Josh Ross on Cementing Whirlwind Year With Debut Album ‘Later Tonight,’ Working With Akon & Prioritizing Health for a ‘Long Career’

Ontario, Canada native Josh Ross is riding a wave of considerable career acclaim as he releases his first full-length album, Later Tonight, which dropped Sept. 19 via MCA/ Mercury Nashville/ Universal Music Canada and CORE Records.

His song “Single Again” rose to the top 5 on the Billboard Canada Country Airplay chart and triumphed at the pinnacle of the Billboard Country Airplay chart, becoming his first U.S. country chart-topper.

He also just won his second entertainer of the year trophy at the Canadian Country Music Association (CCMA) Awards, while “Single Again” was named single of the year. He also picked up awards for video of the year, top-selling Canadian single of the year (both for “Single Again”) and top-selling Canadian album of the year (for his previous EP, Complicated).

“It’s great to have the support and love from Canada, embracing me playing shows and also trying to be an international act — it’s a time for me to reflect when I’m there on the progress we’ve made in the last year and all the things that have happened,” he says. “I’m happy and just appreciative of the awards and recognizing everybody involved.”

The 15-song new album, produced by Matt Geroux, offers up an array of sounds, all of them reflecting different facets of Ross’s artistry. The set includes his latest release, “Hate How You Look,” which debuted at No. 46 on the Canada Country Airplay chart, as well as his Akon collaboration “Drunk Right Now (Na Na Na).”

“It goes from rock to rap to country to piano, singer-songwriter. I think the coolest part is that it is cohesive with who I am as a person,” Ross says. “I very much listened to so many different styles of music. For me, that translates to, when I write a song, I write the song and let the musical parts find it after. And if it calls to be more rock or country, or whatever it may be, I just allow that freedom to happen.”

Ross has been pursuing a country music career for nearly a decade. His first independent EP, Do What You Love, released in 2020 and he followed it with 2022’s Live Sessions and 2024’s Complicated EP. In 2023, he earned his first Canadian Country Airplay chart No. 1 with “Trouble,” and quickly followed with “Ain’t Doin’ Jack.” He earned his first CCMA Awards win in 2023 for breakthrough artist or group of the year.

Ross moved to Nashville seven years ago and has since toured with Bailey Zimmerman, Lee Brice, Nickelback and more. Earlier this year, he wrapped a stint of Canadian shows opening for Jelly Roll‘s The Beautifully Broken Great Northern Tour. This year, he’ll open shows for Dylan Scott, before headlining his own 17-show Later Tonight Tour next year in Canada.

Ross spoke with Billboard about the new album, touring with Jelly Roll, the importance of focusing on physical and emotional health, and more.

“Single Again,” which you wrote with Brad Rempel (known for his work with High Valley) and Joe Fox, has been a huge hit for you. What is the backstory on that song?

I had the idea for almost three years and never wrote it. I told Joe and Brad this idea. I was at Losers Bar in Midtown here in Nashville, and there was a girl I had had a crush on throughout high school. I hadn’t seen her in like eight years, and she happened to be in this Nashville bar. I brought her a drink and walked up to her, and found out she had a boyfriend. It was just casual conversation — and then I don’t know if it was me having a couple of drinks that night or whatever, but I was like, “Hey, let me know if you’re ever single again.”

I also thought it was a cool concept, and wrote it on my phone — and underneath that, I wrote, “The one that got away.” I feel like everybody’s had that situation where you both weren’t single at the right time, or you just never get that chance with a person. I forgot about the idea and had it on my phone for a long time until it popped up that day in the writing room. Joe really helped with laying out the hook, and Brad definitely had that anthem chorus idea and the melody to help it all come together.

How did the collaboration with Akon come about?

I’ve always been a fan of Akon. I have a brother and sister that are 10, 12 years older than I, and they were listening to that music when they’d be going out and partying and stuff. I would hear some of those songs as a kid, and they stuck with me. Melodically, he’s just so incredible, and they are really catchy songs and I thought it would be cool to re-write one of his songs. One of the songs I love is [2008’s] “Right Now (Na Na Na).” I thought, “Let’s make a fun, summertime country festival song like, “Drunk Right Now.” I walked into the writing room and we finished the idea.

We live in such an interesting time of trying to figure out when to release music. I was talking to my team and was like, “Before we tease this song, is there any way to get it to his team?” We sent it over, and within like a day he hit back and was like, “I love this and would like to do something with it.” That was so exciting, and he sent me a version where he wrote his own second verse. There was an original second verse that I had written and he re-wrote that. It had been just a party song — but then once he did his part on it, it was like he’s talking to me trying to help me through a breakup situation, and that just brought such a cool new aspect to the song. I’m super thankful for it, and it feels really full-circle to me.

Are there other artists you would love to collaborate with?

Yeah, I think, a female in the pop world. Tate McRae already did the [collaboration “What I Want”] with Morgan [Wallen], but somebody in that lane. When it comes to sad songs on piano, I think Lewis Capaldi would be really cool.

Another song on the new album, “Mad at Me” has a pop/R&B vibe to it and a bit of a lyrical edge. What did you think when you first heard it?

I felt like it touched on a tone that I really had not gotten to do. We tried to record that song more rocking with real drums and stuff, and I was like, “There’s something with attitude about it, kind of being more of a pop, R&B-style track with 808s.” It just really fit the energy of it.

One of the most vulnerable songs on the project is “Scared of Getting Sober.” What inspired you to write that?

Yeah, I think in a way we’re lucky that I get to do a job where I can have drinks on a daily basis and have fun and party and that being kind of the norm. I was starting to get to a point where, if I was being honest with myself, there’s times where it’s difficult. You’re really, really tired, and you’re trying to balance fun with work. And then, also just the relationship side of it — you watch relationships sometimes kind of fizzle away. It reminded me of my song “Trouble,” that I felt really connected with people that kind of struggle with things like that. I just feel like it’s a raw, emotional song that definitely will connect with certain people.

It feels like more artists are being open with struggles around alcohol, and trying to be healthier.

I kind of relate it in a weird way to sports. You think about sports back in the ’60s to the ’80s, people would get off the football field or off the hockey rink and they would have a bunch of beers or whatever. Those were professional athletes. I think now you’re seeing artists starting to realize the benefits to being healthy. I think the second part for me that is the biggest part that plays into me being healthy is just the longevity of having a long career.

What has it been like touring with Jelly Roll?

Just great. I mean, he’s somebody that I say has turned maybe dark times for him into such a bright light for a lot of people. He’s been able to influence so many people through the lessons that he’s learned. Watching him do that every night, just the kindness. I’d just be sitting in catering having lunch or dinner and he’ll just come sit down and be like, “How are you? What’s going on?” Wanting to actually know about you. I think sometimes that’s hard to receive from a headliner, just because they’re so busy and they have to make time for what they can make time for.

And Jelly Roll is one of those people that somehow finds time to look after everyone, including himself. I mean, you look at how much weight he’s lost and he’s really looking after himself. Again, that’s inspiring me and even the younger generations to be healthy and maybe to not let things get carried away.