Home MusicMusic Interviews Whiskey Talks and Rodeo Tales: Caleb Montgomery Delves Into His Debut Single and Album in Our Exclusive Interview

Whiskey Talks and Rodeo Tales: Caleb Montgomery Delves Into His Debut Single and Album in Our Exclusive Interview

by Jonathan Currinn
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Photo Credit: Caleb Montgomery

Embark on a journey into the heart of country music’s ever-evolving landscape as we introduce you to the captivating Caleb Montgomery. In an exclusive email interview, Caleb Montgomery, hailing from Susanville, California, opens up about his debut single, “Whiskey Talks“, and offers a glimpse into the upcoming album, “Food Stamps Don’t Buy Flowers”. Beyond the notes and chords, Caleb Montgomery’s musical narrative weaves rodeo tales, intricate relationships, and the timeless essence of raw storytelling, providing a modern perspective on traditional country music.

As the anticipation builds for Caleb Montgomery’s musical odyssey, join us in uncovering the layers of his journey. In this exclusive conversation, Caleb Montgomery shares insights into the inspiration behind his debut single, reflects on the influence of his father’s legendary collaborations, and discusses the unique dynamics of performing for hometown audiences versus stages in other states, such as the iconic Nashville. Our interview provides an intimate look into the authentic storytelling that takes centre stage in Caleb Montgomery’s musical world.

Hi Caleb, we hope you are having a good day today. To kick things off, could you share the inspiration behind your debut single, “Whiskey Talks”, and the stories that led you to create such a captivating song?

Hey! “Whiskey Talks” was written as a ballad of young cowboys. The plot of the song follows us young men from a day at work to our night following. The song portrays me and my friends who like everyone, have our struggles, stories, and pride. The deeper meaning behind the song is that during the day we are all respectful, well-mannered cowboys, but when you reach the bottom of that bottle, you start sharing the things that you can’t bring yourself to talk about, things that aren’t to be talked about in other situations, or pipe dreams that seem unachievable in any other moment.

The song was written to show the understanding and comradery amongst a group of kids that I feel others may be able to relate to. I was inspired to write this song by the stories that we all share when we’ve had a little too much to drink, from the ghost of an old cowboy standing on the porch, to the Bronc ride that won the buckle on the belt, to the “Have I ever told you how my dad died?” and everything in between. At the end of those nights, I always pulled out my guitar and sang our favorite songs, and everyone sang along. Those moments inspired the creation of “Whiskey Talks”.

According to the press release for “Whiskey Talks”, you draw inspiration from the likes of Conway Twitty, Sturgill Simpson, and Tyler Childers. How do these influences shape the unique sound and storytelling in your music?

These influences are certainly more apparent in my upcoming album “Food Stamps Don’t Buy Flowers”. A lot of the influence that I draw from Childers and Stu has to do with the sound. I fell in love with it because it was so different but still played with traditional ideas. This sound has a lot of different names, like “amerijuana” or “cosmic country” for example, but it is genuinely hard to pigeonhole that kind of sound. It takes root ideas from bluegrass, Texas swing, and blues and adds a modern twist as well as a deeper layer of unique sounds and effects that make a listener pause and think “Woah… what was that?”

As far as Conway goes, I just love his swingy style and it shows up in a few tracks on the new LP. I started writing and playing the way I do after falling in love with the raw writing and delivery of guys like Tyler and Sturgill. It showed me that I don’t have to put myself in a box either and that I can experiment and sing about real things. My music reflects the raw modern-day outlaw sound with hints of bluegrass, old western tunes, and classic country, as well as some interesting new ideas!

As a newcomer in the country music scene, what emotions and experiences do you hope your audience will connect with when they listen to your debut album, “Food Stamps Don’t Buy Flowers”?

I designed this album very intentionally from the lyrics, to the instrumentation, to the song order, and everything in between. It is a lot of fun to see people put the little references and easter eggs together so I won’t give too much away but, this album was designed for thought and to meet people on a personal level through my experiences.

As far as the stories/lyrics go, there is no shortage of thought about my listeners. A great example of this is a song I wrote last year called “A Song For Them All” which sings about people from all walks of life, their struggles, and how they all connect. I have always said, since I put these songs together, that the album might not be for everybody, but everybody will be able to take something from it.

The sound is an experience all on its own. The mix of traditional bluegrass and classic country instrumentation blends with the metamodern and experimental sounds and ideas to create a special and exceptionally different experience. The music, in my opinion, does a fantastic job of telling the story by itself with every little fill and lick saying something all on its own. It’s the kind of arrangement that can give you chills from the first note.

Can you tell us more details about your new album? What can we expect? We know there are 10 tracks, so are there more singles coming? Have you got an official release date, yet? Our anticipation for this debut album has us truly keen to know everything about it.

We’ve been hard at work getting our ducks in a row to get this project set to be released this spring. We are doing an exclusive presale campaign through iTunes. If you preorder the album through iTunes, at a discounted price I may add, you will be among the first to be able to listen. With preorders, you will instantly be given a copy of the title track “Food Stamps Don’t Buy Flowers” and maybe more than that in the weeks leading up to release…

I’m extremely excited to say that “Food Stamps Don’t Buy Flowers” [is] available for presale [right now. It was made available for presale] on iTunes on Friday, February 23rd! On top of that, those who preorder the album will get full access to all of the tracks before they are released on other streaming platforms. I don’t think I’m allowed to say much more at this time, but if there was ever a time to get excited, it’s now!

Promotional image for "Whiskey Talks" which sees Caleb Montgomery holding a saddle as he walks past a cow, wearing a jacket and a cowboy hat.
Photo Credit: Miah Jimenez

Having signed with Label22 Records, how has the collaboration influenced your approach to creating music, and what can fans expect from this partnership in the future?

Working with Label22 is a privilege that I am grateful for every day. The entire Label22 team is like family and everyone is a go-getter. I love working with Label22 because they embrace my creative freedom and give me what I need to run with it. They don’t intrude on my creative process but if there is something I can change to take something to a higher level, then they never hesitate to let me know and are always super helpful and open to suggestions.

Stephen Cochran, the CEO of Label22, was in the studio helping produce the new album and it was very clear to me that he and the people working around us had a good grasp on the sound I was trying to create and he did everything in his power to help turn those ideas into sound. I feel as though my thoughts and ideas are genuinely understood and cared about by these guys. I am not being urged to change my sound or my ideas, I am instead being encouraged to continue with my ways and I’m being given what I need to execute them!

We’ve heard about your performances across the United States. What’s the most memorable moment you’ve experienced on stage so far?

I think the most memorable moment was a performance I did at the HardRock Cafe in Nashville when I was first starting my journey. It was my first time in town and one of my college buddies managed to get me a spot in a writer’s round. In the hours leading up to that performance, I had been all over town doing the tourist thing all day and seeing all of the artists and bands entertaining. I thought it was so cool to see so much live music in one place. I soon realized that nobody was paying attention to any of these extremely talented individuals. It broke my heart to see the people putting on awesome little shows and spilling their hearts out into the mic being treated as though they were just the cheap sound system in the corner.

I expected the same thing to happen to me at my performance that night but I was mistaken. Expecting the same treatment, I sat down on the stool, closed my eyes, and began to sing a song and just enjoyed playing it. I had no idea that I would open my eyes to see everyone in the room staring at me, staff included, you could hear a pin drop and that continued with the other couple of songs I played. I was terrified and thought that I sounded awful and that was why I got that reaction, but I got off stage and everyone was excited to talk to me. I was told my sound was new and refreshing and flat-out good, “We need more of that in Nashville.” That was an awesome experience and solidified my place in music.

Your family has a deep musical history. How have your roots, both on your mother’s and father’s side, shaped your artistic identity and approach to creating country music?

This is a great question! There are songs on my upcoming album that are tributes to and inspired by the older generations of musicians in my family. I have some Texas two-step and some swingy Conway Twitty style songs on there that came from both my taste, and to honor and remember those who came before me, and not just in my family. It feels good being able to carry on the tradition of music in my family and it is so special to me that I can create songs that you might hear them play back in the day! I feel honored and privileged to be able to raise my hand when George Jones sings “Who’s gonna fill their shoes?”

Your father, Chris Montgomery, has worked with iconic artists such as Willie Nelson, Kris Kristofferson, Tanya Tucker, Toby Keith, Marty Stewart, and Little Texas—the list just goes on. How does having a father with such a rich musical history influence your own musical journey? Are there specific aspects of his experiences that you find particularly inspiring as you carve your own path in the industry?

I wouldn’t be where I am today without my dad. He’s done a great job of pushing me to be a better musician, performer, and overall person. He’s saved me from so much misfortune and so many pitfalls because he had to learn the hard way when he was doing this. Some say those pitfalls are “paying your dues” which my dad has assured me I have done in other ways. I can say with confidence I would not be standing where I am if it weren’t for him.

It’s super cool to my family that we get to add another layer of music to the bloodline, and it has been extremely fun for both me and my dad to learn about how things are done these days. I think the most inspiring aspect of my dad’s journey was the fact that less than a year went by between him doing his first tour to his performance at the Ryman. It reminds me that if I keep my nose on the grindstone I can get to where I want to be.

We’re curious about your journey with the guitar, starting at the age of five. How has your relationship with the instrument evolved, and how does it contribute to the unique sound of your music?

At that age, I was signed up for classical lessons and didn’t enjoy them for that long so my parents had me stop doing it. A few years later at the age of around 8, my dad had taught me just a simple D major chord and all the things I could do with it and that’s where I got my start. Soon after I took to the old guitar books lying around and to YouTube and started becoming a player. Over the years I would move from learning old country songs to playing metal and classic rock, my first gig ever was playing classic rock at 11 years old.

At another point, I had taken a good break from playing my guitar. I believe I was 16 when I put it down and didn’t pick it up again until I was almost 18 when I would end up falling in love with the traditional and the unusual and beginning my writing journey. I started playing and writing in college, however. The only acoustic guitar I had ever had was an old $200 Ibanez that my dad had picked up at a yard sale. A few months after I had left for college I had proven to my family that I had truly mastered my instrument and got good at the songwriting process so they surprised me with the Martin D-18 that I still play today.

You’ve got upcoming performances in Nashville, including the Country Radio Seminar showcases. What excites you the most about these upcoming events, and how do you prepare for such significant moments in your career?

The most exciting and also most terrifying part of these events is playing my spread of music for a brand new group of people. I love sharing my experiences and sound with anybody willing to listen because I love the little moments on stage where just for a second, everybody understands what you’re saying, and as a result, in that moment everyone understands each other.

I do a lot of mental preparation for these moments. The biggest thing that I always remind myself is, “You’re here for a reason.” This means that I like to imagine that I’m awarded these amazing opportunities through my hard work and dedication. I also remind myself to just get up on that stage and enjoy the music and the energy, that’s what all of this is about after all.

How does your approach to performance change when playing to hometown audiences, like at the Lassen County Cowboy Festival, compared to performances in other states such as Nashville? What unique feelings or considerations come into play when connecting with your local community versus broader audiences in different locations?

Not a lot changes believe it or not. I know my people and their lifestyles better than my Nashville audiences, but at the end of the day, I’m still just sharing my stories and the stories of those around me. As I said earlier, I love sharing my experiences and sound with anybody willing to listen no matter where it is or how many people are in the room. My music is personal and always leaves room for interpretation among listeners and it is always amazing to see how my words are perceived among different walks of life.

With the recent release of your debut single and the release of your debut album now on the horizon, what message or feeling do you hope your music will evoke in your audience?

I want people to listen to my music and think, “He’s singing to me right now.” I wrote every song on this upcoming album with intention. I write music about my personal experiences and struggles, hoping to connect with those who may be going through similar situations. My goal in this career is to meet people where they are and let them know that they are not alone.

I want my music to be an outlet for connection and healing, at the end of the day, that’s what I’m here for. I’m here to play my music for as many people as I can, but if I can mend one heart, change one mind, or save one life then I believe that I have accomplished my goal. This album gives me a nostalgic feeling that I believe my listeners will also feel through the unique sounds and deep cuts. Like I said, I believe that this album is not for everyone, but I know in my heart that anyone could take something from it.

Promotional photo for "Whiskey Talks" which sees Caleb Montgomery in a brown-and-white striped shirt, jeans and a baseball cap, sitting in a producer's chair in a studio.
Photo Credit: Caleb Montgomery

As we look ahead, considering the exciting developments in your career, what plans and endeavours can your fans anticipate for the summer and fall of 2024?

We are adding dates every week! This summer and fall, we will be playing numerous fairs, music festivals, and smaller, more intimate gigs all over the western states. Stay tuned for updates, it is so exciting to see these new opportunities coming forward and I can’t wait to see you all!

And, lastly, what are your aspirations for the future of your music career, and how do you plan to navigate the evolving landscape of the country music industry?

I don’t need to be on the cover of Rolling Stone, I just want to be heard. At the end of the day, I aspire to help people with my music. I’m on this journey to explore the great plains of sound and to tell the stories I live and hear along the way. I plan to navigate the future of country music by planting my feet. I will always continue to write genuinely about real things in a way that allows people to find comfort.

The real magic of country music comes with the term, “Three chords and the truth.” Country music was once a gorgeous collage made up of the lives and experiences of genuine people who took a risk and let the whole country know how they were feeling. We don’t seem to see as much of that nowadays. I aspire to be a part of putting that magic back into country music!

Official single cover artwork for "Whiskey Talks" which sees Caleb Montgomery posing in a cowboy hat, a blue and gold neckerchief, and a dark green jacket, with a fence and a field behind him as well as a blue sky.
Photo Credit: Label22

Thank you, Caleb Montgomery, for taking the time to answer our questions. We love your debut single “Whiskey Talks”, and we are looking forward to your forthcoming debut album “Food Stamps Don’t Buy Flowers”—which is available to preorder right now from iTunes.

“Whiskey Talks”, the debut single by Caleb Montgomery, is available to download and stream, right now, across all platforms. Look out for his forthcoming debut album, “Food Stamps Don’t Buy Flowers”, which is set to be released on April 7, 2024, according to the iTunes presale.

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Share this article and tag us @GoodStarVibes to let us know what you make of Caleb Montgomery’s debut single “Whiskey Talks”.

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