In “Never Kissed a Cowboy,” rising country star Lily Meola turns little acts of chivalry into bighearted moments, and gives a first peek at her upcoming album.

Stream: “Never Kissed a Cowboy” – Lily Meola

Lily Meola has always written like someone who understands how fleeting and meaningful a moment can be.

While working on her upcoming album, she stumbled across a statistic that provided some unexpected inspiration: the odds of being born are roughly one in 400 trillion.

“We are so freaking rare, and I think we lose sight of that in our everyday lives,” she says. “That perspective came at a time when I really needed the reminder. It was so eye-opening that I ended up using the statistic in one of the songs.”

It’s fitting because Meola, herself, is pretty rare.

You can hear it in her current single, “Never Kissed a Cowboy.” Among the classic country instrumentation, she tucks in lyrics about rare courtesies in modern life, like holding doors, pulling out chairs, or giving his jacket when it rains.

“Ain’t that some gentleman shit / Chivalry ain’t dead I guess,” she sings.

Never Kissed a Cowboy - Lily Meola — Never Kissed a Cowboy – Lily Meola

The track offers the perfect setting for her distinctive vocals to settle in. But it’s her songwriting that gives those vocals their depth. She has a gift for noticing small details and shaping them into scenes that draw you into the story – a skill she was lucky to learn from a couple of legends.

Willie Nelson helped her sharpen her storytelling, and one afternoon in Los Angeles, Jackson Browne sat with her at a piano, walked her through the songwriting process, and gave her the confidence to believe in her artistry.

That gift for turning personal experiences into something relatable isn’t new — it’s the same quality that reached millions when Meola stepped onto the America’s Got Talent stage in 2022. She shared her story about caring for her mother through cancer, losing her record deal, and wondering whether the dream she’d chased since childhood was beginning to slip away.

By the time she sang the first note of “Daydream,” audiences across North America were already rooting for her.

The ache in Meola’s voice is hard-earned, shaped by grief, perseverance, and a lifelong relationship with music that began long before any reality show.

She landed her first gig around age 10, playing cafés around Maui. With her mother’s encouragement, she sang everywhere she could – bars, private parties and events.

All of that experience feeds into her upcoming album, which she says is untethered to any specific genre. After years of moving between Nashville, Hawaii and Los Angeles – and trying to be everything at once – the singer/songwriter stopped chasing labels.

“This project feels different on so many levels,” Meola says. “I’ve been on a journey to this moment for over half of my life, so in a way, it feels like arriving somewhere. All the poems and tears that turned into songs along the way led me here. At the same time, because this is my debut album, it also feels like just the beginning.”

Atwood Magazine caught up with Meola to talk about chivalry, working with legends, and the wild odds that made this moment possible.

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:: stream/purchase Never Kissed a Cowboy here ::

:: connect with Lily Meola here ::

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A CONVERSATION WITH LILY MEOLA

Atwood Magazine: “Bolo Blues” and “Never Kissed a Cowboy” mark the beginning of a new era for you. What feels different about this chapter compared to Heartbreak Rodeo or Postcards to Heaven?

Lily Meola: This project feels different on so many levels. I’ve been on a journey to this moment for over half of my life, so in a way, I see it as finally arriving at a destination. All the poems and tears that turned into songs along the way led me here. At the same time, because this is my debut album, it also feels like just the beginning.

With “Bolo Blues” and “Never Kissed a Cowboy” being the first glimpse of the upcoming album, how does it set the tone for what’s coming next?

Lily Meola: All I’m going to say is: I’m a 6/8 slut, and I hope you are too.

There’s such a nostalgic feel to “Never Kissed a Cowboy.” It leans heavily into old-school romance and chivalry. What inspired you to write about that kind of love in such a modern setting?

Lily Meola: For some reason, my picker isn’t keen on gentlemen – so when I experienced one for the first time, it honestly threw me off a little bit. Like… I can open my own door?! But now I love it. It’s fun to feel like a lil princess sometimes. So unnecessary, but so dang sweet. This song is really inspired by that feeling of finding someone who makes you feel like you’re worth the extra mile.

There’s a lot of visual storytelling in the song – the Texaco stop, feet on the dash, being walked to the door. How important are small, specific moments to your songwriting?

Lily Meola: I think it depends on the song and what story you’re trying to tell, but I love it when a lyric can take me to a moment in time where I can not only visualize it, but also smell it – or sometimes even taste it. (laughs)

How do you want listeners to feel the first time they hear it, and where does it fit in the larger story of your upcoming music?

Lily Meola: The record touches on a wide variety of emotions. I write about all the things life throws my way – the good, the bad, the lovely, and the ugly. For this one, it’s all about that warm, fuzzy feeling of falling in love and being loved.

What can you tell us about the album? Any interesting collaborations or stories while writing or recording?

Lily Meola: Yes, there will be some collaborations on the record, and without giving any away, all I’ll say is my dreams are really coming true.

What’s one lyric from the upcoming album that plays on repeat in your head?

Lily Meola: While I was in the thick of writing, I stumbled upon a statistic that absolutely floored me: the chance of you being born is 1 in 400 trillion. We are so freaking rare, and I think we lose sight of that in our everyday lives. That perspective came at a time when I really needed the reminder, and it was so eye-opening. I ended up using that statistic in one of the songs.

Circling back to “Postcards to Heaven”… That song has helped so many people who’ve lost someone they love. How does it feel knowing your tribute to your mom has become a source of comfort for others? And was there a particular memory of your mom that inspired “Postcards to Heaven”?

Lily Meola: This is a hard question for me because I have so many answers, I don’t know where to begin. Having writing as an outlet has been the most healing thing for me throughout my journey with grief. And the connection these very personal songs have made with other people is such a bittersweet experience. It’s so beautiful to have this community of people who make you feel less alone in it all, but it’s also so sad to know they know your pain.

You’ve moved fluidly between country, folk, pop, and Americana. Do you see yourself as genre-less, or do certain sounds always feel like home?

Lily Meola: I’ve always felt a little funny when I’m asked what genre I am, because I’ve never wanted to be put in a box. I grew up on such a wide variety of music and I’m genuinely inspired by all of it, so for a long time I tried to do it all and stay untethered to any one sound.

But I also went through chapters where that freedom didn’t feel as good as I thought it would. I learned to write songs in Nashville, then moved from Hawaii to LA, and the pace, and the music I was making, never really felt right in my gut. It took me years to put music out because something felt missing. I even lost my record deal, and it brought me to this moment of realizing I couldn’t wait for everything to feel “perfect” before I started sharing. I had demos I’d written all over the world, and I found a way to release them as I was still figuring it out.

What changed with this record is that I finally felt truly free in the creative process, no pressure, no outside noise, just writing what that day had to hold. I stopped trying to force an identity and let it be a pure flow state. So I don’t know if I’d say I’m genre-less as much as I’d say I’ve stopped chasing labels. This project is the most “home” I’ve ever felt, like I’ve come back from a long work trip and I can finally breathe.

You’ve been mentored by legends like Willie Nelson and Jackson Browne. Do you ever hear their voices in your head when you’re writing?

Lily Meola: I met Jackson Browne at an event we both played in Bend, Oregon. At that point I was playing lots of shows, but I had never written a song. I’m heavily dyslexic, and growing up, the thought of writing anything felt so overwhelming that I never even gave it a chance. After my set, he asked if I wrote. I explained what I just explained to you, and his response was that he could teach me everything I needed to know about writing a song in one sitting – and the next time I found myself in LA, to stop by. So I did. We sat at his piano and he showed me his process. It was so special.

I could go on and on about Willie as well – he’s just the greatest of all time. I’m forever grateful to the people who believed in me and gave me the courage to keep trying and keep going all these years.

Your audition on AGT is one of three that stood out to me. Did it feel as big in the moment as it looked from the outside?

Lily Meola: Thank you so much! I had honestly never seen a full episode of the show, so it was all very different from what I was expecting. I went alone and didn’t really tell anyone I was doing it. I had put out my song “Daydream” earlier that year and got a taste of what the message of that song could do for someone’s life – and I wanted to share that with as many people as I could.

I don’t have a competitive bone in my body, so throwing myself into a show like that never felt right for me. But it was a really big stage with millions of listeners who could maybe benefit from hearing “Daydream,” so I went for it. It was wild.

When you look back at the girl playing cafes at 11 years old, what do you think she’d be most proud of today?

Lily Meola: That’s a really sweet question. I think she would be most proud of her perseverance.

You started performing really young in local Maui cafes. Do you remember the first moment you realized music could actually be your life?

Lily Meola: I got my first gig when I was, I think, 10-ish. I always loved to sing and knew that’s what I was going to do. I didn’t know how or when, but I just felt such a deep connection to it that I couldn’t even focus on anything else. My mom really nurtured my fascination with it, and she started getting me different gigs around the island – bars, private parties, events, and cafes. And I literally just haven’t stopped yet.

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