At country music festival Stagecoach last month, one of the fest’s most-watched artists wasn’t even officially on the bill.
Country-pop artist Stella Lefty, whose breakthrough hit “Boston” has reached No. 27 on the Billboard Hot 100 and the No. 7 on Hot Country Songs, was seemingly everywhere during the weekend, jumping up onstage with artists including Cameron Whitcomb and Wyatt Flores.
“I’m a huge fan of Wyatt and also Cam,” she says. “It’s so crazy to be so embraced in a genre that I’ve always loved. Country music has been such a huge part of my life. And I feel like it’s always scary when you start making music that kind of bleeds into a genre. Country is so specific about who they embrace and how they go about things, so to be accepted in that world is truly the greatest honor.”
At Stagecoach, she joined former tourmate Whitcomb for a rendition of Tyler Childers’ “All Your’n,” and sang her hit “Boston” at during Flores’ and Diplo’s respective sets.
The Chicago-born Lefty is no stranger to the genre, though. She grew up on a mix of country and pop, including Taylor Swift and Miley Cyrus, but also soaked in music from Tim McGraw and Brad Paisley that her father played around the house. Lefty dabbled in songwriting for most of her life but pursued studies in public health at Tulane University. She began posting music on TikTok, but says, “I had no plan of doing anything in music. I always loved to sing and I was always writing, but I didn’t know anybody that did that.”
After graduating in 2024, she began writing and releasing music in earnest, including 2025’s “Cynic” and “Grace.” Since signing with Atlantic Outpost earlier this year, she’s been piling up impactful releases. In January, she rolled out “Thinking ‘Bout You” and “Slow Dancin’.” During a Nashville songwriting trip a few months ago, she quickly sat down at a piano and wrote a snippet of a song to share on social media. That snippet, which subtly interpolated the melody of Noah Kahan’s “Stick Season,” was the basis for “Boston” and quickly went viral. (“Stick Season” writer Kahan is credited on “Boston”).
“It was just for fun and I wasn’t thinking anything about it,” Lefty says. “So when people started to like it, I was like, ‘Oh, shoot, I need to finish this.’ I wasn’t thinking about anything so intensely, and that was honestly the most fun part. Building around something that kind of already existed was cool and I’d never done anything like that.”
Lefty followed “Boston” with the banjo-laced “I Know I Know,” which depicts the complexities of trying to move on from a relationship, while acknowledging those fragile intentions on lines such as “one glass of wine and you’re on my mind.”
“I feel like all of my friends, this is the thing we always talk about,” Lefty says. “You go out and you want to have this night out with your friends, then all of a sudden you start drinking and you start thinking about that one person that haunts you. So, we wrote about it, but in a really lighthearted, fun way.”
As her career picked up steam, the seeds were planted for her six-song EP, Is This Heaven?, out Friday (May 15).
“I just want good writing and super fun and just honest songs,” she says of the EP, which includes “Boston,” “Thinking ‘Bout You” and “I Know I Know,” as well as a collaboration with Vincent Mason on “Something To Lose.”
“I’m obsessed with this song. It’s one of my favorites that I’ve ever written, and obviously, [he] and I started dating a few months ago,” she says. “I wrote it about being in this place of not wanting to be in a relationship, and then all of a sudden this person comes along and you just have no choice. That’s totally how I felt about him. When we sang it, it just felt so natural and fun. I was like, ‘If I’m going to have any features or collaborate with anybody, it has to be him.’”
Lefty’s real name is Stella Lefkofsky, but she’s been known by Stella Lefty her whole life. “My uncle, my Dad, my brothers, have gone by Lefty… so it was the easiest thing and I didn’t have to change anything,” she says. Lefty says her family, including her father, Groupon co-founder Eric Lefkofsky, has been a bedrock of support and a model of work ethic.
“My whole family is super hardworking. I think the biggest takeaway is there’s a grit that I feel, like ‘Keep your head down and just keep going…’ I’ve been working as hard as possible and learned that from them. They were super emotionally supportive. They definitely pushed me in that regard and I’m grateful for that.”
She’ll take her music on the road this year, opening tours for Myles Smith and Tucker Wetmore. She’ll also make her Lollapalooza debut.
“I just want to keep playing shows and meeting people, because it’s crazy to see the number on your screen, like, ‘This is how many people are listening.’ But it’s a whole other experience to meet those people and see the people that love the song. So that’s what I’m most looking forward to.”
She also dreams of more collabs. “I’m obsessed with Ella Langley, she’s amazing, so anything with Ella would obviously be a dream. I’m also obsessed with Gracie Abrams, I’m so inspired by her. And I think if Tim McGraw asked me to do something with him, I would die.”
That duality of unrestrained love for both the country and pop spaces threads through her own music.
“I’ve been super particular about wanting to live in both spaces as best as I can,” Lefty says. “Every time we’ve been talking about doing something, it’s like, ‘Maybe it would be helpful for the audience if they really understood what lane you wanted to be in,’ and I’m always like, ‘No, I will not pick a lane.’ I won’t, because it wouldn’t be authentic for me. Music now is so genre-bendy and so fluid. I don’t want to put myself into a box because whoever is going to love the music is going to love it.”
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