“Music is my dream:” Orlando Caston chats ‘Tennessee Whiskey’ and creating a legacy

Orlando Caston set out to defy expectations on Tennessee Whiskey, the country ditty that serves as the musician’s latest single.

Coasting on bluesy guitar melodies and the infectious drawls of Orlando Caston’s vocals, Tennessee Whiskey is a masterclass in sonic restraint and lyrical storytelling, and we simply can’t get enough. 

“Songwriting is definitely my main focus when creating songs,” Caston said of the force behind the single.

Orlando Caston interview

Below, we caught up with the singer-songwriter for a deep dive into Tennessee Whiskey, the stereotypes around genre, and how “music is my dream and everyday is surrounded by it.” 

Catch our full interview with Orlando Caston below, and scroll down to listen to his new single Tennessee Whiskey.    

HAPPY: What are you up to today?

ORLANDO: Reading a Stephen King novel and trying different techniques to record electric guitar.

HAPPY: Tell us about where you live, what’s the scene like?

ORLANDO: Well, actually, I live in a caravan and I travel. No particular place is home, because everywhere is home.

Being able to see new places and be in different areas has always been great and I love that aspect of my life. It also really helps not being tied down in one area for my music.


View this post on Instagram


A post shared by Orlando Caston (@orlandocaston)

HAPPY: Are there any specific artists or musicians who have had a significant impact on your own musical development?

ORLANDO: I have many musical influences, from many different musicians, from many different genres of music. But, there are three musicians that really influence and inspire me and my musical development quite a lot.

These being Kris Kristofferson, who fueled my love for writing lyrics and telling stories in interesting and creative ways, George Young, who inspired me to want to be a producer and stand my ground on who I am musically and in life.

Above all, Buddy Holly, who sparked the start of my love for music, my dream to be a musician, and later my desire to do my songs my way… And, who I think of in every step of my music.

HAPPY: Could you share a memorable or influential musical experience that has shaped your approach to music?

ORLANDO: Recording in a studio with a producer for the first time has definitely been an experience that has shaped my approach to music as it taught me that while recording quality is important, the performance and song-feel is much more.


View this post on Instagram


A post shared by Orlando Caston (@orlandocaston)

HAPPY: What is your creative process like when composing or creating new music?

ORLANDO: When I write new music I like to focus on the lyrics first. For me the lyrics are the foundation of any song and, unless it is an instrumental, have the biggest influence on making the song memorable and likeable.

Of course the music, melody and riffs etc, are very much a big key element but I feel that lyrics are the best start. After getting a start on the lyrics, I focus on making a simple accompaniment usually on guitar.

Once I start getting a flow of music and lyrics that blend nicely, I try to listen to the song from another perspective (not a songwriter’s) to see what else the song needs or should have.

Sometimes this takes recording the lyrics and guitar and listening to it that way instead of playing it live so I don’t feel like the musician. I then play around with adding what I think the song needs.

Most importantly of all, for me, in this process is, I try not to force write or force myself to come up with other elements. If it feels complete with just lyrics and guitar – leave it, if it feels like there needs to be something else but I can’t work it out – leave it and come back to it later.

@orlandocaston Are you ready for this song in 2024? #tennessewhiskey #orlandocaston #countrymusic #newmusic #newrelease #2024 ♬ original sound – Orlando Caston

HAPPY: Lyrically, “Tennessee Whiskey” seems to touch on defying stereotypes and choosing your own path. Can you elaborate on a specific experience or situation that inspired this message?

ORLANDO: I have a few experiences and situations that inspired this message over time. Growing up I was home-schooled, due to travelling, and outside people had their stereotypical ideas of what type of person a home-schooled kid was.

For instance, multiple times I was tested on my knowledge – especially mathematics problems. I was a quiet kid, and still am a quiet person, and I didn’t have social media so I was stereotyped as being someone that was “behind the times” and so wasn’t worth their time outside of the social platforms.

I have also seen people do things and act in certain ways just because they want to fit in, so I’ve always tried to be myself and make my own decisions.

The latest situation I’ve been in, which tipped me to write this song, was staying in an outback Queensland town (where I have been for too long haha) and have been classed as a local and someone from the country.

But, I’m not local. I’m not country. I don’t live in the city, but I’m certainly not country either. And people also said and wondered why I sang with an American accent, but it’s just the way I sing.

It’s me. And that’s all I ever try to be. I wrote the lyrics to this song as a way to reflect all of this.

Orlando Caston interview

HAPPY: “Tennessee Whiskey” is your second single, but your first foray into songwriting and recording came at a young age. How has your musical journey evolved since then?

ORLANDO: My musical journey has evolved very much since starting to play guitar. At the beginning that’s all I wanted to do – play guitar. Buddy Holly’s music showed me the love I had for music but that’s as far as I went into music at that time.

I never wanted to write songs. As I got older I started to pay more attention to song lyrics, especially Buddy Holly’s. And, out of nothing, I started getting ideas that kept annoying me haha.

So, I finally gave in and wrote down my first song at 15 hoping to get it out of my head. It worked… but then another idea came to me haha. This went on for about the first 10 or so songs that I wrote.

Once I got to that point I started to like writing down my ideas and I was still paying more and more attention to song lyrics. I then started to really listen to Kris Kristofferson’s songs and how he wrote them, the words he used and settings he created.

And I fell in love with writing songs and trying to write in different styles and different ways. After that I discovered The Easybeats and George Young and Harry Vanda and got very interested in producing my own music.

Now, I want to be a songwriter, producer, and musician haha.

Orlando Caston interview

HAPPY: You’ve worn many musical hats – guitarist, songwriter, vocalist, aspiring producer. How do these different roles intersect when you’re creating a song like “Tennessee Whiskey”?

ORLANDO: Songwriting is definitely my main focus when creating songs. I love being a guitarist and I always will play guitar but I try to not smother my songs with too much guitar or music. At the end of the day I try to let the song be its own when I start putting it together.

I’ve never labelled myself as a vocalist and don’t think I ever will haha, there are many more better singers out there than me, I just decide on how the lyrics should be sung when writing it and singing it myself as an independent artist is the easiest way to get my songs heard. Then learning to produce is a whole other world but I’m slowly getting there haha.

But again, songwriting is my main focus when creating songs and all of the other roles take a step back when I am going through each process from start to finish. I feel the song needs to become its own before there can be a guitarist, vocalist, or producer.

HAPPY: How do you balance your personal life with your musical pursuits, and how important is that balance to you?

ORLANDO: To be honest, my personal life is my music haha. Music is my dream and everyday is surrounded by it. If I’m not writing, recording, playing, or listening to music – I’m thinking about it haha.

For now, music is my number one and will be for a long time but I have a second dream of wanting to have a family. So, one day music may take a step back to balance in family life but not just yet.

HAPPY: Can you talk about any upcoming projects or collaborations you’re excited about?

ORLANDO: Well, there are no release plans as of yet but I’m currently working on a ‘Rock-N-Roll’ style track to mix up my previous two releases which have been heavily country influenced and to show more of my musical taste.

And later on in the year there might be plans to collaborate with my cousin who is also a singer-songwriter… a duet with her maybe, who knows haha.

HAPPY: Lastly, what makes you happy?

ORLANDO: Watching movies, reading books, playing video-games, and above all – listening to and playing music… What else? Haha.