An upcoming concert at the Regent demonstrates exactly the synergy of talent and goodwill the County tends to foster.

For Justin Rutledge this County synergy has happened in many ways. “I’ve had a place here since 2015, and lived here for two years initially. Over that time, I met my wife, Sarah Keenleyside. She was doing really well in the city, so I moved back for a few years. But then we had a couple kids and we moved out here.

“This place gets its claws in you, and it just doesn’t let go!”

And it’s not just the place, but the people—the community. The centre of a community, says Mr. Rutledge, is the spirit of the arts.

“I’m a fan of arts organizations,” he says. His day job involves marketing for the education, outreach, and artist development departments of both Massey Hall and Roy Thomson Hall. “I think that they are really the heartbeat of a community, especially a smaller community. Building pride in a community, fighting isolation, they’re essential to the fabric.

“I’ve been an admirer, a small donor, to the Baxter Arts Centre. It’s a vibrant hub, offering creative outlets and skill-building workshops.

“There is so much happening here in the County, but I feel like the Baxter is sort of at the core of a lot of great things that are going on.

“It takes belief in the people around you; it takes dedication to seeing to the health of a community. And I think that’s what the Baxter Arts Centre does.”

As a member of the community, Mr. Rutledge gets involved in his unique way.

This singer-songwriter came to his successful musical career through “a collection of luck and hard work, and kind of a haphazard way of stumbling into it,” he says. “I started like most high school guys, I guess. You know, I picked up a guitar to meet girls.”

He stuck with it through university. “In the back of my mind I never considered it a viable way to make a living.”

Nevertheless, after his third year, he decided to take a year off and make a record.

“And I still have yet to go back to school,” he laughs.

By 2004, Mr. Rutledge had landed a standing-room-only Monday night residency at Toronto’s Cameron House.

That gig has now developed into nine albums, and a 2014 Juno award in the Solo Roots & Traditional Album of the Year category.

While his sound is very much like the title of his last album, “Something Easy,” behind it stands a carefully honed skill in songwriting meticulously assembled in his recordings.

Mr. Rutledge admires the early Leonard Cohen’s songcraft.

“The minimalism of his melodic approach—it’s almost hypnotizing you in. And then, of course, what he’s doing with the words is creating this world that is so clear, but so mysterious. I’d never heard anyone do that before. Or since, really.

“So I sort of took what I learned in school and the courses I was taking, and I tried to sort of elevate the lyrics to a certain degree.” 

Setting literary influences within the context of a traditional country ensemble piques the interest. “The lyrics really sat outside of that, and didn’t identify with the backdrop, which I thought was a cool juxtaposition.

“So Cohen really got me into what a song could do.”

The gentle tempos and consistency of the soundscapes on his albums marks his commitment to “building something that I believe in.”

“But live,” adds Mr. Rutledge, “live is a different story. There’s definitely a lot more energy.” For the upcoming Regent gig, he says, “I’m bringing everyone with me to the region. I’ve got my whole band. Everyone’s available, so it’s fantastic. It’s a lot more nuanced.

“Making a record is a wonderful thing: you’re sitting in a studio, and you’re mixing it, and you can take days to tweak a sound. … But live is where it’s at.”

This show in support of a community organization aims to build a community within the theatre. Mr. Rutledge is well-known for his closing song, “Jellybean”—a participatory sing-along.

“The history of that song was, when I had my residency at the Cameron House, I needed a good way to end the night. You know, it was 1:30 in the morning, and everyone’s feeling good. I just thought it was the silliest thing I’d ever written—it was just something I’d sing to myself while washing dishes.

“But then one night I jumped up on the bar started singing this song, and everyone just started to sing along, and so I would shout out the words, and they’d sing it all. Over the next 20 years, it became this thing that people really loved to do at the end of my shows.

“It’s so unlike the rest of my set. It’s a nice palate cleanser.

“The great thing about ‘Jellybean’ is that it really connects the people in the room, it centres the crowd. Something happens to the room during that song, where people hear their voices together, and I’m up there sort of conducting it. We get to finish the night in solidarity and community, and it’s a wonderful thing.

“So, hey, I might break it out at the Regent, you never know!”

We certainly hope he does. Nothing could be more fitting.

Justin Rutledge plays the Regent Theatre on October 9. For tickets, visit theregenttheatre.org