Caskey: No Limits

By: Todd “DG” Davis

We caught up with Brandon Caskey, better known by the mononym Caskey to talk about his new project CADILLAC MUSIC and more.

After almost ten years of releasing mixtapes independently, Caskey signed to Birdman’s Cash Money Records and Republic Records in August 2012. He has released a large catalog of music including his biggest solo project to date Black Sheep 2. Since then, he has released a steady stream of singles, mixtapes, feature verses, and has released multiple albums including a project called $100 mixtape that was only available on physical CDs and never released to digital streaming platforms. After parting ways with Cash Money Records he has resumed releasing singles and albums independently. In February 19, 2021 Caskey and Yelawolf created a collaborative album titled Yelawolf Black Sheep. His most recent project Cadillac Music is out now and builds off his fan favorite song Cadillac produced by his long time producer and collaborator Anonymass.

Now let’s hop right into this lead single / video, “DIXIE — Tell me about this particular track; how did it come to fruition? 

Over the years since I started making music, I’ve talked extensively about my dad and losing him, but I haven’t spoken much about my mother, how she inspired me to get sober, her perspective through all the tragedy, or even just paid homage to her. This track was a step for that. It spawned from a conversation we had at dinner a few months ago where she talked about being fearful for me when I signed to Cash Money, just because she felt like I was heading in a direction she couldn’t control, and she wasn’t sure if it would be positive or negative. 

“DIXIE” comes courtesy of your new solo collection, CADILLAC MUSIC — Conceptually, what does this title represent both to and for you? 

So still to this day, my song “Cadillac” music is one of my biggest songs. It was produced by my brother, Anonymass, when we first met. So for starters, it’s an ode to that single, and the journey we’ve been on since creating it. But “Cadillac Music” to me represents our sound a lot. I have a ’69 Cadillac Coupe De Ville, and this music is what you listen to when driving that. It’s cruising at night thinking about a come up music. It’s dark, eerie, hard, not really meant for the club, but meant for you to dive into yourself while listening, but not in like a nerd rap way. 

How then does CADILLAC MUSIC either differ and / or compare to previous Caskey efforts?  

I think Cadillac Music is a journey back to my original sound. The “Black Sheep” sound. The bag I was in when I made “Black Sheep 2.” Over the years I’ve experimented a lot with sounds, but this is a re-focus on what my sweet spot is. Dark ominous underwater feeling music, with loud 808s and trap influence. 

As a lyricist, when you sit down to pen your rhymes where do you draw inspiration from? 

It’s cliché to say, but really just my entire life. I don’t think too much when I write. I try to black out and go into the ether and let my life experience flow into the music. I have no aim when I go into making a record. I’ve found the more I try to conceptualize where I’m headed, the less I make anything of value. 

Reflecting, tell me your whole inception into music — When did you first become interested in it? And, how did it all begin for Caskey?  

I owe a lot of my music journey to my sister. She had an eclectic taste of music, and since a young age influenced me with everything from Three-6-Mafia to Linkin Park to Eminem to Metal. I’ve really always been drawn to Metal music, and growing up the hardcore scene was where a majority of my attention was. I always knew I’d be some type of front-man to a band, but when I discovered Nas in high school I fell in love with the poetry of rap and the path for me was laid out clearly. 

Now you’re a native of Orlando, FL, correct? So growing up in ‘O-Town,’ who all did / do you consider to be your strongest musical influences?      

Technically I’m from Winter Springs, a little city just outside of Orlando…but nobody knows that place. So Orlando is easier. But my musical influences have always come from music that wasn’t local. I didn’t really know many artists from where I grew up. To this day I’m the biggest thing to come out of Winter Springs, maybe even Orlando. But I’ve always loved rap from the south. Everything from OutKast to Three-Six to Trick Daddy to Gucci. 

In having said that, how do you classify your overall sound and / or style?

It’s always weird describing my own sound. I tend to like for people to figure that out for themselves, but it’s lyrical trap if I had to put it simply. It’s motivation music. 

Switching gears here, what exactly do you want people to get from your music?       

Perseverance. Motivation. Inspiration. I want people who have been through hard shit to know that there is light at the end of the tunnel, and what we do with this life is entirely up to us. Our past doesn’t have to define us. 

If you could collaborate with any one artist, living or dead, who would it be and why?   

SADE and Anthony Green [of Circa Survive] have always been at the top of my list. Anthony and I have a few songs on my hard drive already.      

If you could play any venue in the world, which one would you choose and why?    

Red Rocks is at the top of my list just because of how iconic it is. But the Sphere in Las Vegas is looking cool recently.     

On a more serious note, are you happy with the current state of Hip Hop? 

I am actually. I don’t buy into the “music is trash nowadays” narrative. There is a plethora of good music out there if you are looking for it, and I don’t think there’s been an era that lacked good music since music’s inception. Plus…I’m here. 

What do you feel has and will continue to be the key to your longevity?   

Authenticity. I’ve built my fan-base and my career off of something sustainable, and that’s being myself. I don’t chase sounds, or chase trends, or try to be something that’s not me. And that has always served me well.      

Do you have any other outside / additional (future) aspirations, maybe even completely away from music?

I’m an artist in every sense of the word. I paint and write poetry and play piano, I’d like to take all of those things further down the road. And maybe in my later years I would enjoy teaching, my Mom’s a teacher and some of the most influential people in my life were good teachers. But for now, music has my spirit. 

To date, what has been your biggest career moment(s), at least thus far anyway?        

Obviously signing to Cash Money Records when I was 20 was big, but honestly that turned out to be more of a learning experience than anything. I was young, didn’t know how to carve a path for myself, had a terrible drug and self esteem problem, and so it didn’t amount to much. Doing the album with Yelawolf in 2021 was more of a highlight to me, because I was sober, clear headed, I A&R’d the project, and really made that happen on my own merit. Plus, the friendship with Wolf that transcribed since then has been life changing. 

What’s an average day like for you?

I wake up at 5. Do some reflection. Hit the gym. Sit in the sauna afterwards. Wake my fiance up with some coffee. Get to work on whatever business needs to be handled. Spend time with someone I love. And make music at night. I’m simple. 

Please discuss how you interact with and respond to fans… 

 I do my best to give as much as I can to fans without compromising my own space. I’m on social media a lot and respond to as many messages as I can, and everyone  that ever sees me in real life gets a good experience from me. That’s important to me because these are the people who my music resonates with and they have changed my life in more ways than one. 

What is your favorite part about this line of work? Your least favorite? And, why? 

My favorite part is the magic of making music. It’s something I’ve spent my life pursuing and still barely understand. I lose track of time when I’m creating, and never know what’s going to come from it. That pursuit will fuel me till the day I die. My least favorite part is the unwarranted opinions of people. It comes with the territory so I take the good with the bad, but the age of social media is weird…you can spend an entire year working on a piece of art and someone can shit on it within hours of it being put out. I’ve gotten better at dealing with that though because it’s rare that anyone who comments negatively is in a position I want to be in.

What advice would you have for someone wanting to follow in your footsteps?

Don’t do it. Haha! Or at least be absolutely sure that you would happily spend 10 years pursuing this with nothing to show for it. Because it’s never a guarantee. Your heart has to be in it for the right reasons. 

Looking ahead, say five or maybe even ten years from now, where do you see yourself?     

Continuing to ascend, making better music, taking care of my loved ones more. More tattooed. 

You’ve been out on the road supporting Yelawolf — How’s that been going for you? And for someone who has yet to experience you live what would you tell that person can be expected? 

Tour has been unforgettable. Yelawolf is not only a great friend, but one of the best performers I’ve ever seen, so getting to study him and learn from his stage presence has been incredible. What can you expect from a Caskey show?…to rage, to get drinks thrown on you, to let out all of your frustrations in a healthy environment, and to connect with great people. It’s not the typical rap show experience. 

As for the immediate, what’s next for Caskey? 

Cadillac Music the album. The J.A.W.S. album. More tours. and possibly some Metal music. Time to revisit the roots. 

Is there anything I left out or just plain forgot to mention?        

Just the fact that I’ve been killing freestyles over classic hard-to-top beats on my YouTube. I encourage everyone to check those out. 

Any “parting” words for our readers?

ANYTHING IS POSSIBLE. There really are no limits in this life. And the more things you remove from your life that don’t serve you, the more room you have for that which does serve you.