Time has never felt more elastic than at this moment. Days feel like weeks and decades like years, while streaming makes all cultural eras instantly accessible. But to artistically embody this elasticity is a challenge—how does one create timeless songs that feel equal parts modern and retro?

Amy Winehouse did it. Adele, too. Rihanna dabbles. And now Elise LeGrow is threading this needle with new single “Evan,” similarly blending temporally disparate elements into a more powerful whole.

“Experimentation is the first step,” says LeGrow of her contemporary throwback vibe. “It did take time to get to where we’re at with ‘Evan.’ We played a lot with instrumentation—so you hear a Hammond organ and live horns alongside programmed drums.”

“It gives you that sense of nostalgia and familiarity while also feeling fresh,” she adds, “and that’s really what I’m going for on this album as a whole.”

But “Evan” also has a familiarity specific to LeGrow. It’s a tribute to her friend, shot and killed more than a decade ago, far too young and full of life.  When she hits that line about OutKast’s The Love Below, she recalls 17-year-old Evan singing in the driver’s seat of his souped-up VW.

“This song was by far the hardest to write,” she says. “About five years ago, I was alone on a lake playing guitar, and started singing about Evan. It’s been percolating for a really long time.”

Then while in session with award-winning Nashville writer/producer Angelo Petraglia, best known for his work with Kings of Leon, she had a breakthrough. After two weeks of enforced silence from laryngitis, she had an “emotional and verbal unraveling” as her voice finally returned. They finished “Evan” that night.

“It’s really my reflection on friendship – and what it means to lose a friend,” she says. “And when I sing these words, I’m transported back in time.”

“Evan” is the first salvo from her upcoming album, the follow-up to LeGrow’s acclaimed debut Playing Chess, which saw the Millennial crooner reinterpreting tunes from the legendary Chess Records. She’d first learned to love 1950s and ‘60s music as a kid growing up in Toronto’s hardscrabble Parkdale neighbourhood, where LeGrow’s mom filled their apartment living room with songs from her own youth. Elise was as enamoured with the Beatles and Stones, and Nina and Ella, as she was with Whitney and Mariah.

“My musical journey has been circuitous—and my sound has elements from all the places I’ve been. Some of my songs lean more pop or R&B, others more rock’n’roll. They’re all pretty soulful.”

Playing Chess brought LeGrow touring across Europe to incredibly enthusiastic audiences, as well as landing TV gigs like “Later…with Jools Holland” in the UK. “He is one of the kindest and most vibrant people I have ever met,” she recalls. They instantly hit it off, and Holland invited her back to perform on his BBC Radio 2 show a few months later.

Now the Canadian powerhouse is ready to walk through the doors that Playing Chess opened for her. After showing off her interpretive skills—like her viral ballad version of Chuck Berry’s “You Never Can Tell” which clocked over 3 million streams—LeGrow is ready to debut her original songwriting, which combines those same musical elements with her own unique experiences.

“Finally getting to share these songs, to tell my own stories, is really exciting. ‘Evan’ is simultaneously joyful and somber, past and present, and the entire album follows that non-linear pattern, revealing the whole gamut of experiences and emotions—good and bad—that make me the person I am today.”