Stella Lefty Celebrates the Chartbreaking Success of ‘Boston’ With Billboard Canada

The minute that Stella Lefty joins Billboard Canada, her bubbly personality bursts through. Immediately, the rising 23-year-old singer-songwriter gushes about her love of Canada.

“My cousins are Canadian,” Lefty tells Billboard Canada, explaining that she has spent a decent amount of time in the country over the years, despite hailing from Chicago and now based in Los Angeles. “I feel a natural tie to Canada. I love coming here — it's so fun,” she says.

Lefty is continuing to spend a lot of time in the country. We're speaking after the singer-songwriter performed an intimate first-of-its-kind Chartbreaker edition of Billboard Canada LIVE at Toronto’s Rock 'N' Horse Saloon to celebrate her chart success. A couple of days later, she headed to Montreal’s Osheaga, making her Canadian music festival debut, which she said she was “so excited” about.

Evidently, the love is reciprocated. Lefty’s viral single “Boston” has reached the top three on the Billboard Canadian Hot 100, rising one spot to No. 3 on this week's Aug. 8-dated chart. During her Toronto show, Lefty was presented with a Chartbreaker plaque by Billboard Canada National Editor Richard Trapunski for the song’s success.

“It's just such a surreal feeling,” she says.

The song is also No. 5 on the U.S. Hot 100.

Gabriel Di Sante

While Lefty had a knack for songwriting as a child, it wasn’t until she graduated college in 2024 that she started posting original songs on TikTok from her bedroom. Lefty’s single “Thinking ‘bout You” had its own viral moment on the platform at the beginning of the year, which helped Lefty secure a deal with Atlantic Records/Warner Music Canada.

She recalled feeling anxious about whether she would be able to top that track’s success. Two months later, she did. Released in March of this year, “Boston” has become Lefty’s biggest song to date and an undeniable breakout. But it started as just a short snippet posted to her TikTok, an interpolation of Noah Kahan’s “Stick Season.”

“It was a different type of virality,” Lefty explains. “It wasn’t necessarily that the videos had the same amount of views as ‘Thinking ‘bout You,’ but other people were making videos [to ‘Boston’] and I had never seen anything like that before. It was really cool.”

But Lefty had more work to do. She had only finished the track up until the middle of the chorus, and while the clip was taking off, she revealed that she “didn’t necessarily love” the clip that she posted.

“I didn't feel attached to it in the way that I had felt to my other songs,” she says, unable to pinpoint exactly what she didn’t connect with. “But a couple of weeks after posting the clip, I went to finish it and I loved it when it was done. I loved the production, the verses that we wrote, the bridge — the song felt perfect to me. It took me a second to really see what everybody else was seeing.”

It’s not the only song by Lefty that’s charting in Canada. The cheeky “I Know I Know” and “Something To Lose,” featuring Lefty’s boyfriend and fellow rising country star Vincent Mason, sit at No. 57 and No. 70, respectively. They’re all featured on Lefty’s debut major label EP, Is This Heaven? which recently hit the top 10 on the Billboard Canadian Albums chart.

Lefty says there’s a relief that listeners are responding to more than just her viral hit. “The fact that the EP is resonating with people as a whole is just exciting, because the other songs that I've written I love so much, and I feel so attached to,” she explains. “It's just fun to see other people falling in love with them the way that I have.”

She continues: “It'd be very stressful if it was just ‘Boston’ [that was going viral]. I'd be tweaking right now.”

Country music is having its own moment on the charts — topped by hitmaker Ella Langley’s “Choosin’ Texas” for 13 weeks on the Canadian Hot 100 — but Lefty strives to strike a balance between country and pop music.

“ It’s just what I love,” she says matter-of-factly. “When I started making music, I just went back to the music that I grew up loving,” citing artists like Rascal Flatts, Carrie Underwood, Taylor Swift and what Lefty describes as “early” Miley Cyrus. “It just naturally was this in-between of both worlds. That's what I feel like I'm best at making.”

Often, mainstream fame can amass negativity. In the wake of Lefty’s success, the internet discovered that her father is Groupon co-founder and Tempus AI founder/CEO Eric Lefkofsky and many have dismissed her as a "nepo baby" or "industry plant." Lefty says that she’s grateful for her family’s support, but doesn’t dwell on negative comments.

“There are days when it bothers me, but ultimately, I do this for the people that love the music," she says. "It's been a long time coming to get to where I am now. I do this for the relationship that I have with the people that are resonating with me and the songs.”

Still, Lefty isn’t showing signs of slowing down. She hints at the release of her debut album, saying listeners will get their first taste of it “very soon.”

In a short time, Lefty has developed a strong fanbase. When she performs on-stage, she explains, it's similar to a group sing-along. "It’s like when you're in the living room with your friends and you’re all singing together and dancing."

As she pushes forward, Lefty shares that she’s channeling her past self.

"I feel really in tune with the girl I was before moving to L.A. and the girl that was doing this as a hobby instead of a job. I really want to feel like this is fun, and I want to feel that love. Because otherwise,” she pauses to think, “there’s no point.”