(photo credit: Cris Slater and Geoff Mau)
In just the past six months, singer/songwriter Stella Lefty has emerged as a bright new star in country & pop music. She currently has one of the hottest singles on the Billboard charts in both country & pop. Impressively, her single “Boston” is already a Top 10 hit (#7) on the Billboard Hot Country Songs chart, and it’s #27 and rising fast on the Billboard Hot 100 pop chart.
It was six months ago that Lefty (who is 23) had a creative breakthrough, when she wrote “Thinkin’ ‘bout You” with two music friends (Grace Enger & Sadie Jean). This song was joyfully created in a country/pop style, which is the she grew up with. But it was a departure from the pop/alternative direction she had been exploring.
After writing “Thinkin’ ‘bout You,” Lefty posted the song on TikTok, and it became clear that music fans loved her country/pop sound. So she began writing more songs in this style, and with each new song she realized that this country/pop sound felt like home to her.
Since then, Lefty has written many new songs and she’s taken trips to Nashville to co-write. One song is “Boston,” a charming, appealing tune that immediately connected with people. And with the help of TikTok, Instagram and YouTube, the song has not only gone viral but has become a hit on country & pop radio. It’s now easy to envision “Boston” continuing to rise higher on the country & pop charts.
This week (Friday May 15), Lefty is releasing her excellent new EP called Isn’t This Heaven? (on Atlantic Outpost Records). This EP contains six songs, four which have been released this year (“Boston,” “Thinking ‘bout You,” “Slow Dancin’” and “I Know I Know”) plus two brand new songs: “Something To Lose” (featuring hit country artist Vincent Mason) and “Why Wouldn’t We”. These six songs demonstrate that Lefty is a talented singer/songwriter with her own distinctive style and personality.
Lefty grew up in the Chicago area, and she learned to play guitar at a young age. It wasn’t long before she started writing songs, and she posted her first song online in 2021. Then two years later, she made an impact with her independent singles “Stay” and “Kiss Me,” and in 2025 she released her first EP, Tragic, Really.
Currently, Lefty has formed her new band and she has begun playing shows as a headliner. This spring, she’ll be on tour opening for country artist Cameron Whitcomb, and this summer she’ll be playing at several festivals.
Here’s the lyric video of Stella Lefty’s hit, “Boston.”
We are pleased to do this new Q&A interview with Stella Lefty. She tells how she got started as an artist and her path to country & pop music, how she co-wrote her hit “Boston,” and she discusses the songs on her new EP.
DK: I read that you’re originally from the Chicago area. How did you get started with music and writing songs?
Stella Lefty: I’ve been writing songs my entire life since I was really young, when I was 5 or 6. I’ve also been playing guitar my whole life and I was a huge Taylor Swift fan fron early on. So I was like rewriting a lot of her songs, like “Back to December,” and a song would come out. I would listen to the melody, and then put my own random words over it. So I feel like I’ve been writing forever.
DK: You’ve had success posting your songs and videos on TikTok and Instagram. Was there a certain video early on, that went viral and was a breakthrough?
Lefty: “Thinking ‘bout You” was the most viral video that I had, which was at the top of this year. But prior to that, I’ve been posting since 2021. I think I was in college posting, and I had a viral song called “Kiss Me” that was the most viral thing I had when I was starting out. But “Thinking ’bout You” is the biggest one that I had.
DK: A year ago, you released an EP called Tragic, Really, which sounds more pop & alternative. Were you exploring different musical sounds at that time?
Lefty: Yes, I was definitely exploring different sounds, although the music that I had been writing my whole life was this blend of country & pop.
When I moved out here (to Los Angeles) I had a lot of noises, a lot of voices in my head of people telling me that I should stick to a certain lane and steer away from country because I wasn’t from the South. I had so many people telling me what to make and it really got in my head, so I went for more of a pop-alternative direction because that’s what they all wanted me to do. But when I started listening to myself and making the music that I loved, it circled back to what I was originally always making—country & pop.
Here’s the video of Stella Lefty’s song, “Slow Dancin’.”
DK: In a recent interview, you said it was about six months ago that you and a friend wrote “Thinking ‘bout You,” which is more country & pop. Can you talk about writing this song?
Lefty: I wrote it with two of my best friends, Sadie Jean and Grace Enger, and we literally had an hour to kill before Grace was going to a session. So we had an hour to kill, we were sitting on Sadie’s bed and we were like, “Let’s write something—whatever comes to our mind. Let’s not think too much about it.” Then we wrote “Thinking ‘bout You” in like 30 minutes and we immediately loved the song. Although I didn’t know who it was for, because at the time I wasn’t making the (country-pop) music that I make now. It didn’t directionally make sense, so I sat on it for a few month, but I was listening to it all the time in my car. And I was like…I love this song so much. So Grace went out and produced a demo, and then I posted it. And that’s when it all happened.
DK: You’re currently having a big hit with your song,”Boston.” Can you tell the story of how you wrote “Boston” with the other songwriters?
Lefty: It’s a funny story with “Boston.” I was on a writing trip in Nashville; it was about a month after “Thinking ‘bout You” came out. I was super-excited about all the music that I was creating and the direction and sound I finally felt like I’d found. I was there in Nashville sitting at the piano for a writing session, and no one had come yet. I was waiting for everybody to show up. And I was seeing this boy that I’m now dating, and I had a huge crush on him at the time, and I had an hour before he was gonna pick me up for a date or something. So I sat at the piano and I was like…Is there anything that comes to mind? And literally, I wrote the chorus to that song and then posted it, and then I got in the car and left. I didn’t think anything of it. I was like…I don’t know if this is even good, but then it really started resonating with people. So I finished the song a week later, because I was like…Okay, I love this now too.
DK: You’re about to release your new EP, called Is This Heaven? Can you talk about the making of this EP?
Here’s the lyric video of Stella Lefty’s song, “Thinking
’bout You.”
Lefty: It came super natural to me. I think it was all these songs that I’ve been making that felt like the most me. So I wanted to put together this mini-project with some songs that are already out that people love, and then some new songs that people haven’t heard. And it felt like the most me thing that I’ve done, which is why it’s called Is This Heaven? Because it feels like (1) it’s a reference to my favorite movie of all time, Field of Dreams. There’s this line in the movie…”Is This Heaven? No, this is Iowa.” It’s my favorite movie, so I wanted to have that. But then also (2) this is my heaven, like being able to perform these songs and to connect with people. This is all I’ve ever wanted to do.
DK: On your new EP, I like your song “Slow Dancin’,” which has a fun video. Can you talk about writing this song?
Lefty: I wrote that with Grace (Enger), the day after I posted the “Thinking ‘bout You” video. I was like…Oh my God, maybe we write really well together and this is so fun. And writing with her is so casual—she and I just sit around and write a song and it’s not overthought the way that it sometimes is in a session. So we were sitting down and writing just to write—we were just enjoying each other’s company and having fun. And we ended up writing “Slow Dancin’.”
DK: Another song I like is “Why Wouldn’t We,” which is very catchy and it has good harmonies. How did you write that song?
Lefty: It was on another writing trip. I’ve been going to Nashville a bunch to write because I love it there. I think it was the same week that I wrote “Boston.” It was one of those days, because I was crushing on this boy. I still am, but it was in the peak of that. It was during a writing trip and I was with three friends who I loved to write with. And the song came super naturally. It was one of those things where that whole week felt magical because it was really organic. I felt like I was writing songs that I had been waiting my whole life to write, and “Why Wouldn’t We” was one of those.
Here’s the lyric video of Stella Lefty’s song, “I Know
I Know.”
DK: Also on your EP is “Something To Lose,” which is a duet with Vincent Mason. How did you connect with Vincent to create that song?
Lefty: Well, Vincent and I are dating. He’s the boy that I write all my songs about. But I wrote that song with Grace (Enger) that same week.
All of these songs came together rather quickly. When I wrote that song, it was about him, and I loved it. It’s one of my favorite songs I’ve ever written. Then I showed it to Vincent and he was obsessed with it. And I was like…”This is about you.” And he was like…”Okay, I love that.” Then one day we were sitting around and I was like, “Do you want to see if we can sing it together? Because I think it would be awesome.” So we sang it one day and it sounded great. I’m so happy about it.
DK: I want to ask you about your upcoming live shows. This week you’re headlining sold-out shows in Los Angeles and New York. Can you talk about your live show, and do you play with a band?
Lefty: Yeah, we do have a big band for the first time ever. I’ve never played with this many people on the stage, but I’m so excited about it. There are four band members and so it feels super organic. It feels exactly like how you want the songs to be heard. There’s banjo, there’s pedal steel. I hope that it’s a great time. Hopefully, everyone will be singing and dancing, which is the general vibe I want it to feel like. Like we’re all close and we’re all out together.
DK: After your headline shows, you’ll be opening shows for Cameron Whitcomb, and then you’ll be playing festivals this summer. Can you talk about these shows?
Lefty: Yes, I opened for Cameron this past month, which was amazing. I got to go onstage with him at the Stagecoach Festival. He’s such a great friend and he’s the nicest guy, and watching him every night was surreal because he’s one of the best performers I’ve ever seen. So shout out to Cam, and I’m excited to play the festivals. I’m playing a bunch of festivals that I’ve always dreamed of. I’m so excited to meet all the fans out there that I have never met, because I’ve never sang or performed in any of those cities. I think it’ll be great.
