Josh Ross Is Riding a Wave of Musical Milestones, From Canadian Country Hits to His Opry Debut

Growing up in Ontario, Canada, music was far from a focus for Josh Ross, who spent his time playing hockey, football, soccer, track and field, and motocross racing.

“It was always some kind of sport,” Ross tells Billboard, while seated in the offices at Universal Music Group Nashville. “I’d maybe sing at a karaoke night or in the weight room sometimes.”

But away from friends and family, Ross was keeping a secret.

“I had a little three-ring, blue book where I would write short stories, lyrics, anything that was going on in my life. I would hide it under my bed,” he recalls with a laugh. “Now, it all makes sense to me. I wish I could find that book now. My family moved when I was in college and everything was piled into boxes. It would be cool to find it.”

He went on to play football at Western University, until he was sidelined by an injury. The time away from the sports fields offered a chance for Ross to rekindle his love for writing and music. He took up guitar, pairing it with his lyrics and stories — no hiding needed.

“I got to the point where I thought, ‘Do I keep forcing through the injuries of sports or do I pursue this thing I’m definitely falling in love with?’” he says. He opted for the latter, and just before training camp during his final year of college, Ross left sports to pursue music.

The decision has paid off. Ross has notched two top 5 hits on Billboard’s Canada Country chart, the viral hit “First Taste of Gone” and its follow-up “On a Different Night,” over the last three years, while his official debut U.S. country radio single, “Trouble” currently sits at No. 21 on the Canada Country chart. Now based in Nashville since 2020, he made his Grand Ole Opry debut in July and is now touring with Nickelback and Brantley Gilbert.

The Core Entertainment agency, who also manages Nickelback and hot country newcomer Bailey Zimmerman’s career, took notice. Ross inked a management deal with The Core Entertainment, and a label deal with Universal Music Canada. Earlier this year, he added UMG Nashville to his team — a clear signal of his global career intentions. He also issued the five-song EP Do What You Love in 2020.

Now, he has six nominations heading into this year’s Canadian Country Music Awards (including male artist of the year and single of the year, for “On a Different Night”). Next year, Ross will be opening shows for Zimmerman.

Billboard spoke with Ross, August’s country rookie of the month, about his breakthrough career moments, moving to Nashville to pursue his dreams, touring with Nickelback and more.

What were your first weeks and months in Nashville like?

I would go out four or five days a week, to Red Door or Midtown, and just meet people. Sometimes I’d find roommates. And at the time, I slept in my car for a while. I always joked, like, “How do I break it to my parents?” They used to help me out, and they thought they were paying rent, but they weren’t paying rent — I would pay for my songs to get recorded, and then either stay with someone or sleep in my car instead.

Not being from the U.S., you can’t just go get a job [without a work visa], so it was figuring how to make cash money — building furniture, selling stuff — and balance that kind of stuff. It was tough in the beginning, because you have to have someone to vouch for you and I didn’t have that yet. You do what you have to do to make money.

What is the story behind “First Taste of Gone”?

When I moved [to Nashville], I was trying for a few years to chase what everybody else was doing—the writing style, melodically and sonically. A couple of years ago, I had just broken up with a girlfriend. Mason Thornley, who I wrote the song with, took me out to a bar. He handed me a drink at the bar and was like, “Here’s your first taste of gone.” It just sounded like a song title. I remember walking away from that songwriting session having been really vulnerable and honest. It felt like for the first time, I wasn’t chasing phrasing or anything; it was just organically me.

How did “Ain’t Doin’ Jack” make its way from a ballad to this angst-fueled rocker you ultimately released?

We were on a writing retreat in the Smoky Mountains. I got a call that day letting me know that the Nickelback tour had been locked in. I was excited, called my family to let them know, and then I remember sitting down again with the writers and thinking, “I’m going to need something more rocking for the live show if I’m playing with Nickelback and Brantley Gilbert. We can only play so many ballads.” We totally changed the momentum of the song to fit that. It’s fun to play.

What has the tour been like?

Chad [Kroeger] and all the guys in Nickelback have been so cool. We get up and sing a cover song every night with them. They have been awesome about welcoming me into their world, and I’ve been able to pick up on so many things, performance-wise. In country music, as a new act, I have 30 minutes and I have to fit in as much as I can. But watching Nickelback’s set, [Kroeger will] engage with the crowd and make jokes. It’s cool to see just how they deal with situations — if there’s a fight in the crowd, watching how they calm that situation down — situations I’ll have to learn to navigate.

How is catering on the Nickelback tour?

It’s so good that I had to sit down a couple of weeks ago and be like, “Okay, I need a meal plan.” You have everything — chicken, salmon, steak, huge dessert tables and salads. It’s like a cruise ship or something. It also opened my eyes to how massive that undertaking is on a tour — feeding 200 or so people every night.

Are you working on a full-length album?

We are planning out on some more singles, probably before the end of the year. But I’ve also been working on a body of work that I, personally, feel like will help listeners get to understand me. But we are definitely working toward an album for next year, depending on where the songs land.

Who is in your writing crew at the moment?

We started looking at some outside songs for the album, but I always try to write as much as I can. I’ve always written with Mason Thornley, and Matt Geroux, my producer, and Ben Stoll. But I’ve also been writing with Heath Warren, Taylor Phillips, John Kraft. But I definitely have a solid foundation of people and bring new people in.

What was the first major performance you did?

I played coffee shops and bars in college, but my first major performance was the Boots and Hearts Festival [in 2017]. I literally threw up before I went onstage, because I was so nervous. I only had to play three songs, and it was my first time playing with a full band, too. It was in front of like 7,000 people. I played Jon Pardi’s “Dirt on My Boots,” an original song I wrote called “I’d Be Lying,” and Aaron Goodvin’s “Don’t Ever Let Go.”

What is your go-to country music album?

I love Morgan Wallen’s older stuff, the If I Know Me project, though his new stuff is great, too. I always go back to Alan Jackson’s stuff, and I love Chris Stapleton’s Traveller album.

Who are some of your dream collaborators?

Lewis Capaldi. He tends to do a lot of the octave stuff, with the verses being a lower register and the choruses being higher. Doing a feature with someone like Halsey would be cool.