Love at First Listen with Gavin McLeod

Gavin McLeod Interview Love at First Listen 2025

We all have those artists and songs we hear that strike the right chord and make us fall in love at first listen. They’re the reason we refresh social media pages, tour schedules, and Spotify profiles — because we can’t miss a single release. This is Love at First Listen — a series introducing you to the emerging, and established, artists with new music guaranteed to upgrade your playlist.

Blending classic and modern rock à la The Strokes, Inhaler, and Sam Fender with the blues music he grew up playing, emerging Canadian artist Gavin McLeod is one to watch. With an EP and several infectious live performances under his belt, Gavin has found his musical footing with ‘The Constant Astonishment,’ his debut album released last month and written over four years, including several pandemic-era writing stints with his bandmates. Songs like “Marigold” (which almost didn’t make the final tracklist!) and lead single “Things We Used To Do” shine with their folk-leaning, intimate-sounding production, but are perhaps most memorable for being pure, timeless head bobbers that will find a home on any playlist.

In this edition of Love at First Listen, scroll through Gavin’s thoughts on maintaining a healthy balance with social media, finding support in the music industry, and the behind-the-scenes scoop on auditioning for America’s Got Talent.

You released your debut album, ‘The Constant Astonishment,’ on Valentine’s Day. Let’s start there: when and how did you come to fall in love with music and songwriting? Who were some of the first artists that you loved at first listen?

I was around seven or eight when my dad put me on a drum kit. He always played drums growing up, so it was a natural thing. There was also just a lot of music in the house. My grandfather introduced me to Neil Young, Fleetwood Mac, and all that early ‘70s stuff on vinyl and then some ‘90s alternative grunge, and that is still the basis of what I listen to. I started playing guitar, singing, and met my guitar player when we were 11. We loved playing blues music early on, and then shifted to playing at bars covering Jimmy Hendrix and Led Zeppelin. We’ve had some lineup changes throughout the years but the two of us have been playing in a band since then, so it’s just been non-stop.

What inspired the album name, aside from your career being a fast-growing success and probably a constant astonishment in and of itself?

The title track came from looking outward and seeing how people are so addicted to their phones nowadays and constantly needing stimulation or anything to keep them occupied and me kind of feeling disenfranchised with all that stuff. I liked the name; it fit in with a bunch of themes that I was writing about at the time, and it rolled off the tongue, so it just became the record name.

As an artist today, that’s an interesting position to find yourself in with so much growth happening on TikTok and YouTube, and then having this feeling of it all being a little too much.

Yeah, it’s scary. I feel like most artists go through this, but you could be really hot on it one day and be like, this is great. The next day, you might feel real down on it. You have to find a way to work with it and be creative. It’s not easy, but back in the day there was nothing like this to be able to self-publish or do anything yourself. So, there’s probably more positives than negatives, but it can be a lot when most of your day is working off of screens. It becomes much less about the music.

Your album release was supported by FACTOR Canada. As an emerging Canadian artist, what does it mean to you to have their financial backing, and what advice would you give to future cohorts of breakthrough Canadian talent?

For people doing this moving forward, there’s a lot of support out there, but it doesn’t mean much unless you’ve got your foundation and your plan and you know what you want to do. That said, the support being there really does help. The fact that you can get this kind of support from FACTOR, and that the government supports that, is crucial because it’s obviously a very hard industry to breakthrough in. I don’t think there would have been a chance that we would have been able to record the way that we did if we didn’t have them. We were able to go in and do a live off the floor thing at this beautiful studio for a couple weeks, and it was all because of FACTOR. So, definitely a lot of love there.

Although your America’s Got Talent audition didn’t air, what experience and exposure did that time bring you?

It was a couple years in the making where they had reached out on Instagram and asked if I wanted to do the show. What you see on TV — the audition in front of 2,000 people — they’ve curated those people to get to that point, even though they make it seem like that’s the first audition. I was able to go and perform in front of the judges and a big audience down in Pasadena, and I met some cool people from Brazil, Poland, and all over the world. The scale of the show is crazy, so I’m glad I got the experience and the opportunity. I’ve never felt that weird and nervous for anything I’ve done.

You’ve played some of Toronto’s favourite venues, including Horseshoe Tavern, Rivoli, Drake Underground, and Velvet Underground. Do you have any other venues on your wish list?

I’ve always [said] if there’s any way we could play at Massey Hall, that would be insane. That would be number one bucket list. But I don’t know if that’s going to happen.

We need to have positive energy here. You’ve played TD Music Hall, which is in the building.

Yeah, that’s in the building. We’re almost there. [We] got to go in the elevators and stuff. I was like, this is close enough. (Editor’s note: For now!)

Singer Gavin McLeod photographed performing live on stage in Toronto. (Photo courtesy of Gavin McLeod)
Singer Gavin McLeod photographed on stage in Toronto. (Photo courtesy of Gavin McLeod)

Spill the tea: which of these venues has the best green room?

The El Mocambo green room is amazing since the renovation. They’ve done some something really nice there, although I also like a crusty, sh!tty looking green room as well. But yeah, it feels like a five-star hotel. It’s very nice.

Speaking of Velvet Underground, that’s where we were introduced — when you opened for Winnetka Bowling League earlier this month. For those who aren’t familiar with the behind-the-scenes intricacies, where are you and what are you doing when you get that invite?

We were meeting with one of our guys from Dine Alone [Records] and he had an email come through. He was like, “Do you guys want this gig?” There’s a song that they came out with a couple months ago called “This Is Life,” and my guitar player Patrick and I [have] played that song a million times. It’s with Medium Build and Dawes, and we love those guys. Sometimes you open for someone, you don’t really know their music, and you get to know it. But we were big fans of their stuff beforehand, so it was quite cool.

Now that ‘The Constant Astonishment’ is out, I’m sure you’re still riding that high and living in the moment, but can you tease where you’re hoping to take this music next?

Everything we’re writing and recording right now is very UK indie rock inspired. We’re hoping to start putting new stuff out in the next couple months — some singles, maybe leading up to an EP. We don’t really have a concrete plan yet, but there’s a lot of new stuff in the tank, and we want to get it out there. We’ve got some festivals and shows in the summer and a couple other slots coming up. Everything will be shared on Instagram.

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Love at First Listen with Drake Milligan

Drake Milligan Interview Love at First Listen 2023

We all have those artists and songs we hear that strike the right chord and make us fall in love at first listen. They’re the reason we refresh social media pages, tour schedules, and Spotify profiles — because we can’t miss a single release. This is Love at First Listen — a new series introducing you to the emerging, and established, artists with new music guaranteed to upgrade your playlist.

Giddy up, country music fans — there’s a fresh face on the scene ready to take over your playlist and your heart. Drake Milligan first caught the attention of the A-list judges on America’s Got Talent last year as the ever tough-to-crack Simon Cowell praised his “real charisma.” Quickly becoming an AGT fan favourite, his debut, critically acclaimed album ‘Dallas/Fort Worth’ grew his audience to more than 3.4 million Spotify listeners locally and internationally, including here in Canada. Did we mention he also scored his first Canadian country radio #1 with The Reklaws on their joint hit single, “Honky Tonkin’ About”?

Drake is days away from kicking off his first Canadian headlining tour with stops in Regina (Dec. 5), Saskatoon (Dec. 6), Edmonton (Dec. 7), and Calgary (Dec. 8) supported by Canadian country songstress Kalsey Kulyk (our next Love at First Listen feature!). He’s set to wrap up his whirlwind year at home with a performance at one of the world’s largest New Year’s Honky Tonks in Fort Worth, TX, before he opens for Cody Johnson on tour across the U.S. next spring.

Ahead of his final shows of the year, Love at First Listen caught up with Drake Milligan to chat all things AGT, #1 songs, and why, even if you’ve seen him live before, his next shows will be a whole new experience.

Welcome to Love at First Listen! You’ve had an absolutely stacked year and you continue to add to a seemingly never-ending string of milestones, having just landed your first-ever Canadian country radio #1 and kicking off a new tour. Is it even possible to take a moment and absorb all that action?

Not at all. It’s all happening so fast. I got a week off back home before gearing up for tour, so that was my one opportunity to sit back and kind of take it all in. With these Canadian shows coming up, this is my first time visiting some of these cities, so it’ll be a lot of fun.

Fans watched your America’s Got Talent journey play out on TV, but how was it for you? What was the biggest lesson you took from your time on the show and how did it help accelerate your career?

As a new artist that had been on the road, I had material recorded but not released yet, so that show was a perfect opportunity for me to showcase it to the world. After the show, I really learned that I can perform on a high level. Those live shows are no joke — it’s truly live. And you’re in front of not only a big theater of a few thousand fans, but you’re in front of millions of people who are watching live at home. So, it’s pretty daunting, but if you can get on the other side of it and pull it off, you feel like, okay, there’s really nothing I could be fazed by.

You were raised in Texas and moved to Nashville at the age of 19. What was going through your mind as you made that big leap and invested in yourself and your career at a young age? Take us through your first couple of months in Music City.

I think I was too naive to really know what I was doing. I really jumped in and started writing songs. My sole focus was finding great songwriters. People that had written some of my favorite songs and some of these ‘90s country songs that I love are still around Nashville writing great music. So, that was my first objective — finding them, seeking them out, and trying to learn from them. I was lucky enough to do that and learn a lot about songwriting and still am learning a lot.

What advice would you give someone who has watched your journey and wants to follow in your footsteps?

Go for it and stay true to yourself, and make sure you go in there knowing what you want to say and how you want to say it.

Coming back to that impressive and exciting Canadian country radio #1 for “Honky Tonkin’ About,” how did you initially connect with The Reklaws (our favourite Canadian country duo!) and how was it playing the song live for the first time to open the 2023 CCMA Awards?

It’s been incredible! My label first reached out and said there was a great Canadian group that wanted to do a song with me. I had heard a little bit about them before then, but as soon as I met them, we became fast friends. They’re amazing and I was really honoured that they wanted me to be a part of the song.

Who is on your bucket list of collaborators for 2024? How can we help you manifest them?!

There’s a few I’d love to work with. On my first record, ‘Dallas/Fort Worth,’ I got Vince Gill to come sing a song with me. He’s one of my heroes and we’re gearing up to hopefully cut another record. I would love to get another country music legend in there. Obviously for a Texan, George Strait is at the top of the list, but you know, any legend will do!

The end of the year always seems to inspire a lot of self-reflection and thanksgiving. When you think back on 2023, what was your career high—if it’s possible to pinpoint one—and what are you most looking forward to in 2024?

I feel like this whole summer has been on a high. We played so many shows this year; I know it’s over 100 shows all over the States. We played in London, across the UK, and we played in Glasgow, Scotland, which was definitely a highlight. But I just feel like being on the road was all one big highlight for me — playing so many shows, watching the shows get bigger, and watching as our show got better. The more we play, the better we are, so it’s been a really great year for just keeping the train rolling.

Are you working on anything else that fans can look forward to as you wrap up this jam-packed year and prep for the next one?

With all of the shows we played this year, I feel like mostly everybody’s got to see a little bit of it. So, we’re going to change things up and totally revamp the live show. We have some new songs recorded and I’m hopefully going back in again and cutting some more songs soon. So, there’ll be new music coming out and lots to look forward to in the new year. I want to be doing this for a long time, and this year felt like the first one of a long career.

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