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Stella Lefty Reaches No. 5 on Billboard Hot 100 With ‘Boston’

Stella Lefty, 23, of the Chicago area, has become one of music’s fastest-rising names as her breakout single, “Boston,” climbed into the top five of the Billboard Hot 100. The…

Stella Lefty performs onstage during Lollapalooza at Grant Park on August 02, 2026 in Chicago, Illinois.
Joshua Applegate via Getty Images

Stella Lefty, 23, of the Chicago area, has become one of music's fastest-rising names as her breakout single, "Boston," climbed into the top five of the Billboard Hot 100. The song's ascent marks a dramatic turn for an artist who, not long ago, watched her early videos struggle to find an audience.

Lefty's path to the spotlight began in 2020, during the pandemic, when she started sharing songs publicly as a personal outlet rather than as part of any calculated plan. That grassroots start eventually gave way to viral attention on TikTok, a spot in Variety's Power of Young Hollywood "Up Next" class, and a headline-making run up the charts, all ahead of the release of her debut album, Long Way Home.

Speaking with Variety backstage at Lollapalooza, Lefty described the gap between where she started and where she is now: "There was this period where I moved to L.A., where I was grinding, and nothing was happening, which, you know, happens," she said. "Every video I'd post would get, like, f**king one view, so I think it's crazy to see what happened from those TikToks and how this has all played out. It's also just so refreshing for me because I feel like I was getting so bogged down by where I was at before. I feel like I've circled around in terms of the sound and where everything is at, to a place that I feel really good about."

The success of "Boston" has also opened doors professionally, and Lefty said her list of dream collaborators is a moving target. Names currently on it include Hozier, Taylor Swift, Miley Cyrus, Chris Stapleton, and Gracie Abrams.

Lefty's rapid ascent has drawn scrutiny, too, largely tied to her father, Eric Lefkofsky, the Groupon co-founder who now serves as CEO of Tempus. The connection has fueled "nepo baby" commentary online. Still, Lefty has largely avoided addressing the label directly, choosing instead to focus on her music and stay true to the mindset she had when she first wrote songs alone in her room.

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