So True with Caleb Hearon - Ziwe is a Delight

Episode Date: August 7, 2025

Welcome! This week’s guest is the iconic Ziwe! Ziwe and Caleb talk dating in New York City, Colbert getting cancelled, a special encounter with the TSA, comments, and much more! Join o...ur Substack for an exclusive post-episode chat with Ziwe and other bonus content! https://calebsaysthings.substack.com/ Follow Ziwe! @ziwe Follow the show! @sooootruepod Follow Caleb! @calebsaysthings Produced by Chance Nichols @chanceisloudGo to Quince.com/sotrue for free shipping on your order and three hundred and sixty-five -day returnsHead to https://www.squarespace.com/SOTRUE to save 10% off your first purchase of a website or domain using code SOTRUE. About Headgum: Headgum is an LA & NY-based podcast network creating premium podcasts with the funniest, most engaging voices in comedy to achieve one goal: Making our audience and ourselves laugh. Listen to our shows at https://www.headgum.com. » SUBSCRIBE to Headgum: https://www.youtube.com/c/HeadGum?sub_confirmation=1  » FOLLOW us on Twitter: http://twitter.com/headgum  » FOLLOW us on Instagram: https://instagram.com/headgum/ » FOLLOW us on TikTok: https://www.tiktok.com/@headgum So True is a Headgum podcast, created and hosted by Caleb Hearon. The show is produced by Chance Nichols with Associate Producer Allie Kahan and Executive Producer Emma Foley. So True is engineered by Casey Donahue and engineered and edited by Nicole Lyons. Kaiti Moos is our VP of Content at Headgum. Thanks to Luke Rogers for our show art and Virginia Muller our social media manager.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Transcript
Discussion (0)
Starting point is 00:00:00 this is a headgum podcast to be a true individual i'm not claiming that i am one i just think that we're losing that like the sense of like the weirdos and the freaks and the you know i think it's kind of getting like beaten out of the broader culture it's literally the book divergent which i haven't read nor have i so let's talk about it your show again that's like maybe we had lightning in a bottle and it won't hit i no not for you like that i won't show up the way that i need to for the second one i think there are people who i would not talk to again but you are not one of those people it's like adam pally right adam pally is someone who can you whatever he delivers it's new and weird and funny you are the same way yeah yeah i love
Starting point is 00:00:51 adam i love adam i love adam he's really so sweet he's really funny you're really funny like him you remind me of him he really one time we were at a party at i don't know it's like shot Tomarmon or something. Okay. Some fancy place that I have been twice and shouldn't have been in the first place. Yeah, right.
Starting point is 00:01:05 And he was like, he was like, hey man, did you drive? And I was like, yeah, I brought my car. And he was like, oh, nice. Can you drop me at a sushi place after this? Shut up.
Starting point is 00:01:13 And I laughed because I was like, oh, he's kidding. And he was like, no, I need a ride to the sushi place. And then I did drop him at a sushi place. And he's just like, thanks. Nice meeting you? No, we knew each other.
Starting point is 00:01:24 But he was like, he was like, he was like, thanks, man, have a good night. And I was like, all right, Adam, see you around, I guess. He's insane. That tracks. That is so funny. That's really, really wild.
Starting point is 00:01:32 He did match games the day after I shot mine in Montreal. And so it was just nice to like cross paths. What is match games? Match games. Oh, it's a really important show. That's from 90s, like the 50s or 60s. And Martin Short is hosting it now. It's like a game show on ABC.
Starting point is 00:01:52 Yeah. And I did it with Selena Gomez and Kara D. Delavine. And, yeah, and so it just cycles in a bunch of comedians, flies them all in Montreal, and it was just a fun time. I haven't been asked. You haven't been asked yet. I haven't been asked.
Starting point is 00:02:05 But, you know, I have the mightest touch. Yeah. Yeah. Put it on there. Tell them, actually, don't tell them. I don't tell them. I don't do panel shows. Oh, you don't?
Starting point is 00:02:11 I don't do it. I don't do it. I don't do it. I had, that was my first one ever, but I would do it again. Really? Yeah. I can't do them. Every time I get asked, I'm like, it just feels like too much to me.
Starting point is 00:02:19 I feel like I'm competing. I feel like I'm in like a sack race with other comedians or something. And I didn't know how to play until the second game. So my first showing was pathetic. But hopefully the second showing isn't. Have these aired yet yours?
Starting point is 00:02:31 Yeah, one aired like three weeks ago, two weeks ago. Well, okay. I need to tap in. I need to get up on my Z-way lore. Oh, please don't. No? You don't want me to? No.
Starting point is 00:02:39 Okay, I have a question for you. Doing an interview like this where we're just being ourselves. Yes, just being. Do you prefer this or do you prefer, also do you view your show as being a character? Do you view that as being different than... Yes.
Starting point is 00:02:51 Yes. Yeah, for sure. Yeah. For sure. Well, I feel that it is, but I'm like, I don't know how much you want to talk about that. Oh, yes. Yeah, I don't want to give away my trade secrets. Right.
Starting point is 00:02:58 Yeah. But do you think that... Do you prefer this or that? I don't like to do podcasts at all. Really? Really? This is my first podcast since 2023, maybe. Whoa.
Starting point is 00:03:06 Yeah, I really say no, but I have respect for you. And I want you to come back, didn't do another interview. And so I know that I have to do the work and show up. So here I am. That sucks. I'm so sorry that you have to do this. It's okay. I don't have to do anything. What was the, you really don't? What was the, 2023, what made you stop doing podcast? Was there a particular experience? Or were you just like, you know what? I'm Zway and I'm good.
Starting point is 00:03:30 I don't think podcasts, by and large, are very good. I agree. So it's just a taste thing. I think that they need to be edited. Obviously, I have like a really strong POV. So I don't find that in a lot of podcasts. And the work is just like two people in front of a camera. And it's like, this is our new talk show. and I have such esteem for the talk show format that I just, it's not something I'm inclined to do, yeah. What's your favorite talk show of all time?
Starting point is 00:03:56 I can't even say, because I go through phases. Like, I went through a big Barbara Walter space. Obviously, she's talked like news. But, so I was watching her top 10 interviews, including the one where she, like, makes Ms. Lewinsky cry, which was hard to watch. And then I, obviously, Wendy Williams is just, like, laugh out loud.
Starting point is 00:04:15 It's unbelievable. funny it's offensive and imagine being the celebrity in that place like i would feel so bad i would be so afraid to to attend that show and be a guest but man oh man those clips are sticky she's the blueprint i saw your episode with marie recently yeah that was really sweet i love marie she's really funny i tried to get her to do an interview but then she wasn't also in canada actually yeah people are shooting in canada i know yeah well everyone wants this uh skirt unions so we're going to have to film everything now in Canada and London, which is awesome. I love that we can't film things in here anymore because the companies don't want to pay
Starting point is 00:04:48 the unions. That's awesome. But you don't want me to say that on camera. I don't really, I don't have an opinion. I shoot in America. I shoot in New York City, baby. We shoot in America. Hey.
Starting point is 00:04:56 These shows, our shows are American made, baby. Made in the USA. Me also not getting my camera. Hello, it's there. Hello, it's there. Wait, what was I going to ask you? Oh, okay. I saw, I came to your, a live show that you did.
Starting point is 00:05:11 Oh, yes, with Alex English's live show. Yes. Yes. And you were so fabulous on it. Thank you. And you talked about your Wiki feet score. Yes. My WikiFeed score.
Starting point is 00:05:19 How is it going? What's the journey? Has there been any improvement that you're proud of? Yes. I'm actually in the top percentile. I have like 4.58 Wiki feet. I think that's exact. So they're going well.
Starting point is 00:05:30 I don't like feet, but I've just learned to not have shame around my feet as much as I did before. But I still do. How did you get the score up? Did people really go to back for you? I literally went around the country and around the globe like to Europe and was like vote for my Wiki feet please please please and people did they rock the vote and so I'm up up up I am up
Starting point is 00:05:49 yeah they rocked the vote they went to the ballot box and they made their fucking voices heard exactly and so now I'm I'm 4.5 which is I think great feet excellent feet amazing feet someone checked me on that I don't think I'm even on there yeah they're not a lot of men they're not talking about me Don Lemon is yeah I think he is how's his rating I don't remember I think it's probably good but like a lot of the anchors are the male anchors are because I talk I talk about
Starting point is 00:06:13 WikiFeat more than I should. But, yeah, I'm on it. How did you start doing Bated? This was in 2016. It was the day after Hillary famously lost, and I just shot an interview series. And I just think it's really funny to make people uncomfortable. And so that was the brain child behind that. It is really funny, the way that people squirm on your show.
Starting point is 00:06:40 Well, also, I think it has to do with, well, let me not spill. too much to you. I think we live in an era of surveillance and as a result, people are hyper-conscious of the self that moves through
Starting point is 00:06:56 public spaces. And I find that to be interesting. Yeah. So the day after the election, you, what, just called up some friends and we're like, I want to do this show today. Let's do it. No, I was planning on shooting like a web series that day regardless. But I was inspired.
Starting point is 00:07:13 to kind of shift the idea to be more incendiary, I guess. Yeah. How was the process for you of moving from you were doing that show online and then you were doing a lot of interviews on Instagram Live? Yeah. So it started on YouTube and then
Starting point is 00:07:30 it changes, it reiterates and becomes an Instagram live show during the pandemic when we were all going live. And then it became a television show and then it became a YouTube show again. Yeah. How was that transition to,
Starting point is 00:07:46 because I'm very inspired by the fact that you took it from what it was on your own to a network and then kept it going afterwards. And it seems to me like it's going really well post-network. Oh, wow. Thank you. How has that transition been through all the different phases? What's been difficult about it or interesting? I think every single iterative,
Starting point is 00:08:06 this is something I think I'll be doing until I die, honestly. And so I think every single iteration, you just learn from the medium what sticks, what doesn't stick, what's functional, what, it changes and grows and evolves. So like it started off with really baiting people. And obviously the interview with Jinks Monsoon, which is the latest, doesn't feel as much in that space, even though the questions themselves are sort of wild and inappropriate. So yeah, I'm just always kind of trying to, with each guest even, I think the show evolves.
Starting point is 00:08:36 Like I thought our interview was sort of like this watershed moment after I had done a couple criminals who have been, you know, arrested and are serving time. And your interview was so different than that, but still in the same, like, accusatory manner. I don't know. Yeah. Yeah, I work through, I work through my process with each guest. Yeah. Until I find my final form. It does really feel that you are treating each guest as their own individual thing. Yes. It feels that you're approaching it in a very specific way every time and you're not asking. I'm glad it's not the same questions across the board and just seeing how people react to them differently. I appreciate the individualized effort.
Starting point is 00:09:14 Thank you for saying that. Yeah, I never want to get stale or dusty. Yeah. And you're dating in New York right now, by the way. I've got so many things in my mind to ask you about. Yeah, I'm dating. I'm dating in New York City, but not really. I'm open to dates.
Starting point is 00:09:29 People really don't approach me with the sexual energy, even though I think that I exude. Yeah. Exude horny I've always said that about you Thank you Zeeway exudes horny I exude horny And so
Starting point is 00:09:44 So people never ask me on dates But I'm going on a date tomorrow Which I'm excited about Yeah And I guess I went on a date yesterday But I don't like to think about it Are you on the amps? No
Starting point is 00:09:54 Yeah you're too chic for that huh I like obvious I go on and off Raya Depending on how depressed I am But I haven't had any success Raya to me I think jail everyone who made it, I think jail, everyone who continues to work on it.
Starting point is 00:10:10 Yeah. I think Raya is one of the most depressing places I've ever been. It's not cool. But I hear it's good for gay men. I'm sure that it is. Everywhere's good for gay men. Because gay men are getting active. Yeah.
Starting point is 00:10:20 Gay men, well, you know, gay men find sex in bathrooms. I know. At the airport. Yeah. It's crazy to me. Gay men are fucking at the airport in a big way. That's wild. Yeah.
Starting point is 00:10:28 I would never feel horny after TSA. Yeah, they do. Maybe even it's part of it. I mean, really, I almost, I got this close to fucking a TSA. are you joking once at an airport yeah no he like i went through the line and then he messaged me on grinder and was like you just came through my line you're so cute and i was like okay i'm in the delta lounge and he was he was like he was like yeah i'm i have to work because it's like a national security risk yeah and then he was like he was like i get off
Starting point is 00:10:54 in like an hour is your flight gone before then i was like yeah i'll be boreded and he was like uh next time i was like all right but i was down i was like if you want to come to if you can get yourself into the Delta Lounge. Yeah, but I don't know. And it's just, you and a man in like yellow vest in the Duttle Lounge? Would have, yeah. In the bathroom. Because the doors go all the way to the floor and the bathroom.
Starting point is 00:11:18 I would have, I would have had sex with in there, no problem. Well. I love a story and I like to have a good time and I like to be myself and be free. And in any space that can happen. Sometimes that happens in the Delta. You know, really what the Delta Lounge bathroom is for is going to the bathroom right before your flight. Oh.
Starting point is 00:11:36 You have to go to the bathroom right before your fight. Yes. Peep poop, wash your hands, brush your teeth. I think I know what you meant. Do whatever you need to do in there, y'all. Including. Including up to peeing, pooping, brushing your teeth. Getting active with a TSA agent.
Starting point is 00:11:49 If it goes that way. Okay. Well, you're really putting me on game right now. Yeah. Yeah. Gay guys, yeah, but that's the thing. You can't ever judge the effectiveness or the goodness of a thing by whether or not gay men can use it to get laid. I know, but you all have so much fun.
Starting point is 00:12:02 We do have fun. I know. It is fun to be a gay guy. I know. But then in many ways it's not, is it? Who are you talking to? Me? See, wait, you know enough gay guys.
Starting point is 00:12:12 We've talked about this before. You know enough gay guys to sound off on this, I feel. I'd be like you could. But I do feel for, I feel for straight people. Oh, you do. People are going through a lot over there. Yeah, I mean, I think we're, you know, we're at a time where it's like super straight,
Starting point is 00:12:27 be as straight as possible, like wear your darker jeans, right? Yeah. I guess. I don't know. I don't know. It's really hard. We live in an echo chamber. it's like fabulous like it's like literally free to be me and then you go anywhere out of the this
Starting point is 00:12:40 wherever you are and it's like hyper authoritarian and like really i do feel that yeah so it's hard for me to say beyond my community i don't see i went to a walmart in missouri recently and i saw no seen kids i saw no kids with big swoopy black hair weird makeup odd piercings and i thought in a suburb of kansas city in missouri this used to be those kids used to run this fucking I know, but they change the living wage. They can't get on that damn bus. You know? Seen kids have been priced out.
Starting point is 00:13:09 Yeah. And yeah, it's weird. I do think the like weird individual, somebody was talking about this reason. I don't remember if it was like in a video or in an, I don't remember how I consumed it. But the idea that like identity is flattening because of the internet. I agree. Well, speak on it. Speak on it.
Starting point is 00:13:25 I mean, I think that there are people who would not know culture unless it was served to them in an algorithm. Yeah. and as a result we are watching people dress alike and sound alike like we're even losing like regional like dialect it's now the internet voice gen z voice which is like black voice from like the hood like 20 years ago yeah people saying dead ass and they're like gen z it's like no that's always been around but i find that everyone is we're buying the same things and watching the same movie is and having the same culture of real references so it's hard to find new and fresh and different and exciting.
Starting point is 00:14:00 Yeah. Yeah. Everyone's dressing. Yeah, they see a trend. They're like, oh, this is what everyone's wearing right now on TikTok. Yeah. And then they're doing that all across the country. It used to be, at least, like, there used to be a big joke in the middle of the country
Starting point is 00:14:10 that, like, if you went to a hip coffee shop in Cincinnati, it's whatever was happening in Williamsburg seven years prior. Yeah. You know, or whatever was happening in the East Village seven years prior. That was the big joke is that it took time for those things to travel over. And now it's actually this flatter, weirder thing where everything is equally mediocre all at the same time. And so you are.
Starting point is 00:14:29 You're losing. You're losing regional, like, ways of dressing and things. And it is really interesting to watch, like, to be a true individual, I'm not claiming that I am one. I just think that we're losing that, like, the sense of, like, the weirdos and the freaks and the, you know, I think it's kind of getting, like, beaten out of the broader culture. It's literally the book Divergent, which I haven't read. Nor have I.
Starting point is 00:14:52 So, let's talk about it. That's podcasting, by the way. I haven't read this book. Neither have I. Let's discuss. What happens in Divergent that you know of? It's bad to be divergent. I know what the word needs.
Starting point is 00:15:07 I've been saying this, yeah. So I imagine that's like the internet. Well, you shouldn't diverge. Yeah. That's the lesson of divergent. Exactly. And if you do. But then they win.
Starting point is 00:15:16 The divergent people win. When you diverge? Yeah. Fuck. But maybe it's like the giver. No, that's just about seeing color. Yeah. What's the giving tree?
Starting point is 00:15:23 That's what I'm thinking of. That's, uh, Dr. Seuss. Nice. And the tree, of course, gives. Right? I'm like we don't have children we don't have children have I ever read a book by the way yes have you read Harry Potter I never read the books I never read the books either I wasn't allowed heroes I grew up in the church did you heroes yes well kind of okay I grew up in a very
Starting point is 00:15:45 religious community yes Missouri Missouri but my mom was my mom's always been like a like we're Christian but that just means to be nice to people and we don't have to be crazy about it so she was like the cool version of it chic yeah it was pretty chic where did you grow up Massachusetts. Right. Yeah. And it was not, it was like, you will go to hell!
Starting point is 00:16:02 Yeah, not chill at all. No. What part of Massachusetts? Like Boston, north of Boston. I just wondered if you were close to Taylor Garon. Did you see her on TV as a kid? Yeah, of course.
Starting point is 00:16:13 In course. Yeah, I remember seeing her Zoom Boomifu. Yeah. Yeah, she was a star. I know her from the New York comedy scene. And so we connected over that. Yeah. She was that girl.
Starting point is 00:16:26 It was like the black girl on Zoom Boomifu. which even though PBS is canceled. Is it? It's not canceled like cancel culture. It's canceled like they defunded it. Like they defunded it and like offices are closing. I know. Public radio is in a really tough spot.
Starting point is 00:16:38 I'm really worried. I donated to NPR. I know. It's really tough right now. But you know what? This is what I say. Say lovey. Oh.
Starting point is 00:16:46 What am I supposed to say love you? And what does that mean in this context? In this context it means I can't fund public radio. Oh, personally. I can send my little donation and continue listening. But like, yikes. It's the best. Bedrock of democracy.
Starting point is 00:16:59 Public radio is so important. I know. Let's go to, let's move on. What was that sound? There's a weird sound in the space. Beep up, boop, beep, pop, boop. Don't cut this, by the way. Leave this in.
Starting point is 00:17:11 Something's happening with the door and chances going out to find it. Anyway. NPR, wait, what's your favorite NPR show? Do you have one? No, I just listen to the daily news show. Yeah. Oh, I listen to podcasts, but news podcasts exclusively.
Starting point is 00:17:24 Which are your favorites? So time, I think time up or up? Time up. Is that what it's called? Time. This time. Up first. Up first.
Starting point is 00:17:31 Up first. And then I listened to Wall Street Journal's. This something or another. I forgot the name. What's News? I don't remember the names. What's News? Up First.
Starting point is 00:17:41 And then I listen to a bitch, like a Housewives podcast called Bitch Sash. Oh, I know Bitch Sash. Yeah, those are my three podcasts. Yeah. Danielle and Casey. Yeah. Yeah. I think those girls are so funny.
Starting point is 00:17:52 And Danielle is such a brilliant TV writer too. She can write. She can write. Yeah. We worked on a show. together. Which show? It never came out. It got canceled by Hulu during the strikes, but it was a Dan Levy and Ali Panku animated show that Danielle wrote on and the Britannic guys and Norie Reed and Dang, that stinks that it didn't get. Greenlit. Yeah, really great room. A bunch of other people
Starting point is 00:18:14 do. Sabrina Jalise. Whoever, if anyone's listening, I'm sorry I didn't mention everyone. But yeah, it was a, it was a really fun room. We were, uh, we were in the middle of the room when the strike started. And then it just never came back. Never came back. They paid out our contracts and then we didn't finish it. Sorry. I think it was going to be good. It was Dan and Allie created it together, but Danielle, yeah, she. She's funny.
Starting point is 00:18:33 She's very funny. She's a really, yeah, so I just think they're so funny until I listen to episodes. That also introduced me to a lot of comedians like Adam Pally. He did that. He's like a favor, Yasser Lester. But I just think they're funny. Yasser's so funny. He's so funny.
Starting point is 00:18:47 I haven't seen his bowling movie yet. I need to do it. I did. I saw it. It was great. I need to see it. It was fantastic. Like laugh out, love funny.
Starting point is 00:18:53 I really, really love him. He's so funny. Who are, okay. Speaking of funny people that we love, who are your biggest inspirations in comedy I want to know? Ooh, that is a great question. Who are my biggest inspirations? Tina Faye, obviously. I like writers. I'm attracted to writers, people who can write really well. So Tina Faye, I remember reading the Steve Martin book, Born Standing Up. Have you read it? I don't read like any comedy books, but I know of it. Okay. It's like the standard bearer of
Starting point is 00:19:20 autobiographies, especially if you're trying to be an, if you're an aspiring artist or comedian. And it is just about his journey to stard him, Steve Martin. And that's really good. So I really admire him. Who else? Colbert is a huge influence of mine, obviously. Who else? What do you think of his show getting canceled?
Starting point is 00:19:40 Political or no? I think it's both. Yeah. What do I know? I think it's convenient that it, I think it, I think they wanted to cancel it anyway because of the money situation. And I think it's very convenient for them that they have that excuse because they, they, they don't want him saying the things he said. Yeah, I'm excited to see what a year of him unleashed looks like.
Starting point is 00:20:00 I am too. I'm really curious to see what that means. And I'm excited for his, Conan had a really great I Left the Network era. Dave Letterman has a great one. I'm excited for his post network, like, what's he going to do? That's exciting. It's exciting. Yeah.
Starting point is 00:20:15 So Colbert Report, I just remember watching that in high school. And it was my introduction into satire and thinking it was like the coolest thing because you could see anything offensive that would get you otherwise in trouble. But because it has great politics, you're allowed to do it. So I really appreciated that. I think you and I both operate on that. We both operate on that idea, that you can get away with saying very funny, like, audacious or inappropriate things because you trust that the audience knows your actual beliefs.
Starting point is 00:20:44 I think so. Do you know what I mean? Yes. But then sometimes they, I hope so. But then sometimes they don't know anything. Oh, yeah, for sure. Our interview left the target audience a couple times. Oh, really?
Starting point is 00:20:55 What part do you think? Oh my God, I would get comments and DMs that were like, oh God, people DMing me and being like particularly the way, like when you were asking me about apologizing for slavery. Oh. When we were chatting, when we were talking about that. That pissed me off too. I got some texts. And people being like, the way he's dismissing this black woman, I was like,
Starting point is 00:21:11 guys, we are doing a format show. They were mad at me, Zeeway. Really? So I also, I got a lot of messages that were like the opposite, which were, how could you make him apologize or something? Oh, I saw this as well. Yeah. That gets my gear.
Starting point is 00:21:24 Yeah. They were like, they're like, he has nothing to apologize for. Why is she doing this? I'm like, guys, we're doing, we're in a format right now. It gets me mad. It gets me, the comments get me mad. So I'd have to just divest. I like can't invest at all.
Starting point is 00:21:35 Yeah. And even the good comments, because they rile me up. Yeah. Truly. What do you do when you, what do you do when you're feeling that way? Like, how do you get yourself out of that? Do you ever find yourself falling into that hole? I think I just do another interview and they're so different.
Starting point is 00:21:47 Yeah. And so then it's like, I, I'm in a new hole. Like, I'm not really thinking about you like that. Jumping from hole to hole. Yeah, exactly. I'm, yes, I love hole. Much like the gay guys on Raya. Honey.
Starting point is 00:21:55 Honey. And at the Delta Lounge. Hole to hole. Zway is jumping from hole to hole. No, I wish it was. No, that's not you. I wish I was. I'm a Charlotte.
Starting point is 00:22:04 Yeah, fuck. What are you? Well, it's been the subject of much consternation. Really? Really? Yes. I mean, my fans, I don't want you to be offended when I say this. My fans called me Charlotte and it made me want to get myself.
Starting point is 00:22:16 Oh! Because I am, I am not a whore or a slut. but I have trafficked in those spaces so is Charlotte no Charlotte's a freak ho no yes she was she way she's like a she's like a sad virginal figure who like puts up with the guy who won't touch her for way too long because she wants to be married for that lovely apartment see but that's not how I moved and then she hooked up with Harry that's not how I moved got it so you would just you would leave him oh for sure so I just think look I wanted what I wouldn't I would have stayed I want to say longer what I want people to say is
Starting point is 00:22:51 What I want people to say is you're, I want them to say, Caleb, you are the fun, sexy, exciting charisma of Samantha with the lead character energy of Carrie. Of course. I mean, of course I'm a mix of them. Yes, of course. Yes, of course. You do have the lead character energy of Carrie and the sexual rawness of Samantha. I think that I am a Carrie son, Samantha rising Charlotte Moon. Okay.
Starting point is 00:23:16 And will you remind me what sun rising and moon mean? The sun is myself. Yeah. The moon is the. inner self that people may or may not know. And the rising is what the world projects on to me. Yeah. What are your actual sun moon rising?
Starting point is 00:23:28 Pisces sun, capricorn moon, Scorpio Rising. Okay. Which I also tracks with those three women. Really? But maybe it's Miranda instead of Charlotte. Okay. Interesting. Yeah.
Starting point is 00:23:38 But I have weird religious trauma. So that's why I can identify with Charlotte. Where are you at with religion these days? Can I ask? Chilling. I'm fine. Yeah. You're chilling.
Starting point is 00:23:46 Yeah, exactly. I'm like, God. I feel like whenever you talk about the fact that you, if you, if you're we see you performing at a megachurch it's because you need the money yeah that's how i feel about fascism where it's like oh okay if they're really rounded us up you just hear me start singing amazing grace they're banging on the door and you're like oh yeah literally literally i'll be like okay you're really gonna see me get real real handmade stale uh yeah so that's where i stand on it i yeah i think it's like Walt whitman where like heaven and hell are like what we become after death so
Starting point is 00:24:18 it's like oh like we see grass we see that the birds eat the grass and we see that bigger birds eat the birds and you know it's the circle of life like i feel like that is our version of afterlife so god yes or no god yes or god yes or god yes or no i that's a complicated because god is in the trees yeah do you what do you see when you see the ocean that's god so do you see god as a figure that exists and and dulls out judgment when we leave no no you don't think there's it you don't think there's it you don't think there'll be like uh you don't think there'll be a hell for bad people that god said i think this is hell you think earth is hell you and my mom are very aligned on this. You and my mom are very aligned
Starting point is 00:24:52 on this. Well, then why am I having so much damn fun? You are? If Earth is hell, honey, why am I having a great time? Oh God, that speaks poorly of me, doesn't it? No, I think you're all having sex in the Delta Lounge. I get it. Like, you're setting yourself up for fun. I'm almost having sex in the Deltz O'Rounge, which is even better than doing it, by the way. Yeah, it's like the promise. Yeah, it's
Starting point is 00:25:16 the, it's the, you get to walk away being like, I would have done that, you know? You get to walk away being like, I'm somebody who would have done that. Exactly. And then you don't actually have to clean up or anything. Sex is messy, don't you find? No. Nice. I don't think I'm having a fun during sex.
Starting point is 00:25:32 Really? It's very neat and clean. Really? You're keeping it very tidy? I just think if you fuck in the Delta lounge, it's like some things are going to drip. Oh my God. They are. You're at work and I'm traveling.
Starting point is 00:25:45 Nothing's going to drip. I just told you that I'm a Charlotte. Yeah. Wait, you really don't think you're having fun during sex? Because I am very interested in that. No, probably not. No, I'm having fun during sex. I don't have a lot of sex.
Starting point is 00:25:58 Yeah. I related to that, though, because I am having fun during sex, but there have been eras of my life where sex felt like a thing I just had to do. Like, I'm so horny that I need to have sex. But doing it was just like, God, it's like taking out the trash. You know what I mean? No. Say more?
Starting point is 00:26:15 I'm not in that right now. I guess I was depressed. I'm not, not right now, but I feel like there was a chunk of time in my mid-20s where I would, I would sleep with people and just be like, God, I do really want to come. I am that horny, but I just, this person's coming over here. I have to, like, clean my house. And then, like, and then I want to be a good, I want to be a good sexual partner, so I have to, like, invest in their coming as well, you know? And then, of course, I do because I'm a good guy and a really good lover, by the way. But, yeah, it was, there was, there was, there was, like, a period of, like, a year and a half there.
Starting point is 00:26:48 I was like, this is such a chore. I think any relationship, anything, during your 20s is how. You're sort of working through what you like, what you dislike, what you're, you know, you're who you are. So that's not too shocking to me now that it seems like you've aged out of that and you're just enjoying all the smooches that you get along the way. I do. I really do. It reminds me of that Bernie Mac, that set that he did where he's like, I love sex. I love it by the pound.
Starting point is 00:27:16 What does that mean? Just Bernie being Bernie. You just love sex? What are you going to do? Loves it by the pound. I love it. I'm not saying that I don't love it. I'm just saying that, I don't know.
Starting point is 00:27:27 Well, you're not having a lot of it. You did say that. No. Yeah, but you're too chic for that. No, I, what does chic mean? Like, you're like, I just feel like, when are you going to have sex? You're like in glam, you're at the fashion event. You're being too.
Starting point is 00:27:37 And these guys won't come up to you. There's too much cowardice in the culture. I know. I have a lot of power. You do. If I was a straight man, I would not come up to you. That's so hurtful. No, you're gorgeous and intimidating.
Starting point is 00:27:48 I'm dead serious. Thank you. No, I'm at, this is something that I am at peace with. I don't want to be a scary person, but I recognize that whatever I move through the world, I just carry with me, like, I don't know, a stick that says, you know, you know how they say, like walk lightly,
Starting point is 00:28:04 but carry a big stick. Like I carry with me the stick, and for some reason people are intimidated, and that is my blessing and is my curse. I don't find you scary to start there. I do not find you scary, and I think anyone who would say that to you is racist.
Starting point is 00:28:16 kind of, it has some work to do. I don't like that. Thank you. Guys, why drop a fortune on basics when you don't have to? Dropping a fortune on basics. Sounds like my 20s. Quince has the good stuff. High quality fabrics, classic fits, and lightweight layers for warm weather.
Starting point is 00:28:36 All at prices that make sense, no matter what you're looking for. Quince is always a solid choice. The best part, everything with Quince is half the cost of similar brands by working directly with top artisans and cutting out the middle. men. Quince gives you luxury pieces without the markups. I'm always wanting to go direct to my artisans. So you can do that with Quince now and get rid of these middlemen between you and your artisans. And Quince only works with factories that use safe, ethical, and responsible manufacturing practices and premium fabrics and finishes. We love that. I've had my eye on their
Starting point is 00:29:04 cashmere baseball caps for some time now. I just might snatch up a whole bundle of them and send them to my loved ones as gifts to say, thanks for being you. Keep it classic and cool with long, last thing staples from Quince. Go to quince.com slash so true for free shipping on your order and 365 day returns. That's Q-U-I-N-C-E.com slash showtree to get free shipping and 365-day returns. Quins.com slash so true.
Starting point is 00:29:29 Have you ever been sitting around thinking about all the things you wished you had? Have you ever yearned and wished for a different life? Maybe a new bicycle or a new job or maybe a single destination where you can find hours and hours of Laugh Out Loud Entertainment, specifically in the form of animated television shows? Well, if you said yes to that last thing I said, I have something for you, and it's from our friends at Hulu.
Starting point is 00:30:00 Picture a giant magnet attracting all your favorite animated shows. That's Hulu, Animatim, Your Animation Destination. Catch all the shenanigans on classics like The Simpsons, Futurama, American Dad, my personal favorite family guy. of it and many more. Family guy really is a quality show. They really, they really do something special on that program. Hulu and a mayhem, your animation destination, stream now on Hulu on Disney Plus for Hulu and bundle subscribers. Terms apply. This podcast is brought to you by Squarespace. Squarespace is the all-in-one website platform designed to help you stand out and succeed online,
Starting point is 00:30:38 whether you're just starting out or scaling your business. Squarespace gives you everything you need to claim your domain, which sounds like a law that shouldn't exist. Showcase your Offerings with a professional website, grow your brand and get paid all in one place. We all could use a good website in this day and age. I tell you what. And Squarespace has so many awesome features to get yours up and running. Squarespace gives you everything you need to offer services and get paid all in one place. From consultations to events and experiences, showcase your offerings with a customizable website designed to attract clients and grow your business, get paid on time with professional on brand invoices and online payments, plus streamline your workflow with built an appointment, scheduling, and email marketing tools.
Starting point is 00:31:13 Get discovered fast with integrated Squarespace SEO tools. Every website is optimized to be indexed with meta descriptions, an auto-generated site map, and more so you show up more often on search engines and bring in more of your ideal customers. At to squarespace.com slash So True for a free trial. And when you're ready to launch, use offer code so true to save 10% off your first purchase of a website or domain. When I envision myself as a straight man, I think that so many straight men are genuinely
Starting point is 00:31:36 intimidated by brilliant, hilarious women who have their life put together. and I actually do think that if I was a straight man I would be too intimidated to come up and forth with you. No, I'm a pleasure. I'm a delight. You are a delight.
Starting point is 00:31:48 Again, it's not about you. It's about who I think I would be if I was straight. Got it. I only like people with self-confidence. Like I only like high self-esteem people. I think I'm a high self-esteem person. Yeah, I think you are too.
Starting point is 00:31:59 Thank you. You're a high-value woman. Yes. What does that mean, though? I don't know. I started reading that and I was like, is this like a dowry, like, cattle thing? What's going on with this verbiage?
Starting point is 00:32:11 The dowry? You know, high value. What is, yeah. Yeah. I think oftentimes that's, if we're being earnest, I think that's like coded language. Of course. Yeah. For stock.
Starting point is 00:32:21 Stock. And also like, I think when men say that, it's never, when you say you want a high value man, it feels different than a high value woman. I've never said a high value man in my life. We wouldn't say that. But if a woman were to say that, I think she means like he doesn't hit me. And if a man says that, he's like she hasn't slept with a lot of people. You know what I mean?
Starting point is 00:32:36 Oh, really? I think there's a, I think the difference in it is so gendered. I think high value man means. wealthy. Really? But then high value woman means like Madonna. Like the Madonna archetype.
Starting point is 00:32:51 Yeah. Or Charlotte. Charlotte. The Virgin Horde dichotomy. Yes. I've never considered dating a man for money. Yeah, because you're a man. Yeah.
Starting point is 00:32:59 But I do date men. But the highest earning couples, like statistically are men to gay men. Of course. Together, obviously. Makes so much sense. Well, and there's the, you know, a lot of gay guys have that, that, that, thing that people who like they have that ambition that you only get from being bullied when you're like 13 a lot of gay guys have that so you get two of them together and just who knows
Starting point is 00:33:19 what they go off yeah they go off they get active they get active in a real way in the delta lounge okay um yeah yeah i do you want a rich man not inherently i want a cerebral man i don't care if he's short i don't care if he's rich or poor i just want someone who i will learn with every day of my life and hopefully laugh with every day of my life yeah but not like a comedian. Like, I just want someone who's well-rounded and thoughtful. Yeah. Yeah.
Starting point is 00:33:46 So hard. Yeah. That's so hard. I want a genius. You want a genius. Yeah. It's like, okay, let me go to Apple. Like, what do you, you know, how do you find that?
Starting point is 00:33:53 Yeah. I'm like trying to think. I want to find this guy for you. Where would we find him? I guess maybe, well, you know what? I actually last night I went to first Saturdays at the Brooklyn Museum, which I always try to go to. Everyone there is so hot and cool.
Starting point is 00:34:05 Oh, really? Oh, my. Oh, my. Have you been? No. Oh, my God. Everyone there is so hot and cool. it's insane.
Starting point is 00:34:10 Everyone you pass, you're like, how are you this gorgeous? Oh, really? Yes. And you're, I'm like not looking now. I know. I wasn't there looking. I'm all good on that. Yeah, you're happily betrothed.
Starting point is 00:34:20 Yeah, I'm good on that. But I wasn't there looking. But if I was, oh my God. Yeah, yeah. Jeez, it's really cool. And there's people are dancing and they put on their best outfits. And it's like, what is this? First Saturdays at the Brooklyn Museum.
Starting point is 00:34:31 Shout out to the Brooklyn Museum. I am a member. You should be getting a free membership after this. I should, will you guys please. My membership is up in like January. Brooklyn Museum, please. renew for free because I'm doing this. Did you see the Dave Bowie exhibit?
Starting point is 00:34:43 No, no. There's a really a good one on doors right now, though, which I know sounds insane, but it's like a video of a montage of a bunch of doors opening and closing your films. It's really cool. But first Saturdays at the Brooklyn Museum, they have a DJ in the rotunda, and it's like a big dance floor. During the day. No, night.
Starting point is 00:34:59 Oh, we got it. Starts at like 530 or 6. And it gets sexy? Oh, it gets sexy. And it's intergenerational, too. There's like, last night I watched like this very old woman, like a salsa dancing with a bunch of young men. but just being silly.
Starting point is 00:35:11 It was really cute. And then they have like vendors in there as well, food and drink and like Cute. Like local made jewelry and candles and stuff. Wow. And then the exhibits are open. Oh, wow. And on the first four, they have live music, like usually a band or a choir or something.
Starting point is 00:35:24 Are you going to go in September? I want to go with you. Let's go. Yeah. I would love to. That sounds fun. Yeah. I should be in town.
Starting point is 00:35:30 We really should. Okay, cool. I like to go to museums for the cultural experience. Yeah. Yeah. Let's go. Also, we'll find you. We'll find you a partner.
Starting point is 00:35:36 No, I don't, I'm not looking for one. Okay. well if it happens it happens yes exactly i can't help it's like it's like a parent trap where you're like if they happen to get back together yeah it's a side effect of the evening maybe not the main point yeah yeah well and then we have to go get i go i always get dinner at a place nearby oh which where do you go i can't tell the cameras because it's my secret for us okay got it but when the cameras aren't rolling i'll tell you where we're going to dinner after okay perfect perfect i love it and you're going to love it i'm moving to brooklyn are you yeah i am oh my god i know and stop the presses this is
Starting point is 00:36:08 This is a scoop. This is a huge for the culture. Scoop alert. Scoop alert. Oh my God. What has inspired? I used to live in Brooklyn. I used to live in Bushwick.
Starting point is 00:36:14 Yes. And then I moved to Manhattan. And now I'm moving back to Brooklyn. Are you buying? No. Okay. No. I'm a renter in New York.
Starting point is 00:36:20 We had talked about it for a second and maybe you'd buy. And we were looking and I was like, these places all seem like I don't want you to buy them. Not at the current interest rates. You know. You know, let's not even give. That's what I'm saying. Let's not even get into that. Yeah.
Starting point is 00:36:31 I can't wait to have you out there. And it'll be so fun. I'm excited to hang out with young people again. We're going to have a blast. The young people are in Brooklyn. I know. Well, whenever I come here, it's like a homecoming. I know.
Starting point is 00:36:41 Yes. You're back. The queen has returned. Exactly. Versus in New York City that's like, move, you know. Truly. Yeah. How did you, okay, so you come to New York, you start doing comedy, the show goes well, all
Starting point is 00:36:52 that stuff. It doesn't go well initially or for years at a time. Really? Yeah, of course. Oh, wow. I didn't realize that. It's a long and grueling process. Yeah.
Starting point is 00:37:00 The creative process. Yeah. Yeah. A failure in. Negative dollars. Failure in negative dollars. And then one day, it all turns. Yeah.
Starting point is 00:37:08 I feel like that happened with you with your podcast. You said you had had one before, and it was sort of into the ether and gone. And then you started so true. Yeah. And then it took off like wildfire. Yeah. And became one of the stickiest pieces of media on the internet. I don't really know what happened was so true.
Starting point is 00:37:26 I think you came into your own. I got into your bag. I think I took some time and I think doing my own thing. Like I did. I took my time. I, like, did a bunch of other people's shows. I think I began to understand the format. And I really just, like, stopped doing everything else on the internet.
Starting point is 00:37:40 Yeah, exactly. I think that was the thing is, I was like, this is what I do. Yeah. And I think that really helped. Were you, I, what were you doing before in the internet? Nothing for a while. I mean, I had started, I really kind of blew up doing, like, the front-facing character videos on Twitter, throwback.
Starting point is 00:37:55 Like, what was the character that was the most breakout? Oh, I did, for sure, the one. The one that really, like, I went from having, like, 3,000 followers. on Twitter to having like $120,000 overnight. And it was this character I did that was, not even a character, it was like a scenario. I was like, I was on a break from my day job, and I was like standing on the street,
Starting point is 00:38:14 and I was frustrated with my own behavior in an interaction. Yeah. And I was like, P.O.V., you're talking to a friend who's clearly in the wrong. Yeah. And I was like, no, you're totally right. You're totally right.
Starting point is 00:38:24 And it was like me just being fake. Yeah. And, yeah, I was actually the person on the other end of that call in real life where I was like only calling people that I knew would affirm me even though I knew what was wrong. Of course.
Starting point is 00:38:36 And I was frustrated with myself because I was like, why are you looking for affirmation when you know you're wrong? But it went like really viral and people wrote like a bunch of articles about it and it got retweeted and quote tweeted by all these like huge accounts.
Starting point is 00:38:47 Chrissy Tegan quote tweeted it into the fucking stratosphere. And then yeah, after that it was like a lot of that for a couple years and then kind of every time I would do a character that people liked they would want me to be just that guy. Yeah, of course. do the southern pastor character or only do the whatever and I would be like I hate this I don't
Starting point is 00:39:06 want to just be that guy so I stopped and then I didn't do really anything on the internet for a couple of years this actually ties into something I was going to ask you a second ago which is you started doing comedy you moved to Brooklyn the show the show happens no I lived in Brooklyn before I started doing comedy oh really yeah yeah yeah moved Brooklyn like 2015 yeah and you didn't start for a while yeah wow because I was afraid yeah I was petrified first I was afraid it took me a second but I got there but I wanted to ask how you started getting so into fashion because I feel you're such a fashion girl always I've always love fashion I never had like the money
Starting point is 00:39:39 for it yeah but I've even as a kid I remember watching like Lizzie McGuire and being like she's killing him yeah you know so she's throwing looks no she had like the fuzzy little like bees in her head or like the little like tie-dye crop tops she was giving the chunky sandals yeah and this I you know we grew up in the era of like the fresh prince of ballet or with like Hillary Banks yeah and then Clueless. She was fierce. I feel like I'm doing Hillary Banks drag right now. Down. Yeah. Yeah. And so I just remembered these girls looking so fresh and wanting that and not being able to afford that, but trying my best with like, you know, going to the thrift store and getting the cool little button up, whatever. And then as I've gotten older, I've been lucky enough to get to work in the fashion space. And that's been really fun. That's so cool. Yeah. I just love clothes. What's the most like surreal fashion thing? I would like to know as fashion and otherwise. But what's the most like surreal. real fashion moment you've had.
Starting point is 00:40:33 Yeah, I did a Victoria's Secret campaign, which I think is so funny. Yeah. Yeah, that there's a photo of me in my underwear. Like, that's just so funny to me. And I'll just bring that up in conversations where it's like, sure, you know, whatever. Three things are true. Yeah. Yeah.
Starting point is 00:40:50 Did you do it was like for the magazine or what was the Victoria's Secret thing? It was for a billboard. Did they have a magazine? Am I crazy? They did like a catalog back in the day with like Tyra Banks. And I'm like, I'm truly thinking of like 2005. Yeah, yeah. Those were the days.
Starting point is 00:41:02 It was for a billboard? Yeah, it was. Yeah, exactly. It doesn't come up ever. That's crazy. But it happened. It's just funny. That's really cool.
Starting point is 00:41:09 Yeah. So, okay, so one of those. And then, yeah, in general, like outside of fashion, what have been your like, what have been your like, holy shit moments? You've had a lot of cool shit happen. Can I be honest? Yeah. I don't think of my life in those terms.
Starting point is 00:41:22 What do you mean? You know, so people will be like, oh, this was one of the best years of my life. Yeah. I think every year is the best year of my life. Absolutely. Like, I look forward. So I'm not thinking. I just.
Starting point is 00:41:31 I don't even feel like I've made it, if I'm being honest. Like, I feel like I'm still breaking out. Yeah. And I know that I understand to some people that seems very foreign and strange, but I just feel like I'm always growing. No, I'm with you. I actually agree with you and feel the same way. I think that every year is going to be better than the last.
Starting point is 00:41:46 And it has been so far. And I don't feel that I've made it at all. Yeah. But I still have holy shit moments where I'm like, oh, my God, that's so crazy. Do you not have those? Where you're like, oh, I met this person or I got to do this thing or I, things where you just like kind of in the moment are like, wow, it's crazy. that this is my life.
Starting point is 00:42:02 A hundred of those. Yeah. Like every week. But so you're in so much gratitude that it's hard to pin down. Is that what you think is going on? Yeah. I would say so.
Starting point is 00:42:10 Yeah. Yeah, I'm like, I'm racking my brain for the heroes I've met. And each time I've been like, wow, that's wild. And then you're like, back to work. Yeah, exactly. I know.
Starting point is 00:42:22 But that's probably like, that's probably anti-labour or some bullshit, you know? Like, that's me not appreciating that like, I don't know. But I just, it's hard for me to, live there.
Starting point is 00:42:32 I like to live forward. That's really interesting. One time a pop star told me they love my work. That was major. That's really cool. And you don't want to say who. Nice. I'll tell you later.
Starting point is 00:42:42 I know you will. That's people get really, my favorite thing about podcasting is how mad people get when you say you're going to say something off camera. I'm like, yeah, everything just can't be said. But I get to know. That's the privilege of podcasting is that I get to know later.
Starting point is 00:42:59 Exactly. We just don't want to give the little clickies and clippies you know yeah that's the thing and also you don't sometimes also as a comedian sometimes i feel protective over i say a lot of uh off the wall shit and i know where it comes from and i can defend myself yeah but i sometimes do feel protective of public figures that say nice things to me or whatever that i don't want to i don't want to align them with me yeah that i'm like i don't want to get you in trouble that this week the viral clip is me saying like oh this very famous person is very nice to me and text me that they love my work yeah and then the next week i'm
Starting point is 00:43:31 in hot water for saying something about whatever. Do you get hot and hot water? People are always annoyed with me on the internet, but not in any way that's been very consequential. Interesting. Because it's mostly like a loud, small group of people that are just like really fucking annoying and sensitive. Okay, I have two comments.
Starting point is 00:43:44 To go back to the private moments, I think like, obviously we live in a space where the public is private and the private is also public. Or the public is public and the private is also public because of the ways in which we like share everything. We see a beautiful couple on the train and we're like, look at this. And it goes viral.
Starting point is 00:44:02 So I appreciate, like, private moments. And I want to, I don't know, be protective of that as well. So I agree with you there. And it's less about getting them in trouble and more just about, why can't we just have a moment? You know, like, when you hang out with your friends and you're not taking photos and you're like, that was a great day. I don't have any photos. Like, I kind of appreciate that about life. Absolutely.
Starting point is 00:44:23 Like, yeah. And I also think I don't like, there are a lot of very awesome, cool things that have happened to me or that are in the works or whatever that I just like I don't share about because I'm just like well I don't I've just I've always said that I think when people are killing it they don't need to convince you yeah and I'm like I feel really good about what I'm doing I don't need to like I'm killing it you don't have to convince me I don't need to but it's like yeah I just don't need to share every single cool thing that happens to me because I'm just like that's fine it's it's cool that just I know that or just my inner circle knows that it's cool that like only chance knows certain things about
Starting point is 00:44:55 my life or that only you and I talk about things at lunch you know yes I think there's it's nice to keep some things to yourself in life in general. Of course, of course. So I agree with you. I'm, I'm, but maybe it's because we were born before the internet became so pervasive with smartphones. Do you think? I think that our generation is really, really special
Starting point is 00:45:13 for that. Yeah. Yeah, is that we got to be really proficient at the internet. And I had a Windows 95 Packard Bell when I, you know, when I was like five years old. I'm with the family computer. And I got to learn as it grew, but also had the privilege of understanding a world before you where you had to have you have to print out the maps
Starting point is 00:45:34 to get around where you had to like call and memorize people's house phones and I think that that like I guess we'll call it analog I think it's great to have that transition yeah and it keeps me grounded in our reality yeah yeah I think so too what's so true to use you way okay what's so true I've been thinking about a lot and this is based on the internet so I think my so true how do I'm supposed to say it? Is it like, so true, honey? No. Yeah, yeah, yeah. It's actually called, I think so, honey. We're ripping off lost culture. He says, I think so, honey. I think so, honey. Um, however you are, babe. So I, my so true is that if you yourself have found yourself in like the 10th year of scrolling on a reality stars, like, Facebook page to find out that like a young
Starting point is 00:46:19 Dominican woman with green eyes may be posted something problematic. You've gone too far. Lost the plot. You've lost the plot. Lost the plot. Like, get. onto the internet get onto Reddit and find out where the tapes are and release them there are better things for you to do with your time than to be stalking young adults from Love Island that is my biggest
Starting point is 00:46:38 passion in the world I do not understand the morality that we've placed obviously these people are not perfect nor do I want them to be but they're not running for office so we've placed this morality onto the winners of $50,000 after taxes for being able
Starting point is 00:46:54 to hump the best and we haven't thought we haven't thought about our elected officials who need to also be sort of like policed. Yeah. Yeah. Yeah.
Starting point is 00:47:04 I just think also like I it's not my place in a lot of those cases but I'm like I just I don't really care what people said when they were 17 or 19. If they're demonstrably different people now and I don't know the Love Island situation if it's like that but I'm saying a lot of these things like people will drag up something from so long ago
Starting point is 00:47:21 that I'm like if they're demonstrably different people I think we can have grace and just be like, hey, that was weird. Let's keep that in mind and you be normal now. But the Love Island thing, I don't know anything about it. What happened with this girl? Well, I'm talking about a new girl, the winner who everyone loves and who was like a delight and very funny, but she posted something when she was 14 on Facebook. And she
Starting point is 00:47:43 got in trouble. Yeah. And my thoughts behind that are, wow, I wish you guys would investigate some of the worst people in our country. Yeah. Why don't you investigate hacking the student loan system? You know what I'm saying? Eliminate debt. Really? Because it's like if you guys, you guys are so smart. You're so thoughtful.
Starting point is 00:48:00 You have clearly great politics. Yeah. Why don't you invest that in systems that we can change? Yeah. Do something better. Yeah. The one thing I can speak on is they try to do this a lot with when people have said like the F slur or like homophobic slurs when they were younger. And I'm like, okay, that's the one area I can say definitively shut the fuck up.
Starting point is 00:48:17 I just don't care. Yeah. I just don't care. I'm like, unless they are actively being homophobic or transphobic right now in their adult life, I just don't give a fuck. If they have demonstrably changed and are different people and hang out with queer people, et cetera, I'm like, yeah, I just don't think that's ever going to be helpful to us to us to, I think it's actually, okay, my so true, I think it's antithetical. I think you're actually worse for the cause than they are. You are making us seem like woke scolds who are
Starting point is 00:48:43 unreasonable freaks, and you are doing, you are doing more damage to the cause than they did when they were 13 posting a slur. Not to mention, we don't accept apologies. It's all about accountability, but what is the accountability here? And why are they accountable to you, random Twitter user? Who are you? Why are they not accountable to the people in their life and their actual community? Why do they need to be accountable to you a stranger? I don't get that.
Starting point is 00:49:05 There is that, the idea of being accountable to people who don't know you does not make sense to me. Yeah. You need to be accountable to the people who are in your life and they can let us know if that's happened or not. But I just think the idea that some random jaded fucking ex-user in Florida is who I need to be accountable to as a human being is
Starting point is 00:49:23 nuts. It's just, it's not practical. But I'm on the other side where I'm saying reality stars should be problematic because they're getting boring now. And I want to hear a real housewife say the N-word like Ramona Singer. Just kidding. Just kidding. Guys, don't do it. There's some reality stars watching and getting ideas. Don't do it. They're heading to the keyboard now. Yeah. No, that's, yeah, I do miss. I've said this often about figures like Wendy Williams or Lena Dunham that I'm like, have missed the mark for me many times. have not enjoyed certain things they've done or said
Starting point is 00:49:55 but I miss bravery I miss and I miss fuck ups I miss fuckups I miss I miss a figure like Lena Dunham having one of the biggest shows on TV saying something objectively insane and out of pocket and then a week later being like sorry y'all I was just speaking freely
Starting point is 00:50:10 that was bad and I apologize I miss speaking freely I miss when people would just say shit and see if it resonated I don't like this like media trained boring sanitized like devoid of personality devoid of culture or just serve to you in an algorithm.
Starting point is 00:50:24 I'm bored. I'm bored. I'm bored of it. Zway's bored. I'm bored of it. But I'm not bored with you. No, I'm not bored with you either. I have a segment for you.
Starting point is 00:50:32 Oh, wait. There's segments on this show? Yes. Wow. And this is sometimes one of the most loved and sometimes one of the most hated segments on the show. We'll see how you feel about it. The purpose of this is speed.
Starting point is 00:50:42 Speed? I'm going to read you 15 statements as quickly as I can. Got it. You're going to tell me if you think it's true or false. Got it. And Zway, if you get 10 or more correct, I'm going to give you 50 U.S. dollars okay wow you should give me that regardless i know right we're actually we'll talk off mic um
Starting point is 00:50:56 okay you ready yes the largest ocean in the world is the atlantic ocean no false it's the pacific the human eye can observe 10 million different colors sure true the first movie produced by pixar was toy story no it's true oh whoops dog sweat through glands in their paws i thought they sweat through their tongue false true Phillips academy's newspaper is called the philosopher no false it's be in nice the Caesar solid was invented
Starting point is 00:51:23 in Italy it wasn't invented in Italy it was invented in I don't know Mexico Greenland is the world's
Starting point is 00:51:29 largest island Greenland is the world world's largest island I don't even know what that means
Starting point is 00:51:36 I didn't know countries could be islands Australia is also an island sure is it no it's not
Starting point is 00:51:42 is it an island I don't know false true damn succession ran for five seasons I think four
Starting point is 00:51:48 false it was four the moving sidewalk was invented in 1893. Who knows? Who cares? True?
Starting point is 00:51:56 It's true. The New York City Marathon is the largest marathon in the world. Probably true. True. Robin Theed graduated from DePaul University.
Starting point is 00:52:04 Thedie and Northwestern. False. It was northwestern. Applesoth was the first meal eaten in space. I believe that. True. False.
Starting point is 00:52:11 Beef and liver paste. Ew. It takes two weeks for a sloth to digest a single meal. Two weeks. That's true. That's true.
Starting point is 00:52:17 Two more. The Boston Red Sox have the second most most World Series titles. after the Yankees that's got to be false go Pat's false they're tied for third most the liver is the largest internal organ in the human body no the internal organ liver is that the one that goes like this no the liver that no that's not true it is true I thought the intestines were the large organ uh I don't know what to tell you Zuiway it's just
Starting point is 00:52:40 what it says the liver I just read the paper larger than the intestinal organ in the largest internal organ in the human body so larger than the small intestines define large is it by Is it by surface area? Because I don't think that's true. So I think what you're, yes, I hear you and what you're, because the large intestine when laid out, it would like circle around the globe, but it's so micro thin that as far as like actual like mass that you can like hold in your head. Like you can hold the large intestine.
Starting point is 00:53:06 You might have to give this one to Zway. You can hold the large intestine in your hand and it would take a less space than the But what is large meaning in this context? Is it surface area? Is it weight? We might need to give this one to Zway. Chance hates when his questions get challenged. No, but you actually have to be really specific.
Starting point is 00:53:18 Yeah, you're right. we're giving you that one chance how she do 11 yeah let's go how many was allowed to get wrong you did great you were allowed to get you needed to get 10 or more correct and you got 11 well thank you out of 14 out of 15 after 15 11 out 15 is a really good one by I know but go pats I can't believe the red sox lost go pats yeah for real I'm like a Patriots fan I know that's problematic uh why is it problematic because I love this I don't think it's problematic all I mean right now it kind of sucks well yeah but they're they're in a transition okay they're yeah they're in a building Period.
Starting point is 00:53:49 Justice for Bill Belichick. Justice for Bill Belichick. Free, free the homie, Bill Belichick. You should make merch. Free the homie, Bill Belichick merch would go crazy. And you know it. That'd be insane Zeeway merch, actually. I know, it would.
Starting point is 00:54:03 You should get him on your show. You don't think I want to. Have you tried? Bill Belichick, I am calling on you now. Go on Zeych. That would be so huge for him. He needs it right now. I think that he and I would get along
Starting point is 00:54:14 because I've loved the Patriots since they won the Snow Bowl against the Raiders. Yeah. You need this actually You both need this He needs to be on the show And you need to have him on the show Thank you
Starting point is 00:54:23 I need him to come on Z way bad I love I love Go Pats Seriously go Pats I know but I feel like we are both We have the The you know
Starting point is 00:54:32 What's the way to say it Like the axes of evil In terms of our sports love Yeah Because you like the Chiefs Huge Chiefs fan Yeah And people hate that about me now
Starting point is 00:54:40 It used to be cute And charming when we were bad Now people are like They don't like That I talk about it They don't like a winner They don't like a winner I know
Starting point is 00:54:48 Can we discuss? I mean society hates a winner Two divas Two divas Lots of ops Breaking down the ops They hate to see a winner It's so real
Starting point is 00:54:58 I know it's hard But guess what Winners win Winners win and that's what We're going to continue to do Is there anything you wanted to say That you didn't get to today Watch my interview
Starting point is 00:55:05 Hello Am I talking here Am I talking here Watch my interview Well because it's like Also the wide as cute Because then he could be like doing a little dance
Starting point is 00:55:12 Watch my interview with Jigs Monsoon Watch my interview with Caleb Heron and feel free to watch my other interviews. They're coming out monthly until I do more, but who knows when. I gave you lots of different options. I saw. I moved. I did peace signs.
Starting point is 00:55:27 I did hearts. I just wanted you to have the space to play with it. Thank you. I'm sad that I didn't play with both cameras. Can we retake that? Of course. Okay. And we'll leave both in.
Starting point is 00:55:34 And we'll leave both in. Just for the audience. They like this kind of stuff. Yes, this, yes. Okay. They like when we do multiple takes and leave it in. Really? Do they like when you talk about sex, too?
Starting point is 00:55:41 They like when I talk about sex. I hate talking about sex. They like when I talk about sex. they are they like my ads because my ads are chaos oh what who's your sponsor uh we have all kinds of sponsors actually met a sponsor on the street the other day i was walking down the street in brooklyn and this girl in like sweatpants and no sorry love whoa whoa she was on she was on a walk and uh clearly not putting to run into people walk no offense love and she goes Caleb I sponsor your show that's so cute and i went what and she goes yeah and she told me the brand she works for i don't want to out her but she told me
Starting point is 00:56:09 the brand that she works for it's a big brand that does a lot of podcast ones and she was telling me I actually am a huge fan of your show, and I'm so glad that we get to, like, sponsor you guys. I love that. And I was like, thank you for your service. I love that. Chance thanks you more than anyone. Amen.
Starting point is 00:56:22 Yeah, and by the way, I'm courting sponsors as well. Sponsor. Oh, do you do sponsors right now on the show? Oh, my gosh. People are leaving money on the table. I know. Well, I like having control. Yeah.
Starting point is 00:56:32 Being perfect. Yeah. Oh, I can't. But now I like money. Yeah. It's important to like money sometimes. It's actually politically, it's revolutionary to be a capitalist. I've decided.
Starting point is 00:56:42 Oh. I just made it. I just made an opinion. Yes, yes. Das Kapital. That's what that's about. That's exactly what that's about. I've actually said for a long time
Starting point is 00:56:51 that I remember the day I decided that millionaires aren't the problem. Oh, really? That was a political change for me. And where were you in the tax bracket? I woke up one day and I said, no, it's just billionaires.
Starting point is 00:57:02 It can only be billionaires. Let me get this money. Yeah, that is so funny. No, I do. The sponsors, God, we love them. We appreciate them. But I read the ads. I read the ads in a silly way, Zway.
Starting point is 00:57:12 And that's just who I am. Oh, you do. You go like, Ooh, you got to buy Casper mattress. That's exactly what I do. Yeah, yeah, yeah. You actually, now I can't do that anymore because you nailed it so hard. No, I'll just, like, mess up and keep it in.
Starting point is 00:57:23 I'll just be silly about them. Some people like it. Some people like the way I do ads. So if you start doing ads, maybe we could have a summit about it. Oh, yes. An ad summit. Ad summit. Caleb and Zeeway ad summit.
Starting point is 00:57:33 Oh, my, honestly, that's our Los Cultures is. Ad week. Yeah. I think so, brand. Yeah. Brand, I think so. I'm going to start ripping off Los Colch. Wait, that's so funny.
Starting point is 00:57:42 Have you been on Lost Colch? I have, of course. I did it like in 2020. I haven't been back since. They've never had me on. Oh, they haven't? No. I think there's a deep fear that we would slay too hard.
Starting point is 00:57:51 I think so. I think it would be the internet would break. Yeah, I do love both them though. And I love their categories that they do for the cultural awards. I know. They're so chic. They're so fucking funny. Those two.
Starting point is 00:58:02 They're really funny. Yeah. I met them years and years ago because I interned at this Comedy Central, like rotational program with this woman named Sudie Green who went to college. with them and so I met them when I was an intern in like 2013 yeah whoa long time ago I know holy god yeah I love sudie she's so funny she's so funny she can write she can write and you know what that's a dying art form yes being able to actually write oh wow uh Zway where can people find you um at Zway on Zway at Zway on Zway on Zway at Zway on YouTube I'm not on Twitter on YouTube
Starting point is 00:58:36 Instagram TikTok substack substack you're really going in on I I'm bullish on subsection I'm bullish on sub-sac right now. I think it's important to have a following that is independent of an algorithm. Yeah. I think that's really smart. Zeeway, thanks so much being on. We just love you. Thank you. Caleb. We did it. That was a HeadGum podcast.
Starting point is 00:58:57 Hey, I'm Gareth Reynolds, and I have a new podcast on HeadGum called Next We Have. Now, this show is for people with short attention spans, which is everyone. I mean, you're probably trying to skip this ad right now, but don't, because you now legally have to listen to the show. That's how law works. Next we have is very simply.
Starting point is 00:59:13 Each episode has three short segments. For instance, Lisa Gilroy and I write insane revenge, Yelp reviews for callers who had bad experiences with a business. The Do Boys play a game called Meal or No Meal, and Steph Tolliv and I go head to head on a thought-provoking game called Guess That Sound. The show is as dumb as it sounds, and we probably have more fun than we should. But it's a great time, and you should listen or watch new episodes of next we have every Thursday on YouTube or your favorite podcast app.
Starting point is 00:59:41 Hello, I'm Joe Mercosuracy And I'm Russell Daniels And we're the co-hosts of The Downside Now on Headgum We are a safe place to complain Be negative, Kvetch We don't like toxic positivity No
Starting point is 00:59:56 Because it's toxic We're not gonna sit there going Hey, look on the bright side Enough on the bright side That's all anyone's talking about these days The fucking bright side So tune in to some of your favorite comedians Some celebrities
Starting point is 01:00:09 Like Caleb Huron Brennan Lee Mulligan, Alana Glazer, Busy Phillips, and Dan Soder. We let them come on, and we let them share what shitty about their life. We look at the things that seem nice on the surface and we go, why is it shitty underneath? It's a fun time, but it's a place you're going to listen
Starting point is 01:00:27 and go, oh, thank God I'm not any of those three people on that show right now. Yeah. I feel better about my life. So please subscribe to us on Spotify, Apple Podcasts, PocketCast, or watch us on YouTube. New episodes every Tuesday. This is the downside.

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.