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Stella Lefty faced an existential crisis last year. The Glencoe native had moved to Los Angeles to live in a creator compound at the invitation of JKash, a major producer who’d heard snippets of her twang-tinged country songs on TikTok. But the moodier, rockier sound of the EP she subsequently put out didn’t resonate, either with her or her budding online audience. “I got really spun about and confused with all these new opinions coming in,” Lefty says of the L.A. influences. “They wanted me to stay away from country music. But you don’t always have to follow what people tell you.”
Listening to her own muse, she holed up with her songwriting roommates-turned-besties, Grace Enger and Sadie Jean. They got back to basics, writing “Thinking ’Bout You” as a trio. Released in January, the song felt lighter, flirtier, more straightforward, leading Lefty on a new wave of inspiration. But it was the following single, “Boston,” which JKash and Enger helped write, that propelled her into the spotlight. After going viral on TikTok this spring, the song charted as high as No. 3 on the Billboard Hot 100 by the time of Lefty’s Lollapalooza set in August. There, she announced her full-length debut album, Long Way Home. Another sign of her rising star: The next week, she joined Mumford & Sons onstage at Madison Square Garden to perform “Boston” on her 24th birthday. But her rise hasn’t been without controversy: Some of Lefty’s tracks, including “Boston,” have come under scrutiny after fans drew comparisons to other artists’ work.
Lefty developed an ear for country early, abetted by her dad, Groupon cofounder and Tempus CEO Eric Lefkofsky, who’d blast Tim McGraw and Brad Paisley in the car. (“Lefty” is a shared family nickname.) Though she dabbled in songwriting, she had no intention of pursuing it as a career, instead studying public health at Tulane University. But after graduating in 2024, she found herself drawn back to music. Now she’s gearing up to headline shows across the country, with fall 2026 dates already sold out. (A second leg begins in January.) Long Way Home, she says, is the project “most at the truth of who I am. I’m finally making the music I love.”
Lefty plays Lincoln Hall November 23.
Jessi Roti is a freelance writer for Chicago magazine.
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