In the past year alone, Alyssa Flaherty’s hard work has opened doors that have surpassed her wildest dreams. From auditioning for The Voice to sharing the stage with Kevin Costner and joining major country acts on the road, Alyssa has built her career built by brick. Now, she’s taking a leap into her next chapter with the release of her debut EP, Heartbreak, Thank you.
The Annapolis, Maryland native moved to Nashville in 2020 and became the latest up-and-comer ready to show the world her talent. She cut her teeth back home, performing at local schools, charity events, talent shows, and even professional sporting events. But she knew that she was destined to go beyond her hometown in search of bigger ways to showcase her talent.
So with no backup plan in mind, Alyssa and her family packed up and headed for Music City, where she dove headfirst into the scene by playing gigs, learning to play the guitar and honing her songwriting skills.
A major breakthrough came when she performed alongside Kevin Costner and his band, Modern West. This moment ultimately led to her powerful rendition of “Amazing Grace” being featured on the soundtrack for Costner’s epic series, Horizon: An American Saga.
This summer, she’ll cross another milestone when she plays her first international shows in the UK. Alyssa’s upcoming run will give her the chance to showcase her new five-song collection, Heartbreak, Thank You.
This project is as personal as it gets, as she uses five songs to capture a deeply reflective healing journey where heartbreak isn’t the end of the story. Instead, she views it as something that marks the beginning of something stronger. Co-written entirely by Flaherty, the EP includes previously released singles “Broken By You” and “Know You By Heart,” as well as the poignant title track, which captures the growth that follows grief.
We caught up with Alyssa ahead of her EP release to talk about her journey from talent shows to Nashville stages, how heartbreak shaped her songwriting, and more. Keep reading for the full Q&A:
Talk about when you realized music was going to be a bigger part of your life story?
So funny enough, no one in my family is musical or has any kind of musical ability. We always crack up about it, not in a bad way, but it’s just so funny. But when I was literally in diapers, I would just be singing around the house all the time, and then when I was really little, I would sing the little Disney princesses. And so my mom’s girlfriends would come over and be hanging out and they’re like, ‘we think she can sing. We think she’s a singer.’ And my mom was like, yeah, okay. She’s going to play sports. So then I did, I played soccer, basketball, lacrosse my whole life and just did that forever. I’m from Maryland, Annapolis, and so lacrosse is huge up there. So started playing lacrosse and then I was about eight years old and I signed myself up for my school talent show. And my parents were like, ‘are you sure you want to do this? Are you sure?’ And I’m like, ‘yeah, of course I do.’ And they’re like, ‘okay, well, you’re not quitting. You’re going to do it.’ So I was like, ‘oh, done. No worries.’
Did you have any vocal training?
I begged and begged my mom for voice lessons at eight years old. I was like, well, I want to get better at this and I want to learn and be coached like I am in my sports. I ended up getting a voice coach and ended up taking voice lessons for about eight years. And so I was trained classically, and I just kind of applied that to anything I wanted to sing. So I loved all kinds of music. I loved Adele, I loved Bonnie Raitt, I loved Fleetwood Mac, I loved Taylor Swift. I loved country like Shania Twain, Kenny Chesney. And so I just kind of was always obsessed with the music industry and just like music, I just loved it.
At what point did you realize your passion for music might turn into more of a career?
In high school, my aunt ended up signing me up for The Voice. And so we all flew to Houston and I auditioned and did the whole cattle call thing, and that was just such a fun experience. And then came home and ended up finding out that I was going to go to LA. So my mom and I flew to LA, did the auditions there, did not make it on TV or anything, and then we came home. And when you go through those processes, they’re always like, ‘well, who are you?’ And I’m like, ‘well, I’m 13. I don’t know who I am. I just want to sing.’ But I was always just so drawn to country music and the storytelling. And again, love Shania Twain, loved Martina McBride and Kenny Chesney growing up. And I was like, well, we should go to Nashville.
How did you get your start in Music City?
So I ended up, by myself, looking up little independent labels in Nashville and then reached out to them and I was like, ‘I’m Alyssa, I’m 14. Here’s a video of me singing the national Anthem. Let me know if you want to talk.’ And I didn’t tell my parents. I was like, we’ll just pretend this didn’t happen if I don’t hear anything back. But long story short, ended up getting a response back. My parents were kind of like, ‘what did you do? But also you seem very passionate about this.’ And I was like, ‘I really think this is what I want to do. I want to do music and I want to sing, and I want to share it.’ And so we ended up coming back to Nashville and meeting with them and did the back and forth and just fell in love with Nashville. And now we’re here, and now I’m writing and playing and doing shows, and it’s been so much fun.
Did you ever have any backup plan or anything else you wanted to do aside from music?
I remember in eighth grade, our lacrosse coach would be like, ‘give us a list of 40 schools you want to go to and play at.’ And I would be like, ‘I don’t want to do this. This is not what I want to do. I want to sing, and I don’t know how I’m going to do it at all yet, but we’re going to figure it out and it’s going to happen somehow some way we’re going to end up doing it.’ So yeah, again, it kind of has just been slowly unraveling and just kind trusting the process.
When did you officially make the move to Nashville?
My whole family moved. I have a younger brother, and it was March of 2020. I was a junior in high school and we moved March 12th, and so everything shut down on the 13th. So we had gotten here and we’re like, ‘oh gosh, what did we do?’ But it was awesome. Again, it was in a weird way, it was awesome to just not have to do anything and just being able to get to know the area and just kind of settle in and get unpacked and all the things. But yeah, we moved in 2020 and we just love it. We’ve gotten my grandparents to move down here, so it’s a party in Nashville now. We love it.
What was it like trying to get established with the songwriting world in Nashville?
Yeah, it was probably about two years ago. I had just started writing, and a year prior to that, I was like, I need to play guitar. I want to be self-reliant. I don’t want to have to rely on anybody else. And I had an incredible mentor who just taught me guitar. So for a year I was every day learning how to play. The next year I was like, okay, well, we got the guitar down, now let’s write songs. So I wrote my first batch of five songs in the first month, and then ended up going to play my first writer’s round in February of 2023. And so go play the round and end up meeting Erland Wanberg there. And he does so much in town, he’s kind of like a philanthropist. He does everything he writes, he plays, he manages, he does a little bit of everything. And he came up to me after and he was like, ‘Hey, my friend Teddy Morgan, he’s in Kevin Costner’s band, and we would love to write songs with you to pitch to sync, maybe see if we can get a song in Yellowstone, whatever.’ And I’m sitting there, ‘no, you do not want me to do this. I just started writing songs a month ago, I promise you, please go find someone that’s really good at this.’ But he was like, ‘no, we would love to.’ So it was my first co-write and I wrote with them, and I remember leaving that day being like, wow, I love this so much, and I love these people so much, just so encouraging and sweet, and just so nurturing with songwriting. And so we just kind of stuck with that.
How did that friendship lead to the chance to hear your voice in Costner’s series?
So Teddy got a call from Kevin and he was like, ‘Hey, would you produce ‘Amazing Grace’ at the end of Horizons a movie we’re working on?’ And Teddy was like, ‘of course.’ And so he started working on a version with a composer that was out in L.A. and Teddy calls me in July of 2023, and he’s like, ‘Hey, do you want to come in and sing a demo on Amazing Grace? Kevin’s putting it in Horizon, his new movie, his friend’s singing it. She’s already agreed to do it, but we’d love to have you come in the demo.’ So I’m like, ‘okay, my God, this is so cool. I’d love to be a part of it.’ And so go sing the demo, think nothing of it. A month later, it was my 20th birthday, I’m on the way to dinner with my parents and my brother and Teddy’s calling me, and he never calls me, but I was like, am I going to answer? We’re about to walk her into the restaurant. Maybe he could just text me. And I was like, no, I’m going to answer the phone. So I answered the phone and he’s like, ‘Hey, I just got off the phone with Kevin and his friend’s not singing it anymore, and he wants you to sing Amazing Grace in his movie.’ So that was like a holy hell, what is happening right now? So that was just so special and so cool. So we were super fired up about that.
And then you also got the chance to share the stage with Kevin Costner and his band?
Kevin was going out on the road to play some shows in Jackson Hole, Wyoming in Denver, Colorado. And Teddy calls me and he’s like, ‘Kevin wants to have you come with him and sing some duets with him and sing a song that is in Yellowstone. It’s called ‘Killers.” And so it was just such a surreal, I was kind of like, what is going on right now? How is this happening? But it was so special, and I will literally never forget it. It was so awesome.
Talk about how you decided to take the pain of heartache and put a positive spin on it with your debut ep, Heartbreak, Thank You.
I think a huge part of this project has been reflection for me. Even just sitting in the room, it’s like you’re sitting and thinking about certain relationships and You’re hearing about different relationships, and it kind of allows for this beautiful just appreciation for it. You learn so much going through relationships and going through breakups and going through heartache, and I just think it’s such a beautiful thing. You come out so much stronger, you learn so much more about yourself, and I just really want people to take away from this. It didn’t work out for a reason, and it’s not an ending. It’s a beginning and it’s the start to something new and something beautiful, and you’re going to find something that’s worth your love and your time.
What was the thought process behind the sequencing of the track list?
We wrote these songs in chronological order and it was not an intention. It just happened naturally. We were picking songs for a project and we were like, these are the songs. And then I was like, well, this is the order they should be in. And then we looked back at the dates and they were all in order, and I was like, well, this is ironic. This is the total natural progression Of I saw my own growth in it. And you see your own stages of why I was here in this month, and now I’m here and I’m so happy I’m here now. But I just love, I think just with anything in life, it’s like if things don’t work out, it’s not a bad thing. It’s not a bad thing, it’s just not meant for you, and that’s okay. And I think that kind of just mindset is such a powerful thing, and I just really hope I can inspire people and even just help girls and young girls going through that. It’s all up here and it hurts and it sucks, but you got this.
Were there any songs that were you were hesitant to include because they were so honest or vulnerable?
I think for me, it’s the more honest, the better. And I feel like if you’re trying to filter out certain things, people are going to feel that. And so I think for me it was like this just feels so right and it’s so real and it’s so just true to where I was at. But also where people in the room with me were at, before you write these songs, you get into these awesome conversations just about relationships in life and coming from all different kinds of generations. One of the songs on the EP, it’s called ‘Better Memory,’ And this is probably the most gut-wrenching song to me. I was not expecting to write this ballad and journal entry almost of a song, and it was with two guys, Dan Hutson and Jeff Middleton who are older than I am, and they’re just whiskey drinking men. And they’re like, ‘you want a whiskey?’ And it’s like 10:00 AM and I’m like, ‘no, I think I want my latte first, but thank you.’ But even that, it’s such a special thing to get to sit in the room and write these songs and yeah, I think for me, it just felt right. And there was none that I was like, no, it just made sense.
How are you feeling as you prepare for your first international dates in the UK?
I am so freaking fired up. I’ve never been out of the country. I think my family and I, we went to Mexico one time, but I’ve never been out of the country overseas, especially. I’m dying. I’m dying to just see it. I’m dying to see the architecture. I’m dying to go to the restaurants, go to the shops, and then just meet the fans and meet people that are loving country music that makes me so happy. So I’m so fired up and it’s so exciting. All I’ve heard is everyone over there is so fired up about country music, and that to me is like, let’s go, let’s go. So I’m just so fired up. I cannot wait. It’s going to be awesome.
How does this project and these upcoming tour dates set the tone for this next chapter of your career?
I know it’s been such a crazy last couple of months. Again, I just hope we get to keep doing it and keep hitting the ground running. I’m just so excited for this project to be out there. It’s like your baby that you’re like, all right guys, it’s here. But I’m just so excited to just have it out there and see the response, and hopefully just connect with people and keep that rolling and keep that snowball effect going. So I’m so excited. I cannot wait. I’m looking so forward to the rest of this year. We have a couple little songwriters festivals that we’re doing here shortly, which will be so much fun. But yeah, I’m fired up. I’m ready to go. I’m like, let’s go, guys.
Fans can keep up with Alyssa Flaherty on Instagram.
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