Stella Lefkofsky (born August 13, 2002), known professionally as Stella Lefty, is an American singer-songwriter. She gained prominence in 2026 following the viral success of her country-pop single "Boston".
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Early life and education
Stella Lefkofsky was born on August 13, 2002, and was raised in Glencoe, Illinois, before relocating to Los Angeles, California. Her father is multi-billionaire Eric Lefkofsky, a co-founder of Groupon who is also the founder and CEO of health technology company Tempus AI and media advertising company Mediaocean, among others. Worth over $4 billion, he is among the 1000 richest people in the world.
Lefkofsky has been practicing songwriting since early childhood.
After graduating from New Trier High School, she attended Tulane University in 2020 to study public health, with "no plan of doing anything in music". While studying abroad in Amsterdam during a "depressive" period, she began sharing her earliest song compositions on TikTok.
Career
After establishing a social media presence and graduating college in 2024, she started releasing music independently as Stella Lefty, including singles "Stay" and "Kiss Me." She released her debut EP, Tragic, Really, in 2025. In January 2026, she released the single "Thinking 'bout You," which she wrote in collaboration with friends Grace Enger and Sadie Jean. In February, she performed the song "The Kill" for the film Scream 7. Shortly thereafter, she signed with Atlantic Outpost, a country music imprint of Atlantic Records.
Lefty gained prominence in 2026 following the viral success of her country-pop single "Boston", which debuted on the Billboard Hot 100 chart at No. 95 in April and climbed to top 20 a month later. The breakout single is built around a melodic interpolation of "Stick Season" by Noah Kahan. According to Lefty, Kahan's team reached out to Lefty due to similarities between "Boston" and "Stick Season," resulting in Kahan being given a writing credit on "Boston."
In May 2026, she released an EP, Is This Heaven? featuring previously released songs, including "Boston", "Thinking 'bout You", "I Know I Know", and a collaboration with Vincent Mason, "Something to Lose". Is This Heaven? debuted at No. 38 on the all-genre Billboard 200 chart and No. 9 on the Top Country Albums chart with 20,000 units sold.
In March 2026, it was announced that Lefty would perform as an opening act for Tucker Wetmore's Brunette World Tour. After it was noticed that she had quietly dropped out of those dates, Lefty posted an apology to her Instagram stories, stating "I just want to apologize to everyone for not announcing sooner that I’m not opening on the Tucker [Wetmore] dates. I love Tucker and I know the shows are going to be amazing. I wanted to announce that earlier but I was advised not to which was a mistake." The story did not include an explanation for the cancellations.
On August 21, 2026, Lefty released her debut studio album Long Way Home. A few days after releasing her debut album and after apologizing for dropping out of the Wetmore shows, Lefty announced her Long Way Home Tour, set to begin in January 2027.
Musical style
Lefty's music is often described as country-pop and indie-folk, but also genre-agnostic. Her vocals have been described as "raspy".
She grew up listening mostly to country and pop musicians, including Taylor Swift, Miley Cyrus, Tim McGraw, and Brad Paisley. She is heavily influenced by Noah Kahan.
Personal life
Lefty is in a relationship with fellow singer-songwriter Vincent Mason.
Discography
Tours
Headlining
Our First Shows Together (2026)
Stella Lefty Live (2026)
Long Way Home Tour (2027)
Supporting act
For Your Validation Tour (2025) (Alessi Rose)
Worldwide Hysteria Tour (2025) (Jessie Murph)
Fragile Egos Tour (2026) (Cameron Whitcomb)
My Mess, My Heart, My Life Tour (2026) (Myles Smith)
The Brunette World Tour (2026) (Tucker Wetmore)