September’s Artist of the Month is… Stella Lefty

Meet Stella Lefty, the raspy-voiced, piano-playing, country-pop daydreamer who apparently looked at a perfectly reasonable life plan and said, “Hmm… what if I became a famous singer instead?”

Born Stella Lefkofsky on August 13, 2002, in Illinois, Stella grew up in Glencoe before eventually making her way west to Los Angeles. She was raised with plenty of musical inspiration around her—and, for good measure, a dad who happens to be billionaire entrepreneur Eric Lefkofsky. But despite having access to considerably more financial resources than the average person, Stella’s childhood ambition wasn’t exactly “Become a Billboard charting star.”

In fact, when she enrolled at Tulane University in 2020, she studied public health with absolutely no plan whatsoever to pursue music professionally.

Because apparently life enjoys a good plot twist.

While studying abroad in Amsterdam during a difficult period, Stella began posting some of the songs she’d been writing since childhood on TikTok. Rather than disappearing into the internet abyss alongside dance challenges, recipes, and videos of people’s pets refusing to move off the couch, her songs started attracting attention.

After graduating in 2024, Stella decided to give this music thing a more serious whirl. She began releasing music independently under the wonderfully memorable name Stella Lefty, putting out songs including “Stay” and “Kiss Me.” Her debut EP, Tragic, Really, arrived in 2025—a title that suggests Stella understood the emotional possibilities of songwriting from the very beginning.

Then came 2026, when things got considerably less “maybe I’ll try this music thing” and considerably more “well, I guess we’re doing this.”

Stella released “Thinking ’bout You,” collaborated with friends including Grace Enger and Sadie Jean, performed “The Kill” for Scream 7, and signed with Atlantic Outpost.

And then came “Boston.”

The song went viral, debuted at No. 95 on the Billboard Hot 100, and then proceeded to climb into the Top 20. Not too shabby for someone who once went to college intending to work in public health.

“Boston” also features a melodic interpolation of Noah Kahan’s “Stick Season,” which eventually resulted in Kahan receiving a songwriting credit. In other words, Stella apparently went to Boston, but brought Noah Kahan’s lawyers along for the ride.

Her 2026 EP Is This Heaven? continued the momentum, reaching No. 38 on the Billboard 200 and No. 9 on the Top Country Albums chart.

Then came a slight detour.

Stella had been announced as an opening act for Tucker Wetmore’s Brunette World Tour, but ultimately did not perform on those dates. She later apologized to fans on Instagram, explaining that she wished the cancellation had been announced sooner. It was an unusually candid moment in a career that was otherwise moving at a remarkably fast pace.

But Stella wasn’t about to let a little tour turbulence derail the train.

On August 21, 2026, she released her debut studio album, Long Way Home—a title that feels particularly appropriate for someone whose musical journey began with songwriting as a kid, took a detour through public health, wandered through Amsterdam, passed through TikTok, and somehow ended up on the Billboard charts.

And apparently, she isn’t planning on stopping at home for very long.

Just days after releasing Long Way Home, Stella announced the Long Way Home Tour, scheduled to begin in January 2027.

Musically, Stella lives somewhere in the wonderfully fuzzy neighborhood between country-pop and indie folk, with a sound that doesn’t seem particularly interested in obeying strict genre boundaries. Her voice has been described as raspy, which is a nice way of saying she sounds like she could sing you a heartfelt ballad and then immediately ask if you want to split a plate of fries.

Her musical influences include Taylor Swift, Miley Cyrus, Tim McGraw, and Brad Paisley—a combination that makes perfect sense when you hear the blend of pop hooks, country storytelling, and folk-inspired songwriting that makes up her sound.

And then there’s the romance department.

Stella is in a relationship with fellow singer-songwriter Vincent Mason, who also happens to appear on Is This Heaven? in the collaboration “Something to Lose.” Because when you’re both musicians, apparently the logical next step is to make your relationship even more complicated by putting it on a recording schedule.

So who exactly is Stella Lefty?

She’s a former public-health student who became a songwriter. A songwriter who became a TikTok discovery. A TikTok discovery who became a rising country-pop artist. A rising artist who landed on the Billboard charts. And now she’s a 24-year-old with a debut album, a growing fanbase, a national tour on the horizon, and considerably less time to contemplate what she might have done with that public-health degree.

Stella Lefty didn’t exactly take the conventional route to becoming a musician.

But then again, conventional routes rarely make for very good songs.

Random Fun Fast Facts…

• Music wasn’t the plan. She was studying public health, with no intention of making music her career.

• TikTok was basically her musical laboratory. She started posting herself singing. It took off.

• She wanted to be a songwriter for other artists before singing her own songs.

• “Boston” was inspired by her relationship with Vincent Mason. She wrote it after the two met in Nashville.

• “Boston” resulted in Noah Kahan getting a songwriting credit. Listeners noticed similarities between “Boston” and Kahan’s “Stick Season.” Kahan’s team contacted Stella, and she gave him a retroactive writing credit rather than getting into a legal fight.

• She has racked up more than 400 million global streams.