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Caleb
This is a Headgum podcast.
Lizzy McAlpine
I really relate to the Red Rocks moment because I have. In my last hour, I have a huge section about my dead dad. Dads are addicted to dying. They'll just do it.
Caleb
Literally.
Lizzy McAlpine
They're just, like, dropping dead out of nowhere.
Caleb
They're like, bye.
Lizzy McAlpine
They're like, see y' all.
Caleb
See you later.
Lizzy McAlpine
See you later. Like, what is going on with dads? They're just dying left and right. Lizzy, I'm so excited you're here. Me too. Dude, I have to tell you, I almost told you this before, but then I was like, save it for the episode. Caleb. I. Well, first of all, I love your music. I'm such a huge fan.
Caleb
Oh, thanks.
Lizzy McAlpine
But I got to have one of the. I. I don't know if you'll relate to this or not, but I feel like your music is so good for. It was raining so hard when I was coming over here, and I was staring out the window listening to your, like, this is Lizzie McAlpine, you know, Tracks. And I was like, this is what this music is about?
Caleb
I think so, yeah.
Lizzy McAlpine
It's about setting longing. Yeah, it's. I was. I was locked in great love that I love. Love, love, love, love. Love your music. I'm so glad you're here.
Caleb
Yeah, me too.
Lizzy McAlpine
How's it going?
Caleb
Oh, it's good, you know.
Lizzy McAlpine
Yeah.
Caleb
Just locked in Broadway.
Lizzy McAlpine
You're locked in on Broadway? You're doing a show on Broadway right now, and how's it going?
Caleb
It's going great. I'm having kind of the best time ever.
Lizzy McAlpine
Yeah.
Caleb
Yeah.
Lizzy McAlpine
Well, you. You tweeted, like, years ago, you were, like, doing. The urge to do a live theater show is so strong that I'm doing, like, Broadway karaoke alone in my house. And do you. Do you feel like you manifested this 100%?
Caleb
Also, I did tweet a long time ago about working with Jeremy Jordan, and now he's in the show with me, which is crazy. So I feel like I've kind of mastered the art.
Lizzy McAlpine
Yeah.
Caleb
Of manifestation manifesting in public.
Lizzy McAlpine
On Twitter, specifically.
Caleb
Exactly. Yeah.
Lizzy McAlpine
I love that so much. So the show, how long has it been running? Where are we at in it?
Caleb
We opened, like, two weeks ago, but we started previews performances, like, the end of March. So it's been, like, kind of a little bit now, and we close at the end of June.
Lizzy McAlpine
Is this your first. Is this your first, like, Broadway show?
Caleb
Yes.
Lizzy McAlpine
Okay. What does that feel to you? Were you nervous starting it? Do you feel better now?
Caleb
It was kind of Terrifying at first. I am a theater kid.
Lizzy McAlpine
Yeah.
Caleb
I did theater in high school. That's like, my only basis for anything theater related. And so doing this was scary. But honestly, I've been learning so much, and it's. It's kind of like one of the greatest experiences of my life so far. It really feels like I was, like, meant to be doing this. It's really cool. So I'm having a good time now. But it was. It's still kind of scary sometimes because I don't really know what I'm doing. I kind of just like, pretend. Yeah, but that's acting, I guess.
Lizzy McAlpine
Yeah. Well, also, if. When it's a musical, I feel like it's. I. I don't. As a singer, I just feel like it would be like, okay, well, you at least definitely know that.
Caleb
Totally.
Lizzy McAlpine
It's like you kill that part. No worries. Yes, exactly. Yeah. That's so exciting. Dude. Is there. Is there, like, a dream? Like, what are your Broadway. You're a theater kid. I was not. So when I talk to theater kids, I'm like, I learn a lot. What were your, like, your, like, influences, your big favorite Broadway shows, the things that made you love theater?
Caleb
Oh, gosh. Well, my mom listened to Wicked in the car, like, all the time. So Wicked was like a touchstone for me. And then I just loved, like, Disney movies, like Beauty and the Beast.
Lizzy McAlpine
Yeah.
Caleb
That was the first Broadway show I ever saw. And just like, all that stuff. Every. I don't know, my grandparents would take us to see a Broadway show every year for my sibling's birthday. And every time, it was just like watching those people on stage was so. I was like, I want to do that. Like, they're giving an experience to the audience that is so unique and special. And I was like, I want to be a part of that.
Lizzy McAlpine
Yeah.
Caleb
And now I am.
Lizzy McAlpine
And now you are. And now you freaking are. So what, you end it. It ends in June.
Caleb
Yeah.
Lizzy McAlpine
End of June. And then is it end of June.
Caleb
Like, the 22nd, the 20s?
Lizzy McAlpine
That's the end of June.
Caleb
That's the end of June, I guess. I don't know. Get out of there.
Lizzy McAlpine
At the end of June. What are you doing after you have. Do you have any. Are you doing, like, tour. Tour this year?
Caleb
Five dates for you after this is over? I'm kind of, like, writing right now. And so after this is over, I'm going to figure out what the next project is going to be. And I don't love to tour. So if I do tour this next album Which I probably will. But it, it's. It'll probably be less dates, less cities. Like, like maybe like five in a. Five shows in a row in one city. You know, that type of vibe. And I want to do like, because I was playing like amphitheaters and stuff, and the next logical step for any artist would be, like, sizing up. But I, I think I want to go just like medium sized theaters where, like, people can sit.
Lizzy McAlpine
Yeah.
Caleb
And there's. There's no pit.
Lizzy McAlpine
Yeah.
Caleb
And we can just like have a good time like that. That feels like the vibe for my next tour, if it, if it happens.
Lizzy McAlpine
Yeah. Because you, you haven't even worked. You don't even know what the project is yet.
Caleb
I know I kind of know the vibes and I know the, the direction that my music is going in, and I'm kind of refining my sound a little bit more, and it just feels like it would not translate in a bigger, like in a stadium or something. Like that just is not. That's not really the vibe for my music.
Lizzy McAlpine
Yeah. I, as a fan of the music, I would want to see you in the first thing you describe. Like, I'm like, yeah, I want to see you in the theater where we can sit.
Caleb
Right.
Lizzy McAlpine
I mean, I would see you wherever, but, like, I do. I totally know what you mean.
Caleb
Yeah. Because I wanted to feel like intimate.
Lizzy McAlpine
Yeah.
Caleb
I feel like I felt like when I was playing the amphitheater, some of them were like, really, really cool. Like, obviously the Greek was like intelligent, insane and Red Rocks and like all that stuff, but any bigger than that, and it feels kind of like you're losing the intimacy. And I feel like my music is just so specific and it doesn't really work in a huge setting because I feel like those are meant for, like, you know, if you want to come and you want to dance and all that stuff, and that's not really my music.
Lizzy McAlpine
You know, I mean, I'll dance to your music, but it's gonna be definitely like a slow sway, right? Yeah. It's gonna be some tears involved. Your music, Your music is damaging to me. I listen to your music and I worry about that. I go, actually, I'm thinking of things I haven't thought of actually in years. In a beautiful way. In a beautiful way. If I had known. If I had known you were writing Ceilings when you were writing, and I might have come over and said, don't put that out.
Caleb
Don't do that.
Lizzy McAlpine
Don't put that out.
Caleb
Maybe don't do that.
Lizzy McAlpine
But I Love it. But, hey, I've got a life to live. I would have said, hey, what are you actually thinking?
Caleb
Right.
Lizzy McAlpine
Why would you do that to me specifically?
Caleb
I'm sorry about that.
Lizzy McAlpine
I wonder. Okay, if this is an annoying question. You can totally tell me. This is so casual. We can cut anything. Um, but I do wonder. I don't know if you get asked this all the time, but, like, your songs going mega Viral, specifically on TikTok, we, you know, we have a version of that where nowhere near what it's like for you. I mean, so different with a song, but, like, I have very complicated feelings about the Internet and things going off and people talking about me and sharing my stuff. Of course, there's a version of me or a part of me that wants it or appreciates it, and it is, like, the point of the work. Um. But, yeah, what do you feel about, like, we're obviously right now, you know, bridge, Alma Mater. It's, like, everywhere. How do you feel about it?
Caleb
I mean, I'm kind of obsessed. It's different. It's interesting because when I feel like I've had, like, three moments on TikTok. The first one was in 2020 when I posted that, like, you ruined the 1975 song. And it. I still get comments on that video. And that one was interesting because I never meant for that song to go anywhere. And I never really even finished writing it because I was like, this is just for fun. And I'm not. This is not what I want my sound to be. This is just, like, for fun. And I still get people asking, like, release it. And I'm like, no, actually, maybe. No, I'm not going to do it, actually.
Hope
No.
Caleb
And I also think that was at a time where I was not really confident in who I wanted to be as an artist yet. I didn't really know anything because I was just at the beginning of my career. And then the second time was Ceilings, obviously, and that was insane. And I feel like that moment really allowed me to, like, make my last album older because it kind of gave me opportunities that I wouldn't have had without it. And so for that, I am grateful for that moment. But then it's also like, you know, that's the song that everyone wants to hear. And, you know, all artists who have one big hit experience this, but it's nothing revolutionary. But, you know, on my last tour, I was playing Ceilings, like, kind of in the middle of the set. And at Red Rocks specifically. I've talked about this before, but we played Ceilings and Then the song after that, I was playing a song about my dead father.
Lizzy McAlpine
Yeah.
Caleb
And. And I was just watching people, like, get up and walk out because they heard the song they wanted to hear, and then they left. So that was tough. So that's the part of it that is, like, not great feeling. But, you know, I try to hold both feelings at the same time, and obviously, I'm grateful for all of it. And then now with Spring Into Summer, I'm like this. I love this song. Like, I love.
Lizzy McAlpine
It's a great fucking song.
Caleb
Like, I feel like this last album, Older, was really, really an important moment for me in my career. And just not even in my career, just in my. In the way that I think about who I want to be as an artist. And it's the closest that I've gotten to what I feel like my true sound is and the direction that I want to go. And so to have that song have a moment right now is, like, really validating because also, I feel like when I released the album a year ago, I. People were like, we wanted five seconds flat, 2.0. And I was like, well, sorry.
Lizzy McAlpine
Well, that's not happening. Sorry.
Caleb
And it was tough because I was like, this is the music that feels, like, so authentic to me, and people are like, we didn't want this.
Lizzy McAlpine
Yeah.
Caleb
And I was like, oh, okay. But I want it. Doesn't that mean anything? So to have this song go viral now is, like, really, really cool. And I love it.
Lizzy McAlpine
Did you imagine. I mean, I think there are times when we're. When I'm writing a joke or something that I'm like, oh, people will latch on to this. Or I. I think, oh, people will do something with that. And it's not why I'm doing it, but I just. I have an acknowledgment of it that I'm like, oh, that's ripe for people doing. Whatever did. I mean specifically, the line that's, like, so viral right now is bridge Over Water. I'm jumping off. And they do the. You know. Did you imagine that when you're making that song that you're like, oh, this is gonna.
Caleb
I never think about that stuff. It. The same thing happened with Ceilings. I. I put the album out, and then a year later, literally a whole year later, the song goes viral.
Lizzy McAlpine
Yeah.
Caleb
And ce. Not a single. It wasn't like, we didn't promote it. And then it just, like, a year later popped off on TikTok. And the same thing's happening with Spring and December, basically. And I never Think about that stuff. When I write it, I just write the music. And I don't really. I don't want to say I don't care about having a viral moment on TikTok, but it's never like, the priority.
Lizzy McAlpine
You're not going into the studio being like, let's cook up a sound.
Caleb
No, no, no. Never.
Lizzy McAlpine
Let's cook up a TikTok challenge. No.
Caleb
But it's always cool if it happens, obviously.
Lizzy McAlpine
Yeah. The thing you were saying about playing the hits reminds me of this moment. I went maybe like a year or two ago and was. I was in L. A at the time, and I saw Jeff Tweety was playing at Largo. And I love Largo. And anytime someone I like is usually comedians, but sometimes musicians like Jeff Michael try to pop over. And I went over, and I was watching, and I just love Jeff Tweedy so much, and I think he's actually so funny. And my comedy kind of lost out on not having Jeff be a comedian, like, good for music. But I'm like, we kind of missed out on one there. But he. He did this thing where he was, like, interacting with the audience, and he was, like, taking song requests. He's, like, such a huge body of work, and everyone was shouting out a different song. And he made this joke where he was like, this is the problem. Every one of you people has a different favorite song, and I've never had a hit.
Caleb
Oh, my God.
Lizzy McAlpine
And I thought that was so goddamn funny. Funny because it's like a grass is all. He wasn't genuinely bemoaning it. He was just being silly. But, like, the. The other side of that is, if there was just one hit and they were all yelling the same song, it would be a totally different thing. Right. You know, and I. I really relate to the Red Rocks moment because I have. In my last hour, I have a huge section about my dead dad. Dads are addicted to dying. They'll just do it.
Caleb
Literally.
Lizzy McAlpine
They're just, like, dropping dead out of nowhere.
Caleb
They're like, bye.
Lizzy McAlpine
They're like, see y' all.
Caleb
See you later.
Lizzy McAlpine
See you later. Like, what is going on with dads? They're just dying left and right. Like, stick around, brother. Like, what the fuck? Oh, my God. But, yeah, I have material about my. My dead dad that gets a little. Like, there's a. I'm building to a joke, but it gets a little earnest for a second in service of the joke, by the way. And I. Watching people check their phone a couple times during that, I'm like, that's even different than a song because I'm like, there's no guesswork. I'm out loud saying that this is about my dead dad. You know what I mean? I'm like, can we just. Can it wait?
Caleb
Right?
Lizzy McAlpine
But, yeah, there's a. There's a live show etiquette thing about that that can be really tricky when you're doing personal stuff.
Caleb
Yeah. Especially because I felt like, see ceilings and 5 seconds flat in general. Like, I love that album, don't get me wrong. But it just didn't. It felt like an experiment. It was always like an experiment because I made my first album and it was closer to old, what older sounds like. And my. My. I think what I want my music to sound like. And then I was. I. I became very scared of, like, oh, I don't want to be pigeonholed into one genre because I have. I like to experiment. I like to do, like, many, many things, and I want to try something new. So I, like, hard pivoted and made five Seconds Flat. And it isn't, like, totally that different from the rest of my music, but it's more, like pop sounding. And it was very fun to make, and I had a great time, and I loved the music when it came out. Obviously, I wouldn't have put it out if I didn't like it, but now that I'm looking back on it, I'm like, okay, yeah, that stuff is maybe not representative of who I am as an artist now. And also, like, I'm always changing and growing and learning, so it makes sense that I don't resonate with that anymore. But to have that song Ceilings Blow up and then, like, that's all that people want to hear. When I am now making music that feels, like, really close to who I am, it's like, dang. Yeah, that's. That sucks.
Lizzy McAlpine
Yeah, totally.
Caleb
And it's not everyone. It's not everyone. But, you know, no, the real.
Lizzy McAlpine
The real Lizzy heads want whatever. That's the thing is, like, true fans. There's. There's levels to fandom and, like, true deep, like, Died in the Wool fans of your music, they want whatever. If you put out a EDM album, they'd be there for it.
Caleb
You know what I mean?
Lizzy McAlpine
It's like they want what you want to make. They're like, we like that Lizzy was excited about this. But, yeah, it's like, when it gets. When it leaves the target audience, when there's a broader coalition of people who know and enjoy even passively, your work, they it's tough. I've definitely had, like, things with this where, like, I. When I first started doing, like, When I first started getting, like, a big following on the Internet, there were certain characters I did that people wanted me to do over and over again, and then they only wanted me to be that guy for them. And I refuse. I'm like, I will not. If you. If. If it gets to a point where I'm doing a character, I don't really do characters on the Internet anymore. But when I was doing a character, if it got to the point where people were commenting on my. All my other shit, asking for that, I would stop doing it entirely.
Caleb
Yeah.
Lizzy McAlpine
Because I was like, I'm not going to thank you so much for liking it. And it genuinely is so cool that I get to, like, express myself as a human being, as an artist in, like, these silly ways and that you respond to it. But I. I cannot enter into this contract with you where I'll only be one thing for you forever.
Caleb
Right.
Lizzy McAlpine
I'm not interested in it.
Caleb
Yeah.
Lizzy McAlpine
It sucks. I'm like, I don't. And there's some people.
Caleb
We all grow. We're all growing. And, like, to think that someone will just stay the same for you forever is kind of a crazy concept.
Lizzy McAlpine
Yeah. And it's a little, like. There's a. There's a part of it that's like. I don't want to make it this sound infantilizing, but it's. There's a part of it that's like dessert for breakfast, where it's like, if I actually gave you what you wanted, eventually you wouldn't like it.
Caleb
Right.
Lizzy McAlpine
I was only that guy for you forever. You would get tired of it. And you may not believe that, but that is reality.
Caleb
Yeah.
Lizzy McAlpine
Do you know what I mean?
Caleb
Totally.
Lizzy McAlpine
Like, eventually you would. Eventually you would go like, oh, I'm done with that guy. He only does the one thing.
Caleb
Yeah.
Lizzy McAlpine
You know.
Caleb
Right.
Lizzy McAlpine
That. Then. That would, like, be so corrosive to my soul, because I didn't even want to be the one thing for you.
Caleb
I know.
Lizzy McAlpine
But I did it because you were asking. That's so real, you know?
Caleb
Yeah.
Lizzy McAlpine
Yeah. I don't. So. Okay. But enough about. Certainly enough about me. The next album. Do you already know who's, like, producing it? Do you have the team in place? Like, what is it really?
Caleb
No, I. Before I came here to do Floyd, I was writing a lot. I basically had, like, two full albums written before I got here. And then I came here and I was doing this, and I was being exposed to this type of music that is in the show, and. And I started writing new stuff that sounds kind of different and. And more mature even than, like, stuff that I was writing, like, half a year ago. It's. It's kind of crazy. I feel like this past year has been a lot of growth for me, and so the music is reflecting that, and I'm kind of trying to catch up with myself, honestly, in the music that I'm writing, because I'm. I feel like I'm learning so much about myself, and I'm trying to write about that stuff, so I don't really know what it's gonna look like yet because I'm. I feel like I'm still in the process of growing.
Lizzy McAlpine
Yeah.
Caleb
And so I can't. I, like, I have to wait until that's not done because I'm never done growing, but it just still feels like I'm in a period of, like, intense transformation. So I'm trying to live that and then write about that and then see what happens.
Lizzy McAlpine
Yeah. What are. What are you writing about right now? Can I ask? Like, what's going. What are the big. What are the big inspirations? Touch points.
Caleb
A lot about freedom.
Lizzy McAlpine
Yeah.
Caleb
And, like, my independence. Because last. A year ago, like, last month, I broke up with my ex, and I did that with the sole purpose of, like, wanting to have my own life, because I felt like I kind of was. I just kind of, like, entered into his life, which was fun and great, and I had a great time. But at the end of it, I was like, wait, I don't have, like, any friends, and I don't have, like, any of my own things that I do, like, by myself, for myself. And so I really wanted to spend time with myself in my house in la. And then. And then, like, I had two weeks in my house, basically, where I was like, yes, I have a routine, and I'm loving this. And then I had to go on tour, which disrupted all of that. And then I kind of, like, was just seeing someone else at the time after that, and then I was learning things about myself through that, and then that ended, and then it's just like a whole. Like, I'm just, like, experiencing life, it feels like, for the first time, honestly, because after that relationship ended last year, I was like, oh, my God. Like, I can do so many things. Like, I. I'm free.
Lizzy McAlpine
Yeah.
Caleb
Kind of, you know, like, it felt, like, really cool to be free. And so now coming here, and I really am in a routine, like, I feel Like, I crave routine, and I. You do not have that on tour at all. And so that was tough for me to know that I wanted that, but I couldn't have it yet. And then I got here and I've just been, like, loving life because I have a routine. I do the same thing every day, and I kind of am loving it. But then there's also, like, you know, I don't know. I just. I'm just. I don't. Does that make any sense? It makes a lot of sense.
Lizzy McAlpine
Yeah. Yeah.
Caleb
I'm just, like, really having a great time right now, honestly. And, yeah, my. My independence is a top priority for me at this point in my life.
Lizzy McAlpine
And yeah, I think about freedom all the time. And I think about. Specifically. It's funny that you mentioned routine as well, because I think about the way that freedom interplays with routine, where it's like, I have a lot of freedom in my life. Like, I am lucky that my career has provided me the opportunity to, like, we kind of record when I want to record. We kind of. I go on tour when I want to go on tour. I kind of say no to filming projects if I'm not in the mood to film projects. It's like, I don't have the freedom to get anything made that I want to get made. I don't have that kind of power or. But I have a lot of freedom, you know, and it's funny because, like, I was there. There are things I think I did a lot better when I had, like, the forced routine of, like, a 9 to 5 job or like, my survival jobs. They forced a kind of routine on me, and now I'm the guy who has to force routine if I want it.
Caleb
Yeah.
Lizzy McAlpine
And it's. It's funny. It's like, I love my freedom. I prioritize it at every step. I actively. I actively turn down a lot of different kinds of, like, work or relationships or opportunities just to preserve freedom. But. But then when there's too much freedom and no routine, I totally spit out.
Caleb
Yeah.
Lizzy McAlpine
And I need some level of routine.
Caleb
Yeah.
Lizzy McAlpine
Which is not the opposite of freedom, but it's an interesting. Like, the way that they work or don't work together is something I think about a lot.
Caleb
Same because before I came here, I. I did not have a single routine. I was just like, I. We're on tour and we're, like, moving every day, and it was just like, I was just going with the motions. And then I came here and I also went while I was on tour. And in between, I wasn't in my house because it was getting renovated, so I was in this, like, apartment, and it was just. It felt, like, kind of foreign. And I, like, couldn't really settle into that place because I knew I was gonna be leaving again. And being here and being able to create a routine for myself, it, like, feels honestly more freeing than when I had no routine.
Lizzy McAlpine
Yeah.
Caleb
And I was just like, what am I doing with my life? Like, I don't. That just. Maybe that makes no sense, but.
Lizzy McAlpine
No make sense.
Caleb
It just. I don't know. Because I'm in control of what I do, and if I want to do something, I'll do it, and that feels freeing.
Lizzy McAlpine
Yeah. I started thinking a lot about freedom because I was. There was this question I was asking people at, like, you know, dinner and just, like, hanging out a lot where I was asking people, what, you wake up five years from today? What is your perfect day? Like, what does your life look like in five years through the lens of one perfect day? And I asked so many people this question. Like, people who. You know, people have different. All kinds of different experiences. People who are from different places, people who make different amounts of money, people who do different kinds of things. And across the board, there was, like, really only one through line. And it was freedom. Like, yeah. Everyone was like, I have the ability to, you know, move this thing a couple hours and go to lunch with a friend if they call. I have the ability to wake up without an alarm. I have the, like. Freedom was, like, this big, like, river that runs through everyone's answers, which was really interesting to me. Like, type A, type B. It didn't matter. Like, everyone just wanted a level of freedom.
Caleb
Yeah.
Lizzy McAlpine
And they expressed it in different ways, but it was a thing I noticed. And I was just like, oh, that's so interesting. That's, like. That's kind of what we all want. It's just like.
Caleb
Yeah.
Lizzy McAlpine
It's not always freedom from a relationship or freedom from a job or whatever, but everyone generally just wants to feel like on some level, I am free to do what I would like to do.
Caleb
Yeah. And I also was writing before I came here, I was writing a lot about freedom within a relationship. Like, that's also something that I was learning a lot about and, like, needed to, because my last relationship was, like, so not. Not. Not freeing. But I don't. It was just different. And the relationship that I got into after that one was, like, so incredible and, like, so, like, a. One, like, complete. Like, 180 from my last one. And I was learning how to be, like, have my own life and also be in a relationship. And it was crazy.
Lizzy McAlpine
Yeah.
Caleb
So I wrote. I was writing a lot about that. And also, you know, I was writing about. I've been writing about, like, I wrote a song about Tor again because it's. It's just. It's just a lot. So I gotta write about it somehow. Yeah. I don't even. What else am I writing about? I don't know. Just really. Freedom is the main through line.
Lizzy McAlpine
Yeah. Yeah, I. Yeah. When you're on tour, your brain becomes this, like.
Hope
It's like.
Lizzy McAlpine
We just. We just got off a massive one, like 25 cities or something. And it. Or massive for us, I should say. I know other comedians do, like, year and a half long tours. It was big for us. That's so crazy. But, yeah, I just start to think about these little things that are so specific. Like, the specific act. I was thinking for, like, two weeks straight about the specific act of every day. I would get to a new hotel and remove. There's a place in my wallet where I keep whatever hotel key I'm using at the time. I would remove. I would remove the one from the previous hotel from the night before, throw it in the trash can in the new hotel room and put in the new hotel key. And I would do that every single day into the same place. And I'd be like, that is so fucking weird. Like, I don't. There's something. There's not anything really profound about that, I don't think, but it just was like, every fucking day I would remove a key to a place I'm now hundreds of miles away from.
Caleb
So it's crazy.
Lizzy McAlpine
That's weird.
Caleb
It's a crazy lifestyle. Like, it really is. It's so. It's so, like, unnatural.
Lizzy McAlpine
Yeah. Yeah, it is. It's like. We did. There was a. There was a. We also. Comedy tours are routed so differently because we just pretty much can show up and start the show. This was a little different because we had tech stuff, so we did a little bit of a check. But, yeah, we. We did Atlanta one night, in Toronto the next. Like, you just get on a plane. It's like.
Caleb
That's so crazy. No, it's so crazy.
Lizzy McAlpine
That's nutty.
Caleb
Well, yeah, also, it's like, when I was touring before my last tour, it was set up in a. In the normal way that, like, a lot of musicians tour, which is like.
Lizzy McAlpine
It was like a van tour or a bus or what was.
Caleb
Oh, we were on A bus? Yeah.
Lizzy McAlpine
Trying to get a gauge of where we were in it. Yeah. Okay. Bus tour.
Caleb
And this was, like, 20, 23. And, yeah, it was, like, crazy. It was routed, like, you know, the normal way where like, sometimes we're doing three shows in a row and. And then we're, like, showing up to the venue and playing a show later that night. And. And it was just all crammed into, like, a month and a half. And I literally, like, I. I was getting sick, like, physically on every tour that I was going on because it was so such a strain on my body and my. I wasn't, like, eating. It was like, I was miserable.
Lizzy McAlpine
Yeah.
Caleb
And so on my last tour that we just did, we made it totally different, and we spread the dates out, and we weren't on a bus. We were just flying everywhere. And we had, like, we would do two weeks of tour and then two weeks off and then two weeks, and it was just like, so much better. And, yeah, I got a little bit of pushback in the beginning because people were like, well, this is not how you do it. Like, it's more expensive and blah, blah. And I was like, I don't. I don't really care. I need. I need to, like, be sane.
Lizzy McAlpine
Yeah.
Caleb
While doing this. Otherwise, I'm gonna have a horrible time and it's gonna show on stage because I can't keep any emotion inside of my body. Like, if. If I'm feeling a certain way, it will come out, even if I don't want it to. And. And if I'm, like, upset or not having a good time one day, like, the show is going to suffer from that. And I don't want that. Obviously. I want to make sure that everyone has a great experience. And so I was like, no, guys, we got to do it this way.
Hope
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Lizzy McAlpine
Thank you Squarespace.
Hope
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Lizzy McAlpine
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Lizzy McAlpine
S O dash T R U E Also you. I don't understand the. As an artist, the thing of, like, you just get all these. And it's no one's. I'm not. It's not like I'm. It's not. I'm not talking about the agents or the managers or the promoters or anything. I'm just talking about in general, there's this constant influx of, like, ways you can extract more and more and more money. Ways you can save money, you can do an extra night, you can travel quicker, you can make yourself more tired, you can dynamic, you can. The venue will let you flex pricing the tickets so that you can screw over whoever gets to the tickets late. You. Which scalpers were already going to do for you. You can up. You can upsell the merch, you can. Like, it's all these ways that you can extract more and more and more money. And I go, well, wait, if I. If that. If the sole thing I got into this for was to protect the bottom line and extract more and more money and create more and more profit, I think I would have just worked in finance or something, right? I'm like, that's not what I'm doing.
Caleb
That's kind of what the song that I wrote is about. Like, it's. It's like. It's just like never ending. Really. Also. Because I also feel like when I did my 2023 tour, I did the first tour and then they were like, okay, we're gonna do another one in the same. The same cities, just bigger venues. And I was like, for the same album? And they were like, yeah. And I was like, but I already did this.
Lizzy McAlpine
Yeah.
Caleb
And they were like, will you do it again? And I'm like, really?
Lizzy McAlpine
Like.
Caleb
I was like, wait, what?
Lizzy McAlpine
So then I'll do more.
Caleb
Yeah, I was like, wait, what? And then I had to cancel the Europe, like, of that second tour because I was like, Literally unwell.
Lizzy McAlpine
Yeah.
Caleb
And it just, like, never ends. It's just. They get you, and then they use, like, keep going in this. In this cycle, and it just never ends. And eventually I was like, I have to put my foot down. Like, I can't be doing this all the time, because it's not sustainable at all for me.
Lizzy McAlpine
Yeah. They'll put you on the wheel. If you allow yourself to be put on the wheel. Put you on the hamster wheel. You have to. It has to be more like. I think of it more like, I don't want to be in the hamster wheel, but I'm fine doing the like. Like, the motorized walkways at the airport kind of thing, where it's like, I will. I will play the. I will do some things. You know, they're like little stretches of the career where I will do the fast, smart, like. What's the word I'm looking for? Like, optimized thing. But I can't be on the wheel. I'm not gonna just, in perpetuity, stand there and run and run and run and run and run.
Caleb
Yeah.
Lizzy McAlpine
No, I have a question for you.
Caleb
Yes.
Lizzy McAlpine
Which is kind of the theme of the show, right? When you're writing a song, do you. Is there a place you typically start? Do you start more with. Do you start with the melody? Do you start with the lyrics? Like, where are you starting?
Caleb
More often I start it kind of recently, it's kind of been shifting, but for the most part, I start with the chords because I feel like those dictate the tone of the song. And then after that, the words and the melody kind of come hand in hand because it's. It's really just, like, word vomit. I'm just like. I sing things, and then I'm like, okay, that. Either that was horrible, or that was amazing, and I'll write it down, and then that's how I write a song. It really is just like, yeah, yeah.
Lizzy McAlpine
So you don't have a bunch of, like. I feel like it's not two camps, but I feel like some of my musician friends have a bunch of lyrics sitting around that need melodies, or they have a bunch of melodies sitting around the need lyrics, and you're not. That's not happening with you.
Caleb
Sometimes if lyrics are coming to me, I will write them down and then build a song based on those. But that does not happen very often, and if it does, the song is not very good. Sometimes I. I have started with a title, like, a few times, like, the song that I was just talking about. About tour and fame and all that stuff. It started from a title that my friend just, like, said. We were just in conversation and he said this phrase, and I was like, oh, that's. That's good. Yeah, I wrote it down and then I wrote the song. But that doesn't happen very often.
Lizzy McAlpine
Yeah, well, you went to Berkeley for three years.
Caleb
2. I dropped out halfway through.
Lizzy McAlpine
You dropped out? Well, that's. Which is such a popular. Like, I feel like that's a huge joke about Berkeley. Like, if you finish, you know.
Caleb
Right.
Lizzy McAlpine
We were talking to Justin Tranter about that. Like, if you finish Berkeley, you know, who knows. Who knows where you're headed? But if you drop out, that's a really good sign. You know where. When you were. When you were deciding to drop out of Berkeley, was that, like, a big decision or what did that look like? Or were you just.
Caleb
It honestly felt really like, yeah, this is the logical next step, because I was there. It was during my second year, halfway through the second semester, and it was like March of 2020, and Covid happened and they shut down their in person campus, and so. And then my dad died the same day and. Yikes.
Lizzy McAlpine
Same day.
Caleb
Yeah. But they shut down everything. It was crazy time. It was crazy time.
Lizzy McAlpine
It was crazy time.
Caleb
It was crazy time.
Lizzy McAlpine
So I guess I would just say, if I had to sum it up, it was crazy time.
Caleb
Crazy time.
Lizzy McAlpine
Yeah, it was crazy time.
Caleb
Oh, God. Yeah. Then I went home, and I had been making my first album, like, through that whole year, and I finished the semester online, which was horrible. Doing songwriting classes over Zoom. I was like, no, guys, I can't do this anymore. And then my first album was scheduled to come out in August, so I was like, okay, I'm just going to drop out. And I don't really feel like I'm. I didn't feel like I was needing it anymore.
Lizzy McAlpine
Yeah.
Caleb
And I don't really know if I got anything out of, like, the classes that I was taking because I had to take a lot of, like, tonal harmony and, like, ear training, and I don't know how to do that stuff. Like, I don't know how to identify a chord if you play it. If you just play it. Like, I don't know how to do that. And that stuff never factors into how I write music. Like, I'm not thinking, like, okay, I'm gonna write this chord progression and. And, like, I just. I don't think about it that way. So I felt like I. What I really got out of it was the. My community and the people that I met and. And I still have really close friends from there. And that was what I needed, I think. And also just being exposed to all the different styles of music. Like, I had never listened to jazz before I went to Berkeley, and that's, like, basically a lot of what that is, is there. And so that definitely influenced what I was writing and the risks that I was willing to take in my music and. Yeah, but dropping out was logical because I was like, my album is going to come out, and I feel like I'm good.
Lizzy McAlpine
Yeah. One. It was just crazy time.
Caleb
It was.
Lizzy McAlpine
It was crazy.
Caleb
It was crazy time.
Lizzy McAlpine
Yeah, I do. You really tapped onto something, though, that I think is so true of, like, artistry in general, which is, like, you don't necessarily have to go to Berkeley School of Music. You don't necessarily have to train comedy at IO in Chicago. You don't necessarily have to go to any of these places, but you do have to find a community of people who give a shit about what you give a shit about. And these places do create that. So it's there if you want it, but you can also find it elsewhere. But, yeah, that's the thing is, like, the people you meet when you're starting out, who are going to inform your sensibilities, who are going to, like, help you figure out what's actually good, whether you're actually good, what being good even means. Like, all those kind of questions are not necessarily something you're going to get from, like, a class.
Caleb
Right.
Lizzy McAlpine
But something that you might get from being in. Experience those people.
Caleb
Yeah.
Lizzy McAlpine
Yeah.
Caleb
I also met my ex, who I wrote my entire last album about, so it was good.
Lizzy McAlpine
God bless.
Caleb
Yeah, God bless. Thank you.
Lizzy McAlpine
You know what? God bless.
Caleb
Thank you.
Lizzy McAlpine
Thank God for everybody I've ever met that taught me something, even if it was bad.
Caleb
Exactly.
Lizzy McAlpine
That is in Boston.
Caleb
Yeah.
Lizzy McAlpine
Is that where Berkeley is?
Caleb
Yeah, there's two. They always get. People always get it mixed up.
Lizzy McAlpine
Yeah.
Caleb
I say I went to Berkeley College of Music in Boston, because if I just say Berkeley, they're like, oh, in California. I'm like, no, no, not that. That one.
Lizzy McAlpine
Not that at all, actually. Yeah. That makes so much sense to me. I mean, music. Oh, God, I. I can't. I'm not. I don't have. I have such an appreciation for it. I love music so much, and I listen to music all the time. I listen to music more than I do anything, but I have no idea how y' all. I don't know how you do it.
Caleb
Honestly, like, me Neither.
Lizzy McAlpine
You go, you know, like when you. Like I work on the chords, I'm like, totally right.
Caleb
Like, I don't know. Honestly, it kind of feels like when I write a song, this might sound insane, but sometimes it feels like I'm literally just a channel.
Lizzy McAlpine
Yeah.
Caleb
Like it's coming from me, but it's also not coming from me. Like it's coming from somewhere else. And I. I have to. I right.
Lizzy McAlpine
You're just like the Pope. It's flowing through you. You're the Pope. Lizzie McAlpine is the Pope of music.
Caleb
You heard it here first.
Lizzy McAlpine
Amen.
Hope
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Yeah, y' all.
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Caleb
But I really feel like because when I when I try to write a song and I don't have the inspiration and it's not there, it feels like it's just, like, not time yet. And sometimes I'll feel like I have a song. It's, like, in the back of my head. It's on the tip of my tongue, like it's about to happen, but it's not ready yet. And then when it is time, I'll just, like, know that it's time. And it just, like, all comes out of me. And it feels, honestly, like, kind of spiritual. Yeah, a little bit. But, yeah, that doesn't sound crazy to me. It's. It's. Yeah.
Lizzy McAlpine
I feel that way about writing. I mean, there's. There's definitely jokes that I'm like, there will be. I don't sit down that often with a pen and paper and go, this is what this is going to be. I often have a thought that is, like, persistently bugging me and with me for a long time, and I'm just. I just trust. I'm like, that will come out as a joke eventually. And then, yeah, eventually it does. And sometimes it's bad, and sometimes it's good, but either way, it happens. And then sometimes through continuing to do it, I may get better and it actually ends up being something, like, worthwhile.
Caleb
Yeah.
Lizzy McAlpine
But, yes, of all my. All my favorite jokes or all my favorite lines in a script or all my favorite things I've created have been something that just persistently bugged me and then eventually just kind of happened.
Caleb
Yep.
Lizzy McAlpine
Doesn't mean that, like, routine and, like, practice don't.
Caleb
No.
Lizzy McAlpine
Totally help. But.
Caleb
Yeah. Because I wrote. I've been writing for so long, and I've written so many bad songs. It's like, it a lot. It. Yeah. I don't know. It's like allowing that to happen now because I've been doing it for so long, and I'm like, okay, I know how to do it. I know I can do it. Sometimes I'll write a song, a good song, and then I'll be like, I don't think I could ever write a good song ever again. Like. Because then I'll try and write after that, and I'll be like, oh, God. Like, I think it's just done for me.
Lizzy McAlpine
Yeah.
Caleb
I think it's over. I think I have to quit.
Lizzy McAlpine
Like, it's over. I did my.
Caleb
It's time for retirement.
Lizzy McAlpine
Yeah. Yeah, yeah, yeah. It's time to go to Boca Raton. Everything is over for me. I wrote a couple good songs, and my latest one was my last one.
Caleb
Yeah. Like, it always feels that way. But then I'm like, okay. I know it's gonna happen again. I just have to wait.
Lizzy McAlpine
Yeah.
Caleb
Because also I'll be experiencing something, and I'm like, I want to write a song about it, but I'm in the middle of it and I haven't. I have to wait until I've processed the thing to be able to write about it.
Lizzy McAlpine
Yeah.
Caleb
And that's frustrating sometimes because sometimes I'm, like, deep in it and I'm like, I need to write about this, but it just doesn't happen yet.
Lizzy McAlpine
Yeah. So many musicians that I talk to allude to this idea of having all of these horrible, allegedly horrible songs they've written. And I'm like, I want to convince y' all to put some of those out. Because I'm like, I want to know. I'm like, some of my. All my favorite musicians have said this exact same thing where they're like, oh, yeah, I'm good at writing because I've written so many bad ones. I'm like, put a couple of them out. I want to know. I want to know.
Caleb
I mean, it wouldn't be the worst thing in the world, probably, but unless it was, like, stuff that I wrote when I was, like, 13, you know, like, that would be. I have. Oh, my God. I. I found this one song.
Lizzy McAlpine
Let's go.
Caleb
Sometimes I. I, like, look through my voice memos or my files, but one time I was looking through my emails because when I was, like, 14, 15, my mom, like, got me email. Like, she, like, bought studio time, and I went in and, like, recorded some of my own songs and, like, recorded a cover of a Demi Lovato song. I don't know. I was just, like, having fun, you.
Lizzy McAlpine
Know, as one does.
Hope
Yeah.
Caleb
And I was looking for that, and I found this song that I made in GarageBand. And it's so. It's honestly hilarious. Like, it's so funny. And I'm like, this is kind of a banger.
Lizzy McAlpine
What's it about? Be honest.
Caleb
I don't even know what it's about. And also, like, what. I don't even know what the lyrics are. It's called heartless.
Lizzy McAlpine
Okay, first of all, let's start there.
Caleb
But, like, what was I writing about? Like, I was probably, like, 12, 13. Like, I didn't have any life experiences to draw on.
Lizzy McAlpine
Yeah.
Caleb
But, like, stuff like that, I'm like, that can never. That can never see the light of day. But stuff that I've written, I can play it for you after.
Lizzy McAlpine
Yeah, yeah, yeah, yeah, yeah, yeah. Play it at least for me. Yeah, yeah, yeah, yeah.
Caleb
But the Stuff that I've written in the past couple years, it, like, wouldn't be the worst thing in the world. It's just like, sometimes also it's. I. I don't release a song because. Not because it's bad, just because it doesn't, like, fit.
Lizzy McAlpine
Yeah.
Caleb
The story that I'm telling.
Lizzy McAlpine
Yeah. So what. What's. What's. If I. If I was okay. If I was like, hey, you have to make a Mount Rush more of songs like this. The best songs. The best songs ever.
Caleb
Okay.
Lizzy McAlpine
What are there, like. Are there some that you would put in that category?
Caleb
Like, what my own songs are of Just songs in general.
Lizzy McAlpine
I would make you do that of your own songs. Jesus.
Caleb
Oh, my God. How many people are on Mount Rushmore?
Lizzy McAlpine
I actually. I asked that recently, too. Someone asked me to do a Mount Rushmore.
Caleb
Who is on Mount. And how do they pick if they're on Mount Rushmore?
Lizzy McAlpine
Rose of Teddy Roosevelt and Thomas Jo.
Caleb
Who, like, gets to choose up there?
Lizzy McAlpine
I'm like, what is wrong?
Caleb
Who chooses what's on.
Lizzy McAlpine
I think it was. I think it was probably just one white guy who picked.
Caleb
Right.
Lizzy McAlpine
Or maybe Congress, which is just a couple more white guys.
Caleb
What was the reason for it at the time?
Lizzy McAlpine
I. Who knows? I'm sure they did something evil. It was probably like, the site where they killed a bunch of Native Americans or something horrible. Like, there's no chance it was just cool. You know what I mean?
Caleb
Right.
Lizzy McAlpine
No, that's legitimately, like, the land is constantly in dispute. Yeah. Yeah. That's not good.
Caleb
Great.
Lizzy McAlpine
But okay. If you had to pick a statue, we'll call it something else. If you had to put four songs on a banner. What are like, four. Like, what are four songs you think are just incredible?
Caleb
Oh, my God. Okay. I kind of need to look at my Spotify for this.
Lizzy McAlpine
I'm trying to think. I've. I've done something like this before. I said, Godspeed is up there for me. Me, Godspeed is so like. I just think it's such a beautiful song.
Caleb
Yeah.
Lizzy McAlpine
And I. Anyway. Okay. Godspeed. Maybe Tion Lauren Hill. I'm trying to think. I'm trying to think. I'm trying to think. I mean, all my. You know, you think. You feel like you should say something so old or so, like.
Caleb
Right.
Lizzy McAlpine
Classic. And I'd be like, yeah. I always be like, I know Canon and Taco Bell's Canon and D. You know, I'm like, like, that's.
Caleb
That's what we're going to Taco Bell's Canon Indeed.
Lizzy McAlpine
Taco Bell. Taco Bell's canon. Indeed. Like, you want to say something smart, but I'm like, no, of course. I think it's like, all stuff I've listened to in my lifetime.
Caleb
Right.
Lizzy McAlpine
I don't know. What do you got?
Caleb
It's tough cuz I have, like, my favorite songs right now. But I think overall. Oh, gosh. Okay. Probably like Amelia by Joni Mitchell. Yeah, it's like one of that whole album. Hashira is just like.
Lizzy McAlpine
That's a really cool, insane, like.
Caleb
Oh, my God, all those songs. Coyote, Amelia, Hashira, whatever the other songs are. I can't. I can't think of them right now.
Lizzy McAlpine
What are my four favorite songs? Four songs from one.
Caleb
Jody Mitchell.
Lizzy McAlpine
No, I love that.
Caleb
What else? I just. I've really, like. I started listening to Joanie, like, recently, kind of.
Lizzy McAlpine
I was gonna ask if she was an influence for you in the past year.
Caleb
And it's like, opened my world up. I'm like, where have I been? Literally? So lots of her songs are probably on there, but also Nick Drake is probably on there. Like Road. That song is so cool. And then maybe like the song Zanzibar by Billy Joel. It's just like kind of a banger.
Lizzy McAlpine
You gonna put a Demi song on there or no?
Caleb
Oh, I can. I love her older stuff. Oh, what is that album? Yep, it's gonna come to me.
Lizzy McAlpine
Don't even worry about it.
Caleb
Here we go again. That song. Do you know that song? Or. Or then like, get back, come again.
Lizzy McAlpine
Or here he comes again. What's that? I'm thinking of a Dolly Parton song.
Caleb
Oh, yeah, that's not. Yeah, I know that song. I don't know who that is, though.
Lizzy McAlpine
It's Dolly, but I can't remember what the name of the song is for some reason. Here you come again. I think it's here you come.
Caleb
Yeah, maybe.
Lizzy McAlpine
Or here he comes again. Anyway. Wait, that does. That does inspire another question for me, though. What? What? What? Who are your influences? Like, who are, like, when you. When you think about, like, Lizzie McAlpine. Body of work. Who. Who informs.
Caleb
Right now.
Lizzy McAlpine
Yeah.
Caleb
Or like in general, I think.
Lizzy McAlpine
And I was probably asking in general.
Caleb
But guess whatever you changes. Because I feel like when I was writing my first album, it was like Sara Bareilles, like, Dodie, God, who else? I don't even really remember. And then like 5 seconds flat was like, Phoebe Bridgers, Holly Humberstone, like, that type of vibe.
Lizzy McAlpine
Love Holly. Love Phoebe. Of course.
Caleb
Yeah, yeah. And then now I feel like I'm.
Lizzy McAlpine
Also me saying love Holly. I think it's just known that I love Phoebe. I want to be clear about that.
Caleb
Right, right.
Lizzy McAlpine
Yeah.
Caleb
Yeah. And recently with older, it was kind of like Andy Shaw. I don't know if you know Andy Shaw. I love his music so much. He's so good. And like Lee Fullback and like, more indie.
Lizzy McAlpine
Yeah.
Caleb
Artists. And now the stuff that I'm writing is very inspired by Joanie. Like, heavily Joanie and like, Crosby Stills in Nash. Come on. Who else? I made a playlist for it.
Lizzy McAlpine
Yeah.
Caleb
I make playlists for, like, inspiration for my albums. And it's. Yeah. Neil Young.
Lizzy McAlpine
Do you ever share those? But you've never put those out and been like, this was the inspiration.
Caleb
That's kind of cool. Maybe I should.
Lizzy McAlpine
That'd be kind of interesting, actually.
Caleb
Yeah. Sufian.
Lizzy McAlpine
Yeah, of course.
Caleb
But like. Yeah, it kind of changes a lot. But that's what I've been into recently. That's been really inspiring. And also, like, like the composer of this musical that I'm in, Adam Guettle, is like, very inspiring to me also. Even though it's Broadway. But it's, it's the, the. The way that he writes music is so crazy because it's so non intuitive. Like some of the, the melodies that he chooses or like, I did not expect that to go there. The chords that he uses, like, it's crazy. And I've really been. Been inspired by that too.
Lizzy McAlpine
Yeah. Yeah. That makes so much sense to me.
Caleb
Yeah.
Lizzy McAlpine
Well. Well, you know, we always ask people on this show, what's so true to you? Do you have a.
Hope
So true.
Caleb
Okay. I think it's that sometimes it's okay to cancel.
Lizzy McAlpine
I think in a big way it's okay.
Caleb
I think so too, because, like, I do it all the time. Sometimes you can't. Sometimes you just can't.
Lizzy McAlpine
Yeah.
Caleb
Emotionally.
Lizzy McAlpine
Also, literally, you're correct about this. And also it's like, so, like there was a. Sometimes showing up in a bad mood is. That's almost always the wrong thing to do.
Caleb
Right.
Lizzy McAlpine
If you're gonna be in a bad mood, I would prefer you cancel on me. I don't want to go to dinner. And you're clearly, like, struggling through it.
Caleb
Right.
Lizzy McAlpine
Stay, stay home. I'll do something else.
Caleb
Sometimes I'm like, I just can't. Like, my social battery goes so fast that it's like, if I. If I am scheduling like a dinner with you after a long day of, like, doing things in public, I'm like, I'm sorry. I. I have to. I Have to stay inside and stare at a wall, right?
Lizzy McAlpine
Yeah. I need to stare at a wall sometimes. Same in a big way.
Caleb
All the time.
Lizzy McAlpine
Canceling is. Canceling can be kind. Canceling is kindness in some ways.
Caleb
Exactly.
Lizzy McAlpine
Almost always acceptable.
Caleb
Yeah.
Lizzy McAlpine
I've gotten better about this. I will say. When I was younger, I had a beef with people who canceled on stuff. I'll be like, for what? Like, just power through. And I've really gotten to a point where I'm like, no, I. Thank you.
Caleb
I fully also, like, what if you're sick? You know?
Lizzy McAlpine
Yeah.
Caleb
I don't want to be around you if you're sick.
Lizzy McAlpine
Yeah. You know, I do like canceling. I do think it's good.
Caleb
Me too.
Lizzy McAlpine
And it feels so good.
Caleb
It does. Oh, God, the relief.
Lizzy McAlpine
Yeah.
Caleb
I've canceled on, like, work things before at the last minute, too, because I'm like, I just like, I thought I could do this, and I said yes for some reason, but I just don't think I can do it. And then once that text is sent.
Lizzy McAlpine
Yeah, it's like, oh, yeah, I just got high. Like, that felt so good. Even just to remember the times I felt that when you've been stressing, I really don't want to do it. And then you send that text or that email and you're like. You're like.
Caleb
And then they're like, all good. No worries.
Lizzy McAlpine
Yeah, dude. The fucking cathartic release of like, I didn't want to do this and I didn't, and it all worked out fine. That's so special. Yeah, that's so special. And even, by the way, even I don't even really need it. I've gotten to a point with, like, I know that I am a. I know that I'm a nice person. I know that I'm a thoughtful person. I know that I'm a reliable person. Even if I know that it is worries on their end, that if it's like, it actually up their day that I had to cancel this. But I know that I had to for some reason, like, I didn't have the battery or something else came up. I've gotten to the point where I'm like, I. They will just have to make peace with that. Yeah, I do it for other people all the time. There are plenty of times someone has had to cancel on me or had to change something on me that I've had to just be like, that really sucks for me, but I'm gonna figure it out, and you'll get me back. They're just gonna have to have the same mentality or not and be miserable about it, but I can't control it. It.
Caleb
Right.
Lizzy McAlpine
I get relinquishing that control of like, I think when I was younger, I was like, you cannot be mad at me. You have to understand. I'm now like, you don't have to. I hope you do.
Caleb
Right.
Lizzy McAlpine
Do you know what I mean?
Caleb
Yes, totally.
Lizzy McAlpine
You actually don't have to, and I can't force you to, but I would understand if the roles were reversed. And if you can't, I'm. That really sucks for both of us.
Caleb
Yeah.
Lizzy McAlpine
But you're just gonna. You're just gonna have to do whatever you have to do.
Caleb
Yeah.
Lizzy McAlpine
Do you know what I mean?
Caleb
Totally.
Lizzy McAlpine
And not in a mean way. It's just like, I'll do whatever I like. If I had to cancel on a work thing, I almost always, of course, try to do it with as much laid out time as possible. And I've offered like a show. I'll offer to be like, I'll try to find a comic to replace me on the lineup or whatever. Like, I will try to help. But yeah, sometimes it's just unavoidable. And you have to cancel.
Caleb
Yep.
Lizzy McAlpine
Especially if it's like a low key social engagement. It's like, we can reschedule coffee.
Caleb
Right.
Lizzy McAlpine
You know?
Caleb
Yeah. But those I feel less bad about because it's like, we have all the time in the world.
Lizzy McAlpine
Yeah. Life is long.
Caleb
Yeah.
Lizzy McAlpine
And of course I want to see you. I will say there is a. There's a cap. I do have some friends who have gotten so comfortable with canceling that they're like, oh, yeah, if we're rescheduling coffee for the fourth time, that's probably when I'm going to go, hey, I'm not going to be texting about this anymore. And we might just not be hanging out. And that is actually also okay.
Caleb
Yes.
Lizzy McAlpine
But there is a cap to the reschedule.
Caleb
Yeah.
Lizzy McAlpine
At a certain point, it's a full cancel. And then we come back later and try to do a new plan.
Caleb
Right.
Lizzy McAlpine
We're not rescheduling the same thing, you know, I mean. Yeah, yeah, that. There is a cap on that.
Caleb
Totally. You know, I mean, Yes, I do.
Lizzy McAlpine
I do think that's true.
Caleb
Yeah.
Lizzy McAlpine
I do think that at a certain point it's like, yeah, we're no longer rescheduling that coffee from April when it's December. We're actually now talking about a new plan. Yeah. We might want to, like, let's start talking about the zoo or something.
Caleb
Right?
Lizzy McAlpine
Yeah. We need to. We need to just change the whole plan altogether. I will do that. Sometimes if I've had to cancel twice, when I reach out for the third time, I'll be like, hey, I know we said coffee, but do we want to do dinner? Like, I'll change the. I'm like, this might change the kinetic energy of what we're trying to do. Maybe it's the afternoon that's with us. Maybe we needed the sun to be down for this to work out. Yeah, maybe I do start thinking about that. That's so funny. Kids song is good. I like this. So true. Yeah, this is a really good one. I have a segment for you.
Caleb
Okay, great.
Lizzy McAlpine
Okay, I'm. This is a true or false segment, okay? I'm gonna read you 15 statements. You're gonna tell me as quickly as you can if you think what I just said was true or false.
Caleb
Okay?
Lizzy McAlpine
And then if you get 10 or more correct, we're gonna give you 50 US dollars. Just a little treat.
Caleb
Okay?
Lizzy McAlpine
Just a little treat. Okay. You ready? Julie Andrews has an egot.
Caleb
True.
Lizzy McAlpine
False. The Master Chief from the Halo Games. Real first name is John.
Caleb
False.
Hope
It's true.
Caleb
Oh, my God.
Lizzy McAlpine
The Scottish language only has three words for snow.
Caleb
I should know this. I'm Scottish. True.
Lizzy McAlpine
False. 421.
Caleb
421.
Lizzy McAlpine
Apparently, Meg White wanted to be a chef before her drumming career took off.
Caleb
What is that? Oh, true.
Lizzy McAlpine
True.
Caleb
Okay.
Lizzy McAlpine
The original London Bridge is now in Arizona.
Caleb
False.
Lizzy McAlpine
True.
Caleb
What?
Lizzy McAlpine
Next to Normal debuted on Broadway in 2005.
Caleb
True.
Lizzy McAlpine
False. 2008. That was a tricky one. Alaska moves three inches closer to Hawaii every year.
Caleb
True.
Lizzy McAlpine
True. Kylie Kelce went to Lower Marion High School.
Caleb
True.
Lizzy McAlpine
True.
Caleb
Need that one.
Lizzy McAlpine
Plastics take 20 years to decompose.
Caleb
I feel like I take more. False.
Lizzy McAlpine
False. Four hundred and fifty years. Oh, God. Amazon was originally an online travel agency.
Caleb
True. False.
Lizzy McAlpine
False. It was an online bookstore. Big Bear Lake is south of Los Angeles.
Caleb
South. False.
Lizzy McAlpine
False. It's north.
Caleb
Yeah.
Lizzy McAlpine
You're killing it.
Caleb
I've been there.
Lizzy McAlpine
Batman was created before Superman.
Caleb
False.
Lizzy McAlpine
False. The mascot for Wawa is Wally the Seal.
Caleb
False.
Lizzy McAlpine
False. It's Wally the Goose seal.
Caleb
I've never seen that.
Lizzy McAlpine
If you wish. Spring Awakening is set in Germany.
Caleb
True.
Lizzy McAlpine
True. There are no dinosaur bones in the Grand Canyon.
Caleb
True.
Lizzy McAlpine
It's true. I don't know how we know that.
Hope
It is true.
Lizzy McAlpine
How'd she do? One of the greatest comebacks of all time.
Caleb
Really?
Lizzy McAlpine
Wow. Okay, that's actually crazy. Wow. You went on legendary A. I really.
Caleb
Thought that I was not going to do well.
Lizzy McAlpine
You went on a legendary run, dude. That was sick. I actually. We haven't had that before. No, we've had. We've had people do really well out of the gate and then win. We've had people do really bad out of the gate and then lose. We have not had a comeback like that.
Caleb
Oh, my God.
Lizzy McAlpine
You did something legendary today on the so True Pod. That is so funny. Well, okay. So, okay, things that people can do right now. Where can they find you? What should they listen to? Where, what should they watch? Tell them about Lizzy.
Caleb
Okay. You can find me anywhere.
Lizzy McAlpine
Yeah.
Caleb
On Spotify, Apple Music, all the streaming platforms, Instagram, just my name, tick tock, you know, all that stuff. What was the second one? What should they.
Lizzy McAlpine
Oh, she comes to you in your show.
Caleb
Yeah, I'm in Floyd Collins right now on Broadway at the Lincoln Center Theater. Yeah, come see that.
Lizzy McAlpine
Come see Floyd Collins before the end of June.
Caleb
Yes.
Lizzy McAlpine
That's so exciting. Congratulations, dude.
Caleb
Thanks.
Lizzy McAlpine
And thanks for being here.
Caleb
Thank you for having me.
Lizzy McAlpine
I love the music so much and I can't wait to. I can't wait to hear the rest of it. I'm so excited for the new stuff. Thanks for doing it, dude.
Caleb
That was a Hitgum podcast.
Allison Williams
Hi there. My name is Allison Williams. If you know who I am at all, it would probably be thanks to my job as an actress on shows like Girls and in movies like M3gan. Recently, when I was having a moment of gratitude for my group chat, I thought, I wish everyone could have these geniuses at their fingertips like I do. Well, now you do.
Jamie
Hi.
Hope
Hi, it's Hope.
Jamie
Hey, babe, it's Jamie.
Allison Williams
Welcome to our podcast Landlines where we share our life sustaining and shame extinguishing friendships. We have known each other and we've been friends for a very long time.
Jamie
Hope was my first best friend. But it wasn't mutual. I mean, I asked, I distinctly remember, I feel so calling her on the phone and asking if she'd sit next to me on the bus. And she said maybe.
Allison Williams
She didn't say no. Maybe she was like discerning. When I was pregnant, I started this group chat to prepare and crowdsource and it, it's been such a delight to troubleshoot with our friend group and we just had this thought. Should we invite other people into our group chat?
Jamie
I'm a therapist.
Allison Williams
I'm a trained early childhood educator and I'm, well, you know, whatever I am. I guess someone who has the vibe of having it all together. And still the three of us find it hard to be moms, partners, friends, family members, professional women, and just, you know, adults.
Jamie
The stuff we're talking about, whatever the recent fight was with our partner or the parenting concern we have or a funny thing with our kids or it's like, what's going on with my body? I feel like I have like a family of squirrels living in my lower abdomen. Like, I feel affirmed. I feel normalized. I feel like I'm not going fucking crazy.
Allison Williams
And I had to talk it out with you guys with different perspectives and different identities that you're juggling totally. Lifelong friendship has been our lifeline. We sincerely hope our conversation makes you feel less alone in whatever you're going through. So subscribe to Landlines on Spotify, Apple Podcasts, Pocket Casts, or wherever you get your podcasts. New episodes are out now on Hudcum. Love you.
Episode Summary: "Lizzy McAlpine is The Pope" | So True with Caleb Hearon
In the June 26, 2025 episode of So True with Caleb Hearon, host Caleb Hearon engages in an insightful and heartfelt conversation with singer-songwriter Lizzy McAlpine. The duo delves into a variety of topics ranging from Caleb's Broadway endeavors to the complexities of songwriting, the impact of social media on an artist's career, and the delicate balance between freedom and routine in their personal and professional lives.
The episode kicks off with Caleb sharing his exhilarating experience of performing on Broadway. Reflecting on his initial nerves, he expresses how terrifying yet fulfilling stepping into the world of live theater has been for him.
Caleb [02:03]: "It was kind of Terrifying at first... But honestly, I've been learning so much, and it's... one of the greatest experiences of my life so far."
Caleb discusses the process of manifesting his Broadway role through social media, highlighting his excitement over collaborating with Jeremy Jordan, an opportunity he feels he attracted through his active engagement online.
Caleb [01:32]: "I feel like I've kind of mastered the art of manifesting in public... exactly. Yeah."
He also touches upon the duration of his Broadway show, revealing that performances began in March and are set to conclude by the end of June.
Lizzy McAlpine brings attention to Caleb's viral moments on TikTok, particularly focusing on how unexpected viral success has influenced his career trajectory. Caleb reflects on how some songs, like "Ceilings," gained unanticipated popularity a year after their release, impacting his relationship with his audience and his artistic direction.
Caleb [08:40]: "I had to figure out what the next project is going to be... It just feels like I'm learning so much about myself."
While appreciating the opportunities virality has provided, Caleb also shares the challenges it brings, such as audience expectations and the delicate task of balancing hit songs with personal artistic growth.
The conversation shifts to the creative processes behind Caleb's and Lizzy's songwriting. Caleb explains his organic approach, often beginning with chords that set the song's tone, allowing lyrics and melodies to flow naturally.
Caleb [33:18]: "I start with the chords because I feel like those dictate the tone of the song. And then the words and the melody come hand in hand."
Both artists acknowledge the seemingly spontaneous nature of creativity, likening it to channeling from an external source. They discuss how persistent thoughts and emotions eventually crystallize into their art.
Caleb and Lizzy explore the contrasting demands of touring and the need for personal routine. Caleb recounts his previous strenuous bus tours and the subsequent shift to a more balanced approach with flying between cities and taking breaks between tour segments.
Caleb [27:05]: "I need to be sane... Otherwise, I'm gonna have a horrible time and it's gonna show on stage."
Lizzy relates by sharing her experiences on long comedy tours, emphasizing the importance of finding a balance between maintaining freedom and establishing a manageable routine to sustain mental and physical well-being.
A significant portion of the discussion centers around the concept of freedom—both in personal life and artistic expression. Caleb speaks candidly about his recent breakup, highlighting his pursuit of independence and the freedom to shape his own life and career.
Caleb [19:48]: "My independence is a top priority for me at this point in my life."
Lizzy expands on this by reflecting on how freedom intertwines with routine, and how both artists strive to preserve their autonomy while managing the structured demands of their careers.
Caleb shares his struggles with evolving as an artist and the frustration when previous works continue to overshadow his current creations. He emphasizes the importance of staying true to his authentic sound, even when it diverges from what initially garnered him attention.
Caleb [09:51]: "I feel like this last album, Older, was really, really an important moment for me in my career."
Lizzy echoes the sentiment, discussing the challenges of meeting audience expectations while pursuing personal artistic growth. They both underscore the necessity of evolving without being confined to past successes.
In the latter part of the episode, Caleb and Lizzy engage in a playful true-or-false segment, showcasing their camaraderie and mutual respect. The conversation wraps up with Caleb promoting his Broadway show Floyd Collins and encouraging listeners to follow his journey across various platforms.
Caleb [59:13]: "Come see Floyd Collins before the end of June."
Lizzy extends her gratitude towards Caleb, expressing excitement for his ongoing projects and the new music he has to offer.
Artistic Growth: Both Caleb and Lizzy emphasize the importance of evolving as artists while maintaining authenticity, despite external expectations and prior successes.
Balancing Freedom and Routine: The conversation highlights the delicate balance between valuing personal freedom and establishing routines necessary for sustained creativity and mental health.
Impact of Social Media: Caleb discusses the unpredictable nature of virality and its dual role in providing opportunities and presenting challenges in managing audience expectations.
Personal Experiences Shaping Art: Caleb's personal life events, such as relationships and independence, significantly influence his songwriting and artistic direction.
This episode offers a deep dive into the lives of two creative minds navigating the complexities of artistry, personal growth, and the ever-evolving landscape of social media influence.
Notable Quotes:
Lizzy McAlpine [00:05]: "Dads are addicted to dying. They'll just do it. They're just, like, dropping dead out of nowhere."
Caleb [09:04]: "I feel like this last album, Older, was really, really an important moment for me in my career."
Lizzy McAlpine [14:40]: "True fans... if you put out an EDM album, they'd be there for it."
Caleb [33:18]: "I start with the chords because I feel like those dictate the tone of the song. And then the words and the melody come hand in hand."
Lizzy McAlpine [19:48]: "I started thinking a lot about freedom because I was asking people what their perfect day looks like in five years."
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