Chloe Tucker Caine Is Taking New York By Storm

Many folks who start their careers on the national tour of Mamma Mia! end up working all over Broadway. And then you have Chloe Tucker Caine who is selling multi-million dollar homes up and down that very street. 

Since pivoting to the world of luxury real estate, Chloe has become a breakout star of the hit Netflix series Owning Manhattan. Following Ryan Serhant’s team, season two just dropped and boy is it a great watch. 

I recently caught up with Chloe to discuss bringing her love of Broadway to this season, Dancing With The Stars, and of course Legally Blonde: The Search For Elle Woods. Our conversation has been edited for clarity and length. 

Theatrely: So how's it going? Season Two is now out. 

It's going great. The show came out and I was terrified because you never know what's actually going to make it on air. And the response has been really incredible. It's really the first time I put myself out there when it comes to performing, especially in the real estate world of it all, so it was nerve racking, but the response has been great. I've been getting a lot of messages, especially about the audition scene and how it touched a lot of people and people really connected to it. So it's been a joy.

So I was doing a deep dive on you.

Oh boy.

And I was reading how you went to the Boston Conservatory…

I was actually only there for four months because I went and then a lot of people don't know this, but I was on that show about becoming the next Elle Woods on MTV.

Oh trust me, we know. Let’s jump into that. 

Yeah. So I literally went to an open call for that TV show with all my friends from Boston and they were like, "okay, you made the top 10. You're going to be moving into this house." And I was like, great, I'm leaving school to be a big Broadway star, like see you never. And then got kicked off on the very first episode, scene one beat one. I was like, "I can't go back to school, this is horrifying!" So I went to LA, I went home.

How did that show prepare you for reality TV now? 

God, that's a good question. I mean, that show, I was so young and it was such a gut punch and I literally became a recluse in LA. I couldn't leave, I couldn't leave the house, I couldn't be seen. That show kind of changed the course of my life because after being in LA, because I left school, I was doing everything but performing for a beat. And then I said, "wait a minute, what are you doing? You know, you want to perform, go perform." So I was like, "I'm going to go to an open call." The first open call I went to was for Sophie in Mamma Mia! and then booked the role and was off for two years on tour.

Have you seen it since it's been back on Broadway. 

I'm actually going on Saturday. We're taking my little cousin and I'm so excited.

Talk to me about that touring experience and going out on the road. And also, we have to know, who was your Donna?

Kaye Tuckerman. She's incredible. The whole experience was incredible. I learned so much about myself. And also, you know, that was my college experience. It was on the road. It was the years I should have been in school, but I really got a lot of hands on training. It also, I will say, messed me up a bit mentally because I booked it so fast. So when I got to New York, I was like, "hello, I'm here. Where's the parade? Where are the roles?" It definitely took me a beat to really understand how theatre works in New York.

So you finished the tour and you moved straight to New York…

You know, it's funny: I didn't realize it at the time, but I was actually doing really well. I had a huge agent and I was always getting callbacks. I was in the room. I was also in the conversations. But I think because I was so young and I didn't really understand the business of the business, to me I was like, "well I'm not making it here. I'm not good enough." And so I really got in my own head. And I kind of have this joke with my mom that the truth is no one told me I wasn't good enough but me. I was really hard on myself. I really, really struggled mentally with the industry. And I hate to say it, but I essentially ended up just giving up on myself and it's sad when I really think about that little girl in her twenties who thought she couldn't do it, but really she was doing great. Listen, it led me to here and now I'm in real estate and now we're back to the performing of it all. But you know, life, what can I tell you?

So was there always that passion for real estate there?

I had no passion for real estate. It was never on my bingo card. I've had people in the past be like, you should go into real estate, and I'm like, that's embarrassing. Absolutely not, over my dead body. But in between theatre gigs, I was bartending, and I was just such a bad bartender, I kept getting fired. So then I was like, "okay, how can I make money?" So I started Airbnb-ing my apartment in Midtown in Hell's Kitchen. And I was doing great, like I was booked and busy. I was running this little business and then it started getting really illegal in New York. And my landlord was like, "I see what you're doing, you better pack it up." My boyfriend, my now husband, at the time was like "why don't you just go get your real estate license? It's like basically what you've been doing, but legal." And I was like I guess that's a good idea. I mean, why not? It's a two week course. So I got my license and I was like, wait, I'm really good at this. Like, I could kill this. Like, screw theater, screw Broadway. I'm going to be the biggest real estate star you've ever seen. I think I did like 150 rentals in my first year. And from there, you know, I always have had this itch to perform and be on camera. And so I started stalking Ryan Serhan, as you do, as after watching Million Dollar Listing. And I said to myself, I could do that. So I started copying the way he made his YouTube videos and I kind of told myself, when I get to 10 videos, I'm going to reach out to Ryan Serhan and I'm gonna go work for him. But I actually got to six videos and someone from his office called me and that's how it all happened.

Tell me about starting the show last season, what was going through your head at the time. 

I was one of the first people to join Ryan's new company, and even from the very beginning, there was always this kind of rumbling that he wanted to do his own real estate show. I can't remember how it happened, but I was always in the mix for this. I always kind of knew that this is something we were going to do and that I was going to be a part of it. Maybe it was just me being delusional, being like, "I'm going to be on his show." But in my memory, I was always in the mix. But eventually, they had a big casting team come in and we all had to do a casting audition and then it ended up happening. I was very excited. I always was like, put a camera on me. I'm ready.

I love it. So then after season one aired and it came out, how would you say your life changed?

I think I was just definitely a lot more known. I don't know that anything changed drastically, but it definitely gave me a bigger platform to go out and start creating stuff, which then did lead to, you know, the musical series I started, Chloe in Manhattan, the musicals series. But it definitely just opened up the possibilities of what I could do.

Why was creating this series so important to you?

I was focusing on real estate, but secretly was still singing, dancing and acting. I was renting rehearsal spaces at Ripley-Grier and singing in between listing appointments, so it was always on my heart and my conscious, but it was not something I was putting out into the world and out of the blue. In the same week I had Michael McCrary, who I went to BoCo with, reached out to me, who is now a huge director choreographer. He said, "hey, I've really been thinking about you. I really think you need to start creating stuff again. What should we make?" Literally within three days, I had Michael Farrar reach out, who was my musical director on an Off-Broadway show I did called Death of the Moon. It was a one woman show. And he kind of had the same sentiment of you've been so on my mind. Why aren't you singing? Why aren't your performing? Like, let's figure out what you wanna do. And I was like, this is Kismet. Not only is it both of them reaching out to me on the same week, they're both Michael. I was, like, the world is trying to tell me to do something. I always knew I wanted to make a version of The Wizard and I, but turned it into Ryan Serhant and I would sing it to myself, walking into the office in SoHo. And I know what I wanna make. And they just happened to be the only two people in the universe that I think could take exactly what it was in my brain and turn it into a reality.

So now we are at Season Two. Talk to me about what you wanted with this season. Just seeing you in Open Jar Studios was everything…

I really went into season two, not really sure where my storyline was going to go, but I knew that I was coming into it as a new mom. And for me, it was such a different version of myself, especially than the one you saw on season one, that I wanted to show the world what it had been like for me trying to balance both motherhood and real estate. And it really switched something in me because I thought you only had to be one thing. I thought, going back to theatre, I can't do theatre, I can only do real estate. Being a mom really showed me that you can be a multi-dimensional human. You can be more than one thing and I just wanted to, I didn't know that we were gonna go down this path of theatre, but I just knew that I wanted to say yes to everything and go into this season a lot more open that I may have been last season.

What have you been seeing lately around town that you've been loving?

I love Death Becomes Her. I thought it was one of the funniest things I've seen in like forever. Dying to see Chess. That is the next on our list of things to see. And then Mamma Mia, which I'm so excited to see.

If you could jump into any show on Broadway right now, what do you want to do?

Ooh, I have two. I would love to do Chicago, but I want to do Velma. I want do a Velma stunt cast, and I'd love to do a Satine stunt cast in Moulin Rouge. Like, let me sing Firework, please, I'm ready.

I see you love Dancing With The Stars. I think let's start the campaign now. Who do you want your pro to be?

Obviously Val. I mean, I just think he's like such a winning ticket. He's so good. I'm ready. Sign me up. I have my dancing shoes ready.

If Ryan was going to be in a Broadway show, what do you think, where should he be?

I've already thought about this a million times and it is so clear to me. It’s Billy Flynn. He needs to play that role like he would be phenomenal.

You are at a really exciting moment in your career right now. When you think back in twenty, thirty years to now, what do you want to remember?

I want to remember that I didn't give up on myself like I got out of my own way finally, Chloe got out of her own way. I think I feel like that's really been my theme up to this point is, like I said before, the only person that was telling me I wasn't good enough was me. I've always found a way to psych myself out of things that I don't think I deserve. And now that I have this kid, I have this daughter, I don't ever want her to look at her mom and say, "oh, God, my mom had so much talent. She had so much potential, but she couldn't get out of her own damn way." So I'm in my era of that.

I recently saw Brittany Bateman from Real Housewives 54 Below.

How was it?

It was so iconic. I couldn't believe what I was watching. But when are you gonna come do a cabaret here in New York?

You know, you're not the first person to ask me that, so we are working on it. I will be doing a solo show, dates, TBD, but it's coming.