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A
This is a headgum podcast.
B
That script was a perfect example of the types of films and television that I'm trying to get made. It was so funny, so hilarious, but so true. Nice. Nice. Sweet.
A
We'll be clipping that. Lily, hi.
B
Hi, Caleb.
A
I'm so glad that we're here. Yay.
B
Me too.
A
I just love you.
B
I love you too.
A
I'm so excited to have you here. I. We have been friends for a while now.
B
Yes. And work in progress.
A
Days back in work in progress. How did you get involved in work in progress? I actually don't know if I know that. This is the Showtime show with Abby McEnany.
B
Yes.
A
Yeah.
B
Well, Abby lives seven minutes from my house.
A
Yeah.
B
And we're old friends. After I transitioned, I went through this searching phase where I was not sure I wanted to be in the movie business anymore. And I started. I struck on this idea to do stand up comedy.
A
I didn't know this, but I'm loving it.
B
I took comedy classes when I was in college and I liked it. And it was, I thought it was like, I think it was like part and parcel of like the trans experience where you have to, you know, build up that callus of being out in the public. And so I started doing this and because Abby worked in Second City and IO theater here, I went and had coffee with her because she was friends with my partner Mickey, who, you know, and we went and had coffee and, you know, I started asking her about doing stand up and stuff and she didn't know who I was. And then we, you know, we started, we started hanging out and we became super fast friends. And you know, some years after that, like a couple years, she started working on this show with her friend, the co creator, Tim, and they cooked up the. Basically the open of the show where the therapist dies and they shot it. And I said, oh my God, this is brilliant. I sent it around and I was still like, not sure what I wanted to do. I was painting at that point. I left comedy for a second and I started painting and really enjoying myself. And then Abby and Tim made the pilot of this show. So a year after I had sent it out, the little teaser, they made the pilot, came back to me and said, do you want to executive produce this? And I said, yeah, executive producer. You don't have to do anything. And. And I hopped on. It was like the first thing that brought me back to film and television. So.
A
Yeah.
B
Yeah.
A
That's so interesting.
B
Yeah.
A
How. I'm curious, like when you transitioned.
B
Yes.
A
And that big feeling of, like, I don't really know if I want to do this anymore.
B
Yes.
A
What made you decide to keep doing it and how. What were. What were those feelings?
B
I guess I was. I walked away because I felt like I was. I wasn't. There was a grind. Number one, I was. I had made three things back to back to back. So posting one and prepping the other at the same time. So we made Cloud Atlas and then Jupiter Ascending and then the first season of Sensate. So right in the middle there, my life was falling apart. And my partner, my wife, who I had been married to for many, many years, like, almost 20 years, she was like, I think we're breaking up. I said, okay, I think I'm going to go on hormones. She said, good, and then started hormones on Sensate. And I was. I was exhausted and extreme, like, emotionally just down to a nub. And I came out of that experience, and I was just like, I didn't. The stuff that we were making was fun and cool, but it wasn't like I had lost a little artistic spark for myself. And so I, like, had started hormones on Sense8 and then got to post, came out to everybody on post, started living full time as my, you know, as a woman, trans woman, and then kind of went through this, like, beta stage. And I would be in my little. My little gerbil run where I could, like, you know, go to work and then get in my hamster habit trail, go to my home, and then go back to work. And it was like this little thing that I was like, you know, doing a test run of my transness and came out of it. And I was like. I was like, okay, now I can go do the next season of Sensate. But there was no mana left. I didn't have. I didn't have any juice. And so I was like, you know what? I think I'm gonna stay so long. And I walked away. And it was like, it was a good time for me because my mom and dad's health were declining. I got to. I started painting with my mom, who's a painter, going to her art class, and then when she couldn't do that anymore, I would go and just bring her to the studio and we. I would paint with her and my aunt, and we'd have this, like, fun, like, Thursday where we just paint all day. And, you know, I started. Yeah, I started. It started sparking something for me as an artist again, and I began to enjoy creating. And so work in progress came in, like, right as my mom and dad, they died. This story is taking a turn. It's also very long. So mom and dad, we're here for it. Yeah. My mom and dad both died. They both decided that they would go off their meds simultaneously. They got the kids together and said, hey, your mother and I decided that we would stop taking our meds. And we were all like, what? And we were like, how can we help? And so that was, like, in the spring, by the fall, they both died. They died, like, five weeks apart. And then Work in Progress was, like, kind of like tumbling around in there, and. And they brought Work in Progress to Sundance. They got some buzz. And then off of that, I went with Tim and Abby to LA in January, had three meetings. Showtime bought it, and by that spring, we were writing the show. Being on that show was a. Was a revelation for me because the thing that, like, I was missing, like, that had kind of been fulfilled for me as an artist was that I had. I had, like, satisfied a lot of stuff for myself as an artist. But getting to work on that show and, like, hiring the people that we hired, you know, queers and trans people and, like, the crew looked like Chicago. It was, like, completely diverse, and the show was too. And I was like, okay, there's something that's left for me to do in this business, and that is to try and, like, you know, bring underrepresented voices to the forefront and get them, you know, and positions that I was typically in. And so I said, you know, I. The. The. I've been doing that for the last four years trying to do that. Yeah, you might want to edit that one down a little bit. Not sure where you're gonna cut, but.
A
We'Re gonna put some air into it, actually. We're gonna find a way to nice it. Yeah, it makes total sense to me. And I really. I was a fan of your work, obviously, because I'm a living, breathing person. And then I really fell in love with you working on Work in Progress because of how warm and generous you are. Right when I'm saying something earnest. You're gonna open the sparkling water.
B
I couldn't.
A
Really silently. You really did. And I saw the care and the carefulness, but I. Yeah, you were so warm and so generous. And you and Abby and everybody who worked on that gave me two of my first shots at TV. And Abby McEnany, who is so brilliant, is somebody who I met because I was working in the box office at IO in exchange for free classes and no money. And Abby was just so warm and Lovely. And you really got to know what performers in that building were playing at being warm and lovely and who it really was.
B
Yes.
A
And luckily, Chicago comedy scene in general, it was mostly people who really were and are. And Abby invited me to her birthday party and as like, an intern at the box office. And I felt, like, so excited that someone who was, like, so talented and so kind of like a. I mean, Abby was and is like a stalwart, like a pillar of the scene. And I feel like, oh, my God, I'm invited to her birthday party. That's crazy.
B
Those parties were bonkers.
A
They're crazy. And it's like, it's such a testament to what kind of person Abby is that it would be like. It would be like some random intern from the box office that half the people didn't know, be friends that she knew her whole life. And then it would be like her mailman.
B
Yeah.
A
Like, it would be the most random UPS guy.
B
Yes.
A
Like, beautiful. And so, yeah, working on Work in Progress. I was so excited to go and do it in general. But then when I found out you were going to be involved and I got to meet you, and then we. I brought Trash Mountain to you and was like, would you ever consider slumming it and working on this. This movie that I wrote about my dad dying? And we just finished making it and we really only got it made. Not only, but a huge part of the reason we got it made is because you believed in it and championed it. And. Yeah, I'm. It's funny because I have gotten a lot of DMs about. Like, you were on as the director originally. Yes. And then things. We lost Windows and things shifted and it was circumstances and you executive produced the film. Thank God. And. Yeah, I'm curious. I'm curious how you felt about the script and what you thought of the movie and how it feels now that it's over after, like, years of us trying to get it made. How was it for you?
B
I mean, that script was a perfect example of the types of films and television that I'm trying to get made. It was so funny, so hilarious, but so true. Nice. Nice. Sweet.
A
We'll be clipping that.
B
It just like it had so much heart in it, and I could tell that it came from this absolutely hard and real place. So immediately I was drawn to it. And, you know, getting to work with you and Ruby on the script was. Was just. Was just a blast. I'm curious. I haven't read, like, the latest draft, so I don't know what the shooting draft is like. But every. What I appreciated about the writing process, like, even after I kind of, like, sort of took a step back, was seeing how you and Ruby kept on making these, like, improvements in the script. And it's. It's something that I think, like, a lot of writers don't understand that, like, once you write something, that writing is rewriting.
A
Yeah.
B
That you can constantly make something better. And you will continue to write, actually, now that it's shot, because you will write new lines that have to fit into people's mouths and, like, you know, trim up ADR and stuff. So it's not done until it's super done. But, yeah, I can't wait to see it. You know, I love Chris Wray so much. I think she's wonderful. And I was sure that she could make something that not just bring the page to the screen, but bring all that heart that was in the script initially.
A
Yeah. She directed the hell out of it. We got so lucky. Andy, the dp, like, everybody who worked on it, it was so. It's just so good at what they do. I feel like we. I feel like we pulled off, like, a heist or something.
B
Yeah.
A
It's interesting. I feel a bit of. I'm so excited. I'm so glad that it's done. It was so difficult and fun and awesome and exciting and cool. And also, I have this weird kind of, like, anxiety about. Not anxiety, but this interesting feeling of, like, it was based on my experience of my dad dying. And there are still many kernels of truth in there, but, like, I actually never wanted the character to be called Caleb because I was like, I know we're gonna change things. I know that making a movie is negotiating and, you know, like, there are characters that are invented for the movie, and there are conflicts that are invented. And I say things to my grandma as this character that I would. In ways I would never speak to my grandmother, you know, and we created conflict, and we added things that need to happen to make a movie compelling, because you can't just meander through a personal experience you had for a whole film. I guess. I mean, in some ways we do, but, yeah, there are things we changed about it to make it a better script. And I really believe in the changes we made. But now I. It was interesting in writing it. I only ever felt like we're making a great movie inspired by something I went through. And I feel really passionate about all the changes we're making. And I fought for the things that I felt had to stay And I did other things that I felt needed to happen to make it an interesting movie. And then while we were filming it, I had this weird sensation several times when I had to film some of these scenes of being, like, for the first time, thinking about what the audience is going to think of me. And I try not to create from that place ever and not think about, like, what is the perception of me as a person going to be when I say this? Because that's not a good place to create from. But for the first time, I got real anxiety filming this movie about, like, oh, God, are people gonna think that that's how I talk to my family or how I. How I acted when I was grieving my dad. In some places that is true, and then other places it's fabricated. It's an interesting thing because it was the most challenging role I've ever done. Not only because I was in every scene of the movie, which is probably a choice I won't make again. I think this will be the last time I do that. But not only that, like, the rigor of it, but then also this interesting thing of, like, when I've performed characters in the past, it's never really mattered whether I, Caleb, would do that because I'm playing a character. But then when the press around it or the idea around it is that this guy is me, all of a sudden I'm having these conflicts. Do you know what I mean?
B
Yes. Well, I mean, like, I don't know how to address. I don't know how to address that feeling. I do know that when I write nowadays, I try to write from a place of a very conscious place. So, like, I am specifically looking for my writing to be of service to me. Right? And specifically, like, I will look for ways to, you know, heal holes in my heart. And you can do that unabashedly through, you know, fictitious characters. You can draw on stuff. There's this moment in the second season in work in progress where me and Abby have this commonality that, you know, both of our moms are the dead mom club. And, like, her character in the story is going through all of this, carrying a lot of grief about her mom and has her ashes on this shelf, and she will carry the ashes around in the show a little bit. And because my mom had just died, I was like, all of those scenes were very intense but purposeful to write. And so there's this scene where she's going through it. It's like, you know, we're in the height of COVID The height of the, the protests and the murder of George, Floyd and Abby character is like, you know, completely spiraling down this, you know, doom chasm. And there's a painting that my mom did that I'm using for set dressing. So there's this moment where it's like the room is just filled with all of this grief. And some of it is real grief and some of it is, you know, grief expressed through storytelling. And so I would never want to like, write something that isn't coming for, from that kind of perspective that it's not like I want my work to have a level, level of catharsis for myself. And so to do that I need to put myself into my. And you know, if people want to read into it, you know, you just gotta go, well, do whatever you want. You have to let go of your work too. You gotta let go. You know, people are gonna interpret it however they interpret it. You know, it's like I look at all of the crazy mutant theories around, like the Matrix films and what the, the crazy ideologies that those films create, helped create, and I'm just like, what are you, what are you doing? No, that's wrong.
A
Yeah.
B
But I, I have to, I have to let it go to some extent or else I am engaging in. You're never going to be able to make absolutely every single person believe what you initially intended. So I don't know.
A
I know. And I do actually know that at this point in my career, which is nice. It was just the first time, I think I've ever had that much trouble with it, that I know that once you do something, once you put something out, it's not yours anymore. It belongs to everyone else. And I feel so sacred about the time in a creative process when something is yours.
B
Sure.
A
When it's just yours and you've created it and it's just with you that then when you open it up, it becomes everyone else's. It was a very interesting creative process to for the first time like grapple with that in any meaningful way. I did. I was going to ask you, I'm glad you brought it up, about the Matrix and the specific, like how you've dealt with. Yeah. These loser freaks like co opting this thing to make it something. Yeah. That just must be so crazy for you to be like, why are members of the Trump administration like talking about the Matrix like it was made for them and their ideology when it came from you and you're not. That's not you at all. I mean, what do you even do with that, other than love it. I know you voted for him.
B
I did. Twice.
A
Yeah.
B
Going to vote for him next time, too. I don't know. I don't. I don't. I mean, yeah, I. I have no idea. I have no idea. You. When you make stuff, you want your art. Let me back up. I think it's a mistake to want your art to let me back up. I don't make stuff anymore with the idea that I wanted to reach as many people as possible. I make. To make right. It's like you just finished Trash Mountain. That experience is the reason you're there, not what comes after. And so as an artist, I try to be as present as possible. Now, this isn't what I always did. It's taken me a while to get to this point of view. I want to be present and relish every single day of the making that I have. Because the beauty of filmmaking is that you get to come together in this community, all these different artists, and bring this thing that is in your brain into this new form. And that new form is a collective art piece. And so when I think about, like, the Matrix and, you know, this, you know, success that it had, I mean, that's something that I think like artists or filmmakers or any. Any artist really, they place too much emphasis on those kinds of successes. And I don't think that that's necessarily a success. That's like, I don't know how the, okay, right wing ideology appropriates absolutely everything. They appropriate left wing. Points of view and they mutate them for their own. For their own propaganda, for their own to obfuscate what the real message is. This is what fascism does. And so, of course that's going to happen. They do it with absolutely everything they do it with, you know, I mean, make America healthy again is like. It's like, are you. What is going on? This idea of, you know, putting scientific gender in our. In our. In the words of our. I mean, where. Where are they putting this? There. There is only two biological genders. It's. It's this. They're calling it science, but it is not science. And that is what fascism does. It takes these things, these ideas that are generally acknowledged as questions or investigations or truisms about humanity and life, and they turn them to something else so that they are. They remove the weight of what those things represent.
A
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B
Yeah, that was a classic rambler, but.
A
I don't know what you're talking about. I'm having a nice time over here. You said something to me that I have thought about a lot since you said it during the initial stages of us working on Trash Mountain together. That kind of recontextualized the film for me and, or added context to the film for me and also that I've thought so much about in. In relation to my work since then that you said like, oh, on some level this movie is about the way that queerness springs up everywhere and takes up purchase in any place, even in the most hostile environments. And specifically the way you said that queerness takes up purchase in hostile environments. And I hadn't thought about my work being about that really in those terms. And I. But it's so obviously true and so like. So like one of my favorite things about us, you know, and so like what I love about us and what I feel proud of about us and why I feel connected to us, all of us, any of us. And I just love that. And I think about it all the time and I think it's such an interesting time to put it lightly for queer artists to decide what we're doing right now and why we're doing all of this. And I wonder if you have any as an artist that has benefited from your words and thoughts and generosity. I'm wondering if you have anything to say to the like, you know, 22 year old painter or the 19 year old filmmaker or listening to this about the purpose of making art right now and how to approach it when things are so bleak.
B
Yeah, they sure are. They sure are. I mean, one thing for sure that I always say is that we are in this period of unmaking. And I think that the. For me, I feel like the only way to counteract that is to make. You have to fill up that black hole, that widening void that is being fostered and is festering in front of all of us is to make shit. Make your art. And because I think queerness for me is about joy. And so queer artists in their making, that is really about those kinds of stories, those kinds of objects, you know, I think that kind of stuff is so effective because it gives us. Like, I've been. During this past year, I've been trying to. I've been doing this trans Mana refill event where I just. I get together all of every single trans person that I know, and that group is slowly expanding, and we just go bowling or we go see a movie together, or we just have drinks. And there's something about just being in that space together that pulls you away from this portal into hell that we're all, like, looking at constantly. And it affirms each other bodily. We get to see each other. And, like, when you talk about, you know, finding purchase, I find purchase when I see another trans person alive and in this world at the same time that I am alive and in this world, and I say, ah, I see you. Here I am. Look at me. I'm here. I'm here. I see you. And so that sort of stuff is amplified in our art and our stories, and it is a way to send out these signals to each other that we're not going any. We're not fucking going anywhere. And you can unmake as much as you want, but our joy is going to. Those voids are nothing compared to what we bring to the table here.
A
Yeah.
B
Keep making art. Young queers.
A
Young queers, make some art.
B
Yeah.
A
Young queers, make some art, please. Yes. Yeah. I. I do feel so inspired by queerness, especially right now. And I think, yeah, I feel maybe naively. We talk all the time in the tenant union about the belief that things can and will get better. And I do think that it's radical to have hope, and I really do. Even though it's really fucking hard, I really do think that we will win. Overall, I don't know what path that takes. And that's not to diminish at all how hard and awful it might be on the way there. I'm not dumb, but I do, yeah, I do have hope that things will get better. And if I didn't, I don't know that I could create anything. And, yeah, I. I just Want our art so badly. And I hate that we have such a commerce driven, like venture capital affected and mimicking industry right now that there's all this talk of, like a contraction. But I'm like, there's no contraction. They're making the money they've always been making. They're just not using it to pay people for their art or make things. I feel. I do feel discouraged by that. But I think, if anything, and making Trash Mountain really lit me up in a way that I'm like, this is the kind of stuff I want to be making. I actually don't personally have a desire to be making 75, 80 million, $120 million films. I really do want to be making this kind of stuff. I do want to make, like, sub five indies. I do think that at this moment is where the most exciting storytelling is taking place from my perspective. But I'm curious, how has transness affected, like, coming out and living as a trans woman? Has it changed the way that you look at storytelling and the way you approach making art?
B
Yeah, for sure, for sure. I mean, you know, like, I look back, I say this thing where I look back on all of my previous work, and I see it because I'm, like, looking at it from this higher place. I see. I see it from. It's just like, creates this different perspective from my own. This point of view up here. And I can see, like, bound. The first shot of the movie is a closet. And it's like, okay, looks like we're gonna be working on some stuff. And so it starts there, and then, you know, you go through Matrix and it's about, you know, liberation and. Identity and, yeah, like, freedom and like, I mean, all of those things are so definitely working on. This is a thing that's cool about making art, is that you can will things into being that you need to see in the world to help pull yourself along. So, like, a lot of the things that me and Lana were also writing about was love. That we needed to create stories that. That. That gave us a grounding to see that love was possible. Like, as a trans person. The dark question that every trans person, like, has or not everybody. The dark question that I had as a trans person was who will ever. Who will ever love this? And it just. It's just. It's like an Edgar Allan Poe story where you're just, like, cementing yourself up in the closet longer and longer.
A
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B
Here'S me and Lana. And we're like, this story is about love. Love is possible. These two people found each other. Corky and Violet, Neo and Trinity. And it gave us this. It gave us this reminder that there was a future for us. And so now, I mean, all of that is great. I wouldn't not make a story or put that in a story because we all need to be reminded that there is love out there, there is love in the world. And it doesn't have to be like a romantic love of between two people. It can be like just fucking love. And. But I think I don't, like, have. The things that I'm working on in my subconscious are probably a little bit different than the things that I was working on with my subconscious, you know, 20 years ago. Now I'm like. I think about, like, I just wrote this script with Mickey, and it was just a way for us to process all of our trans rage that we have, you know, about the world. And so we. Mickey's. He was. This project started before even work in progress for me where he was like, he wanted to make something with me. And he was like, I was completely done with movies. And he was like, come on, we can. We can make a. We can make a story and put some, you know, kick ass trans people in it and, you know, they can kick a lot of ass. And I was like, well, I mean, that does sound kind of good when.
A
You put it like that. Yeah.
B
And so, you know, this is in 2017. And we were. It was. Everything was horrible. And we started right. We had. We had no idea what the story was. We knew how it started, and we wrote about 30 pages or so and it became this, like, this way to just like, ah, I'm purging all this rage and horror out of the world onto this page. And. And it was great. And then work in progress came along and I put it down. Mom and dad, endless horrors. Fast forward to 2021. And the world is, like, way shittier for trans people. So we picked up the script again and started writing again. And I was like, oh, this is good. I'm gonna. Oh, yeah. And then this happens. And so, like, for me, that kind of catharsis that I got out of. Fighting back about completely creating caricature buffoons of the right wing to create an idealized family, a network, a Weather Underground of trans people coming together and supporting each other and holding each other up, trying to create a story that is the best of us. That was like. That was. It gave me a new Way to like think about what I want to put on the page now. And so I try to like, I try to be a bit more conscious as opposed to unconscious when I'm making work.
A
I would categorize you in so many ways, but maybe my favorite one is Midwest legend. I'm just like, this is a Midwest legend, dude. Why you live in Chicago?
B
I do.
A
How come you're not off in LA or New York or somewhere? Why are you in the Midwest and how does the Midwest affect your work?
B
I don't know. I spent some time in LA and I grew to love. Took a little while. There's something about Chicago whenever I come back. It's always, I feel. Because it's been here longer. I feel like Chicago, it just like it's got so much history. There's so many people that have come through this town. I mean obviously there's like good and bad things about Chicago. But the best of what Chicago is, I think is that's the reason I'm here. I mean, I think also because I was pretty young. As we got started in this business, going to LA as a young person, I feel like the industry feels absolutely everywhere. And it really did back then because this is, you know, the mid-90s and so this is like the height of like the film industry. There is, you know, it's before like there's been all of these like mergers happening. I mean it was always box office based back then, but you still were feeling like you were walking amongst giants. And it was just, the industry was just felt like it was everywhere. I mean it was everywhere because when we would go, we would be like hanging out with, you know, muckety mucks and stuff and they would just take us to their muckety muck places. And so you didn't get a chance to see anything outside of that. And to be that, to feel that much saturation of the business kind of made me scared. And so I didn't feel that at all in Chicago. I could walk around in Chicago and be just another Chicagoan anonymous. And so I always came back here. I mean, my mom and dad were from Chicago, my sisters were here and I don't know. It's beautiful. I like the seasons. There's catharsis in the seasons.
A
Seasons is a big one. Yeah, that was my biggest thing in la. I like LA a lot. I had a lot of fun living there. I just felt like time was like escaping me all the time because nothing changes.
B
Yeah.
A
And I was just like, oh fuck, it's Christmas. And it doesn't feel like it at all or shit. I've been here for four years. What happened? Yeah, like, you just feel like you're in, like a. I love la. There's so many beautiful things about la. It did not, in the time I was there, feel like the industry was everywhere. I felt like the industry was nowhere. And it felt like, why are we all living here? To work in this industry, but there's no work happening. But, yeah, the seasons thing was huge. I was just like, God, I can't believe weather's the same every day.
B
Yeah, you get autumn, fall, it gets cold and then it gets really, really cold. And then you go in your house and you make stew and you warm up your house by. Oh, my God, we're going through the polar vortex. I gotta cook something, make some banana bread and make that in the morning, and then in the evening, make some chicken stew or something like that, you know, a roast chicken, you know, and it, like, warms up your house and your house smells good and. Yeah. And then you get to spring and the buds start coming out and everybody's, like, running around in shorts and it's 40 degrees. And that's just, you know, you get that, like death and then birth and then life. That cycle is like. It's a microcosm of what it means to be a human being. And I think, like, in la, that it's just different. You don't get that as much. And so, I mean, you get other things, like, you know, fire season and.
A
You know, floods and then just other stuff.
B
Just other stuff.
A
Just other stuff that you get other.
B
Kinds of death and birth and reliable.
A
And I don't know why it's escaping me right now, but there's a poem about spring that I love. Not even a poem. Like a. Maybe I would call it an article. Is it. Who the hell wrote this? Chance. It's called the Common Toad, Like In Praise of the Common Toad or something. And it's not Oscar Wilde. It's like the most obvious. When I hear it, I'm gonna be pissed off.
B
Is it Some Thoughts on the Common.
A
Toad by George Orwell? Yes, of course it's Orwell. Yes. And have you ever read this? I know, it's so great. I love it. Makes me. It really lights up my love for seasons. And there's a piece of it where he's talking about, even if they lock all of us away in prisons for ideas or whatever, they can't take away that when it turns to spring, the birds are still singing and the trees still bloom, and we can still see that. And so there'll be joy regardless. And as much as they'd like to take that, they can't. And it. It's really, really pretty. I'll send it to you. What's inspiring you right now? What's making you want to. What's making you feel good and excited and creative?
B
Well, Thanksgiving is coming up.
A
Yeah.
B
So I'm. I'm. It's. I'm hosting.
A
You are?
B
I am hosting. It's a small group, and I don't have a big house, so the group sort of just fits around my table. So I got nine people, and I'm pulling out all my old recipes. Mom and dad, Thanksgiving was always big in my house growing up. We're good eaters. My grandma was an amazing cook, and so all of those recipes get passed down and shared. This knowledge passed. The sacred knowledge passed to all the family. And so this meal is, like, it's super important, and it takes days to prep and plan it. So I'm in the throes of that cooking, to me, is something that I've really used lately as, like, meditative practice. And, like, so there's something that's healing about it when I make this. I just made this chicken stew for Mickey that he really loves. That is the cook's illustrated chicken stew recipe, and it's called the best chicken stew, and it is a labor of love, but it takes me a good part of the day to make. And so that's what Thanksgiving is. I've started. I've. I've started buying my ingredients. The gravy, Caleb, is just. It's just knockout gravy.
A
Yeah. It's its own dish.
B
What's that?
A
It's.
B
What's that?
A
You told me the other day, you're like, the gravy is its own dish.
B
It's its own dish. You have to make this gravy stock that becomes eventually the gravy, but you need all of the drippings from the. From the turkey to finish it off, to finish it all off. But you make the gravy, like, a day or two in advance, so. Damn.
A
Yeah, I'm. I'm really. I'm jealous of these nine people. They're living. They're living my dream. They're over there. They're over there having this gravy that's been much talked about. Yeah, I love that. So we're inspired by Thanksgiving right now. I feel that I'm excited. My family comes to my house every year now.
B
Oh, Good.
A
And I hope they come on Tuesday.
B
So are you having this in your new house that you just.
A
Yeah. And my new place is bigger, so I have room for everybody to stay because they come. My family used to be. My grandma would host my whole childhood, and we would all go to her house and stay for, like, four days. Like, everyone stays.
B
Yes.
A
We barely leave the house other than to get ingredients or go on walks or whatever. Like, it's just like we're stationed at the house. Everyone's coming on Tuesday. They're staying till Saturday. And then on the night of Thanksgiving is one of my favorite. I love Thanksgiving. It's my favorite holiday of the year. I love the way it started, the politics of it, everything. And I wouldn't change a thing about the origin or the. The ideas, but I love it. I do love it. It's like, just. It's the one holiday that my family has always, like, gotten together for.
B
Yeah.
A
And, yeah, the night of Thanksgiving, it's become this tradition since I've started hosting that, like, a bunch of my friends in Kansas City will come over and we'll, like, play music, have pie, play cards, sit on the porch until, like, 2, 3 in the morning. Gossip. My family is also still there, so it's like. But people just. After they've finished their thing with their family or whatever, they come over to mine and have dessert.
B
Oh, that's so nice.
A
It's the best. And it's my organizer friends, my artist friends, my buddies from college and high school. School. It's like this beautiful tapestry. It's like one night of the year that I really get. Like, the only time I come close to that is if I have a big show.
B
Yeah.
A
There'll be many people from different areas of my life in one room. But Thanksgiving, I. It's like every period of my life, I have somebody there, and it feels so. I just feel so happy.
B
That's nice.
A
I'm excited about it. It's a very special thing. And I. It's like, man, if it only happens one day a year, it's like, that's crazy to think about, like, one day a single year where you get to do that. It's pretty nice. I'm excited about it.
B
I love it.
A
Lily, what's so true to you?
B
Okay. I wasn't sure I could come up with so truism, but then I started, you know, plumbing the depths a little bit.
A
Did a process with your process?
B
Yes. Well, I mean, I guess, like, when I think about art making, it's like, I Don't like to. I don't like to cast aside art of any kind. I think all art making is. I think all making it can be art is art. And if you. Sometimes it's like it's okay or it doesn't speak to me. But I think it's all good. If we're all out there doing stuff, that's great. When I was learning how to be a writer, I read this one, how to Book. And one other piece of advice always stuck to me. It's a very specific thing. And that is. The guy was saying, don't use. Don't put smash cut in your scripts. Don't say smash cut to this. Just write the next scene. It's implied. What are you going to do? Are you going to hit the edit button harder than a normal edit? And that thing stuck with me for forever. And so I've refined that into this other pet peeve that I have that writers will do and that writers will put in their script, though, for a scene direction, they'll put the word beat, and that will be the only sentence in that line. And they'll use it to break up two moments of dialogue. And this. This word beat. I do not like it because I think that it is a. It is a. It is. It's lazy writing. There's no. You could write anything you can give. There's so many people that read a script and are using that script to help bring the film to its final form. You know, your production designer, your sound designer, your dp, your actors. And so the word beat is a way for the writer or director to put in a placeholder between two characters that doesn't tell anybody anything about what's going on. And I think it is like a very ungenerous way for a writer to tell their story.
A
Yeah, I like that. I like that. That's a good. So true to me. That's a good. So truism to me. Yeah, I like that. I also, I. It falls in line with a similar thing that I look out for when I'm reading scripts now of if someone has written too much of the acting for me that they. They're writing like they go so deep into it that I'm like, are you planning on not hiring an actor you trust? Like, they'll write such granular little things that I'm like, like what? Like they'll do. Like, they'll be like, he. He. Like he takes a pause, looks into her eyes, cocks his head to the right, and I'm like, well, like, did. There are times when that level of detail is necessary because you're setting up something so specific, but when it's not setting up anything specific and it's just going towards an action you'd like to see.
B
Yeah.
A
It's like. Well, now you're dictating the acting to the actor.
B
Right.
A
It gets to a certain level at a certain point, and it's a hard thing to, like, pin down.
B
Yes.
A
That I'm like, there are times when that's called for, and you can feel it in the scene where it's like, we need to see him look into her eyes because he hasn't done it so far in the scene. Or it's conveying a certain emotion.
B
Yes.
A
That is always necessary.
B
Same with camera moves, too, I think, like, when you're telling the director how to direct.
A
Yes.
B
That's another thing. Push in on this person. It's like, really? Are you gonna. You're really gonna push in?
A
Yeah. No, it's like all the side. It's like, maybe it's just a cut.
B
I can just, like, cut into a punch in.
A
Well, maybe it's a smash cut.
B
Maybe it's a SM whiplash smash cut.
A
Yeah, I love that one. Lily, we have a game for you.
B
A game?
A
Yes. We've played this game with everyone who's ever been on the show.
B
Okay.
A
It's a storied tradition. It's one of the only things we actually. It's funny, when Chance and I were, like, concepting about this podcast, we had so many ideas for segments, and one of the only ones that we have stuck with is this one. Yep. Not one of the only one. Yeah. And people would kill us if we got rid of it. We tried once to maybe not do it on a live show or something, and I mean, the dismay. Yeah. It's a hit. We're so excited to have you play. It's. This is our true or false segment.
B
Oh.
A
I'm going to read you 15 statements.
B
Oh.
A
You're going to tell me as quickly as you can if you think what I just said was true or false.
B
Okay.
A
And there's a prize if you get 10 or more correct. We're going to give you US$50 for gravy.
B
$50 for gravy. That's some walking around money for bread.
A
Okay. You ready?
B
I'll do my best.
A
Okay. The Empire State Building has its own zip code.
B
True.
A
True. Winston Churchill's mother was Irish.
B
False.
A
False. She was American. The shortest war in history lasted 38 minutes.
B
True.
A
True. Speed Racer debuted in Japan in 1966.
B
True.
A
It's true. Amazon's Alexa is named for a French queen.
B
False.
A
False. It's named after the Library of Alexandria. You're killing this. Okay, Woodrow, would I get the 50 bucks yet?
B
I want that $50.
A
Woodrow Wilson's face was on the $100,000 bill. False. True. Chicago has a larger population than Iceland.
B
Chicago or Chicagoland?
A
Oof. That's a great question. It's just written as Chicago.
B
I'm gonna say true.
A
It's true. A cockroach can live for nine days without its head.
B
That's very specific. I'll say. True.
A
It's true. Samuel Beckett wrote A Streetcar Named Desire.
B
False.
A
False. It's Tennessee Williams. Carrie Anne Moss was born in Scotland.
B
Oh, my gosh. That's very specific, too, but I don't think so. False.
A
False. Canada.
B
Yes, Canada. I knew that.
A
Since 1912, Olympic gold medals are actually silver with gold. Gold plating.
B
Oh, that's very specific, too. I'm gonna say no. I'm gonna say false. Oh, it's true.
A
We got you on that one.
B
Cheapers.
A
Monster. Monster Energy drinks were invented in 1989.
B
False.
A
False. 2002. The space between your eyebrows is called the Glabella. Wow.
B
My eyebrows.
A
Just yours. Just yours. We made one up for you.
B
I'm gonna say true.
A
It's true. A monkey was the first animal sent to space.
B
False. It was a dog.
A
False. It was fruit flies. Technically, I guess, is the creature. The being Michael Jordan was.
B
That's in that lossy Hellstrom movie, which is really nice.
A
Oh, I don't know that movie.
B
I can't remember the name of it. But there's this. My Life as a Dog, it's called. And the opening is this kid narrating, thinking about that dog that goes into space.
A
Yeah.
B
It's very nice.
A
I need to tap in. We have one more for you. Michael Jordan was drafted to the Bulls in 1984.
B
True.
A
True. How'd she do? Thirteen.
B
Yeah.
A
That's $50 in your pocket. Might be the best performance we've ever had. Very good. Wow. We've never had a perfect 15. I know that.
B
No. And we've never guessed at quite a few. I'm. I. I didn't. I don't have an encyclopedic.
A
It was a beautiful performance. We're all.
B
Thank you.
A
We're all stunned by the performance. I would say our most common is probably, like, nine.
B
Nine is by far the most.
A
That feels like where people land. Yeah. Never had a zero. Never had a 15 I would look for. I. I think once we get a zero and a 15, we'll probably end the show.
B
Yeah. Zero.
A
Once we get both, we'll end the show.
B
Yeah. I want to know who that zero is out there.
A
Oh, you will be someone. We'll make a big deal out of it.
B
Yeah.
A
Lily, thank you so much for doing this. Yeah. I just love you. I can't say that.
B
Thank you so much for having me.
A
How much you mean to me.
B
I'm so proud of you.
A
Stop it. Don't say that. Thank you. I love you so much. Do you?
B
Love you, too.
A
Is there anything that the people listening can do to support Lily right now?
B
What can you do to support me? I don't know. I think just, like, hold each other up. That's all we got to do. That's how we get through this. Keep getting into community and grabbing hold of people and make sure they're staying on their feet.
A
That's beautiful. Thank you very much for doing it. Yeah. Love you. We did it.
B
You too.
A
That was a Headgum podcast.
Date: November 27, 2025
Host: Caleb Hearon
Guest: Lilly Wachowski
In this heartfelt and wide-ranging conversation, comedian Caleb Hearon welcomes filmmaker and writer Lilly Wachowski for a deeply personal, funny, and moving discussion just before Thanksgiving. The pair dive into their creative histories, the challenges of being queer artists, the ever-mutating meanings of art in a hostile world, and the importance of community—culminating in a love letter to chosen family, queer resilience, and bomb gravy recipes.
This episode captures the warmth, humor, and honesty that define both Lilly Wachowski’s and Caleb Hearon’s creative worlds. It explores the deep interconnection between life and art, the joy and rage of queer existence, the power of community rituals, and the imperative to keep making art—no matter how hostile the wider world may feel. As they close, Lilly summarizes:
“I think just, like, hold each other up. That's all we got to do. That's how we get through this. Keep getting into community and grabbing hold of people and make sure they're staying on their feet.” — Lilly (66:51)
For listeners: Whether you’re a young queer artist, a film lover, or just prepping your gravy, this episode is a nourishing, affirming call to keep making things—and to find joy, connection, and healing in art.