Josh Ross Interview - Single Again, Later Tonight Album

Country music hitmaker Josh Ross is seeing his star power rise with the release of his first full-length album. Later Tonight. It debuted #1 on the Canadian Country Albums chart and also did well in the U.S.. Hailing from Ontario, Canada, the singer/songwriter scored his first No. 1 hit with “Single Again” earlier this year after a remarkable 71-week climb.

The lengthy trip on the charts was worth the wait, though, with the success etching him in an elite category as the first male Canadian country singer in decades to top the Billboard Country Airplay chart. Meanwhile, in his home country, Ross took home two of the night’s biggest honors at the Canadian Country Music Awards. He picked up trophies for Entertainer of the Year and Single of the Year for “Single Again,” bringing a total of five CCMA awards to his collection.

Earlier in life, Ross hoped to be a professional motocross rider. That desire came to an end as did another passion, football, after he was sidelined by injuries. Thankfully though, his joy of singing music took center stage, and he began honing his craft and learned to play guitar and write songs. From the person on the football team that sang country songs at parties, the singer got serious with the music. In 2019, he made a pivotal move to Nashville to grow and learn from the singers and songwriters. Notably, Ross also won the Canadian Juno award for his 2024 EP, Complicated, which featured the gold-certified breakthrough hit, “Trouble” as well as “Single Again.”

Ross’s new 15-track album also includes “Single Again” along with the new single, “Hate How You Look,” the recently released track, “Later Tonight” and a collaboration (“Drunk Right Now”) with rapper Akon. Josh says he’s excited for fans to see the various sides of his musical personality in his new music. In the past he felt like more of a content creator for social media, but now he feels that he has come into his own as a songwriter and artist. While the album contains many of the songs Ross penned, he didn’t shy away from enlisting the best songs that fit him from other songwriters.

In this new interview Josh Ross talks about the new album, and his hits, “Single Again” and “Trouble.” He tells about why recording with Akon was a full circle moment, building a fanbase in two countries, and his adamant stamp of approval for one of his album’s songs.

BC: How did “Single Again” develop in your co-write with Joe Fox and Brad Rempel?

Here’s the video of Josh Ross’s hit, “Single Again.””

Josh Ross: I had that song idea for two or three years on my phone. I saw a girl that I knew at Losers Bar & Grill in Midtown. I never had a chance to date her or anything like that. I sought her out, and I bought her a drink. I must have been feeling pretty good about myself that night. I went up there and had a conversation. I found out, while I was talking to her, that she had a boyfriend. We just caught up real quick, and I was about to leave and walk away. I said, “Hey, let me know if you’re ever single again.”

Then to be totally honest, one day I was a little hungover heading to a writing session with Joe and Brad for the first time. Joe definitely helped land that hook, and Brad is such a great high tempo, uplifting chorus kind of guy. He had a great melody for the chorus. People have been in those situations where they never got a chance with somebody, because you or the other person never lined up at the same time. That’s kind of how it was for her and I.

BC: Tell me about your debut album, Later Tonight.

Ross: I really tried to focus on allowing people to get to know my process and the growth that I’ve had since I moved to Nashville. Also sonically, I’m a consumer of a lot of different music when I listen to music. It could be rock, could be pop, it could be traditional country. I think you can hear that and feel that through my own music. I want to allow people to go on that journey and go through the songs and the find the ones that resonate with them. I built the track listing as if it was a live show and taking you through what the flow of a live show would be like.

For sure I have the fun party songs like “Drunk Right Now,” “Single Again,” and “Hate How you Look.” Those are fun uptempo songs. Then there’s songs with a little more depth to them like “Scared of Getting Sober,” and “Songs You Gave Me,” which I think people who have been in those situations will definitely resonate with.

BC: You are very popular in Canada and you’re building a strong following here in the U.S. How did you go about building your U.S. audience?

Here’s the video of Josh Ross’s single, “Hate How You Look.”

Ross: Most people don’t know that I had more of an audience here in the U.S. before I did in Canada. I moved to Nashville premature without knowing much about the music industry and much about songwriting. I just knew I wanted to write songs, and I knew that I needed to be a better vocalist. And the best place in the world for that for me was Nashville. To have a fanbase here early on in 2022, and then it started to catch up in Canada in 2023. Now, to watch all the support from Canada has been amazing. There’s definitely been some barriers to break. A lot of the bigger challenges for me were always the financial side of it, not being able to earn money when I moved to Nashville and figuring out different ways to go back home, make money or cash jobs here in town. Those are some of the biggest struggles. Then at the end of the day, you’re not from the same country, so I’m sure there’s always a bit of that too and trying to prove yourself that you’re worthy of hanging out with the best singers and songwriters in town.

BC: Your new single is “Hate How You Look,” that was written by Nicholas Sainato, Chris McKenna, Jessica Farren & Christian Yancey. It’s one of the few songs you haven’t had a hand in writing.

Ross: Up until this album, I’ve always wanted to try to write everything. What I realized was over the last three years I’ve probably played 500 or 600 hundred shows. I didn’t have as much time as I did in 2021 and 2022 to write 150 songs a year. I’m very judgmental and hard on myself. When I write 150 songs, I maybe think 10 of them are good. When I’m only writing 40 or 50 songs a year, I’m only getting two or three that I think are really great.

When it came to putting the new album together, I didn’t have enough solid songs that I think represent what I want to say. The coolest part about being here in Nashville from these relationships is having friends that send you songs that know you, know what you like to say, and know what you’re looking for. I would say to people that I have to be able to feel like I’ve lived that situation or wish that I wrote it. And it’s got to feel like it’s good for my live show. “Hate How You Look” checked all three of those boxes. It’s my favorite song to play right now on the road.

Here’s the video of Josh Ross’s song “Leave Me Too.”

BC: You have another cut on the album that features rapper, Akon. How did you two get together?

Ross: My brother and sister are 10, 12 years older than me. So growing up, I was 6 or 8 years old, and they were going to the clubs and doing all that kind of stuff. Akon was really popular at that time. I probably shouldn’t have been listening to his music and the things he was saying, but I always remembered his melodies. I always remember feeling really good and making people happy. There was an emotional feel to his music, and that’s always kind of stuck with me. I was having a hungover day one day, and I had this idea about rewriting one of the songs called “Right Now” and called it “Drunk Right Now,” and making it more of a summertime, party fun song for country music.

We found out who his management was and sent it off to them. He wanted to be part of it, and I wasn’t sure what that meant. He ended up sending his own version where he wrote a second verse. That’s such a full circle moment for me. He’s an awesome guy and comes from a different time in music, but a time that was really pivotal for music.

BC: Another album cut that caught my attention is named after the gun brand, “Smith and Wesson.” How did you decide to write that one?

Ross: Ben Stennis had sent me that. I was missing a couple of spots on the album that I wasn’t sure what I wanted to do yet. I absolutely loved it. A few people loved it, but a handful of people were like, “Oh, I’m not so sure.” That was on a Thursday or Friday and the session was a few days later. If’ I’m being honest, I didn’t tell anybody, but I was like, “We’re gonna cut this song in the studio.” If there’s one song on the record that I didn’t care if people agreed or not, I wanted to put it on the record.

BC: Your first single in the U.S. was “Trouble,” that you and Mason Thornley wrote. Tell me about that song.

Ross: It was just a very honest song about me and my process. I moved to Nashville, was out partying on Broadway, doing that whole thing. One night I left a voicemail for an ex-girlfriend that basically said, “If you could, could you come back home because I’m in trouble?” And the song kind of wrote itself.

Here’s the video of Josh Ross’s song “Namin’ Names.”

BC: You’ve opened for a variety of artists including Jelly Roll. What was that experience like?

Ross: His show and the power of his music and how healing it is for his fans, is something that I think even translates to some of the life songs that I have on the record that I normally have never done. I would definitely say it comes from watching shows like his. The biggest thing I learned from him is how much treating people goes a long way. He really treats his people really well, and me also, being an opener…he treated me well. I’ll never forget sitting in catering a couple of days into the tour, and he come and sits and pulls up a chair beside me, asking me about my life and what’s going on. He’s somebody that has so much going on, and for him to be able to take a moment out of his day and see if I need anything, see how I’m doing, want to know more about me, was really cool.

BC: What do you want people to understand about your new album?

Ross: For the first time, it’s not just singles about girls or drinking and that kind of thing. Not that it’s all been that. But I feel like this is the first time that I didn’t have to put one song at a time out and get promoted on social media and be a content creator more than an artist or songwriter. I feel like this is the first time that I’ve got to be a true songwriter and a true artist and think about what I want to put on something, and it not be a rush. I feel like you’re going to learn a lot about me, especially if you’re somebody new. There’s definitely some new style stuff on there that I’m very excited about—some things vocally that I’ve never tried in songs that I got to try on this record. I’m really excited about it.

Bill Conger has been a freelance music journalist for more than 30 years, writing feature segments for shows on the former TNN and Country Music Television. He has written for various publications including Bluegrass Unlimited, Bluegrass Today, Fiddler, American Songwriter, CMT.com, GACTV.com. He can be reached at [email protected].