Love at First Listen with Riley Taylor

Riley Taylor 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.

Whether headlining a show or touring with the likes of Kip Moore, Sacha, and Owen Riegling, Riley Taylor and his band approach every performance with the same attitude: be loud, proud, and always jam. With a 30-track debut album released earlier this month (April 18) fusing multiple influences and narratives, that’s an easy—and extremely fun—task. ‘Story to Tell,’ out now on Honky Tonk Record Co, is primed to fill every country playlist with its blend of bar songs, country storytelling, and celebrations of life, love, and everything in between. Soon, you will catch Riley on his Small Town Hometowns acoustic tour across Saskatchewan, Alberta, and Ontario or opening for Cooper Alan. Don’t see your city? More dates are already in the works (details on that below!).

Just before hitting the stage at his packed album release show at Rivoli in Toronto, Riley dished on making his album as relatable as possible, calming down to the sounds of Matchbox Twenty, and returning to play his favourite festivals.

With 30 tracks and an hour and 44-minute runtime, there are certainly multiple stories to be told on ‘Story to Tell.’ Can you describe the process of pulling these 30 tracks and stories together?

Especially with it being a debut album, [I] kind of have my whole life to choose from as far as what we want to focus on [with life] moments [and] certain things. I think we chose pretty well a lot of things that would encompass what has made me who I am today. And I think as far as what I would be curious to know from the fans’ perspective is, which one of these songs relate[s] to your story? I think we wanted to make a lot of it as relatable as possible.

With this album release show being your first big headlining performance and celebration of the project, are there any tracks you’re especially excited to share with fans live?

The first one that always comes to mind is “Fucked Up.” My grandmother wasn’t very happy with that title, but that one really stands out to me because I’m proud of it as a songwriter. It comes from a dark place, but there is a sense of optimism about it. And I think it translates well because I also think everybody’s felt at least some of what’s in there at one point or another. Outside of that, I adore “Off the Liquor.” It’s just a big, loud, fun energy song. I also like a lot of the old, more traditional sounding stuff that we recorded too. That was all done in an old school way with live recordings off the floor and it was a cool process.

Boots and Hearts Music Festival plays a big part in your story, with you winning their Emerging Artist Showcase in 2021. How did it propel you to go all in on music, ultimately bringing us here today?

Yeah, that was a really crazy, validating point where I wasn’t sure I could do this or if it was worth pursuing because I didn’t feel good enough. So, it meant a lot to me, and it was very eye-opening in the fact that these people know [the industry] and they thought there was something there. So, I’m still trying to find “it,” and I kind of hope I never do. I hope I’m always kind of chasing whatever that is.

When you talk about sources of validation like that, what is one of the best pieces of advice that you’ve received along your musical journey that you can pass along to the next gen of artists?

Just keep your head up and be kind. It doesn’t cost anything, and in this business, there are not a lot of things that don’t cost anything. And ironically, that tends to lead to more opportunities than not. Some people will throw you a bone just based on the fact they like you. So, I think that’s really important, along with just caring about the craft of it—putting your time into your songs and making sure that you know your stuff. And try to have fun along the way.

An artist, Riley Taylor, stands centre stage singing into the microphone on stage at Rivoli in Toronto.
Riley Taylor performing on stage at his ‘Story to Tell’ album release party held at Rivoli in Toronto on April 22, 2025: “I never thought I’d have an album—let alone a release party.” (Photo credit: Angela McLean/Love at First Listen)

You first released one of the tracks on ‘Story to Tell,’ “Good Things,” as part of the Boots and Hearts contest, but have since reimagined it with more drawl and personality. What inspired you to revisit and revamp it?

I’m glad you asked that. I don’t want to be misunderstood—I didn’t redo it because I hated the original. I still love the original, and it will always be special to me. I just always wondered [how it would sound] if we had a different style of production that was more twangy and rootsy. The first time we tackled it, the song had more of a pop production. I’ll always love the original, but the way we redid it made it easier to deliver live as well. It almost sounds like it’s live in the recording. That’s what I wanted to re-imagine, while keeping it true to the original.

On the album, you also cover three songs: The Rolling Stones’ “Dead Flowers,” Matchbox Twenty’s “3AM,” and Live’s “Lightning Crashes.” What about each of those songs resonates with you and led to them needing to be part of this project?

All three of those songs were just clear [studio] cuts. We played around with a few, but “3AM” was probably the one that’s nearest and dearest to me. Growing up in Alberta, my mom had this Matchbox Twenty CD, and I was a colicky baby. So, I don’t remember, but allegedly whenever “3AM” would come on, no matter if I was in a fit or if I was being bad or a little brat, I’d go right to sleep. When I got older and I started playing [music], I was looking at easy three-chord songs to play on guitar and that one came up, and I knew all the words. I was pumped up because it was the first one that I could play and sing at the same time, so I was like, “Mom, you’ve got to check this out!” She was blown away because I didn’t know that story about when I was a baby.

The other two, to be honest with you, are songs that I just love inexplicably. Something about them is so cool, and they just make me feel a certain way. So, when we were looking at songs that would be cool to cover, they stood out. They’re also songs that I think are undervalued nowadays. It’s a fun way to recirculate them.

With this series being about the music we love at first listen, who are some of your Canadian country peers whose songs you’ve loved at first listen?

Love at first listen for me… there are so many, but “Do It Anyway” by Jade Eagleson, “Home Less” by Owen Riegling, and “Pillow Talkin’” by Tyler Joe Miller.


Riley’s newest single “Hometowns” is quickly rising on the country radio charts with airplay across Canada and major looks on streaming services.

As the summer concert and festival season fast approaches, do you have any live shows or festival performances that you can tease?

We were just looking into getting the festival season booked up. This May, I’m going to be doing an acoustic tour across Alberta. We’re calling it the Small Town Hometowns tour and it’s going to be more of a stripped back, almost singer-songwritery atmosphere where I’ll get the chance to explain how each song came to be. The goal is to get introduced to those fans and say, “If you like this, maybe I’ll be back with a big band.” There’s one festival back home that I’m doing—FundyFest in Sussex, New Brunswick—and that’s always been one of my favourite places to play. It’s always been the most responsive crowd. Then, I’m heading back to Cavendish Beach Music Festival in Prince Edward Island for the kickoff party the night before the festival starts. There are a couple others that we’re in the middle of booking right now. My message is if you like what’s going on, you like the sound, and you want me to come to your town, reach out. We’re always looking to see where the fans are and gauge where we should go to next.

Continue Reading

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.

Continue Reading

Love at First Listen with MacKenzie Porter

MacKenzie Porter 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.

Canadian country queen MacKenzie Porter is the definition of booked and busy. If it feels like she’s been racking up a new set of career milestones every few months, it’s because she has—she was named to the CMT Women of Country Class of 2021, earned Academy of Country Music Award and American Music Award nominations for her duet with Dustin Lynch, “Thinking ‘Bout You,” which also marked her first U.S. Country #1, and landed a sixth #1 at Canadian country radio with her latest single “Chasing Tornadoes.”

Shockingly, despite years of homegrown and international success, MacKenzie has yet to have a moment to celebrate with Canadian audiences. That will all change when she embarks on her first nationwide headlining tour this week, starting Friday (November 3) in Toronto. Soon after, fans will gain a whole new set of songs to memorize and play on repeat when MacKenzie releases her long-awaited debut album in the first quarter of 2024. So, it’s safe to say the MacKenzie Porter country reign is just getting started.

In this edition of Love at First Listen, MacKenzie reflects on her whirlwind journey and shares a first look at her new tour setlist (read to the end to find out how you can meet her at the shows!).

“Chasing Tornadoes” is the lead single off your upcoming debut album. Amongst all the material you had written to date, how did you decide this song was the one to officially kick off a new era?

The new record is way more country than some of the other stuff I’ve been putting out before. We still have my pop influenced parts of it, but I think the overall sound is more like wooden instrumental—like there’s fiddle on almost every song. So, “Chasing Tornadoes” is a good bridge between “Pickup,” which is a lot more poppy, to this record.

For anyone who hasn’t heard “Chasing Tornadoes,” can you describe the story behind the song?

It’s about being in a relationship or a situation that you know is probably not good for you. It’s chaotic and messy and might not end amazingly, but there’s something that’s fun about that. I think we’ve all been in situations where you’re like, oh well, I’ll deal with the consequences later. So, that’s what the song is about and it’s actually kind of cool because I did not write this song. There’s going to be 20 songs on the record, and I’ve written probably 12, but this is one Lainey Wilson wrote. I love Lainey and her record was finished, so this song of hers worked perfectly on mine.

Given all you’ve accomplished in a few short years, is it even possible to take a moment and let everything sink in, or is life just a constant string of pinch-me moments?

It sounds sad because obviously I should be enjoying those moments, but by the time something like a #1 is announced, I’d put the song out months ago, so we are already working ahead on the next project. But of course, we’ll always have a glass of wine or do something to celebrate.

Let’s talk tour! Aside from the fan favourites, how much new music can concertgoers expect to be amongst the first to hear?

I’m definitely going to play new songs. I want to make sure I play all the ones that people want to hear and that they know because when I go to a concert, I want to hear the hits. But I also really want to bring people into this new record, and that’s what you’ll get when you come to the show. I’m going to do some old, old songs that I first put out, and then this era of the last three years, and then the new era, including my favourites off the record. So, it’ll take us through the whole thing.

On Instagram, you’ve been asking what songs fans want on the setlist. Was there anything they were requesting early on that made you stop and go, ooh, maybe I actually should add that?

A lot of people were saying early, OG songs like “I Wish I’d Known,” which was the first song I put out in like 2013. I was not planning to play that song, but now I’ve got to go back and listen to it and relearn it. I also want to have moments where if somebody’s yelling from the crowd, you’ve got to play this song, I want to make sure that I can play it as well.

Performance outfits are half the fun of touring, and you’ve shared some try-on videos online. Talk to us about your on-stage style! How does it differ from your day-to-day fashion?

It differs quite a bit. I wouldn’t wear a sparkly dress—I’d actually probably be in sweatpants most of the time. But I always think that my stage style has the exaggerated outfits of my life. I love unique pieces. That process of shopping is so fun for me.

Opening these shows is our friend at Love at First Listen, Griffen Palmer. How did you connect, and how excited are you to have a fellow Canadian and labelmate on the road with you?

I actually cut a song that Griffen wrote called “Drinkin’ Songs,” so hopefully we’ll get to write some songs on the road too. But I’m really excited. His music’s incredible, and Canada has been the place that I have really been able to build a career. So, I always want to bring other Canadian acts out and support that industry because it does mean a lot to me and it is really the reason I get to do this for a living.

You’re also hosting your inaugural Country vs. Cancer benefit on November 20, where you’ll be joined in Nashville by Dustin Lynch, Walker Hayes, Lily Rose, and Nate Smith in support of the American Cancer Society. Why is it important for you to use your voice to amplify causes close to your heart?

What’s the point of having an audience if you can’t try to do some good with it too? I mean, making music and having people relate to your songs and being able to help get them through a hard time is incredible. But I do feel the responsibility to try to do more, and that cause is really close to my heart because my mom had breast cancer. So, this is raising money for all different types of cancers, but October was Breast Cancer Awareness Month. We had help in those times from family and friends and I want to be able to pay that forward as well.

Event poster announcing MacKenzie Porter's inaugural Country vs. Cancer benefit concert in Nashville on November 20, 2023.
After wrapping her debut Canadian headlining tour, MacKenzie Porter will head to Nashville to host her inaugural Country vs. Cancer benefit concert with former collaborators, labelmates, and other peers.

Spending so much time on the road, have you picked up any self-care secrets that help keep your mind, body, and voice healthy and ready for the next gig?

I definitely warm up for every show. I actually used to do a shot of vodka or something, but I’ve stopped doing that because I do feel like rest and keeping your body healthy when you’re going that much is so important. We do grueling days where it’s a 5 a.m. start, you travel all day and you play the show, and then you do it again the next day. So, I’m really trying to be healthy and clean to keep up with the schedule and not get rundown.

Do you have a message to send to your fans who will be seeing you at an upcoming show or to anyone who needs a final push to buy a ticket?

This Canadian tour is a first for me, so it’s a really special moment for me to get out and really thank people for the last five years or more of my career. They’ve shown up for me, and I hope we really show up for them on this tour. And after the show, I’m just going to be hanging out and meeting people and thanking people and taking pictures and all that until literally the last person leaves the venue. So, it will be a more intimate experience than just a regular show.

Continue Reading