A Transgender Woman on the Internet Crying: Cassie Hamilton on Her Hyperpop Hit

Welcome back to Let's Be Perfectly Queer Podcast, your go to LGBT Australian podcast for all things queer.

In this episode of Let’s Be Perfectly Queer, we sit down with playwright, composer and performer Cassie Hamilton, creator of the bold new hyperpop musical A Transgender Woman on the Internet Crying.

We dive into what it means to create trans stories for the stage; loudly, proudly and without compromise. Cassie shares how her own transition shaped her journey in musical theatre, why traditional theatre spaces often exclude trans performers, and how she decided to build the kind of work that showcases transgender people and performers.

We talk about:

• Creating a fully trans cast musical
• Why hyperpop and trans culture are deeply connected
• The realities of transitioning as a singer and performer
• T4T relationships and trans love stories
• Letting go of perfection and embracing trans joy

This is a joyful, honest and funny conversation about art, identity, and making space for trans voices on stage.

Whether you love musical theatre, queer art, or want to hear from trans creators changing the industry,  this episode is for you.

🎧 Listen in and find out more about this hyperpop hit musical... and until next time, stay perfectly queer!

Want more of Cassie Hamilton:

• Instagram: https://www.instagram.com/cassievehamilton/
• Website: https://cassie-hamilton.com/
• Pretty Perfect Track: https://open.spotify.com/track/37iZ0XGomDXAPxvd75qX0J?si=012ab3973bbf45a9
• Melbourne tickets (concert preview version: https://www.ticketmaster.com.au/a-transgender-woman-on-the-internet-crying-in-concert-melbourne-26-02-2026/event/25006397E8A96970
• Sydney tickets (From $29.70):
  https://tickets.iwannaticket.com.au/event/fair-play-copy-txnbty?eventId=691bc02fcd7b825a613f790f

Transcript

Welcome to Let's Be Perfectly Queer, a queer podcast creating space to talk about all things queer. My name is Archie and I'm joined today by Cassie Hamilton, playwright, screenwriter, songwriter and writer of the musical A Transgender Woman on the Internet Crying. Questions of how you identify, seeking answers to clarify, whether you're queen or somewhere in between.

Let's be perfectly queer. Felt cute today, but it was not in the usual way. Rolled out of bed, got my cats fed, and made some macrame.

Got the topper stitching inside, white, pink, and blue for trans pride. It's kind of family. I don't know what you want me to take away from this.

What do you mean? They're nothing like me. You're pretty, pretty, perfect. I think you're pretty, eh? You're pretty, pretty, perfect.

Who cares what they think? It's not that serious. Let your worries shrink. Cause you got all of us.

We think you're perfect. Pretty, pretty, perfect. I think you're perfect.

Pretty, pretty, perfect. Transition, go fade. You look so cute.

You're so pretty. Perfect. I think you're perfect.

Pretty, pretty, perfect. Welcome to the show, Cassie. Hello.

Happy to be here. Thank you so much for the listeners today. What we are going to talk about is Cassie Hamilton's musical.

It's called A Transgender Woman on the Internet Crying, which I love the title. That sold me. If I saw that at Fringe, I'd be like, I'm buying tickets to that straight away.

But before we get into that episode, did you want to tell the listeners a little bit just about who you are? For sure. What can I say about me? I am a writer. I work predominantly in theater.

I am a director. I kind of do a whole bunch of things. I was writing down recently all the things that I do for a bio thing recently, and I was like, oh, fuck, this list goes on for a really long time.

But predominantly, I'm a writer, I'm a performer, I'm a director, I write music, I produce music, and I also am a theater producer. So I do a whole bunch of little things, but predominantly love creating new work, new work in the theater world, also the screen world. And yeah, and I love gay shit.

So you're the perfect person to be on the show then. Absolutely. You came up in our newsfeed and I was like, this is so interesting.

I need to know more. Did you want to tell us about the musical? I would love to. So it's a, how would I describe it? A transgender hyper pop musical about two trans people sort of overcoming their differences and accidentally falling in love through the most high stakes, sort of like intense kind of online political discourse that a girl could have.

But yeah, it's like entirely sort of based in like hyper pop music. It's very electronic. It's very online and it's very high energy and very electric and intense, I would say.

Very cool. And you don't usually hear hyper pop and musicals together. What made you want to do a hyper pop style musical? I think it was, look, it was a journey.

I came up with the plot and the story that I wanted to tell first. And I knew I, look, I'm a musical theater diehard. I love music theater.

I have been doing it since I was a little baby. And I sort of like grew up in this musical theater world. And I transitioned when I was like 17 and I realized I was getting ready to like be this like pristine little tenor that goes off to Whopper and like trains or whatever.

And then I transitioned and I realized that there was sort of no roles for me anymore because music theater is such a like rigid sort of form in terms of like voice types and how you need to look to play specific like female characters. And I think all of a sudden I was like, huh, how do I keep doing this thing that I love and is my like the thing I'm most passionate about in the world? Whilst there aren't any like roles for me, there seemingly isn't a place for me where there was, I mean, like we know how music theater like pumps up like little twinkie tenors to like the nth degree. And it's like, oh my God, that's the best thing ever.

And so I went from like the top of the food chain to like not on the chain anymore. And I was like, well, fuck, what do I do? But then I was also like, well, surely I'm not alone in this either. Like surely there are other trans people who are like experiencing the same thing.

I cannot be the only one who's experienced this. And so I was like, okay, I want to write a trans musical. I want to write a musical for trans people to be on stage and to play trans characters, not have to worry about like trying to fit into the sort of this like cis normative mold and also like tell a like revolutionary trans story, right? Like I think I'm a big believer in this idea that like if we tell a story with like honesty and specificity, universality will be found in that and cis people will come to that and they'll be like, oh my God, there is so much of myself I see in like different parts of this story that maybe it's not the specifics, but it's these like overall like themes.

And I think I was like, I think if I make it specific, then people will be able to see things and relate to things and like have a deeper connection to it rather than making general and wishy-washy and then making it feel not real, I guess. And also it was just important for me to be like, to like tell a story that had trans people on stage. I think like trans representation in media is like so important. 

And especially in musical theatre, we don't get a lot. I think we're getting more now, which is freaking awesome. Huge, huge ups for Dylan Mulvaney in Six. 

That's awesome. Get it, Dylan. But I think, yeah, I think I originally wrote this story and I was like, I've written some bops, but like, I didn't feel it was anything like holding them together. 

And then I was dating this trans guy in Melbourne and he was like, there's like this huge like hyper pop scene down here. And he sort of introduced me to it as this like genre of music that is so dominated by trans people and like bi-gender diverse people. And I was like, oh, okay, this feels like it's probably the style of my show. 

And then I started repurposing a lot of the tracks and stuff that I've written to be in that style. I started writing new tracks, like specifically in that style. And then I was like, oh no, this is like something really special. 

Cause I think there is something like, I think the whole thing of hyper pop is it's so in your face. Like it is so many feelings and it's like such a like sensorial and like deep and like complex experience just listening to hyper pop. And I feel like in a big way, that's kind of the same with musical theatre.

Like it's like these big, like emotional moments. And I was like, kind of makes sense that they kind of like sit next to each other in a kind of comfy way. And yeah, so I started just like made some discoveries through that. 

We started like bringing like live vocal processing into it. Cause I knew I was like, I knew I didn't want to have instruments on stage. I knew that we're going to be like, cause I was like with pre-recorded tracks, we can do stuff that is like more, I can do crazier stuff essentially if it's pre-recorded, but I wanted there to be this live element still. 

So I think we have a couple of three out of the four cast members have their own like vocal processing units that they use in different points in the show, which is super hot. But yeah, so that was, that was my journey to hyper pop as a genre for the show. For those of the listeners who are listening, who've never heard of hyper pop, if you could describe it in one sentence, how would you describe hyper pop? I would describe it as sort of this maximalist glitchy genre of music that is like pop music on steroids dialed up to a thousand tempo in the like higher than you would expect it to be and louder and overstimulating, but like in a really satisfying kind of brain scratchy way.

I was going to say that sounds like a very neurodivergent brain scratchy kind of thing in there that you're kind of aiming for. I think you described that perfectly. Thank you so much.

And you said there are some trans people also in the musical besides yourself. So was it important for you to really have that trans and gender diverse representation? I was like, I want to make a full trans cast. And I know that's crazy. 

And boy, has casting the show then been difficult because I wanted that, but we did it. And the cast is so good. They're so amazing. 

And they're so hot. And they're so talented. And everyone has such beautiful chemistry on stage. 

And they're like, we've performed a concert version of the show sort of like twice with that group now. And we have a third one coming up in Melbourne as well in February before we do the full thing. But we've just become such a little family through doing it all these times now. 

But yeah, it's like a fully trans cast. They're very, very talented. No, that's awesome. 

I guess because, you know, like you mentioned before with Whopper and you know, for those of you who are listening who don't know what Whopper is, that is the Western Australian Academy of Performing Arts. And it is in Perth. And it is very clicky. 

And there are boxes that they like you to fit in. And so was that your original plan to go to Whopper? And then you kind of, I can't do this. I'm doing my own thing. 

I'm forging my own path. Totally. I mean, every, all the music theatre girlies go to Whopper. 

Like that is like the place to go if you're like, if musical theatre is your dream. And I was like, yeah, I was fully getting ready to audition. I was like going to like workshops and stuff purely with the intention of auditioning for Whopper. 

And then, and then, yeah, I sort of was like, actually, I need to sort out this whole like gender thing. This feels like maybe it's more important. And yeah, and then I was sort of like, I actually I did give up on music theatre for a little bit after that, because it was really hard. 

And also, I don't play any instruments. Like I don't, I don't do those things. I just was like, okay, I'm gonna be a playwright. 

And I'm gonna write like straight plays. And I'm gonna maybe I'll write some music for them a little bit. But like, I don't really know how to write music. 

And then Eve Blake came into my life, the wonderful writer of Fangirls, and Mackenzie coming up this year of Belle Shakespeare. And she, I don't remember how I met her, but she got on a Zoom with me. And she just started talking to me about what I needed, what is like the bare minimum you need to do to be able to write music and to write songs and where I should be putting my energy. 

And then I downloaded Logic Pro. And I just started like fucking around in there and seeing like what I could do. And I got like, I just like fell into this world and started like training myself how to use it. 

I just found it so addictive. It was like playing a video game. Like it was just like moving through. 

And I had like, obviously, I've been listening to musical theatre for like years and years and years. And now I listen to hyperpop. Like hyperpop is now the primary genre of music I listen to, to a like a really extreme level. 

And I am obsessed with it in I think a healthy way. But I don't know. Hard to say. 

But um, yeah, that's sort of how I came to then like musical writing. It was like it was it was a long, it was a long journey, I guess. But I'm very, very comfortable now. 

And now I can write songs really quickly. And it's really fun. That's amazing. 

Because I do the singer songwriter thing. I'll be honest, I'm average. People don't realise how much transitioning actually affects your whole body. 

Your muscles change, everything changes. And so then you have to relearn. Did you have any difficulty relearning how to present yourself and a new voice or anything like that? 100%. 

Because I had a singing teacher when I was going through my transition. I had two singing teachers. That was the first mistake. 

One of them was really great. And the other one was very like, you need to sing mezzo stuff now. And so just like I was also I was very lucky, unlucky, hard to say. 

When I went through like boy puberty, quote unquote, my voice, my voice didn't break very much. I stayed with a pretty high voice. And so my singing teacher was like, oh, well, we just need to make you like sing higher. 

And I was like, what? And so she's fully just like getting me to like a belt out these mezzo songs. I'm shredding my chords all over the shop. And I'm like, this can't be good for me. 

This can't be healthy. And I'm like cracking all over the place, which is then making me like dysphoric and like nervous and making me not want to sing at all. Sometimes I can like I'd be able to belt a C really confidently, right? I can now belt a D5 really confidently, which is a huge, huge win for Cassidy. 

Thanks. It's a very recent thing I have acquired. But back then I was like, like all these songs, I was like transposing them to the top note was like a C5. 

And I was like, this is like hard. But then I think I slowly became more acquainted with my voice and what I should and shouldn't do. Because I also I had a very like rich, tenor-y sort of like sound before I transitioned as well. 

And I think it was like the journey of like letting go of this like darker, like fuller sound and transition and like getting more comfortable with my mix, which is something I'm still working on. And being able to sort of like take up this like lighter space so I can sing the rap that I want to be able to sing. But oh my God, that was a journey. 

And it's still it's still a journey. Like I think it's yeah, it's a forever thing. Oh, yeah. 

And so people don't realise how much you have to go through mentally as someone who loves musical theatre or loves music and you are transitioning, you have this whole other element to think about. Because sometimes I know at the start, because when I went through a second puberty and my voice was lowering, and I sounded like I was choking a like it wasn't great. It was just really bad. 

And then I was like, have I screwed up? But then mentally, I'm like, but this is me. And then so you go through all those kind of things as well. And then now to come out on the other end, and you're you're hitting that notes that you never even thought you were going to hit. 

That's absolutely incredible. And it really shows for all those young trans kids who are listening who want a career in musical theatre that it's still in reach. Totally. 

100%. Couldn't agree more. And with the musical, if you could only choose one of the songs to sing forever, and is your absolute favourite. 

Why is that your favourite? And why should people also love that song? That's a wonderful question. Oh, okay. I love, I'm addicted to the finale number. 

And this is a bit of a cop out, because the finale number is kind of like three songs sort of smashed together over 10 minutes. But it's just this euphoric extravaganza of trans joy. And also some of the most bubblegum hyperpop in the show as well.

But whenever we want to get hyped before a show or something, it's like end of warmup or something, we'll all sing the finale number. And it just gets us all in this headspace. It's a mashup of two songs, primarily. 

Compet is the first song, which has this addictive chorus with this incredible sample that I've sort of manipulated through it. It's like the character, the protagonist, Avis, who's this conservative influencer character, it's like her finally coming to her understanding of her own queerness, and that she doesn't have to fit into this mould of being a cis, passing, heteronormative girly. And she can finally be herself. 

And also finally opening up to the idea of the community that she is in conversation with being the trans community for the first time. And it's this really intense moment of self reckoning. And then the other song that it's mixed with is kind of the anthem of the show, which is called Pretty Perfect, which a version of is on Spotify if you want to listen to it. 

But is this anthem of trans community, and this idea of letting go of the idea of needing to be perfect, but pretty perfect is enough, close to perfect is beautiful. And what it is for trans people to have community and to celebrate that and the joy of being seen by other trans people and being able to celebrate each other. And it's just a beautiful, euphoric song. 

And also a song like that, and being transgender, you do see these kind of icons on social media and these kind of really unrealistic, sometimes expectations because of people who have a lot of money and they can make themselves look like an ideal perfect of what they feel. I feel like then that song does have that double meaning for those who are trans and they're listening to it as well. That you can get close to perfect.

You don't have to reach these ideals, who you are and who you want to be is just perfect enough. And I think that's really beautiful. Yeah, 100%.

And how have people's response to the musical been so far? Really nice. People have really loved it. It's been really beautiful.

I think we've gotten a standing ovation after every performance that we've done, which I'm trying not to get accustomed to because if we never make the whole show and everyone's sitting down politely clapping, I don't want to be upset with that. But the track record's really good. People and the messages and stuff I've been getting from people, not even just trans people, but also musical theatre people who are quite high up in the industry being like, this is so, I've never seen anything like this. 

This is fully changing the game of what musical theatre is and how we understand musical theatre. But also trans people have been loving it. And I've been getting into some really big conversations with trans people after the show. 

Just especially, I think the show deals with this idea of passing a lot, this idea of being cis-passing and holding that up and what it is to be someone who is cis-passing, what it is to be jealous of somebody who is cis-passing and how that hinders you from connecting with other trans people in all its various shapes and forms. And I think I've had some really, really interesting conversations with other trans people after the show. And obviously ending in this place of, it doesn't matter what you look like or how other people perceive you. 

Yeah. That has been some of the most interesting and exciting conversations I've had with people post-show. No, that's awesome.

Do you have any plans to tour Australia or just like the, are you doing the East Coast? So the only venue that is currently confirmed is the Old Fitz Theatre in Sydney. We have deep hope and aspiration to then come to Melbourne at some point. Nothing is confirmed yet, but we have a lot of very, very, I would say with quite a lot of confidence that it will happen, that we will go to Melbourne. 

Beyond that, who's to say? Yeah. Who's to say? But I feel like now in the climate of the world, this musical is very much needed because people turn to musicals for escapism, but it also can be political commentary on the world. And a lot of the world with trans people and what they think about trans people is a little bit backwards and very conservative.

And so I definitely feel like a musical like this is very much needed. And I have not heard of a trans musical before. So that's why I was like, oh my God, I need to learn more. 

This is amazing. And so it's really nice that you are doing this. And I really do hope that this can take you as far as you'd like it to go, because it's something that I feel like Australia needs to have right now before we then follow the footsteps of places like the UK and the USA. 

100%, 100%. And I think it was so important to me that the show was very like loudly and authentically trans as well. Like I didn't want it to be like a secret reveal that like I keep from the marketing copy or anything. 

I wanted it to be in your face and like just present. I was like, I don't want it to have any shame about what the show is and who the show is for and what the show is about. I think a few years ago I saw a show by a Greendoor theatre company called Seven Methods of Killing Kylie Jenner. 

And I think a brilliant, hilarious show and the way that that show, it was two black women on stage sort of discussing racism and that experience. And that show just did not, if you were not in the black community, it did not hold your hand. It just went straight into the language and the things that they were familiar with. 

And it just expected the audience to catch up regardless of their background. And I was like, I want to be able to do the trans equivalent of that essentially. I'm like, I'm going to drop us straight into the lingo. 

This is my community. We're going to go straight there. We're not going to sugarcoat anything. 

And people will pick it up. And people do pick it up. It's so fun watching an audience of three or four trans people at the back scream laughing at something and all the cis people around them being like, oh, is that, okay, that was funny because, okay, well then that means, and then putting the pieces together as the show goes on.

There's a lot of cis people who have seen this show that have been like, I've never seen anything like this. I didn't know some of this stuff before I saw this show. And I am very grateful to now know these things. 

And I'm really grateful that the show can do that. No, that's awesome. And if there is one thing that the audience take away from the musical, what would you like that to be? One thing, one thing you can take away. 

I think, it's also interesting because I wrote the show so long ago, right? It's like, what's a baby Cassie you want people to take away? I think at the show's core, there's what I want cis people to take away. And there's what I want trans people to take away. I think there is a bit of crossover, but I think one of the big things I wanted to talk about with this idea of like T for T relationships and what that is. 

And for trans people, the profound sense of being seen and being understood and not feeling the need to be anything other than what you are, that can come with that. In my own personal experience, that is what that was. And I think I really wanted to have, I just thought it was weird that like all the trans people around me were dating other trans people. 

And then in media, it was always a trans person and a cis person in relation to the cis person. And I was like, this doesn't feel indicative of like what my actual experience of this community is and what romantic relationships are. And I think I really just wanted to show that this is like a beautiful, I just wanted to show that T for T relationships were like really, really beautiful and how electric and like beautiful that can be. 

Yeah, I'm repeating myself, but that is how I, that was like kind of one of my big motivators, I guess, for like writing the show and what I wanted people to take away from it. And that trans people don't need cis people to validate them to be valid, you know? Validity of your transness does not depend on the validation of cis people. Yeah, that's probably the main one.

Yeah, that's great. I've seen a lot more online of trans people who aren't worried about fitting into heteronormative ideals of what it means to be masculine or what it means to be feminine. You can actually just be yourself and that is masculinity and that is femininity if you say it is, and that's all it is. 

And so, you know, that is beautiful. And for those who are listening who don't know what T for T is, do you want to explain what that is? Because we do have a few allies, so I'm not 100% sure they know what that means. 100%. 

A relationship between two trans people, essentially. Yeah. A romantic relationship. 

Yeah. We do get some listeners who are like, you say all these abbreviations and I don't know what they mean. And it's like, oh, which is really nice that we do have a lot of allies who listen to the show and stuff, which is really, really nice. 

We even had an ally come onto the show. He was like, I'm an ally, and they did a whole documentary on a trans bill in Canada. And I was like, wow.

So it's sometimes you just have to explain a little bit. 100%. And I am awful at explaining things. 

So thank you for helping. No, it's all good. It's just my brain is like, oh, wait, I need to remember that part that we need to explain what that is. 

100%. So when is this show performing next? So the show is coming up at the Old Fitz Theatre in Sydney. We open at the end of March and then run through until around mid April. 

Amazing. If you were going to sell this show, think you are an infomercial, like a 90s or early 2000s infomercial. How would you sell this show for our listeners to go watch it? Yeah, I'm putting you on the spot. 

No, and I'm so bad at marketing copy. That's so not my thing. I would describe it as a hyperpop cyber war rave about two transsexual divas falling in love and making a mess. 

So if you love divas, if you love hyperpop and craziness and absolute hilarity, is it funny? Is it enjoyable? It's very funny. It's deeply, deeply funny. So if that is your thing, then go watch this musical and you will have a great time.

Sydney, you may be the first ones ever to see it in the first true musical form. You can say you saw it first. So go ahead and go check it out. 

And that will be towards the end of March. And do you know roughly how much tickets will be? I don't know. It's hard to say. 

If you get it now, tickets would probably be about 50 bucks, I would say. But they scale. So get in earlier because then later on the tickets will become more expensive. 

And then you'll be like, fuck, I'm paying so much money for tickets. But if you get in now, 50 bucks. I'll put all the links and stuff in our show notes so that people know where to access the musical. 

I'll put in that song as well so that people can have a listen to that and see if this hyperpop, maybe that you've never had a taste of hyperpop and you can see if it's your kind of thing. And then go check out the musical as well. Thank you so much. 

Thank you for coming on the show and chatting. It's been lovely. I really can't wait to see what happens with the musical and what you're doing next. 

And yeah, it's been great talking to you. I'll post links to everything in the show notes. So all of our listeners, if you'd like to check out any more of Cassie's stuff, you can check it out there. 

Go check out the musical. And until next time, I hope that we have been perfectly queer. Let's be perfectly queer.

(Transcribed by TurboScribe.ai. Go Unlimited to remove this message.)