that's who they are when they're not fully performing it. And then you get to another part that's funny. So as you said, you did cut out a large section about the sort of grieving process of losing your father, but there is a large section about your father. And you do a really interesting thing, which is you first just, just Talk about him. You don't go like, my dad died however many years ago, I'm going to tell you who he was. You sort of tell him who he was. And I think Eagle eared watchers or whatever will notice. You say was a lot.
B
Right.
A
Or just people who have lost people, like, are more akin to that. Can you talk about approaching that entire section? Because as you said, there's probably tons of things you could talk about that you probably had other material you did. But, like, this was the section I'm going to do about it. How you wanted to balance the heart of it and the sort of comedy of it.
B
Yeah, well, a big question for me during that section of the hour was who cares and why? You know, like, I don't want people to enjoy this just because they're a fan of mine and they want to hear more about me. I want this to hopefully appeal to somebody who doesn't know who I am and doesn't care about my life. And so I, I think I tried to hone in on like, okay, the interesting parts of this are loving someone who you had a complicated relationship with and loving someone even though they were quite bad at being a parent and love, you know, that. Trying to find the more universal things about it. And the thing about talking about him first and not bringing up him dying first is that when you bring up. I wanted to walk people down the road a little bit because when you bring up the bad thing first, then you have to do this like, kind of saving the room energy kind of thing where you're like, don't worry guys, it's gonna be okay. We're gonna be funny about it. But instead, when the way that I approached it made me feel more like, you know, I'm just setting up jokes. And I said, I considered for a while the was and is thing about my dad. Yeah, the tense was something I debated for a long time and tried it a couple different ways. For there was a while there were on tour where I tried it as is. And then when it got to the part to bring up his death, I actually would say, you know, I've been saying is, but it's actually was because he's dead. And then. And getting into it that way felt like too much of a device and felt like dishonest. Yeah, but yeah, that, that section is like the one part of the special where I was like, it doesn't really matter when the laughs come, how loud they come. This is a, this is a section for you to tell the truth. And that if people really just wanted to, like, watch a. A joke, a second kind of thing, they could watch a sitcom.
A
Yeah.
B
This is a moment for this to be a piece.
A
Yeah.
B
This is a moment for you to, like, tell the truth about what you're actually going through. And also, I think it is quite funny, but that I gave myself the space creatively to say it doesn't matter if it is. You can try, but if it does, if it's not, that's okay. I think we landed on it. But, yes, the was and is of it all was a big consideration.
A
Yeah. I mean, it's to the tone of it. Like, it's. It ends both. It just sort of ends. Like, it doesn't end like a big story. And that's when I realized my dad was always my dad or whatever. And then it was like, yay. And then you move on. It just sort of, like, ends at. Ultimately, I think, your takeaway from the entire experience, which is, like, how you reconciled the fact that he wasn't, like, didn't want to be a father who wasn't meant. What? And then you just sort of, like, have it. And then you have a pivot, obviously, which is sort of. He wasn't the first straight man or whatever.
B
Yeah.
A
How did you. Were there times you tried it with, like, a bigger finish or whatever? Or did you. Or you're just ultimately, like, this is how the story ends. And I don't want to play with.
B
Had so many different permutations. I can't even remember where I landed on it so many times. But I was always trying to. I was always trying to put the most saccharine moment of that material up against the next funniest thing, which is the straight guy joke. I wanted to move on quickly. I didn't want to sit in it for too long. To me, that was like. I gave myself that space to be like, hey, this is a piece. You're an artist. This is a space for you to just talk and maybe it'll do something. And then as soon as that's over, it's time to be funny again. And so to me, that was always. The plan is just get out and do something else. But, yeah, I didn't want there to be a big lesson. I didn't want there to be like, a. And so if I could leave you with anything.
A
Yeah, that's, like, not at the end of the special. Yeah, that could be. I think what's really impressive is you. You have to. In the first section of the joke, think of an example of your interaction that will be funny and characterizes your entire relationship with your father. And you have this story where you come out to him. Is that. Were you thinking of it that way? You're like, okay, what is the one definitive thing that has ever happened to me? Because I think it's hard. I mean, like, really, you're like, you don't have a time. You can't. It's not a one person show. Or like, I remember my dad did this and then when I was nine, you know, that's the easy way of doing. You're sort of like, I need one example. And is that how you landed on it?
B
It was like, no, it was more like. It was more. It does serve that purpose, but it was more like I just had a bunch of jokes from over the years of like, experiences and conversations I'd have with my dad. And then when I was building the hour, it kind of started to develop that. It was like, oh, you have this because, you know, you're building an hour and you go, well, it's kind of like four 15 minute chunks is typically how you start out. And then you go like, oh, okay. So this material is kind of wanting to be grouped together. This material is kind of wanting to be grouped together. You know, you want to have kind of a closer at the end of each segment. And the dad stuff just kind of. It was like, oh, you do have like 10 really fun jokes about your dad. Maybe you just do like a dad segment of the special.
A
Yeah.
B
Or of the hour at the time. And so they just kind of glommed together. And then that story was just the. My favorite one. And the audience liked it the most. And so it just kind of became the thing.
A
Yeah. Yeah. When did your dad pass away?
B
2022.
A
So that is three years ago. So much of the sort of career success that we were talking about is happening after that period. How did it influence sort of how you approached your career or just your, I guess, your life as. And as a. In your career as being part of your life?
B
They're not. They're separate. Yeah. I mean, my dad was just like, not a big part of, like, he wasn't. He wasn't super interested in what I did. I would send him stuff sometimes and he. I remember I sent him my. My first character, like, reel that I did in Chicago and there's a great taping of it that was like, I was really proud of it and I sent it to him. He was like, I didn't get a lot of it, but the Audience seemed to love it. I was like, okay, sounds good. But yeah, affected my work in that it became a big part of the hour. And I did write a full movie about it, about his passing. But really, it's just funny. It's just funny that I don't. I don't know that I didn't have any conception of my career going this way necessarily. Certainly not at that time when he was alive. And I don't think he did either. And so I'm like, oh, he's just not here to, to see what's going on. But I wonder what he would think of any of it.
A
Yeah.
B
If he would, like, be more interested now. He was proud of me, but I just don't think he, like, he doesn't like any of the same people or things that I do.
A
Yeah.
B
So if I was like, oh, I'm. I'm doing a movie with such and such actress that's like such a leg or whatever, he would be like, oh, yeah, I think I've seen her in something, you know, it wouldn't be like a big thing for him. But I'm. Yeah, I'm happy. I'm, I'm happy for you, buddy. You know, it just be like, like I got a new car or something.
A
But it didn't seem, at least in a sense I got. It didn't seem to, like, light a fire underneath you, as some people that.
B
No, no, nothing like that. Nothing like that. Like, like his death.
A
Some people go life short. I'm going to. You know, this is a. Lots of people have different reactions to these things. One is light a fire underneath a person.
B
I had a. I, I will say that not in my work life at all. In my personal life, I definitely. Losing a parent so young. My dad was 50 and losing someone so young, I definitely, I definitely think about the things I'm doing and how I'm spending my time on earth. But I will say my dad was so depressed and unhealthy and such an alcoholic and a chain smoker that. That was kind of always a part of his death, was a part of my life long before he died.
A
Yeah.
B
That I was like, this guy is not gonna live super long. You know? And so I thought about being 45 and being that close to death as I felt that he probably was. And I thought about that when I was 18 and 20 and I was like, oh, I don't, I don't want to get to that point and regret not having done any of the things that would be exciting to me. Just Because I was scared or whatever. So his death kind of loomed large in my life before he ever even passed. Just in a way that like, he wasn't really living a life even when he was here. He was like a shut in and a hoarder. So. Yeah, maybe that's part of it.
A
Yeah. What's the state of the movie Trash Mountain?
B
It's really funny you asked because I'm. We've been trying to get the money together for a long time. Indie filmmaking is pretty much dead, but we, we got the money and it seems like we're making it next month.
A
Oh, wow.
B
Well, like it seems like there's been this like looming timeline for months and months and months that's been like I tapped out a long time ago mentally that I was like, I wrote the script, I'm ready to star in it whenever. Colin Trevorrow and Lily Wachowski, who are producing and Chris Ray, who's directing now, I was just kind of like, you guys let me know if you need anything. If you find a rich person who wants to talk to me about giving us the money, I'm. I'll get on the phone. But otherwise, go with God and I'm going to go work on other stuff.
A
Yeah.
B
And, but, but this whole time it's been like, we have this great crew in Chicago that's kind of available in this window and the other lead actor in the movie is available in this window. And so it might happen in this window. And then like a week ago I got a call that was like, hey, we got the rest of the money. It's probably happening.
A
Did you consider like crowdsourcing? You like being hey, fans, like, you know that movie like now it's unfair making for the people who legitimately do, I think a reasonable thing which is trying to crowdsource. But like, like you have this fan base. I'm sure if you're like, can you all give me $10? They'll be like, Please let me give you $10 so you can make this movie.
B
Yeah, it came up. I mean, it comes up every time. I don't, you know, every single time you talk about a project now, if you have any kind of following self funding, it comes up immediately. It's like, are you sure you want to go deal with pitching this or would you rather just try and crowdfund it or self fund it? I just felt it was too much to ask of people. People are like, money's tight. And I just feel like buying tickets is something that makes sense to me, you know, Spending. If you want to spend an extra, like, four or five bucks a month getting the bonus content from the podcast, that makes sense to me. It feels more direct. But asking people to put in money so that we can pay a PA to, like, bring food to set while we make a movie just feels too far removed from the payoff. I just felt. I felt like it wasn't right. And so I felt like. Like, I also felt like, look, a lot of garbage gets made. A lot of garbage gets made. People get paid $20 million to do movies. This industry has money. If they don't want to spend it on telling this kind of story, then maybe we just shouldn't tell it. I just felt like there's money here we're asking for. It's a shoestring indie budget. We're. I'm. I. Everyone, many of us are going to lose money doing this movie, you know, But I believe in it and I love it, and I think it's so good, and I love the team and I want to make it, but. But I just feel like there's too much money in this industry to be asking, like, working people to donate to it. And that's no shade to anyone who's crowdfunding at all, but not me.
A
I want to talk about a little bit more special and your career as it stands, but I think we need to. I want to take a step backwards and sideways to sort of get there, to paint the picture of where you are, which is. So you discover improv in college. You like it. I'm sorry for putting that on the record.
B
God, humiliating.
A
You moved to Chicago. Yada, yada. I wanted to smash cut to SNL audition. Can you talk about that process of, you know, you're pretty young when they're like, oh, do you, you know, like, people audition? And then you don't think you're going to be the person that are going to go through the different steps or you got pretty far in the steps. Can you talk about that process?
B
Yeah. I was in Chicago. I. It was like 2019. I was doing characters and improv and working day jobs, and I did a character showcase at Iowa Chicago that, you know, it was like five or six hundred people would do the first round or something. It was huge. And then the second round would be like. Like 100 people or something. And then the third round would be like 25 people that would go in front of the producers and Lorne Michaels and the writers when they came to town. So it'd be a showcase just for them. And I actually did that. I was. I had been prepping for like a year because I knew I worked at the theater as an intern and I knew that they were coming up, and I was like, I'm gonna start practicing now. And then that first year I did it. I just got through to the round in front of the producers and I killed, to be honest. Like, I. I just really murdered that night. And it doesn't always go that way for you, but it was a good night for me and they love my stuff. And then they ask you to. I mean, everything with that place is so archaic, but they. They ask you to go to drinks at the Ritz with Lauren, you know, if inch before he leaves Chicago, if they like you. And so you get in a van with a bunch of other comics, like the six other people who got asked to go or whatever, and you're. You go down there, you have drinks, them. You kind of speed date, you go around, you talk to people, and then they fly some of you. I think they flew three of us out to screen test or something. And then you go to New York and you screen test on the stage and everything and hear all the different stories about, like, oh, it's going to be dead silent or one person will be laughing or you don't know what to expect.
A
Yeah.
B
So you practice your set. What we. Something we would do for each other is we would practice our sets like 15 times in a row to complete silence with our friends sitting and staring at us. And it's the most minutes past, like, days. I mean, it's horrible, but yeah, I went and did it. I would have killed for that job. The first time. The first time I had no. I had no career, I had no followers, I had no team. I was just making comedy in Chicago. I would have killed for that job. It would have changed my life. Glad I didn't get it. Not a place for me to work for many reasons, not the least of which I'm fat. And they're telling people to lose weight who work on that show. No one likes to talk about that, but that's reality. And then when they didn't hire me, I was. That if anything lit a fire under my ass, it was that I was pissed. I was like, what are you talking about? I have this great set. But I. I was just like. I was like, you should have hired me. I'm really good at this. I love, I love sketch comedy. I'm quite good at it. I did a killer audition, you know, and maybe it was great in the room. Who knows when I taped it, maybe it sucked. Who knows why it didn't happen. But I started making videos right away. And I want to say that was late summer, early fall of 2019, and I had maybe like 3, 000 followers on Twitter or something from like college. And I started posting videos. And by the end of that year, I had like 120,000 followers. A team. I had agents and manager. And so shout out to Steve, he was right.
A
Yeah, it's wild because that conversation of being like, well, I'll just go to SNL so I don't have to do the Internet stuff. And he's like, we'll do the Internet. Like, that is now. That is the two paths that sort of now exist for all talent, which is like, maybe I can skip being an Internet famous person. I can just ride the line of what was once the traditional arc. If not, you are in the minds.
B
Yeah.
A
Like making common things.
B
And thank God, by the way, that it went that way. I so much prefer I didn't know it at the time, but I genuinely mean it when I say the two best things ever happened here. That I didn't get that job twice because I am not meant for that place. I. I don't like being told what to do. I don't like routine. I don't like crazy schedules. I. The way that it all worked out for me, that I get to be in charge, that I get to hire the people I want to work with, etc, way better.
A
What was Haunted Mirror? Are you willing to discuss what it was?
B
Yeah. Haunted Mirror was my favorite bit at the time that I auditioned the first time. It's just this Southern woman talking about she has a haunted mirror. And she was being very blase about it. The joke was just kind of the way that Southern and Midwestern people, women in particular, will talk about. Like, the most harrowing thing, I think maybe the first time I tested it was a woman coming home from the grocery store and talking about how she got shot. And she was like, I couldn't find the ham I wanted, but I got this guy shot me in the leg. What? Oh, yeah, I got. I got shot while I was down there. Like, it's just like so blase and like anything else is important than what I'm going through. And yeah, Haunted Mirror was like my first big closer for character set.
A
How do you feel about the character videos you put on Twitter like now, like when you look back upon them and those videos, do you. You know, they're harder to find now? I mean, you can find them, but they're harder in so much. Are you embarrassed by them? Are you proud of them? Do you feel like that representative a time represents who you are?
B
I'm proud of them, yeah. I'm really proud of them. I don't want to do it anymore. And I don't think that they necessarily hold up. I don't. I haven't watched them in forever. But I. When I imagine them, I don't imagine that I would be cracking up about it, but I'm really proud of them. At the time, they were good, and I. I think that at the time, they made a lot of sense. I got really. I've always have a problem with authority in general, and I've always felt like when someone wants me to do something or tells me to do something, that I won't. And for better or for worse. And when I first started doing videos on Twitter, people really wanted me to do kind of the same thing over and over again. And then, tick tock. It's. That's what it is now. It's just trends. You do the trend, you hop on the trend, which is inherently in. Not creative and hack. But I tried really hard on Twitter. One thing that was a really interesting experiment that I did was after I got some followers, I tried to do a series, a storytelling series, of gossiping to a co worker about your weekend end. The story never ends. It's one long story. Every video is about two minutes, and it ends on a cliffhanger. And then I wouldn't say when I would do the next one. Then, like a week or two weeks or three weeks later, I'd pop up and do another addition to the thread. And it was me trying to test the limits of, like, can I get people to care about a story in a sustained way on a platform that's not designed for it? And I had a lot of fun with it. I thought it was a really neat experiment. People really liked. Was demoralizing, though, to see, like, you know, you would start. The first one did so well that I was like, oh, I should make this a series. And then, you know, the numbers would go down and down and people would fall off. And then you. By the end of it, you know, at first, if you were getting 20,000 retweets on the video, you know, by the 15th one, you're getting like 3,000 or 800 or something. But I was always just trying to experiment and goof around on there. And I feel like it was my playground to, like, figure things out.
A
Yeah, you've described the sort of origin of your podcast so true. Both as sort of a cynical need for clips in a time where people want clips and a reaction to a feeling of like, I want more freedom in my career. Is it both? Is it one or the other?
B
It's both. Yeah, it's both. It's that, that we. I want freedom in my career. I'd like to be able to make things that I care about. I care about the podcast to the extent that it makes people happy and that they enjoy it. I hope that that's what they're getting out of it. But I want more freedom in my career. The only way it seems like you can get freedom in this career right now is to have a large audience. The only way to get a large audience is to feed the clip machine. So what do you do? I mean, every comic is like struggling with this right now. Do you do crowd work clips? Some people do it really well. Stavi's incredible at it. You know what I mean? Do you post your actual material and burn it? That's not sustainable unless you're doing a show every single night. John Marco can do that. John Marco gets up every time he gets a chance. You know what I mean? Everyone has to figure out their own way to come at it. And for me, I was like, I'm a chatter. I like to chit chat that the podcast I had, I had done front facing videos and fallen out of love with it and decided like, I don't want to do this forever. And then I had tried crowd work clips for a little bit. I love crowd work as a practice in the room. I didn't like posting the clips. It felt really nasty. It felt too for me, Caleb. It felt like, no, I'm making my audience like, I don't know, I'm like pimping them out for. I hated it. Yeah, for me. And so then I was like, the podcast is truly the last option. And then if the podcast doesn't work, it was in the back of my head that I was like, you're gonna have to just give up on the Internet thing and like, really focus on like developing and auditioning and like kind.
A
Of asking, you know, it's a quite popular podcast. How do I make my podcast more popular?
B
Video was a good start. Video is a really good start.
A
You've been through half this interview. How could this interview been done in a way to be more popular?
B
Well, you know what sucks for you is you're just a really actually good interviewer and you're gonna have to come up with some slop. You're gonna have to like, you're gonna have to come up with a segment that's like kill or save. And then it's like you pick a celebrity that they can kill or. So you're, you're gonna have to come up with something a little catchier than just being like a genuinely good long form interviewer. Sorry, your talent is holding you back, babe.
A
This is what literally every meeting we have, that's what I say. The what I think think part of what I think your success is or what is special about this is in your stand up as well in, in the podcast is. And, and I should say, like a lot of popular podcasts, I think capture this, which is people talking and joking how they would with their friends. And that specifically means without the fear. Like essentially when you're joking your friends, you're not afraid that they're going to be mad at you for one way or another, regardless if they are mad at you. But like that freedom I think, think you really have, which is not to say like, you know, you're like wild with it, but I think there is a sort of looseness that you're able to joke about like who your community is that I think is really exciting for people who listen to podcasts and want this feeling of friendship. Can you talk about, how would I put it? This sort of like fearlessness you have about like talking about groups of people that you are your, your friends. Does that make sense?
B
Yeah, they get mad. People get mad at me all the time. Yeah, people are presently mad at me. I'm certain that people are gonna be mad at me from the special, whatever podcast episode I'm putting out next week. There'll be people mad at me. It's not that I have this like charmed existence where no one gets mad at me. It's that I just don't care that much. I'm just like, you'll be fine, everybody will be fine. Because I think the reality of it is whether strangers on the Internet know or believe or think this, I am a, I'm a nice person. I'm just. I know I am and I know that I, I know how I treat people and I care about people and I care about doing the right thing and it just is not important or that big of a deal that I like make a wise crack about non binary people. Half my friends have multiple pronouns. You know what I mean? Like, I just think we have got to. Some people are stuck in this moment of that was, you know, kind of in vogue five or ten years ago of, like, being so sensitive and so caught up in, like, the. The correctness Olympics of, like, who can be the most correct all the time. I'm not interested. I don't want to play. I would rather just be funny. And the reality is, like, I want to joke in public the way I joke with my friends in private. And that's what I am trying to do, because this is actual life. I just think, yeah, I'm not. I'm not escaping. I'm not escaping people being mad at me. People are quite mad at me very often.
A
But. Yeah, but I think that allows the people who are not mad at you. Like, I think the acting as if you're trying to not have anyone be mad at you.
B
Yeah.
A
Prevents a lot of people from having people like them.
B
Yeah, exactly. It's boring. I'm bored. I am bored. Board by. I'm so bored by the celebrity culture. People are still trying to cling to this celebrity culture of, like, the 90s, where it's like, you just never say anything. You stay out of it all. You. You pick your charities very wisely. Animals or cancer. You know, things that no one would be offended by. Don't talk about Palestine. You know, people playing this very safe version of existence that I'm like, I am bored. I don't believe you. I know that you're having conversations behind closed doors that are quite opinionated, and I would like to hear them, and I would like you to. What it is, is a lot of times when people talk about decisiveness, you know, some of my friends are like, how do I be more decisive? You are so decisive. And I'm like, it's not a lack of fear that something will go wrong. It's a willingness to handle it. If and when it does, people will get mad at me. And I feel like I can handle that, that they're not necessarily wrong to get upset with me. I just feel like, you know, it's the same math that everyone's doing. If a critical mass of enough people got mad at me about something, I would think about it, and I would handle an apology, and I would figure out, you know, whether or not I was actually wrong to say that. But for the most part, it's like very small groups of people that have other going on that they're projecting on to, like, a sentence I said that they're happy to take out of context.
A
Yeah. I feel like the definitive thing of your podcast is, like, an audience of she. Theys listening to you make fun of people that use she. They pronouns.
B
Yeah, I'm making fun of us. Yeah, I'm making fun of us. I am kidding around about us, about people like me. I am trying to. Yeah, I'm trying to have a nice time and just joke around about the way that we are. I think we're funny.
A
There's a trans. A joke about trans people in the special, and I will not just say that and then move on.
B
That's it. This was so much fun that I.
A
Think is really instructive in terms of this line you're doing of and specific about the idea of trans people exist. And then you pivot it. Can you explain, summarize the basic premise of the joke before we talk about how you went about it?
B
Yes, I have a problem with trans people. And so the joke. No, I'm kidding. Yeah, the. The idea of the joke is just like, I think about trans people a lot. I love trans people and I worry about my trans friends. And I'm so confused. I feel, more than anything, I feel confused about this political moment that we're in where trans people and immigrants and teachers now randomly are into the fold and somehow Jimmy Kimmel's implicated. I'm confused about this moment where these are. So many people are falling for these groups of people being the enemies of the, of the public that, like, it's trans people and immigrants you have to worry about. I don't understand that. They do. They're. They do. They do nothing to anybody most of the time. And even if in the times that they do, compared to what billionaires are doing to you, I just feel insane. Yeah, I feel crazy. I'm like, you've got to be kidding me. You are letting billionaires run your life into the ground. They're destroying the quality of life in this country and you're mad about trans people using the bathroom or whatever. It just feels crazy to me. And so the joke is born out of me sitting with and thinking about often how much I would like to help. I would like to help the narrative change. I would like to help people who might not be like me, very leftist, and have a bunch of trans friends. I would like to help them with a perspective that could be different and that they could maybe listen to a joke and go, oh, I don't have to be like a woke skull who went to a liberal arts college to understand this thing. I could actually just go like, oh, I don't really care about that. Or oh, yeah, that's. I can joke about these things, but still want people to have rights and be left alone.
A
Yeah.
B
So it was born out of my. My love and my care for trans people and also just, like, hanging out with my trans friends.
A
Yeah. I mean, so the premise is essentially like, they ask for a lot of money.
B
They're thieves.
A
But I think what is useful is they are people like you. Friends ask for money, but my friends are trans. It's like. But they're also not immune to having jokes being made about them. And I think that is the sort of line that I think it's very. As I say about all the things that I think is really impressive about your work is that you're. You're able to be reverenced towards these people, but not. Not so reverent that they're not people anymore. You're like, you're still.
B
Well, that's the thing is. Yeah. The joke is that queer people are abusing GoFundMe. Is that. And. And we're. And by the way, that's not just trans people, queer people in general. I got. There's some gay people on there doing a little too much. But, yeah, I think that we create. We kind of create with topics and with people. We create these sacred, untouchable ideas of them that are. It circles back to being actually worse than, like, a lot of white liberals do this with black women, where they're like. Like, they're terrified of black women. They don't actually want to talk to black women. They're not friends with black women, and they're like, but black women are going to save us. I think that is, if not as bad, very closely approaching as bad as just outright disdaining black women. That you're expecting them to be these, like, saviors and heroes, and then you're scared to talk to them and that. That you want. You wouldn't joke with them the way you would joke with a friend of yours who wasn't a black woman. To me, that is weird, selective treatment. And I don't want to do that to anybody who's marginalized in my life. I don't want to cut them out of the joke because if I'm cutting someone out of a joke in my personal life, it's because I don't like them. So I want everyone to be in on the joke, and they can joke about me, too.
A
Yeah. The podcast is called so True, and it's a. In so much as about anything. It's about truth.
B
Yeah.
A
Which is an interesting. Like, it's how heavy of a topic when you think of truth as an ideal, when you're starting it and you're like, we should do a podcast about truth at a time where this post truth reality of the Internet. Are you. Is that part of. Or just like, how can we ground people being like, what actually are things that are true when we literally feel like nothing is true is like, is that motivates you?
B
Yeah, I. I do think a lot about truth. It's. It. We partially came to the title because I made a big list of gay little. Gay little turns of phrase that I say all the time. You know, like these little white conversation fillers because gay people can't shut the hell up that we say so true or totally or yes, queen or. You know what I mean? That it partially came from that. But I do think about truth a lot. And I think something I've thought about my career, this, the era of my career that I'm in, and maybe it'll end up being my career writ large, is this is just the truth as I see it. This is like how I'm seeing the world right now, and I'm offering it. And if someone wants to be like, oh, he's right about that, or, oh, that made me think differently about this, I go, great. You know, hopefully they laugh first. But I do think about truth a lot. It's such a tricky time where everyone gets to have their own trip truth. And that's weird. It's weird that it's weird that truth is so fractured and we can't seem to agree on many things that. I don't know, just there's things right in front of us. Even this, even, even like this Jimmy Kimmel thing. You know what I mean? It's like the fact that people are so able to be like, well, the ratings were down. You know how it is. It's like Trump is using the FCC to threaten his opponents. He views the media as his opponents. Like, to me, I'm just like, like, you don't have to like Jimmy Kimmel. I don't care if you like Jimmy Kimmel show. That's your own business. But the idea that it's just this, like, business decision made in a vacuum to me is like, that's so objectively. You're either being intentionally obtuse to serve an agenda which many people on that side in power are doing, or you're actually just kind of stupid. And that. That's. That's a problem. Yeah, it's a problem that we can't agree on the truth about many things. Right now. Now. And I don't know what to do with that.
A
Yeah.
B
And I don't think that I'm outside of it either. I try to think about the things that I'm ignoring the truth about or the truths that are inconvenient to my world view. I'm trying to think about that stuff all the time.
A
Yeah. You're gonna kill me. And I'm sorry, but I'm gonna bring up Mr. Beast.
B
Oh, God.
A
But I promise there's a reason.
B
Okay.
A
And I'm not gonna make you tell the story about how he called. None of it.
B
Have you seen. Have you seen the press tour for this?
A
But I really promise ever either.
B
I actually believe you and have faith in this line.
A
But like, I can't ask this question without it being brought up, so. And just in case you have to.
B
Say it, you have to tell what happened.
A
So. No, you have to. You're the subject.
B
Yeah.
A
Can you explain the Mr. Beast.
B
Yeah.
A
Caleb Heron controversy as if I was 70 years old.
B
Yes. Hi. 70 year old person watching the show who made it this far in my.
A
You.
B
I. Yeah. Basically, if you. If you work in entertainment for long enough and things are going just well enough and you have a good enough publicist, you'll get put on these lists. And the lists are influential people who are going to change everything in the business or whatever. And it's totally ridiculous. It's not needed. It's like people that are already doing well, who have good publicists. It's fake and we all know that. And you're not supposed to say it because you want to be on the list, you know, or your team wants you to be on the list. And all that being said, please put me on your list.
A
This.
B
But Rolling Stone made one. I really like the writers at Rolling Stone. CT Jones was involved in making the list, who's a writer I really like and. And have done stuff with. I'm glad for the list because it gives, as much as I don't care about them, for Caleb personally, it gives some really great writers some opportunity to work. And so I dig the list for that reason. CT Jones worked on this list and that was cool. I forget the other writer's name. I haven't met them, but shout out to them as well. They made a list of influential people. I don't know. It was like 20 influential. 30 influential people. Something like that.
A
That.
B
And I got put on it. I probably wouldn't have shared it. I don't think anyone would have really talked about it. Most of These things come and go. You think maybe a couple people get convinced to watch your thing, so you do it, you know. And then Mr. Beast, a very famous YouTuber who your grandkids are obsessed with, 70 year old person that I'm explaining this to. Yeah, he, he tweeted out my only my head shot and was like, according to the Rolling Stones, this guy is more influential than me. But he only has a million followers. This guy's got like 990 followers or something. He's right. But yeah, he tweeted that out and then immediately deleted it. Called me to apologize, pretty much not a big deal. But the Internet had a field day with it for several reasons, the biggest of which being many, many, many people just really don't like that guy and they are excited to be mad at him any chance they get. And I don't really know if that's founded or not. I don't know anything about him. I know he does like games and has like chocolate bars or something. But that, that is why it was such a viral moment is people really, there is a kind of a cottage industry around loving to hate him and another kind of set of YouTubers. And I think that in itself is pretty insidious. But I got wrapped up in it briefly.
A
Yeah, the thing about all of this, which is I heard about this list because you posted this thing and I thought it was funny that happened. And I go, it's a list of the top 20 or 25 creators. That's the word they use.
B
Oh, God, yeah. Get me started.
A
Well, this, this is why I bring it up. So I see these people on this list, some are categorized as comedians and I am my age. I'm not seven years old, but I am older than the people that. Well, no, there's plenty of people watch YouTube who are my age. But I was like, Caleb's a creator, he's one of these people. I thought, like I was just sort of. That's what shook me of all it. To me, that was the, that was the insult. And maybe I'm wrong and I'm sorry, maybe I shouldn't say that on YouTube, but like, I just don't. I think of you as sort of operating different thing. And I was curious as a person who seemingly has more feet in that space, the more like has a foot near that world that I am. Clearly I knew the names of all these people at this point. How do you feel about the being called a creator?
B
I don't like it. And, and it, and here's the thing. Though I'm very. I turn this over a lot because it's not offensive to me. There are plenty of people who do identify as creators that are creators first, that are very, very talented, that I love, that I think are great and I appreciate their content, I appreciate their brain. I. It just, to me it's bad journalism. Not that they put me on the creator list. They asked my team, my team said it was like, that's fine. But in general, there's this thing that happens with me where people go, this podcaster is branching out into stand up and acting. And I'm like, that really sucks because it's not good journalism and it's not the truth. I was on TV before I was on Tick Tock and I was doing stand up before I was on Twitter. Like, it just doesn't feel like the truth to me. And so I get a little annoyed by it. It doesn't matter in the grand scheme of the world. Go nuts. But like I do the creator thing kind of bothers me because they try to. The industry is loving right now. This big story about how like old Hollywood is dead. Traditional media is out. It's the new gen from the cre. The creat are going to do it themselves. And I'm like, part of that is true. I did have to go and make this online platform for me to have a traditional career that was furthered. But I was writing for TV before. Like I. It just feels to me. It's like I, I get annoyed when I'm like, that isn't completely the reality. Yeah, but that's all that's. I find it a little slightly annoying.
A
You said that you get offered specifically Internet famous people all the time for your podcast and you say no.
B
And regular famous people.
A
Yeah, well, at that time it was only Internet famous when he said that. Now you get off. But like, how do you think about. I imagine especially get put on the list. They're like, oh, he's now part of this creative circle. We'll just put. I don't know the names of these people, but you see their names that are silly to me because they're twitch streamers and they go by their handles. I think part of it is this desire to sort of have two narratives of like, there are bottom up celebrities, people that have fan bases and that's how they got famous. And they work there, they're entrepreneurs or whatever. And then there's like traditional Hollywood, top down. You've got part of an institution and then you built a fan base by just Sort of being broadcasted out, and your work has largely still been in the sort of traditional space. And I think seemingly you prefer that work for yourself. We don't need to make fun of the work that creators are making. Is that the sort of discomfort which is like, people. I think there is a tendency to treat all artists now as influencers, and then the art they make is like their coffee brand or whatever, but not as equal to a coffee brand happening. It's like, oh, you act cool. That's like your side hustle, your hobby. Yeah.
B
It's unfortunate, but true. Look, if I only this year had done the acting and writing gigs that I did, I would be in a, A, A vastly different financial place because of the podcast and because of commercials that I get because of the podcast. I. It's like, it is my. That is the reality. The. Everything I get to do in acting and writing at this point is bankrolled by the fact that I do podcasting and Internet stuff.
A
Yeah.
B
And I don't love that. I don't. I would love to just, like, go act in three movies a year and make incredible money and. And then the rest of the time be reading and writing and thinking. But that's not the reality, and that's not the landscape that we're in right now. But, you know, when it comes to turning down famous people for the show, it, I, I. Look, I would have a massively bigger show if I didn't do that. That's the reality. I'd make a lot more money and I'd have a lot bigger show. But the thing you mentioned of, like, the point of the show being people talking genuinely without filter. Famous people don't do that unless they really know you and trust you. And so I've had famous people on that really know me and trust me, and I think we're able to have those conversations. But when someone stops by for a press tour and you've never met before, sometimes it's like pulling teeth, getting these people to say one genuine thought. They got the publicist in the corner. No, no. You know.
A
Yeah, yeah.
B
Because they got into, like, one mildly spicy. The only interesting thing they've said in the hour. You know, it just is. It's. It's disingenuous and not fun.
A
Yeah. Do you. I think there is. How do I want to put this? I think a lot of people who started building fan base during COVID are currently having to reckon with their fan base. I think this is a phenomenon of all across the spectrum. Right. Either they or they're blindly just assuming everyone is normal. But I think because of the parasocial intensity of that time of building a fan base, artists have to be like, wait, what is my relationship to them? And I think putting out a special, like, this is a good example, which is like. Like there are comedians who have a certain sort of fan base. Like, that will be like, okay, should be an hour of jokes for these people. They've supported me. They wore the things that they laugh at. Most is that thing that you had to wrestle with, which is sort of like, well, I got to give something to these fans. I mean, like. Or these. That the people that supported me, but also, like, I don't want to be beholden to it. Is it something that you consider.
B
What do you mean? Like in the special?
A
Yeah. I think when you're creating work.
B
You.
A
There's a tendency for people who develop a fan base online, especially one that was sort of intense because of the COVID that you. Even if you don't want to, it's hard not to make work for these people. That's the feedback you're getting. That's the audience who's seeing you live. You have to essentially, to not do that. You have to, like, actually take a step back.
B
Yeah.
A
And I was wondering if you took a step back.
B
Took a step back. Yeah. I'm not. I'm lucky. I'm very, very lucky that I get to. Uniquely. I think if. If I have. I have many privileges in this life, but probably the biggest one is that I get to show up as exactly myself in every single space I go into. That's a privilege that most people don't get. They don't get to be exactly themselves at work. They don't get to be exactly themselves all the time around anybody. And I really do. And so that's really nice, and I'm so grateful for that. And I. I. The only thing really that came into consideration about the online stuff is that I have so many jokes about it. It. Because it is such a bizarre, funny thing to happen to somebody that I cut a lot of them because we were very sorry. Some of my eye. We were very cautious of it seeming like a standup. An Internet creator getting a standup special. And a bunch of people who don't know me are going to see it on their HBO home screen and maybe watch. And then while they're watching, start Googling and going, who is this guy? And. And I want.
A
Oh, the sixth most powerful creator.
B
Yeah, yeah, yeah. Or whatever. Well, now they're going to see a bunch of articles about Mr. Beast. Yeah, yeah.
A
And Mr.
B
Beast. Yeah. And then they'll be on his channel subscribing to him. But yeah, I was just very cautious of being like, this is not that. And I am lucky that I think my fans, they genuinely seem to want from me what I give them.
A
Yeah. This will be the last time I hopefully will say Mr. Beast, maybe in my life. Your producer worked for Mr. Beast at some. And I, I, I, I remember, I feel one time people like, well, his producer worked for Mr. Beast and that's part of how he secretly figured out the.
B
Oh, they've always got theories.
A
Yeah, I was, and I was like, why? Might as well ask him. If, if you think there's anything about the Mr. Beast sauce that is like, you know, that fed to whatever the way in which you immediately were able to find a response to the stuff we were.
B
Putting on, I don't know if I would attribute it to the Mr. Beast sauce, but I will tell you that Chance Nichols, my dear friend who produces my show and is now working for all things comedy, doing all their shows, shows, Chance is just brilliant. Like, he just the show. I think the show would have found its feet in some regard no matter what. But the reason that we found it in the way we did, in the time frame that we did in the spaces that we did is in large part due to Chance and I's collaboration. I met him when I was in college. I've known him for years and years and years. And I'm really glad you asked this because I, I don't often get a chance to, like, very intentionally talk about how brilliant Chance is, but he really is, he's so brilliant. He's so thoughtful and smart and kind and good at what he does. And from the jump, he, he really told me, like, I'd had a podcast before with, with Headgum called Keeping Records with Shelby Wolstein, who was amazing and we loved it and it was really fun, but we had to stop it for a number of reasons. And he had told me, like, hey, no zoom interviews, no missing weeks. Has to be video, has to be high quality video has to go on YouTube at the same time every week. We could never miss a deadline. And like, we have to put out clips at the same time every week on the same days. Like, him really like, enforcing. Him really enforcing to me, like the, that the path to success on this thing was buy in and consistency. And then he's like, you can't just be like, I'm gonna do A podcast on the side and not really talk about it in case it flops. He was like, you have to put your neck out there and try this for it to work. And it totally changed my life and his. So really a huge part of the reason that that whole thing is succeeding is just because of Chance's work.
A
So as you said, you're in the Devil Wears Prada sequel. Do you feel like it should be called the Devil Wears Two Pradas? Two Devils Wear Prada.
B
Yeah.
A
Or the Devil Wears Prada again.
B
The Devil Wears Prada Colon. We're. We're wearing Prada as the Devil. I. The Devil Wears Prada to. I would call it the Devil's Wear Prada. Yeah, that's what I would. I would do kind of a surgeon's general General with it.
A
Yeah. And then who are the devils?
B
Yeah.
A
I don't need any secret details about the movie. You're not going to tell me any. But I'm sure there's going to be one, maybe two stories from working on it. Probably something with Meryl Streep or Anne Hathaway that you are going to tell over and over again in junkets and on a late night shows.
B
Yeah.
A
And I want to see if you have any of those stories already that you want to practice first here.
B
God, you know what it's like genuinely, I wouldn't bullshit you about this. They're just all the nicest fucking people. It's infuriating. It's like really psychotic. I am watching Anne Hathaway navigate this set in a way that I'm like taking notes. I'm like, this person is so kind and thoughtful and intentional and like energetic in a way that I'm like, I'm tired. More tired than her and I'm doing less. Like, it just really some of the sweetest people around. And David, who's directing again, and Alene, who wrote it again. Everyone actually genuinely is so nice. And I don't feel like I have to say that I'm trying to think of any. There was a day. There was a day where I have some very fun clothes in this movie that were all made custom by the costume team over there that are a bunch of geniuses. And I was standing talking to Aline, the writer, Aline Bros McKenna. And Meryl walked by and she just like grabs the back of my shirt and tugs on it and goes, I love this. And I turn around, I was like, hey, Meryl Streep. And she was like, very cool. Kept walking. I was like, it's one of those moments where you're like, like I'm not supposed to be here. Like that is really insane to me. But yeah, I, I don't know what stories I'll tell because everyone's just been so nice.
A
See, that's you now. That's cute.
B
But now you build that out.
A
Build it out.
B
Yeah.
A
And then on the last day of set I pulled her. Now you have to almost manufacture.
B
Yeah, yeah. And so then. Well, the really funny thing is you're talking about these press junkets I'm going to do. I'm number 15 on the call sheet, so I don't know if they're going to have me out.
A
Followers with your followers.
B
Yeah, yeah, yeah.
A
You're going to be out there and they're going to, to, I promise you you're going to be. I mean maybe they haven't talked to you yet, but I, I cannot imagine. You're not going to have to do a heavy press for. Or they'll ask and you'll decide.
B
We shall see. We shall. I will do. Hey guys, I'll do whatever you ask.
A
But I don't know if you what your role is, but I was in so much as if you play a gay assistant, do you think about, let's say you play a gay assistant or don't because maybe you're not allowed to reveal that. But what are your thoughts about the trope of, of the gay assistant?
B
I go back and forth because gay assistant and gay best friend are actually someone, someone came up to me recently at a party and was like, I just saw you in a short film. And I had had two short films that were in the other people's that were in festivals at the same time. And I go, oh, was it gay best friend or gay assistant? And I, I really, I go back and forth because I hate how limited gay men don't get a million shots actually in this industry. And it's funny to me that it's. Hollywood's made out to be this like bastion of gay guys now. All of the hair and makeup and costume people are gay guys. Thank God those are my mothers. But gay actors, I just feel like you've got so many gay actors that we don't get a lot of chances to tell our stories. Especially now people, networks and companies are really, really, really not telling queer stories right now. And if you take it out there, you're getting kind of back channeled notes that are like, what if the character was straight? Like it really is happening right now. So I don't know, it feels like there's this moment where I'm like, I feel at once annoyed about how constricted all these talents are and how so many fabulous, brilliant gay men could play so many more roles if they were given an opportunity. I think Tramell Tillman's an incredible example of that. And he's getting those shots. And thank God. He's like, one of our best. But then I also feel like, thank God. Yeah, thank God they're letting us be gay assistants and gay best friends because I don't know that we would be represented at all if it weren't for those tropes. And so thank God. Pod.
A
Do you think you. You'll get to keep the clothes?
B
Well, there's at least two pieces I'm trying to steal, but it's a Disney production and so everything is a little bit different. But I am, I am on all my movies now. If I see something I like, I'm trying to be like, hey, make that fall off a truck for me.
A
I think you're going to be in the mcu, Disney. Like, I was like, be in the mcu.
B
Come on.
A
Could this be your last stand up special?
B
Yeah. Yeah.
A
How do you feel about that?
B
That'd be okay. I. I don't know if I want to do another one. I, I just don't, I don't want to forecast, like, I don't know what I'm gonna want. You know, I like making movies. I like, I like, I've directed a little bit. I'd like to do more of that. There's a going to be, there's going to be at least a couple of a year or more period in the very near future where I'd like to off entirely and, and do nothing and no one hear from me. Maybe during that time I write some projects or write a book or something. I have. There's a book idea I've been working on for a while while Stand Up Special. Who knows? If I, if I, if I go on tour again and I find material that feels like a piece, I will do it. But I'm not interested in cashing in on that. I think I would just like to make sure that it's something I actually believe in. And so if there's another hour I believe in, I'll make it. If someone will make it with me. But I'm not. Yeah, I don't, I don't want to say. I don't want to say that I'm gonna do a hundred more of them because that's just not really my style.
A
100 would be quite ambitious.
B
Well, that's what Carlin did.
A
Yes.
B
He's doing like three a month.
A
It was before digital cameras.
B
I'm just like him. Yeah, yeah, you said that.
A
Your hope if you do more stand up tours is like, can you figure out how to create a community among these people that all showed up beyond just the service of your laughing together and then you sort of leave. I do think it's really interesting because I do think as community became a sort of buzzword, everyone's like, what I'm doing is creating community. But then all they do is like, just be a stand up comedian like they always were. And then literally everyone leaves and goes in their separate cars. Do you think about that? How can you actually do that actively? Like, I do feel like you are of a generation that forever means like, we're not activists. We hate. Activists exist over there and we're these other things, whatever. And I think you are. Oh, you don't say your comedy is activism, but you are aware of the sort of how it works. Like, how could one actually do that?
B
That.
A
And where does it come from, your desire to do it?
B
Yeah, I, I care deeply about community. I think it's the. I think it's the pro. I think if I could pinpoint one problem that we have, it's the isolation. Everyone feels so separate from each other. And I want us to feel together. And I want. I think when I think about community on tour, I think like, well, look, there's 1500 people in this room who all have at least something in common. Either they like my stuff or their girlfriend does. And so I'm like, okay, we, you know, like, let's. I'm always trying to get people to make a friend and exchange phone numbers. And I experimented. I experimented at a Bellhouse show recently where I. I got $500 cash before the show and I went around the room and I said, who. Who's sitting next to someone they don't know? And then I paired people up and I was like, I'll give you $100 cash if you promise me you'll use it on going out together. Like go out after the show or plan a dinner three weeks from now, Just promise me you'll do it. And a couple of them messaged me and were like, we just split the money and haven't talked since. And I'm like, okay, sounds good. But I would really. I want to do more stuff like that and I want to find ways to like help people connect because I think it's, it's cute and it's special and it's also nice to be a part of and I think it would be fun. ABC Wednesdays Shifting Gears is back. He has arisen. Tim Allen and Kat Dennings return in television's number one new comedy.
A
What what?
B
With a star studded premiere including Jenna Elfman, Nancy Travis and.
A
Hey buddy.
B
A big home improvement reunion.
A
Welcome. Oh boy, that guy's a tool.
B
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A
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B
Young people to figure that out.
A
Now, almost 90 years later, the results are in. There was learning. People who learned and read and read and read and liked to learn. They were much happier as they got older. People who are really good at managing their feelings.
B
But there was one thing that stood.
A
Above all the rest. I'm Henry Blodgett and this week on.
B
Solutions, I talked to best selling author.
A
Arthur Brooks about the science of happiness. Follow Solutions with Henry Blodgett for more. Wherever you get your podcasts. So now it's time for the final segment of the show. It's called the laughing round. It's like a lightning round, but it's a comedy podcast. So laughing round, do you have a favorite joke? Joke, like a street joke?
B
A street joke?
A
Yeah, like a joke. Knock, knock, joke.
B
Oh God.
A
Blah, blah, blah. Went to a blah blah blah with a blah blah.
B
Yeah, there's this one, I always butcher it, but I really love it. I think my dentist told it for me for the first time.
A
Perfect. But the perfect person for a joke.
B
Always, always. I, I always butcher it. But basically the short of it is this guy goes into a bar and he's, he's stressed out, he's had a long day. His tie is, you know, undone and he sits down at the bar and there's no one else in there. He tells the bartender, can I get a beer? And bartender goes, yeah. Bartender walks away to get the beer. He's sitting. The guy sitting alone at the bar, and he hears, he goes, hey, nice shirt. Looks around, there's no one there. And then he calls the bartender over and he goes, hey, did you say nice shirt? And bartender goes, I don't know what you're talking about. And the guy goes, oh, I just. It's the weirdest thing I heard. I thought I heard someone say nice shirt. Bartender goes, not me. Goes back to get the beer. And then when he walks away again, the guy here's like, that tie is really neat. You know, something like that. And he goes, he's looking around, he's going, who's telling me this? Calls the guy over and he goes, I gotta get out of here. I'm hearing a voice. And the guy, bartender goes, what did the voice say? He goes, well, first it complimented my shirt and then it complimented my tie. And bartender goes, oh, points to a basket of nuts on the table, and he goes, it's the nuts. They're complimentary. I just love that. I just love that.
A
That. I've heard a lot of jokes in my day. Come on.
B
Dumbest one.
A
That's. That's up there.
B
That's up there. Isn't that fun?
A
But in a benefit of a joke like that, it really gives a lot of room for a person to like, make it their own.
B
Yeah, well, that's my favorite kinds of jokes are like old men in the Casey's gas station in the Midwest at like 6 o' clock in the morning. And the way that the whole point is kind of they were raised on like Don Rickles and stuff, you know, so it's like the whole point is being like, walk into the place. The guy says, what are you doing in here? I says, I'm not supposed to be in here. You know, it's like the. The whole performance of the, like getting into it and the pageantry of like an old straight man telling a joke he loves. It's the long walk, you know, it's the real. It's the six minutes and you have to sit there engaged and you are.
A
Yeah. I think that's a beautiful thing to think about, which is the part before a punchline of a joke like that is actually where a person actually is expressing themselves.
B
Yeah.
A
Like telling the joke is not that, but it does if you allow yourself to be like. So I told the guy, and you're like, who are you now, you're like an old timey guy.
B
Oh, I get no respect. You know, it's like very. Yeah.
A
Do you have a joke you wish you can steal another comedian's joke? You wish that was my, your joke and you got to tell, but no one get mad at you. It just sort of.
B
Right. Trying to think, certainly. But I'm trying to think there's a couple comics in my head that I, that I love watching that I'm like, what is one of theirs? Kyrisha Boz. I'm trying to think of a specific one of his jokes that I would love to steal. He's just so funny in general. Hayden Johnson is a very funny trans comic and she has a very, very funny joke that I think about quite often that I will of course butcher and trying to tell, but shout out to Hayden, Hayden, you can stitch this with the actual joke. But she says, like, you know, experimenting with gender is so funny because for a while I was non binary. And she goes on this long thing where she's like. And during that time I realized that gender is fake and it's all made up. And we put this on each other and we say, you have to be this way and you have to be this way and there's two ways to do it only. And then you're non binary and you realize none of that is true. And you can be anyway, you know, whatever, whatever. She's walking it out. And then she goes. And then I realized I was a trans woman and it's like, oh, I'm a girl. I'm actually just a girl. And I really. She has another one too, where just thinking about Hayden now, she has one where she's like, she's like, I can't tell if everyone in this dive bar is staring daggers at me because I'm trans or because I'm wearing a ball gown and a dive bar. Really, really, really funny. I think she's incredibly funny.
A
Ball Gown and a Dive is a special name.
B
It's very. It's a special name. And Hayden Johnson and Nori Reed run a show called Trans Girls that is. That is really great that I, that I love.
A
Do you have a short story of an interaction with a legendary comedian, living or dead, you're willing to share with us?
B
Short story, legendary comedian, living or dead, that I'm willing to share with you and, and the world. Really? I'm trying to think of a comedian I've talked to. When have I talked to a comedian? I'm like, when have I talked to a Comedian. I know. I talk to comedians. Yeah, you definitely, you know, here's what I'll say.
A
Yeah, yeah, yeah, yeah.
B
Here's what I'll say. I. IO a debri. She and I did a show. I. She didn't. I don't. She wasn't driving at the time. We were both living in LA and we were both on a lineup at Largo and I was driving her home. And I really think the world of IO. I think she's a brilliant, brilliant comedian and performer. And even more important than both of those things by many miles is how good of a person she is. But she. I had this joke, it was a joke about white people gathering in St. Patrick's Day and how I was like, I'm terrified of St. Patrick's Day because when white people gather, bad things happen. And on the way home, she did something I thought was so brave and cool. And she was like, I want to offer. Can I give you a tag a punch on that joke? And I was like, oh, I would be so scared to do that. Like, I'd be so scared to offer that to someone at that point in our friendship. And I was like, of course, I would love that. And she did. And it was a brilliant punch. And she really. You could just tell when she was giving me the idea how excited she was because she loves jokes. And I was just like, that's. That's a thing I think about sometimes. Cuz, you know her, she's doing all of her big acting stuff and life is kind of going that way for her. And I'm. I'm like, damn. I hope all the people who know her as a brilliant actor correctly also know that she is a dyed in the wool comics comic. Like she is that funny. So that's what came to mind.
A
Nice. We have to wrap up. I have two more. You can choose between the two.
B
Yeah.
A
Or you can do both if you don't care about where you're going next. So the two and is either what's something that people think is comedy that you think isn't comedy or best time you ever bombed.
B
Oh God. Both good ones. I'm trying to think of an answer for either. So what's something people think is comedy that isn't comedy?
A
It's a new one.
B
What's something that people think is comedy that isn't comedy is just like pretty much whatever Joe Rogan's doing. Like, genuinely. I mean, I really do think like you. I. I saw some clips from his last special and I was like, interested. So I Clicked in and watched a little bit further because I was like, you know, here's a guy who, he was like just some sitcom dude and then he was hosting Fear Factor and then got in really into professional fighting. And then now he's like the biggest podcaster in the world or whatever. So that's an interesting journey. I've said about Joe many times, I have a lot of respect for him and specifically in the way that he puts on comics. He puts comics on his show that have nothing to offer him and they are the only ones who will benefit from it. He puts on comics like Brian Simpson, who's a geni. He really, really, really supports other comics. I know that he sent money to people when they're struggling. It's a thing that a lot of people who don't like Joe Rogan, as I do not, will not say about him, and I think it's unfair. He really supports other comics and I think that's cool as hell. That being said, he's one of the worst stand ups I've ever seen. Sorry to Joe. I'm sure the podcast is doing something for someone. The stand up is horrible. I don't know if he was ever good, but he is, present day, one of the worst stand ups. I mean, I have seen, I have seen drunk open micrs who have never touched a microphone do better than his intentional special. And it's, it's, it's okay. Not everyone has to be good at everything, but he's a very, very bad standup. I bet he's great at watching professional fighting. He is a very generous guy who helps out other comics. I like that about him. He's even said some things on the podcast politically that I thought were interesting at times. And I felt like, thank God he's saying that right now. There's a lot of people who listen to him who need to hear a balanced perspective, but good God, the guy shouldn't touch a stage.
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Thank you so much.
B
Yeah, thanks for having me. This was fun. Thank you very much.
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That's it for another episode of Goodbye. Good One is produced by myself, Zachary Mack, Neal Janowitz and Ann Victoria Clark. Music Composed by Brandon McFarland. Write, review and rate the show on Apple Podcasts five stars, please. I am Jesse David Fox and you can follow me at Jesse David Fox. Buy my book, comedy book, wherever books are sold. Thanks for listening to Good One from New York Magazine. You can subscribe to the magazine@nymag.com pod we're back with a new episode next week. Have a good one. Limu Emu and Doug Limu and I always tell you to customize your car insurance and save hundreds with Liberty Mutual. But now we want you to feel it.
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Host: Jesse David Fox
Guest: Caleb Hearon
Release Date: October 2, 2025
In this wide-ranging and deeply personal episode, Jesse David Fox is joined by comedian Caleb Hearon to discuss his new HBO stand-up special, his comedic influences, his approach to happiness and truth in comedy, navigating grief and fame, and the evolution of his career from improv in Chicago to podcast stardom and Hollywood film roles. The conversation balances thoughtful discussion on the craft of comedy with candid anecdotes, self-reflection, and plenty of humor, capturing Caleb’s distinct perspective as a comic who is both irreverently joyful and critically self-aware.
Timestamp: 01:34–02:54
"For a second...I sat with it for a second. I was like, oh, no, I’m not mad at you when you do that." — Caleb (02:19)
Timestamp: 03:18–06:33
"Zach’s comedy was so pivotal to me when I was figuring out comedy...he’s just brilliant...I really think he figured it out." — Caleb (05:44)
Timestamp: 06:50–08:29
Timestamp: 08:29–10:17
Timestamp: 10:17–12:18
"I am a serious artist. And the serious artistry I wanted in this special was the artistry of trying to make people laugh." — Caleb (12:01)
Timestamp: 12:18–18:31
“I have started to become like an older Midwestern woman who can find joy in the simplest things. Part of that's practice." — Caleb (17:05)
Timestamp: 18:31–21:56
Timestamp: 22:50–27:47
Timestamp: 27:56–33:32
Timestamp: 33:49–37:12
"Two best things ever happened to me: that I didn't get that job. I am not meant for that place...The way that it all worked out for me, that I get to be in charge, that I get to hire the people I want to work with, etc. Way better."—Caleb (37:14)
Timestamp: 38:36–59:16
“It’s not offensive to me…There are plenty of people who do identify as creators… I just get a little annoyed by it. It’s not the truth." — Caleb (56:41)
Timestamp: 42:43–50:29
“We create these sacred, untouchable ideas… I don't want to do that…I want everyone to be in on the joke, and they can joke about me, too." — Caleb (50:10)
Timestamp: 50:36–52:43
Timestamp: 53:08–55:34
Timestamp: 72:03–73:16
“I think if I could pinpoint one problem that we have, it's the isolation. Everyone feels so separate from each other. And I want us to feel together." — Caleb (72:05)
Timestamp: 75:02–82:56
“Pretty much whatever Joe Rogan’s doing…He really supports other comics and I think that’s cool as hell. That being said, he’s one of the worst stand-ups I’ve ever seen.” — Caleb (81:21)
Throughout
“If you work in entertainment long enough…you’ll get put on these lists. It’s fake and we all know that.” — Caleb (53:25)
The episode captures Caleb’s blend of sincerity, wit, and self-deprecation. He’s earnest about his craft but keenly aware of the absurdities of fame and the industry. The tone is conversational, warm, and often cutting in its honesty, in both the host and guest’s voices.
Advertisements, show credits, intros/outros omitted.