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.
When country superstar Keith Urban pulled a then 14-year-old Hailey Benedict out of the crowd and up on stage at a 2016 concert, neither of them could’ve predicted the series of life-changing events that would follow. His question to Hailey: “What’s the dream job in life?” Her answer, without hesitation: “Be a singer-songwriter.” An enthusiastic “Yes!” in response led to Keith shining the spotlight on Hailey, passing her a guitar, and letting her sing an original song for a packed arena. Since then, Hailey has grown into a full-fledged performer making that dream—and so many others—come true.
In this edition of Love at First Listen, we’re celebrating Hailey’s biggest Country Music Week yet as she prepares for a jam-packed weekend, reflects on her American Idol journey, and reveals which ‘Era’ of her life she’s embracing this fall.
“Damn You July” was your first single after almost two years and has been the catalyst to multiple career milestones (not to mention that it’s currently Top 50 on Canadian country radio!). How did you know it was the right song at the right time?
I’d written with my friends, Rich Cloke and Elias James, and the moment we finished it, it was one of those feelings of like, we’ve got a special song here. I started playing it while on tour with Aaron Goodvin and found people really resonated with it. It also felt like something completely different than I had written or recorded before. All of that led to me bringing it into the studio and making it part of the Top of the Country competition, and I’m really proud of how it all turned out.
Building on that success, you’re nominated for the CCMA Innovative Campaign of the Year Award and are a Top 3 finalist in the SiriusXM Top of the Country competition. What does it mean to you to be part of this special week for Canadian country music while enjoying these major accomplishments?
It’s absolutely insane and I feel very grateful that I get to just be part of it. I’ve been attending the CCMAs since I was 14. Even with the Top of the Country competition, I’ve gone every year and thought it’d be really cool to be part of. I’m excited to soak it all in.
The Top of the Country concert features a headlining performance by The Reklaws. Considering the country scene is always described as a family, have you met them before?
I’ve met Jenna, and I’m a big Reklaws fan. They don’t put out a bad song. Jenna and I were supposed to write in Nashville back in May and then schedules got moved, so I think that’s still in the cards for one day when I’m back down there. I can’t wait to watch their performance.
You were invited to audition for American Idol in 2020, so you’re no stranger to rocking a singing competition. What advice would you give to someone wanting to follow in your footsteps?
What’s so awesome about music is there are so many different paths you can take and so many things you can explore. I say experiment and do the things that feel right and make you happy, whether it is a local competition, performing for your friends and family, or trying to get on every show you can — whatever is going to make your heart the most excited and ready for your career.
Your CCMA nomination is for a TikTok challenge you created to test your own guitar playing skills and “empower others to take [a] leap.” Having amassed a following online, is it still a shock to come out from behind the screen and see everything come to life?
I remember during the first show back after COVID I was like, this is weird. I felt at home, but because I’d been so used to doing Zoom performances, I almost forgot I had a whole body and real people were watching. As I’ve gone to more shows, even down in Nashville, I’ve had a couple fans who’ve followed me from my very first videos say hi. You see numbers on a screen, but you don’t totally know what that means until you start going out and playing and people recognize your music. It’s been really fulfilling and exciting.
Country fans in Alberta will get to catch you opening for Tim Hicks on a six-show run across the province this October. What experience do you hope to bring to those audiences?
One thing that I love about music and especially country music is the storytelling aspect, and I think with Tim’s upcoming tour, that campfire troubadour feeling is going to probably be a big focus. I hope to just add to that experience and give people something to make them feel a little more celebrated or a little more loved and seen. It’s going to be a fun time.
You’ve shared the stage with several amazing country legends and friends. Has there been one concert that’s stuck with you and inspired your own stage presence?
I saw Taylor Swift on the Speak Now tour when I was eight or nine. That definitely inspired me because she was doing everything that a young country artist could dream of, and she was paving the way for so many artists.
Speaking of Taylor, have you scored tickets to The Eras Tour?
I did, in Nashville! My sister and I ended up getting floor tickets through the Ticketmaster lottery for my birthday. It was everything and more. Taylor is incredible. I’m going to watch the Eras movie when it’s out because I’m sad that the show went so fast.
What Taylor Swift ‘Era’ would you say that you’re in?
My gosh, that’s a good question. I would probably say my ‘Red’ era. Maybe it’s the fall vibes right now, but I also feel like her ‘Red’ era was her exploring different types of genres and that’s where I’m at right now — just experimenting with lots of different sounds and finding my sound.
Do you have a message to send to your fans heading into CCMAs weekend?
I’m very grateful for everyone’s support, and hopefully I’ll get to see you at a show near you soon.
