Walker Montgomery may come from a strong musical pedigree as the son of John Michael Montgomery and the nephew of Montgomery Gentry’s Eddie Montgomery, but he’s an incredibly talented artist in his own right.
The 21-year-old emerging country singer/songwriter, who divides his time between his native Kentucky and Nashville, Tenn., first got hit with the music bug after forming a band and experiencing the true feeling of what it’s like to be on stage in front of a live audience.
After spending years honing his craft, Montgomery independently released his debut EP Simple Town, which racked up over 9 million streams. In the fall of 2019, Montgomery became the flagship artist for Dallas Davidson’s Play It Again Music, where he released tracks including “Saving For A Rainy Night,” “Like My Daddy Done It,” and “Bad Day To Be A Beer.”
Most recently, Montgomery teamed up with Country Now on the audio premiere of his catchy track, “She Don’t Know.” The romantic song, penned by Dallas Davidson, Kyle Fishman and Michael Ray, is part of an upcoming collection of new music expected later this year.
Montgomery recently caught up with Country Now to chat about his musical background, current music releases, and what’s to come.
Read on to find out more about Walker Montgomery in this exclusive Q&A below…
Did you always want to be a country singer?
I was surrounded by a lot of great things as a kid. And, that’s a tribute to my parents. So, the music thing did not hit me until I was a sophomore in high school. I always enjoyed it, but sports was my main thing growing up. But, at one point, I had a three-piece band. As soon as we did our first show, and the first time I got up on stage with other people and sang, that’s when it hit me. I was like, ‘Alright, this is cool right here.’ So, it was later on in life when the music thing came in.
Your dad, John Michael Montgomery, is a staple in the ‘90s era of country music. When it comes to your father/son relationship, has music brought the two of you closer?
It’s kind of weird. I think it’s something that most people don’t expect. But, there’s not a lot of music talk or music played in our house. My relationship with my father is just father-son. And, when we come off the road, he’s dad, and I’m the son. We go fishing, hunting, and golfing, and we do pretty much anything but music. That’s what it seems like to me anyway, and I feel like that kind of relationship makes it that much more special because it’s not a business relationship. He’s a regular dad.
Is it ever difficult to break the ties of your father’s legacy and to showcase who you are as an artist to the fans?
I don’t take it as a challenge. For one, there’s no hiding from it. And two, I’m proud of what my family has done in this business. Hopefully, I can keep the success and tradition going. But I think fans know who my dad is and who my uncle is, regardless. I think with songs that we release, our presence on stage, and with the way we treat people, will let them know that I’m not just John Michael’s Montgomery’s son or Eddie Montgomery’s nephew, I’m my own person, and that’s Walker Montgomery.
Who do you look to for inspiration when it comes to country music?
I love all the guys that are so big right now like Luke Combs. And, Luke Bryan has always been my number one, which is funny now that I’m signed to Play It Again Music. I love Cody Johnson right now just because of the way that he tells his stories. Randall King is also another one. He’s probably in my top two.
What steps did you take to navigate your career in the beginning?
I spent a glorious nine weeks in college. Fortunately, I got a little song up on the radio that did fairly well for me. It’s called “Simple Town.” Then, after that, I knew it was the right time to move to Nashville. After I got down there and got a place and everything, it was just meeting with people and going out and trying to build a brand. I was also getting some buddies together to start writing. It’s just this process that you’ve got to work on and figure out. There’s no rhyme or reason to it; you have to do it your way. For me, I ended up getting signed with Play It Again.
What would you say is the biggest thing you’ve learned so far while on your musical journey?
I would say having patience, especially with the current situation going on right now. It’s hard because you make a living off of groups of people, and then you can’t have groups of people together anymore. And, playing for groups of people is your favorite thing to do. But, I’d say it’s the patience and knowing that the grass is greener on the other side, is what has been the number one lesson learned.
We recently featured your single, “She Don’t Know” on Country Now. But another song of yours is called “Bad Day To Be A Beer.” Can you tell us what drew you to that song?
In college, I was a Sigma Chi, and every day on Saturday, which we called ‘Cat-urdays’ at the University of Kentucky, we would wake up at the Sigma Chi house. We would say, ‘Man, it’s a bad day to be a beer.’ That would always seem to be a true statement! Then, I signed with Play It Again, and I heard that song. It was actually on hold for another artist at the time. But, as soon as it got off hold, Dallas called me. He said, ‘Do you want to cut this song?’ I said, ‘Dallas, I’ve been bugging you about this song for six months now. Yes, I want to cut it!’ But it’s a ‘my age’ kind of song. But, I do think it relates to people of all ages. It’s just a fun song with a cool twist on a party song.
How about “Saving For A Rainy Night.” What was the inspiration behind that song?
That song is a beautifully-written song by Ashley Gorley, Dallas Davidson, and Kyle Fishman. I needed one of those power ballad songs, and we released that song in 2020. I think, once we get to play shows again, that song might take on a whole new life of its own. It didn’t get the live chance that a lot of the other songs did.
You’ll mark your two-year anniversary on Play It Again this year. Reflecting on that experience and the friendship between you and Dallas Davidson, what would you say?
It’s such an honor to work with Dallas Davidson. I think he hates it when I say this, but I grew up on his songs. And, I think that might make him feel old or something like that, but all those Luke Bryan, Jason Aldean, and Blake Shelton songs, that’s what I grew up with in high school and middle school and everything. So, he has been my songwriting hero since I can remember. And, the fact that he’d have the confidence in me to take a chance on me, I’ll be forever grateful to Play It Again and him.
Davidson and the rest of the Peach Pickers (Ben Hayslip and Rhett Akins) have produced your music. What is it like having that team of hit songwriters behind you and supporting what you do?
It’s a dream come true. It’s almost surreal how amazing it is! And they’re great guys, which makes it even better. But there’s no telling how many hit songs or number ones there are between the three of them. But, when Dallas called me and said, ‘Hey, I have this idea. Do you want The Peach Pickers to produce you?’ That’s another one where I was like, ‘Dallas! Why did you even ask, bossman?’ But, of course, I want them too! And we had a great time! We went into record six songs, and I think they’ve turned out so great! I’m over the moon about it, and I think they are too.
Tell me about your songwriting process.
Songwriting, for me at least, depends on the day. I find, most of the time, I’m a melody guy. But, then again, one day, I’ll be a lyric guy. I’m never the track guy, though. The computers and I don’t get along (laughs). But what I have found that works for me the best is if I have a good group of folks around me that I enjoy hanging out with and have fun with, then we’re probably going to write a good song. And, if we don’t, then at least we had a good time. But, the chances of writing a good song do go down if you’re not having a good time with it, in my perspective.
In what ways have you had to adjust your creative process in the past year?
We’ve been active on social media. More active than we ever were before. My saying is: For all the stuff that we can’t do, we’re doing all of the things that we can do. The shows, the meet-and-greets, and everything that we are not allowed to do, we’re trying to make up for it by being creative on social media and just being interactive with the fans.
Have you taken up any new hobbies?
I used to work on antique cars and classic cars and rebuild engines, and that sort of thing. But I’ve got a buddy who has a garage, and he buys and sells antique Rolls-Royce. So I’ve been working with him and rebuilding engines and stuff. I’ve just bought one myself. You know, when you think of a Rolls-Royce, you think in terms of upscale. But the one that I purchased is in pretty bad shape. It needs a lot of work. But hopefully, we’ll be able to get it running and everything.
What can fans expect from you next?
I’m hoping to be able to do more shows. We’ve got some big news on the show-front, hopefully coming soon. But I want to get these songs out and have people hear them. We worked hard on them, and we’re extremely proud of them. So, that’s the main thing, just getting these songs out and letting fans hear them.
Fans can keep up with Walker Montgomery on Instagram.