Meet Caleb Giles, an Artist Who Finds Comfort Under The Shade

“Writing’s always best when there’s ease and comfort.”
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Caleb Giles has body and community baked into his work. The 21-year-old artist quietly stands at the forefront of the moment currently unspooling in the NY underground. Playing saxophone in the ensemble Standing on the Corner, featured on Earl Sweatshirt’s Some Rap Songs and Solange’s When I Get Home, among others, Caleb’s musical skill is vast and comely. His solo music is widely influenced by his ensemble work and his gospel and jazz upbringing.

“Growing up, I only listened to gospel music and Christian music, because my mom is really religious and what not,” Giles tells me over the phone. “But I had a friend, the same friend who showed me Get Rich Or Die Tryin’, and his mom listened to a lot of R&B and hip-hop, so when I would be at his house, we would bump all this stuff I never heard before.”

It was in the eighth grade that Giles began recording raps and making beats, going over a friend’s house and borrowing his recording equipment. In conjunction, Giles always found himself in music lessons, thanks to his father, who was also a musician. Whether pops knew it or not, he was preparing his son for a life in "the game." 

Caleb Giles’ poetics and jazz roots shone through most brightly on 2018’s There Will Be Rain, a quiet storm of a record that imparted motifs of faith and the sensation of being overrun. Giles presented himself as a wellspring of capitulating wisdom. There Will Be Rain was the sputtering sound of coffee percolating and was just as aromatic and satisfying. While he never fully came into his own on the album, it was still an exciting step forward from his 2017 debut, Tower.

On the horizon for Giles is his third album, the lighter and more self-actualized Under The Shade. The record finds as much inspiration in the light as in darkness, with Giles remarking that both states are equally beautiful. He finds his poetic energy in prayer, and Under The Shade feels like a spot of Holy Communion. For Giles, this is imperative.

“I feel as if, what I’m saying, there are people who can relate to my shit,” he explains. “My happiness and my sadness. To be understood so other people can be understood.”

Within that understanding is his mature perspective on the New York hip-hop scene. Giles tells me that it’s not about fitting in and finessing your way to the top, it’s about enlightenment: “In terms of a grand scale, we’re all just trying to come up, and we’re doing a good job of that.” We couldn’t agree more.

DJBooth’s full conversation with Caleb Giles, lightly edited for content and clarity, follows below.

Caleb Giles, 2019

DJBooth: Take me to the first time you realized the power of music.

Caleb Giles: It was when I discovered “Many Men (Wish Death)” by 50 Cent. I became so obsessed with it! I was like, maybe, seven when I found that song.

Where did that discovery lead you in terms of your first tastes?

A lot of hip-hop. Growing up, I only listened to gospel music and Christian music because my mom is really religious and what not. But I had a friend, the same friend who showed me Get Rich Or Die Tryin’, and his mom listened to a lot of R&B and hip-hop, so when I would be at his house, we would bump all this stuff I never heard before.

What drove you to make music?

My father is a musician, so he put me in violin lessons and had my sisters in string lessons as well. But then, I moved to New York. I started playing the sax; I didn’t start making my music until eighth grade. A friend of my friend had recording equipment at his house, so I would go to his house every day and make beats, and write raps.

How did that lead you to Standing on the Corner?

I’ve been playing music my whole life, and I started playing with Gio [Escobar] in 2016. But I had known Gio for a minute. We had mutual friends; we all kind of knew each other. Gio eventually asked me to play keys in the ensemble, [and] it morphed into us playing live with the saxophone.

How has playing sax with Standing on the Corner influenced your solo work?

Gio and I both have a lot of similar music tastes. Even before I started playing with him, in my solo music, I was influenced by jazz. Of course, by my vocation. I came up playing jazz and gospel music. Gio also grew up in the church too, playing keyboard in the church. We had similar upbringings and similar interests, and that’s why we’re such close friends.

Diving into the music, in 2018, you said “[There Will Be Rain] plays on the trope of a flood or an impending, inescapable fate from which nobody can hide.” What does your new project, Under The Shade, play on?

There were a lot of things going on when I was writing this record. I finished There Will Be Rain, and I started working on this next one, and I was thinking a lot about my foundation as a musician and as a person, and how I came up and things like that, and my family. This record has a lot more to do with innocence and how this innocence can be maimed or just replaced as you grow up. It’s about that relationship to innocence and how to be a young kid, while also trying to be a kid. How do I be a kid in this environment? I lived in the Bronx for many years. I moved to Brooklyn to write this record and be closer to where I grew up.

There’s a lot more light on Under The Shade. And looking at the titles of your last two albums side by side, there’s literal movement. A catalyst and the product; was that intentional?

You know what? It wasn’t. Writing’s always best when there’s ease and comfort, and I find that there’s ease and comfort in nature. It wasn’t intentional, but I came to this realization just yesterday. When you write something, it should be natural; it shouldn’t feel forced. It wasn’t intentional, but that’s the motif that kept popping up! The sun, and the shade. So I just called it Under The Shade.

Do you feel there’s more inspiration to take from darkness than from light?

I think it’s equal. The light can inspire you just as much as darkness. It just depends on what you’re trying to do what your dispositions are. The light and the dark are both beautiful, and there’s a lot to take from both. It would be ignorant to be obsessed with one over the other.

Caleb Giles, 2019

You’ve also said, “The rain to me represents anything that you can’t control, that will of course just take you over.” What does shade mean to you?

Right now, the shade is about how you feel trying to get by. It’s how you feel, rather than someone projecting a feeling onto you. Specifically, how I felt. When I was writing about the sun a lot, I wanted to get across the sunshine and goodness, but where there is light there is dark, and there’s a lot of bad stuff that’s happening in the world, every day.

How do you keep yourself so creative and poetic?

I pray. That’s it.

There’s a communicative quality to your music like you’re sitting across a table from the listener, just pouring yourself into them. Where does that communal quality come from for you?

That comes from wanting to be heard, wanting to be understood, really trying to have someone know what I’m saying. Most artists want that. I feel as if, what I’m saying, there are people who can relate to my shit; my happiness and my sadness. To be understood so other people can be understood.

Finally, where do you see yourself fitting into the vast New York hip-hop scene?

I think I fit well in it. A lot of the cats coming up right now, I know well. I know MIKE since high school age. I believe that it’s more just about uplifting each other, and being friends, and making good music together, as opposed to fitting in on some Tetris… In terms of a grand scale, we’re all just trying to come up, and we’re doing a good job of that.

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