Stella Lefty on ‘Boston,’ Stagecoach, and Her New EP Is This Heaven?

Stella Lefty was one of Stagecoach’s most visible artists last month, even though she was not on the official lineup. Her breakthrough single, “Boston,” has climbed to No. 27 on the Billboard Hot 100 and No. 7 on Hot Country Songs, and she kept turning up across the festival weekend alongside artists including Cameron Whitcomb and Wyatt Flores.

“I’m a huge fan of Wyatt and also Cam,” she said. “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, Lefty joined Whitcomb for Tyler Childers’ “All Your’n” and performed “Boston” during sets by Flores and Diplo. It was another sign of how quickly she has moved from online momentum to festival-level visibility.

The Chicago-born artist did not arrive there through a straight country pipeline. She grew up on Taylor Swift and Miley Cyrus, and also heard Tim McGraw and Brad Paisley playing at home, thanks to her father. She wrote songs for years, then studied public health at Tulane University before posting music on TikTok. “I had no plan of doing anything in music,” she said. “I always loved to sing and I was always writing, but I didn’t know anybody that did that.”

After graduating in 2024, she started releasing music more seriously. That run included 2025’s “Cynic” and “Grace.” After signing with Atlantic Outpost earlier this year, she followed with “Thinking ‘Bout You” and “Slow Dancin’” in January. A few months ago, while on a Nashville songwriting trip, she sat down at a piano and posted a short snippet to social media. It subtly interpolated Noah Kahan’s “Stick Season,” and that clip became “Boston.” Kahan is credited as a writer on the song.

“It was just for fun and I wasn’t thinking anything about it,” Lefty said. “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.”

She followed “Boston” with “I Know I Know,” a banjo-driven track about trying to move on from a relationship while knowing how quickly old feelings can come back. “One glass of wine and you’re on my mind” gives the song its specific kind of after-hours tension.

“I feel like all of my friends, this is the thing we always talk about,” Lefty said. “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.”

That stretch of releases led into her six-song EP, Is This Heaven?, out Friday, May 15. The project includes “Boston,” “Thinking ‘Bout You,” “I Know I Know,” and “Something To Lose,” a collaboration with Vincent Mason.

“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 said of the track. “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 legal name is Stella Lefkofsky, though she says she has gone 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 said. Her family, including father Eric Lefkofsky, the Groupon co-founder and Tempus AI founder and CEO, has been a constant source of support.

“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.”

Her year now includes opening slots for Myles Smith and Tucker Wetmore, plus 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 is also looking at future collaborations. Ella Langley, Gracie Abrams, and Tim McGraw are all on her wish list. “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 split between country and pop has been there from the start, and Lefty says she has no interest in choosing one side over the other. “I’ve been super particular about wanting to live in both spaces as best as I can,” she said. “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.”