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When Walker Montgomery called me to talk about his latest song “Bad Day to Be a Beer,” penned by the Nashville dream team of Brock Berryhill, Dallas Davidson, Ray Fulcher and Cole Taylor, I had a lot of questions about the new tune and his collection of music coming in 2021.

But first, I had a lot of questions about his dad, John Michael Montgomery. A man who, in case you didn’t know, absolutely owned the country charts throughout the 90’s. Starting with “Life’s a Dance” in 1992, and then the hits that just kept coming: “I Swear,” “I Can Love You Like That,” “Sold (The Grundy County Auction Incident),” “How Was I to Know,” and on and on and on.

So Montgomery indulged me and let me focus on his father and the influence his music had on his new songs. Before we talk about your music, let’s talk about your dad’s. Was it no big deal that your dad was a big country star? Was that just the normal you knew?

Montgomery: It wouldn’t say it was particularly normal, but it was normal to me. It just so happened that instead of being a plumber, a doctor or a lawyer, my dad was a country music singer. And instead of working on the weekdays, he worked on the weekends. To me, that was just who dad was. And that’s just what he did. His dad — Harold Montgomery — was a picker and a singer around central Kentucky while dad was growing up, so he was really the one who got my dad picking and singing.

So then your dad passed that down to you, right? Did you think about any alternative careers or was this always your destiny?

Good Lord, I hope this is my destiny. I respect my parents immensely for the way they raised me. Because obviously they knew I loved music, but they also surrounded me with all these other great things like sports, acting, and choir. And they let me find my own path to music. Since I found that, it makes it all the more special to me. Once you get the bug in music, there’s no going back. I think I came to the conclusion, and I believe it was the right conclusion, that I’m proud of what my family’s done in this very unique business. I think my music will let the people know I’m not only John Michael’s son, I’m also my own artist and my own person.

Is there one song of your dad’s that stands out to you for any reason?

Look, I love my dad’s music so much. And I don’t know if it’s just because I’ve heard the hits so much, but some of my favorite songs that he had are ones he didn’t even release as singles. But he had great albums, and that’s really hard to do. Ten songs on a record, and they were all great. Especially his love songs. And especially vocal-wise, my dad had a big influence on how I sing. His “How Was I to Know” is how I learned how to do falsetto. Just listening to that song again and again. I mean, he hit notes that I didn’t think I’d ever be able to hit, but it was just practice, practice, practice to that song. Those power ballads of his helped me get better and work out that muscle.

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Now let’s talk about your music and your life in Nashville.

I moved to Nashville in 2018, but now during the quarantine I’ve spent most of my time up here in Kentucky on the farm. I just found that to be a little bit better than a condo Nashville. Just being able to roam free and have some green grass to mess around in is better that black top.

So 2018? Was that right after high school?

I was doing music coming out of high school, but I did go to college. For a glorious nine weeks at the University of Kentucky. And luckily, the local radio station found my song “Simple Town” and they started playing it. So it just wasn’t the right time for college. It was the right time for music. Once that song was on the radio, my class attendance started to drop a little bit. It was the first song I wrote and recorded that I would ever actually show people.

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Okay so then fast forward a couple years, and you release “Growing Up Country,” “Saving for a Rainy Night,” and “Like My Daddy Done It.” And now “Bad Day to Be a Beer,” which is a song you didn’t write. How do you make a song like that sound so much like you did?

My mentality is that the best song wins. The one that best fits me. And if I wrote it, that’s great. And if I didn’t, it doesn’t bother me one bit. I just want the song that fits me and makes it believable. I think it goes back to if I can relate to it, chances are a lot of other people can, too. And if you can pull at somebody’s heartstrings — whether it’s with a sad song or a happy song or a drinking song — they’re gonna react. I try to keep that in mind. I remember when I first heard this song, I thought, “I can drink on a boat to that. And I know about 15 other people who can drink on a boat to that.”

So is it some kind of gut instinct you have, maybe another way your dad’s talents have rubbed off on you?

I don’t know about that. But I do trust the songwriters with just about anything. Every song finds a home, and every song finds the right home. And sometimes you find a hit song, but it’s just not for you. It’s a hit song for somebody else.

When you are doing the songwriting, how do you approach a session: do you walk into the room (or the Zoom) knowng exactly what you want to write, or do you wait for some kind of group brainstorm?

You’ve always got a list of titles or a melody in your voice memos. You never really know what’s gonna happen in a writing room. Sometimes lightning will strike, but sometimes it won’t. It just depends on the day. It’s all about the experience and being around good folks you enjoy writing with. Nobody’s ever written a hit song where they didn’t have fun writing it.

Just one last question that I have to ask, because of the quarantine we’re all living through. What has been a silver lining in your pandemic cloud?

For all the things we can’t do in the music industry right now, we’re doing all that we can. It’s obviously been a journey trying to figure out how to still progress during a time when we can’t play shows. But one silver living is that with Zoom songwriting, writers are more accessible. You can hop on whenever. I’ve done writes at 10:00 at night, and that normally doesn’t happen in Nashville.

And now that the vaccine is on the horizon, I’m hoping we’ll get to hear you live. In real life.

We have some shows at fairs and festivals planned for 2021. God willing, we’re able to do them. Once we book more shows, you’re the first person I’m gonna call.

Do you swear?

I swear. By the moon and the stars in the sky.

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Alison makes her living loving country music. She’s based in Chicago, but she’s always leaving her heart in Nashville.