Florida rapper Caskey about overcoming depression and addiction, learning to find happiness, and why he never listens to any tattoo advice.
By Katharina Moser
808s blasting through the speakers of a shiny cadillac, polaroid-blue sky in the background, the leather-covered steering wheel in the tatted-up hands – that is how listeners might visualize the scene in their mind´s eye when blasting Cadillac Music, the mind-blowing latest album of US rapper Caskey. It is indeed a certain peace that perpetuates this album unlike any other works the Florida-born rapper has done. A newly-found calm and optimism seems to ring through the solid verses and beautifully vibrating melodies of Cadillac Music, which makes Caskey fans wonder – what has the rapper been up to, and how is he doing after another incredibly productive year of releasing and touring?
“I am really happy with the album and the responses it has created”, says Caskey on a casual Friday afternoon, a new Blacksheep hoodie covering only half of his characteristic tattoos. “The fans are super appreciative. You can tell that we put a lot of thought and time into it, and it feels very true to myself. And performance-wise its better than my last couple of albums by a long shot.” The performance aspect, however, cedes into the background in comparison to the significance the album seems to have on the journey of the renowned rapper. It is, he says, the second of two major turning points in his life as an artist. “The first one was the album This Isn´t Even My Final Form, and I already was on the journey of getting sober, going to the gym, changing my habits as an artist, and going through some tough things such as a breakup from a three-year-long relationship. Those things reset me as an artist, and it was the start of getting more personal in my music.” Cadillac Music, produced by friend and partner Anonymass, was shaped by Caskey moving back to his hometown Orlando, looking to be close to his family and friends. “The album has this element of being back around my family and loved ones, it is very focused. It naturally made me more reflective.”
The reflexive nature of Cadillac Music is grounded in the cumulative experience of years of pain and struggle, of visions and never giving up, and it bears witness to somebody who has found his path after a long journey of hardship. “It´s not like I had the worst life from the very beginning. I had a good life up until my teenager years, it felt supernormal”, Caskey explains. “But right around my teenager years, things changed. I always knew that my sister had a drug problem. But when I grew older, I realized that actually also my dad had had a drug addiction pretty much my whole life. He was living the lifestyle with one foot in the street, and one foot out, working construction and selling drugs on the side. As a teen, I was exposed to this much more.” When Caskey was 16 years old, his father committed suicide following longs years of an opioid addiction. “I was hit with a lot around that time. That naturally pushed me to negative things. I gravitated towards the street life, selling drugs, doing drugs. That was the shifting point in my life.” Through all this, Caskey held on to his love for music. “Growing up I always felt a certain tension in our household, even if I didn’t know what it was about for a lot of years, and music was always an outlet to me. I grew up in the metal and hardcore scene. But I have always felt drawn to words. Once I discovered Nas and other more poetic rappers, I knew this was the thing for me.” Ever since Caskey was 15 years old, he says, rap music was pretty much the only thing he put his effort behind.
Originally a metal fan, Caskey loved the creativity of it, the pain, the social commentary of the themes that were important to rock and metal artists. But hip hop as a genre resonated with young Caskey because it is more personal. “When you listen to a band, you´re not hearing the story of the lead singer. Rather it is more abstract song ideas. Hip hop has always been about the street life”, Caskey says. “Because of what I was exposed to with of my dad and sister, I always felt kinship to that. But as I got older, I realized that I don’t want to push people in the direction of self-destruction.” He feels like this is a prominent feature in contemporary music – “drugs, meaningless sex, fast money. All these things that I tried for parts of my life and thought they would make me cooler or happier, but really they made me more depressed. So I´ve grown to be conscious about what kind of message I want to put out. As a kid I romanticized the self-destructive rock artists, such as Kurt Cobain, whose lives ended early.” But then, Caskey recalls, he had a reflective period “where I realized that if I keep pushing this, some percentage of my fanbase is going to do these things because of me, and then I changed my life. That’s important to me.”
Especially when it comes to expressing pain, it might feel easier to do that in genres that are more melodic, where the artist doesn’t have to find the words for what they are feeling. There might be more emotional and intellectual effort behind pressing emotions into verses than into screams or melodies. “Even when I was 16 and lost my dad, I remember specifically the day it happened and I was outside in front of the house, while the police were getting the body. I had a song coming into my head, and it felt really weird because you almost feel guilty for being inspired by such a thing. But it was a big sign that this is what I´m supposed to do with my pain. In some rap verses it comes easier than in others”, Caskey says. “But I´m definitely interested in expressing my feelings with minimal lyrics, too. I feel like at some point I am called to do a metal album. I think there is another side of my emotional expression that might come out there.”
“It still has this rap element of bragging, but it is derived from the things I´ve overcome. And that’s probably the most important element of my music.”
Caskey
With 19 mixtapes and seven albums, not to speak of his countless singles, Caskey has undergone a multifaceted stylistic development, from street music to spiritual music to mainstream hip hop and back to the more personal Blacksheep era. “I went through these waves, but I always get pulled back to what is most genuinely me. Cadillac Music is one of the most potent projects of mine, sonically very true to myself but also content-wise”, Caskey says. “It´s motivational music, not like this meek, woe-is-me music. I have been through hard shit, but I changed my life and am really proud of my accomplishments. It still has this rap element of bragging, but it is derived from the things I´ve overcome. And that’s probably the most important element of my music.”
This element of overcoming is the pivotal point in all of Caskey´s songs, reflexive of what the rapper is proud of and of what he might regret. “I´m most proud of my overall dedication to music, and my life I´ve given it. And of what I´ve done to give back to people that have been supporting my music. I have had so many genuine moments and interactions with my fanbase. And I feel I´ve added to their lives in a positive direction, and that´s the number one thing for me”, Caskey says. “A big part of my fanbase is people that have experienced loss, suicide, drug addiction, like the things I´ve been through. I´m most proud that I´ve overall been a force of positive influence in that regard.” To lead people going through similar struggles in a positive direction, however, is something that Caskey had to learn first, too. “What I´m not proud of is the perpetuating drug use in the past, the meaningless sex, all the things that formed a part of who I am. On the one hand it´s honest to talk about those things. But I also know that early in my career I may have pushed people in that negative direction too.”
“I want my music to be a unifying force. Whether you like Donald Trump or Joe Biden, you can listen to what I have to offer.””
caskey
Alongside Caskey´s personal growth, his following has expanded and changed as well. “In the last couple of years, it has turned towards people that really care about improving their lives, want to put down vices they have, change in a positive way. These are getting a bigger portion of my fanbase. Before, it was just people that had been through the same stuff like me – drug-addicted counter-culture kids”, Caskey explains. “My brand has always been Blacksheep, the counterculture to the norm, tattoos, and living life on your terms. But over the years it has gotten more diverse and inclusive.” He recalls that on his last tour through the States with fellow rapper Yelawolf, there were fans from seven years to seventy years old. “You have to be the type of person that this” – he points to his striking face tattoos – “doesn’t scare off right away. It has the natural advantage of scaring away all the people that I don’t want to be part of this. Anybody that sees this, judges me and doesn’t want to have anything to do with me because of it – cool, this saved myself any inconvenience of talking to somebody like you”, Caskey grins. “Those are not the people I want to attract to my life anyways. But there is also the juxtaposition of looking this way and being somebody of value and intellect at the same time.” With his tattoos, he wants to defeat the stereotypes that are still put on hip hop and street culture. “I´m not the typical face-tat white kid that talks about popping percs and doesn’t care about life. I´m so the opposite of that. For people that are turned off by my tattoos initially, it´s this nice relief moment to just hear me say something of substance and value.”
Caskey has, however, refrained from political dimensions in his songs, avoiding big politics that might divide his following. “The discourse around Trump and Biden, for example, is a way too nuanced topic to put in the scope of just one song. All it does is making people argue in my comment section. I really couldn’t care less. A lot of things we are fed on the internet are just made for the point of being divisive, and I want my music to be a unifying force”, Caskey states without hesitation. “Whether the fuck you like Donald Trump or Joe Biden, you can listen to what I have to offer.”
It is this personal take on music that Caskey wants to maintain as one of the key features of his style. In Cadillac Music, his mother and family are mentioned quite often. “Prior to this album, I talk about my dad more because this was a big pain point in my life, so it was naturally a more potent thing to draw inspiration from. My mom has always been a saint in my life, an angel. It´s harder to rap about a person who has never caused any pain in my life, only made my life better. This year it was finally the first time that that came organically”, Caskey says. In the song Dixie, he apologizes to his mother for the pain he has caused her. “This record came from this place that I´ve really been on a better path these couple of years. I´ve been reflecting more on all the pain I´ve caused her, doing those bad things. After my dad died, I just went off on this route”, Caskey recalls. “She had already been through a lot of pain growing up, from her family doing drugs, one of her kids, her husband – she has gotten it from all angles. I´m finally able to say that I´m on a path I know she is proud of.” Since Caskey moved back to his hometown, he says, he has the best relationship with his mother since a long time. “I´ve always loved and adored her, but only after this period of reflection I was able to really grasp the positive impact she´s had on me. My family influenced this album more than usual after I had moved back to Orlando. They are a big motivator to my life.”
Back in his hometown Orlando, he is being recognized and appreciated. But being the introverted type, Caskey says, he does not like to go out to clubs and bars. “The biggest benefit is being around my family and best friends. In the last year, I spent way more time with friends and nurtured these relations, more than ever since I started rapping.” After leaving Orlando, Caskey had been living in Los Angeles or travelling around the country and internationally. “This year was about relearning to prioritize other things than music. Having relationships that really matter to you, they feed their spirit, more than your career ever will. I´m learning to really value that.”
It really does seem like Caskey is bathing in a newly found sunlight in his life, having found a way back to joy and contentment. Is he the happiest since a very long time? “The happiest in my entire life”, confirms Caskey, and smiles. “When I was very young and wasn’t thinking about my life, I was happy then. But ever since my teenage years, I have really struggled with mental health. I had those phases of depression, drug addiction, suicide – that was the big upward battle that I had to fight. And for a long time I wasn’t really sure if I was ever going to conquer that”, the rapper says. “Now I´m learning to find happiness in my life. Maybe that’s just a thing in your late 20s, that you become more balanced. But definitely getting sober, not over-analyzing my career and being happy with what I have, did a huge part. I´m blessed to derive a lot of purpose and meaning from what I do.” Caskey also got engaged last year, and wants to keep up the happiness he gets from being around his loved ones. “I can even imagine a future as an old guy”, Caskey says, and seems a little incredulous about this new fact himself.
What advice would he give his own 18-year-old self, if he could? “Don’t do anything in your life that you´re not really proud of. A drug problem leads you to do things that you feel a lot of shame and regret for. One of my mentors always said: use regret as your guideline, and if you can remove those things from your life that you regret, you will naturally be sent on a more positive trajectory”, Caskey states. “Put down the drugs, they are never gonna make you any happier, put down the meaningless sex, it´s never gonna make you any happier, and then do all the things that make you proud, not things that you deep down regret. It’s a simple formula. It´s weird, at that age you make it so complicated. It´s really easy when you look back in retrospect, but when you are in the middle of it, it´s hard to conquer.”
“Blacksheep is about adhering to your vision and not giving a fuck what the rest of the world is doing.”
caskey
The one red line that leads through the entire narrative of Caskey´s journey as an artist is embodied in the letters that grace his hoodie today: Blacksheep – a brand, a lifestyle, a philosophy. “It´s about marching to the beat of your own drum and not caring so much about what the majority of society is doing. Constantly we are pushed to do things, through social media, music… On your journey as an artist you have to tune out anything that doesn’t really resonate with your spirit. Every time I´ve listened to my own vision, I´ve had exponentially more success than any other time I compromised. Blacksheep is about adhering to your vision and not giving a fuck what the rest of the world is doing”, Caskey states passionately. “That has been true to me every step of the way. It´s gotten more powerful over the years. At this point I´m mad I don’t have it tattooed on my face”, Caskey says with a daring grin. People would surely like to tell him not to do that? “Well, I don’t listen to any tattoo advise any more”, Caskey laughs.
Right now, the rapper is marketing upcoming mixtapes of which he will only sell 1000 copies for 100 Dollars. On the one hand, this is for financial gains, as, of course, regular streaming does not pay much at all. “But on the other hand, there is this struggle that when I´m working on an album, I´ve got a lot more music for that album than goes on it. I have hundreds of unreleased songs on my hard drive. It´s not that the records aren’t good. But when conceptualizing the album, there is this mechanism in my brain ordering the songs, seeing what fits together, and I have to listen to that. If it doesn’t feel like it fits the vision of what the album is, even if the record is great on its own, it stays out”, Caskey describes. “The mixtapes are for the fans that really want to listen to this music. It´s a cool way for me to share records that are very important to me, with people that actually care about it. It´s not meant to feel cohesive. It’s a creative offering to the universe. I could pocket them, but it was a way of sacrificing them – these I records I care about – in order to make room in my head for new ideas to come.”
Indeed Caskey is already working on new projects. “I always keep my hands busy. If I spend too much time not creating, I just fall into some kind of natural depression. It´s just the universe´s way of demanding a lot of output from me. I don’t really have an off button.” Does Caskey have an infinite repertoire of ideas in his head? “I feel like manic in a way. It feels like I´m always overwhelmed by ideas. Even when we were working on Cadillac Music, I already got three other projects to think about.” He wants to bring out music until he is 80 years old, he says, and means it. And the idea of a metal album is taking form in his head. He also does painting and poetry on the side. “Having so many things to be inspired by makes life exciting to live. Even if I lived to be 200 years old, I wouldn’t have enough time to do everything. Every time I finish a project, new ideas come knocking. And I´ve learned to say yes to everything. It opens the doorway and allows more ideas in”, Caskey says.
But at this point on his journey, it is not only about records and releases anymore for Caskey. He will get married in February and is very excited about that. “I would like to start a family – that’s a cool, new piece of my vision which hasn’t ever been there before. I never romanticized the idea of being a married family man, but now I love the idea. I just think I´d be a great dad”, Caskey imagines. “When I was younger, I didn’t even imagine to get old, seeing as I was struggling with my mental health. But now I´m actually inspired to live as old as I can, so I can forever do more.” After years of struggle and doubt, Caskey, it seems, has found a way to see the beauty and value in being alive, every day anew, with the purpose that music and art offer him. “There are so many artists that we look up to that didn’t make it. It just feels good to have this vision for me. That I really want to live – a long time.”
The Wrapper 