Kaitlyn O’Leary: From San Diego Triple Threat to the National Tour of Hadestown

“I think that’s kind of the, comes with the territory of being an actor, is that you kind of move to New York hoping that you’ll move away, or book Broadway, one of the two.”

Welcome Kaitlyn O’Leary

We’re joined on the Starline by an actor, singer, and dancer. She does a killer Kourtney Kardashian impression, but doesn’t have to depend on it for her latest Broadway project. It’s playing Worker in the national tour of Hadestown. We welcome Kaitlyn O’Leary.

KO – Hello, hello.

SD – Kaitlyn, let’s go Beyond the Mic. The Tony Award-winning musical is on the road. What makes playing Worker, the chorus of the musical, so special for you?

KO – I think the thing that makes it so special is getting to work with everybody else in the ensemble and kind of building this like family unit almost. I think the beautiful thing about Hadestown, this is across the board, it doesn’t matter which role you’re playing, is that it really asks you to bring a lot of yourself to the story. And I think that’s what makes it very special, very fun to do.

SD – If someone hasn’t seen Hadestown, what do you want people to take away from the show?

KO – I hope that people take away the beautiful love story that’s being told. It’s being told through two love stories at once, actually. Orpheus and Eurydice, and you get to see this kind of young, blossoming love, and also get to see it through the perspective of Hades and Persephone, who very much love each other, but it’s a lot more complicated than one might hope.

It’s a lot. It’s a lot, it’s a lot. But you kind of see these two relationships foil each other, and it begs the question, how far would you go for the person that you love? And I hope that’s what audiences get to ponder and reflect on.

SD – How did the musical, which intertwines God and mortals, change you?

KO – Ooh, that’s a good question. I think the people that I’ve had the opportunity to meet along the way, and become so close with, I think that’s the thing that’s changed me the most.

SD – Why?

KO – I met some of my best friends doing this. I met girls who were going to be my bridesmaids. And I think we have a very unique, shared experience that kind of has bonded us for life.

The Rockin’ 8:

Kaitlyn O’Leary from Hadestown joins us for The Rocking Eight.

All this is, is eight random questions. Answer with the first thing that comes to your mind. There is no pressure.

KO – Oh my god, okay.

SD – Which Hadestown character would Kourtney Kardashian play, and how would she play it?

KO – Oh, she would be Persephone, and Travis Barker would be Hades.

SD – What is your typical In-N-Out order?

KO – Ooh, number two, grilled onions, add pickles, extra spread, and a Neapolitan shake.

SD – Number two, grilled onions. I’m writing this down.

KO – You gotta, it’s my favorite. And a Neapolitan shake. Or Diet Coke, depends on what mood I’m in.

SD – Last time you enjoyed a beach bonfire was when?

KO – A beach bonfire, oh my god.

That must have been high school. Last time I enjoyed a campfire was last summer in Maine, though. I was doing a contract up there.

SD – Best flavor for shaved ice?

KO – Anything with red dye 40.

SD – Best breed for a dog is?

KO – A lab.

SD – Labs are the best. What was the final, the last final you studied for, by the San Marcos River?

KO – Ooh, my last final I studied for? Probably my math final.

Not a lot of studying got done, to be honest. But I passed, I graduated.

SD – Texas State, not a lot of studying got done.

Who is the last person you shared a s’more with?

KO – Oh my goodness, some of my cast members and band members and I had a little bonfire in Wichita and we had a full s’mores bar and charcuterie board, it was awesome.

SD – Last Lakers game you saw live was when?

KO – I think the last Lakers game I saw was at Madison Square Garden and we won.

The Back Half:

It is Kaitlyn O’Leary from Hadestown, she joins us for the back half.

Kaitlyn, how have you grown from where you were when you were the winner of the San Diego County Fair Ultimate Triple Threat to now?

KO – Oh my god, honestly not much has changed. No, I think I have a much better understanding of who I am and what kind of art I want to be doing and Hadestown definitely fits the bill.

SD – How old were you when you won the Ultimate Triple Threat?

KO – Oh god, I think I was 12, 12 or 13, maybe younger.

SD – And the video of that is still up.

KO – It sure is, everybody in this cast has found it, they sure have.

SD – When they found it, what was the reaction?

KO – The reaction was, oh you can sing, oh she can sing.

SD – What was a Broadway show that made you saw, when you saw it, it made you think, this is what I need to do forever?

KO – Oh wow, the first Broadway show I ever saw was Annie and Jane Lynch was playing Miss Hannigan.

SD – Wow.

KO – Dude, dude, she is, Jane Lynch, her comedic timing, prowess, all of the above, has been my bible since I saw my first episode of Glee.

SD – Why is it important to master that comedy element to make you a better actor?

KO – Oh gosh, it’s just so, we must make people laugh. Everyone needs to laugh these days, everyone needs to smile, and comedy’s hard. And so I think the best way to learn it and study it is to learn from the greats, and Jane is one of them for sure.

SD – Who influenced you musically growing up?

KO – Beyoncé, I said it in my interview then, I’ll say it now, Beyoncé. I used to listen to, oh god, I used to listen to Listen from Dreamgirls, and I would play it over and over and over again and try to mimic how she sounded on that song.

SD – When was the last Beyoncé concert you saw?

KO – Last was Cowboy Carter. I went on closing night of year one of this tour, we were in Chicago, and we closed, we had a 1pm matinee, and then we all got ready and went to an 8 o’clock concert at Soldier Field.

SD – How was that for you?

KO – Best day ever. Best day ever. We were in the nosebleeds, and I was having more fun than anyone there.

SD – So how many songs do you know of hers off the top of your head?

KO – I won’t sit here and say that I know every single one. I won’t claim that. But I think if we were to play, I’m pretty much up there, yeah.

SD – You’ve been supported by your friends, significant others, and family. How have they encouraged you as you went from San Diego to Texas State to New York?

KO – I think the first people that come to mind are my parents. I think they saw from a very young age that this was all I ever really wanted to do, and they made sure that I had the opportunities, and I was put in places where I could grow and continue to get better. And they’ve always been my biggest supporters, and I don’t think I would be here without them.

SD – How many times have they seen a show that you’ve been involved with? Not Hadestown, but any show you’ve been involved with.

KO – Oh, they’ve never missed one. So I don’t even know if I can count. My dad literally drove out to Palm Desert last weekend. He’s seen Hadestown so many times. He’s like, yeah, I’ll see it again.

SD – How does that make you feel?

KO – Oh my god, it’s the best feeling in the world.

SD – Now, do you look for him when you know he’s in (the audience), or do you’re like, don’t look?

KO – I totally do. I had my lamp, and I was scanning the audience for him to make sure he made it.

SD – Hadestown is all about love, doubt, and second chances. Since this is your first national tour, what theme, love, doubt, second chances, hits closest to you right now?

KO – I think right now it’s love. And I think it’s love in all different kinds of ways. I think that doing this show every night, it’ll get you. I still cry every night at the end of the show. But it just reminds me of all the people in my life that I am lucky enough to call friends or family or loved ones. And it reminds me to tell them when I think it.

SD – I see you have a Clauddah ring on.

KO – I do.

SD – Why is it important for you, for your significant other, for you to show everyone, nah, done.

KO – No significant other right now. But I think the reason why I wear this is because my younger sister got it for me in Ireland. And so it always reminds me of her when I look at it.

SD – So even without a significant other right now, you already know your bridesmaids for the wedding that you’re going to have in the future.

KO – Oh, yeah. The other part, I’ll figure it out. Who cares? I got the bridesmaids. That’s all I need.

SD – Kaitlyn O’Leary from Hadestown joins us beyond the mic. There’s something haunting about Hadestown. What’s the key moment in the show that gives you chills?

KO – Oh, so many. It changes every night. I think after doing a show for so long, one might think that I would get bored with it. But that’s like the furthest from the truth. I think there are someone could say a line with like a different emphasis on a word or take a breath in a different spot. And I go, oh, that’s what that means. Um, or do a new riff or, you know, whatever it is.

I think the last time I got chills was the other night listening to How Long. I don’t even remember what she did. But Namisa did did something beautiful and it gave me chills.

SD – What’s something about being in an ensemble that audiences completely misunderstand?

KO – Oh, I that’s a really good question.

SD – Why?

KO – I think there’s a misconception that everybody’s everybody’s working hard. Everybody’s giving their all to what they do.

Everybody’s giving 100 percent all the time. I think for this ensemble in particular, it’s really interesting because you need to have people who can do the show every single night and then also cover a lot of different roles. So every person, every worker covers principles.

Principles. And so it’s a it’s a different part of your brain that you have to exercise. You may not be getting the last bow every night, but you have to make sure that if something goes amiss, that you can do the role that gets the last bow at curtain call.

SD – How is the nerves of that not knowing in some nights someone might be in warm ups going? Not feeling it tonight. Yeah. And then all of a sudden it’s like, Kaitlyn, Persephone, go.

KO – I think the name of the game is being as prepared as you possibly can be. And that’s a lot of doing work on your own time and making sure that you’re ready for that for that moment.

SD – When you’re out in the road, what’s the one thing you bring with you so you don’t feel alone?

KO – Oh, my mom got me a little I don’t even know, a little stuffed animal. It’s of the red panda from Turning Red, the Disney movie. And she got me that for Christmas. So I have that with me.

SD – What’s the one thing other than the claddah ring from your sister that you have that reminds you of her?

KO – Oh, probably some of her clothes. I love stealing her clothes.

SD – What’s the last…

KO – Sorry, Kylie.

SD – What did you steal from Kylie?

KO – I think I might have a pair of her jeans. I’ll be honest. Oops. Sorry, Kylie.

SD – What’s the first thing you seek out when you hit a new city that might shock people?

KO – This isn’t very shocking, but probably a good coffee shop.

SD – What is your typical coffee order? So what’s that? Are you black, cream, sugar? Or are you like oat milk, one shot?

KO – No, it truly depends. It depends. I mean, you can’t go wrong with my smell latte. Sometimes I’ll get a Cortado if I need a little extra boost. I had one of the best lattes of my entire life in Salt Lake City. It had like lemon and olive oil in it. And I was apprehensive. Wow. It was delicious. It’s really good.

SD – Was there ever a moment, Caitlin, when you thought, this might not work out? And who or what pushed you through it?

KO – Oh, of course there was. I think the whole first year I lived in New York City, I was like, I can’t do this. And I’d call my mom crying every other week. And it was my mom. She was the one who was like, no, you’re going to stick it out. Everything’s going to be OK. You’re going to figure it out. And she was right, as she so often is.

SD – Why is your mom so special for you?

KO – I tend to get very anxious about situations and things, and she’s always the one to talk me down and kind of ground me back in reality.

SD – So what role does your sister and dad have in this whole taking care of Kaitlyn?

KO – My dad’s the same way. My sister is like, girl, get it together. Like, what’s wrong? What are we doing? I always joke that she was meant to be the older sister.

SD – Your sister gives you the tough love.

KO – She does.

SD – What’s the one key detail of the show that most people miss, but means so much to you personally? (She pauses) This question hits you. Why?

KO – I don’t know.

I’m trying to think. I think there are so many, because our audiences are so perceptive of like all of the little nuances of the show. And I think it’s been around for so long that it’s developed such an incredible fan base.

So I don’t want to sit here and say something that’s like, oh, of course we noticed that. I mean, this is the thing on the playbill. But I think every time a carnation is revealed on stage, I still get chills.

And it’s such a—I think that’s such an indication of the beauty and the magic of live theater is this flower appearing because of how much these two characters love their person.

SD – What does the power of that love mean to you? Oh. And what will it mean when you have someone that loves you that much?

KO – I think it’s—I think the thing that’s most meaningful to me about this show is getting to bring it to so many different cities around the country and getting to see how it affects our audiences.

I think my favorite part of the show was Cups when we’re standing on the edge of the stage and we get to see like the first couple rows of the audience and really connect with them.

SD – Where were you when you got the news you got the job, and who did you call first?

KO – I was at—I think I was at LaGuardia because I was flying home to visit my family for a little bit, and the first people I called were my mom and dad.

SD – So you’re at LaGuardia. Your agent calls you. Were you at the gate? Were you before?

KO – Oh yeah, I was about to get on the flight.

SD – So what do you, how do you take that moment of, I’m, Mom, I see you. I got great news. Or did you tell her everything and they’re like, final call, final boarding call?

KO – I think I told her everything. And then I can’t remember.

I was like, but don’t tell my siblings. Like, I want to tell them and surprise them. And then I think she accidentally told them because she was so excited.

SD – What did that mean? What did that moment mean when you’ve been doing San Diego, you’ve been doing shows everywhere, you’ve been auditioning after auditioning after auditioning, and then you got the call that your life’s dream has been made?

KO – It was very—it was kind of the best feeling in the world. It was very affirming… was very exciting.

It was my first big girl job, really. And I hadn’t had the opportunity to perform in a while. So I was just, like, over the moon, so excited to get to do—and this show, of all shows, is like such a gift to get to do.

So I was very, very excited.

SD – How many auditions did you go through to get to Hadestown?

KO – Oh, I gotta go check my audition tracker. It was a lot. A year’s worth.

SD – A year’s worth?

KO – And it’s so funny, too, because that’s, like, nothing in the grand scheme of life, you know?

SD – So no after no after no after no after no. What went through your mind when you finally got the yes?

KO – Hell yeah.

SD – Did you cry? I mean, what was your—

KO – Oh, I don’t think I cried. I think I pulled it together because I was in public.

But I think when I was with my family, I think a tear or two was shed.

SD – So which friend did you call after you told family? Who was the first friend you called?

KO – I think I called—I can’t remember who the first friend I called was, but I do remember I got to tell my two best friends from high school. I got to tell them in person, and that was the best thing ever, because they had been on that journey with me the whole time and seen how difficult it was.

And they’re also some of my biggest supporters and the reason why I’m here. So it was really special to get to tell them in person.

SD – As special as Hadestown is, there is a role in the back of your mind that you know, if you got it, you would say it was your dream. What’s the role?

KO – Sally in Cabaret.

SD – Why?

KO – I’ve always loved that show. I love the music, and I think it’s such a love letter to this art form, and it’s a meaty role, and I’d love to get to play her one day.

SD – What did Broadway mean to you?

KO – I think Broadway is very much a privilege, and I think musical theater is obviously an art form that I love very dearly, and I hope that it becomes more accessible and equitable, and that the people who keep it running are taken care of, so that they then get to take care of audiences by telling their stories.

SD – Tell me about special friends that you made. You talked about them earlier, about them being the bridesmaids, but in a broadway show. They may move to another show. How do you keep together such a core group of special friends when you guys are on totally different journeys, and their journey might leave Hadestown?

KO – Yeah, true. I think that’s kind of the, comes with the territory of being an actor, is that you kind of move to New York hoping that you’ll move away, or book Broadway, one of the two.

And I think the best thing I can say is that you cherish the time that you get with each other, and then it’s lots of FaceTimes, lots of texting, lots of sending each other stupid videos on the internet, and making sure you have plans for the next time you see each other.

Two Childlike Questions:

SD – It’s time for two childlike questions with Kaitlyn O’Leary. Beyond the Mic. She plays Worker in Hadestown. Kaitlyn, what do you want to tell the child in the audience who’s looking at you with hope and wonder in their eyes about being you when they grow up?

KO – It’s going to be tough, but it’s the most rewarding and fulfilling life you can lead. And if it’s what you love, don’t stop until it happens.

SD – If you could sit down with your eight-year-old self right now, what would you tell her about everything this tour has taught you?

KO – I would tell her that the hard work paid off, and that you do get, the dream that you have right now is real. And I would also tell her to be nice to her parents and to not ask your mom to skip dance class, because you don’t need to be skipping dance class. We don’t need to be doing that.

SD – How many times did you attempt to skip dance class?

KO – Successfully? Probably more than I should have. But I went to enough to make this happen, so it all worked out.

The Wrap:

She likes In-N-Out’s number two grilled onions and extra spread, and her last campfire was in Maine. Kaitlyn O’Leary, go see her in the national tour of Hadestown. Thanks for taking the time to go Beyond the Mic with us.

Thank you.

And that, my friends, is Beyond the Mic.

Check out Hadestown on tour here.

Listen to more Beyond the Mic episodes featuring Broadway stars here.