Although he’s 21 years old, Isaiah Gilbert’s journey through rap has allowed him to gain a level of insight far beyond his years. From freestyling with Chance the Rapper in the 9th grade, to collaborating with some of Chicago’s current rap frontrunners like Saba and Supa Bwe, Isaiah has witnessed firsthand the city’s evolving hip-hop landscape. These experiences have given Isaiah confidence in his abilities, and a sense of urgency to evolve his music to a whole new level.
Isaiah has only offered mere glimpses at his progression so far. On his “KNOWSPACE” EP, he familiarized listeners with his signature sound, delivering intricate flows over atmospheric, spacey beats. Now, he’s gearing up to drop a more cohesive body of work titled “CONTACT.” In this interview, the Southside native speaks on the state of Chicago hip-hop and how he sees himself fitting into the picture.
Where did you grow up?
Originally, I’m from 76th and Loomis, then I moved to the far Southside in Roseland, and then I moved to 73rd and Western, and now my peoples live three blocks from where I first grew up. But, I feel like I’ve never been somebody indicative of my environment. I didn’t go outside that much ‘cause there wasn’t really shit to do that was cool to me. I was just trying to hoop, play video games and I got into rapping in 7th grade. I went to Jones [College Prep] which was dope, because when I got to see downtown Chicago with my own eyes at the age of 13, that shit was hella mind opening.
What was the contrast like between downtown and the southside?
Every space is utilized downtown, it’s a symbol of efficiency. There’s something for somebody somewhere. But if I go back home, there’s so many empty buildings. … People from Englewood don’t get out that often. You either get out or you don’t. When you see outside of that, you just realize the potential of things.
Does having that perspective about your environment influence the way you make music?
It made me more versatile from a social aspect. I had to learn to talk different when I was downtown versus at home. It made me develop a unique voice. I just became a chameleon, never sticking to one space in society–just existing. … When it would change from “we’re in a good neighborhood” to “we’re in a bad neighborhood,” I could peep that subtle shift. In my music, it made me have the emotions of the struggle but also have the optimism of what I know is possible. I saw people in skyline buildings and raw-ass views. I could see the worst of a situation and the best of a situation.
Who did you grow up listening to?
In my early childhood, Alicia Keys, Usher, Pac (even though I’m not a fan anymore), hella Kanye, 50 Cent, Common. Lil Wayne held us down as shortys when we were like 8 or 9 years old. He just ran every summer.
Would you say Wayne inspired you to start making music yourself?
I started rapping when I got into Lil Wayne, and then when Drake came out with “So Far Gone” I really started getting into it. Some other projects that inspired me were J. Cole’s “Friday Night Lights,” Kendrick’s “Section.80,” Joey Badass’ “1999,” Childish Gambino’s “Camp.” Then, when I got into A Tribe Called Quest, that caused a major change in how I approached music. I heard their song “Jazz,” and I was like “damn, this is what good music sounds like.”
While you were still in high school, how did you spread the word about your music?
I was in a RapGenius rap battle and they had this competition. I finished in 5th place but I took away the most fans. I got to the point where I was a verified artist on there. At the time, it was a close-knit community, and it hadn’t been monetized yet. I had the moderators fucking with me when they tweeted out my song “Cheesin’” on their twitter, and I also got nods from The Needle Drop.
What was it like rap battling Chance the Rapper when you were in high school with him?
That shit’s wild. He was a senior when I was a freshman. It was my first time skipping class ever. I spat my shit, and it was aight. Then Chance comes out of nowhere and spits his verse from “Brain Cells” and I’m just like “ok…. true” [laughs]. I have a friend who asked him one time if he still knew me and he was like ‘yeah I know Isaiah.’ So one day when I get to that level, I’m gonna have to slip some music in Chance’s ear. He’s gonna remember this kid he used to see around Jones.
Fast-forwarding to where you’re at now, you dropped your “KNOWSPACE” EP in December. What do you have planned next?
I’m working on this full-length project called “CONTACT.” When I try to put an adjective to my music, I feel like it’s spacey. … I’m an aerospace engineering student so I’m into that type of shit and the way I think is off the wall, abstract. The EP is just the fundamentals and “CONTACT” is coming into contact with everything that I’m trying to realize. It’s gonna sound more refined and experimental.
How did you form your AAP Collective?
I came up with my homie Aaron Deux, and he pretty much gave me the background for most of my music. Aaron moved to Houston like after 7th grade, but he would always be producing and I would rap on his beats over Skype. Then, we formed our group AAP which right now consists of me, Aaron and my homie Devon Culbert. We just have this progressive outlook on hip-hop, and we all have our individual styles as well.
Taking a step back and looking at the state of Chicago hip-hop right now, do you think there’s a predominating sound in the city?
I think there’s two lanes in Chicago rap right now. There’s the stereotypical SoundCloud rap–well, stereotypical is the wrong word–archetypical SoundCloud rap. The SoundCloud aesthetic that now exists in every city started here. And then there’s the other side of Chicago where it’s more poetic, more RnB and more rooted in the city. The world sounds like Chicago right now. Chance and Chief Keef are the two most influential rappers of the past five years. … What I’m trying to do is navigate the middle ground of both of those lanes at the same time. I like ignorant shit, I like poetic shit. Good music to me is really about leaving a unique imprint on whoever is listening to it.
Why should the music industry be focussing more on Chicago right now?
Chicago per capita has the most talent. It’s not even close. There’s so many rappers who are so critically slept on in Chicago. My homie Ausar is so good; he’s like a Mos Def-Common hybrid. When I think about the next wave in Chicago, I think about me, Femdot., Ric Wilson, and Ausar. We’re coming with some shit that’s not boring or dry–it’s got energy. … We need more A&R agents and people putting money into the scene here. We are the most talented city in America, no bullshit, and we just need more people here invested instead of just biting our shit from afar.
How does it feel to look back at 21 years old and realize you’ve already been doing this for 6+ years?
It feels amazing, because I’m still getting better especially in these past 3 years. I’m coming up with new melodies out of nowhere, I’m thinking about ad-libs, I’m thinking about breaks in songs, I’m thinking about doing duets. I’m just seeing my creativity flourish. I feel like I’m finna enter my prime.
Photos & video by Mike del Ro.