The dust at Burl’s Creek has a specific scent. It’s a mix of dried fescue, diesel exhaust and the faint, lingering aroma of overpriced light beer. For anyone who has spent a weekend at Boots & Hearts, that smell is the olfactory equivalent of home. This Friday, Aug. 9, the Oro-Medonte grounds will brace for the return of Jess Moskaluke, a performer who has effectively moved past the "rising star" label to become the definitive vocal powerhouse of Canadian country music.
Moskaluke isn't just playing a set; she’s marking a decade of dominance. The industry likes to talk about "burn" and "momentum," but few tracks have the legs of her platinum-certified monster, "Cheap Wine and Cigarettes". It’s the kind of song that defines a career, yet somehow remains flexible enough to evolve alongside the woman singing it. To celebrate the 10-year mark, she’s dropped a series of remixes that strip the paint off the original and find something new underneath.
When I sat down with her to talk about the milestone, the weight of the decade seemed to hit her in real-time. We looked back at where it all started, long before the Juno Awards and the CCMA trophies started crowding her mantle.
"Yeah. Isn't that wild?" Moskaluke says. "I mean, maybe it's not wild to anybody but me. In some ways 10 years seems so long ago, but also, in some ways, it feels like only yesterday."
But the reality is that the song wasn't just a hit; it was a pivot point. I remember interviewing her right after journalism school when that single was first hitting the water. It was clear even then that she wasn't interested in the cookie-cutter Nashville-north tropes. She had a grit that felt earned. While it wasn't her first swing at the plate, it was the one that cleared the fences and forced the industry to stop checking their watches.
"It really is nuts. Yeah, it's crazy," she says. "It really feels like that song and I grew up together. Like you said, I'd released other songs before that, but nothing that had really hit the way that Cheap Wine and Cigarettes did. It really opened a lot of doors."
The industry is obsessed with the immediate gratification of a chart-topper. We see it every week—songs that rocket to the top, stay for seven days and then vanish into the ether of terrestrial radio. "Cheap Wine and Cigarettes" defied that logic. It didn't need the validation of a number one spot to become an anthem. It found its power in the speakers of trucks and the playlists of fans who didn't care about Mediabase stats.
"Well, the weird thing about Cheap Wine and Cigarettes is that it didn't feel as big at the time as it has in the last 10 years," Moskaluke explains. "It seems to be the kind of song that has a second, third and fourth life. It just keeps hanging on. You know, it's funny because the fans really latched onto that it and claimed it as their own, even though it never went Top 10 at country radio. I've had a lot more tracks that have climbed higher on the charts, but nothing else that's gone platinum. And that’s all thanks to the fans."
There is a distinct difference between a hit and a classic. Most artists would trade a dozen number ones for a single platinum record. Platinum means people actually reached into their pockets or dedicated their data to your art. It’s a metric of genuine affection, not just radio programmers doing their jobs. Moskaluke’s first actual number one didn't arrive until March 20, 2020, with "Country Girls", a fact that usually shocks people who assume her 2014 breakout owned the top spot.
"You’re right. A lot of people assume that Cheap Wine and Cigarettes was my first No. 1, but it was far from it," she says. "I didn't have my first No. 1 until 20 March of 2020 with Country Girls. But, if I’m being honest, the very fact that's a common misconception kind of makes me feel good, because it means people feel like it should have been. It's just like an assumption that it went No. 1 and it never, ever did. That said, if you gave me the option the next song I put out would go No. 1, or be certified platinum, I’d pick certified all day, every day because that's a natural thing that happens and you just can’t plan for in any way and it’s an amazing surprise. Basically, it means a lot of people have loved that song enough to add it to their playlist. And even though those certifications come from the radio industry, it’s the fans streaming and buying and playing your music over and over again — and that’s an incredible and rewarding feeling."
It really feels like that song and I grew up together. I'd released other songs before that, but nothing that had really hit the way that Cheap Wine and Cigarettes did. It really opened a lot of doors.
And then there are the remixes. Usually, a 10th-anniversary remix is a lazy cash grab—a slightly faster beat and some synth pads. But Moskaluke went deeper. She brought in Dan Swinimer for what they call the "Vice" mix, which leans into the darker, more visceral elements of the narrative. Then there’s the Jack Trades version, which pivots toward an EDM dance floor vibe. It’s a ballsy move to mess with a fan favourite, but it works because the core songwriting is sturdy enough to handle the weight.
"We did two of them," Moskaluke says. "We had done one quite some time ago that we were holding onto until the 10th anniversary that my friend Dan Swinimer made. It's a lot darker sounding and vibier, and just more unique in that way — we call that one the Vice mix. After we noticed that one was doing really well, we thought let's try one more just for fun. So, we had a gentleman from Calgary by the name of Jack Trades do his own version as kind of an EDM dance mix. So, they're out there and it's just kind of cool to hear the song reimagined. They're not meant to replace the original, of course — they're meant to be their own standalone things, so they're super different. It was a really fun process to hear those songs back, especially since I really didn't have a lot of input. We kind of just gave them the music and said to have some fun with it! What came back was something completely different and it’s really cool."
Returning to Boots & Hearts this weekend feels like a victory lap. The festival has seen her through every stage of her career. She’s played the side stages, the main stages and everything in between. But there is one specific memory from the Burl's Creek mud that sticks out—a moment of pure, unadulterated connection that happened in the middle of a storm.
"I don't know how many times it's been, maybe three, maybe more — I’m not 100 percent sure, but it definitely feels like home at this point," she notes. "I don’t really know if I have a story. I’m sure the best stories come from the fans more than the artists because we’re the ones flying in and out and here and there all summer long. That said, the first time I played Boots & Hearts, the song had just come out, but the weather had gotten so bad that day right near the end of our set — we’re talking torrential downpour — there were literally ponds forming on the ground everywhere, and we weren’t going to be able to finish our set for safety reasons, and we were so disappointed. But, it wasn’t long before the crowd started chanting as we’re coming off the stage, 'Cheap Wine and Cigarettes, Cheap Wine and Cigarettes.' I don't ever remember hearing anything like that at that point in my career before, and so it was pretty cool, but it was devastating because we didn't get to play the song. All of a sudden, the heavens just kind of opened, and the weather took yet another turn — for the better this time. The organizers came over and said OK, you’ve got time for one more song. So, we went back on and played. I think that Boots & Hearts was the first time that I really heard anyone sing my own songs back to me."
And looking back at those early lineups is a trip. You see names that are now global icons tucked into the bottom half of the bill. It’s a reminder that the festival circuit is a grind, and no one gets a free pass to the main stage.
"I guess sometimes you just have to really dig for those memories," she says. "And ya, everyone starts somewhere, right? You don't just wake up and be Chris Stapleton where he is today. That just shows you have to work a lot at it — and we all develop as artists one way or another."
There is a specific energy to a Canadian summer festival that you don't get in the club circuit. It’s the desperation of a population that knows winter is always six months away. People party harder because the sun is out. For Moskaluke, the festival format is less about a structured concert and more about the discovery of a curated mixtape.
"I do really, really love summer festivals," she says. "I think the weather here in Canada really creates a perfect summer environment, and everyone feels good. They're getting out. They know that in a couple of months, everything is going to be covered in snow, and we need to soak up all the summer we can. Festivals are also kind of like listening to a mixtape; you show up and you don't just see one artist on stage or two artists on stage. You see five or six in a day, and you know they might not be artists that you listen to all the time, but you usually learn to love them in that moment that they're on stage and you hear them play live."
But she rarely gets to be a fan. The life of a headliner is a series of green rooms, soundchecks and hurried transport. Still, she finds the time to watch from the wings, catching glimpses of her peers like Dallas Smith or Mackenzie Porter. It’s the ultimate "inside baseball" experience—watching the mechanics of a show from the side stage.
"As performers, often we never get to take in a full show of anything," Moskaluke admits. "But, there have been a few really cool shows I’ve gotten to catch standing on side stage that I’ve really really loved. Sometimes that’s people I consider friends I just love watching, like Dallas Smith or Jade Eagleson, or Mackenzie Porter. Those are always great moments because these are people you talk to on a fairly regular basis, but you don't always get to actually see what they've worked so hard on to make their show what it is. I've also had the pleasure of working with Miranda Lambert and watching her show, Chris Stapleton, Sam Hunt . . . even if you just catch like 30 seconds of the concert, it's a real treat."
Looking forward, the focus has shifted. She’s spent the year writing without the crushing weight of a deadline. It’s a luxury few artists at her level can afford. She’s been road-testing snippets of new material on TikTok, bypass-ing the traditional A&R filters to see what actually resonates with the people who buy the tickets. It’s a raw, unpolished way to work, and it’s clearly revitalized her process.
"Oh yes, we're always working on stuff," she says. "This is the first year that I feel like I've really been able to just focus just on writing without trying to hit deadlines for certain things — so I’ve just been riding that momentum. It's been a really enjoyable year. We do have some plans for some new music, but they're super early, and I want to just hang on to that last little bit of just writing for the sake of writing and trying new things and rediscovering what I want my music to sound like in the next few years. I’m so excited about a lot of the stuff that I've been writing, and I'm so excited for people to hear it. I've been putting a lot of it up on Tiktok, just like chunks of songs. So, if they want to sneak peek at what may or may not be released in the future, they can check them out before I get back into the studio. So, you’ll have some new music, not immediately, soon, but soon enough."
And then there’s the question of collaborations. Country music has finally embraced the mash-up culture that hip-hop perfected decades ago. Moskaluke has always been a proponent of the team-up, and she’s got her sights set on the genre-bending outlaws of the current scene. Specifically, a certain artist who has been blurring the lines between country and rock with surgical precision.
"There's so many, and I have done probably more collaborations in my career than a lot of people, and I love them," she says. "I've always, always believed in them, and I'm so glad that country is really starting to do more of that, especially across genres. I'm a huge Hardy fan. I think that would be such a cool one. I love how he bends genres as well."
As she prepares to take the stage at Burl's Creek, there is one non-negotiable for the fans. They want the hits, sure, but they specifically want the one that started the fire a decade ago. Rain or shine, the expectation is set.
"YES! I mean I hope so — because you never know when a torrential downpour is going to happen, obviously," Moskaluke laughs. "But, as long as the music festival Gods allow, I will play that song.
