Chicago’s Jay iLLA on Staying True Amid National Spotlight

This Chicago DJ speaks about his recent honor from Rémy Martin and what his city gave to Hip-Hop.   

For any dude who got hooked on Hip-hop in the 1980s or 90s, the love affair probably began with a song, moment or an epiphany. 

For Chicago’s Jay iLLA, it was a combination of things. That one time he heard Common’s “I Used to Love H.E.R.” in ‘94 or A Tribe Called Quest and De La Soul, artists who wielded the sort of sonic sorcery that captivated heads around the world. Throw in how he acquired his love for DJing, by hosting an open mic night in Hyde Park back in the day.  

As one of Chicago’s most respected DJs, this “90s Hip-hop dude” is not only a member of the culture, he is one of its luminaries.

For Hip-hop’s 50th Anniversary, Rémy Martin spotlighted Jay iLLA as one of eight “epochal DJs” who have helped to establish the genre’s mixtape culture. Epochal means the man is influential and extremely significant in what he does. But you would never know that by conversing with him.

Recently, The Defender chatted with the humble and unassuming DJ about being honored by Rémy Martin, Chicago’s contribution to Hip-hop and what he wants his legacy to be. 

Chicago Defender: What was it like when you first learned you were selected as one of the DJs for the Rémy Martin Mixtape Street Art Museum?

Jay iLLA: It was very surreal. I’m gonna be honest with you. I really did not know if I deserved it. Because, I’m just a 90s hip hop dude. And I just love hip hop. And so when I got the nod, one of the first things I did was find out who I would be honored with. I actually texted DJ Clark Kent. Because Clark is like a big brother of mine. And I was like, ‘Yo Clark, I just got selected to be in the room with these legends’. And the first thing Clark said was ‘Little brother, you deserve it. They might not know you now, but they will know you’. He was like, ‘you deserve to be in that room’. 

CD: Kool DJ Red Alert, Marley Marl, Spinderella, DJ Yella and DJ Cocoa Chanelle. How did that feel when you learned you were a part of this esteemed group as an esteemed figure yourself?

Jay iLLA: Unbelievable. It was super surprising. I loved it. Seeing as though I am familiar with all of these legends’ works, and they impacted my life somehow, growing up in Chicago, and being the youngest out of all of them to be honored, and knowing what their contribution has meant to me. I picked each of them out individually and let them know how much they meant to me and where I remembered them from. So it was just a super cool moment.

And it was either, if you’re dope, then you were dope, and you had to show and prove. That’s what Hip-hop has always been to me. That’s why it’s so important to me.


CD: Everybody has that origin story of when they were first introduced to Hip-hop, where they fell in love. And I don’t mean to sound like the movie “Brown Sugar” here (chuckles), but what was that moment like for you?

Jay iLLA: I’m a 90s kid, an ‘81 baby. Hip-hop in Chicago back then was super underground…In the 90s, Chicago had that underground element…That’s what we live for, whether we was tagging on buses, or you know, backpacks with your rap book, with your lollipop where you can tag on buses and do all the riff-raff stuff that B-boys used to do. That moment where I knew that hip hop was for me was in grade school…And being introduced to hip hop culture, I remember in 1990 — what was it 94? — when Common dropped, “I Used to Love H.E.R.” breakdancing in my kitchen. 

That subculture spoke to me because Hip-hop was not about being commercial back then. If you were on commercials back then, you were considered a sellout. So, I just embraced that subculture, and I loved being a part of it. And it was either, if you’re dope, then you were dope, and you had to show and prove. That’s what Hip-hop has always been to me. That’s why it’s so important to me.

CD: Can you kind of paint that picture of the Chicago hip hop scene, the artists who were popping back then who were, you know, immediate influences in that era for you?

Jay iLLA: We always had Twista, of course. But in the 90s, that’s a beautiful thing about Chicago, it has so many different branches. You had Twista, you had Do or Die. You had Infamous Syndicate, who was Shawnna and Teefa. That was that different kind of Hip-hop. 

I was leaning more towards listening to Common and underground artists like that. You had Family Tree. You had No I.D and Dug Infinite back in the day. People don’t remember that No I.D. used to rap back in the day, you know. I was leaning more towards that. You know the Twilite Tones, and when Twilite Tone was rapping under the name Ynot. So that’s what it was like for me. 

You had so many different branches, and even Common’s first album, “Can I Borrow a Dollar.” When he explained his album cover, it was like, ‘you have the East Coast of where it started. You have the West Coast, who started the whole gangster rap thing. We were like right in the middle, just saying like, ‘Yo, can we get some of this?’

CD: What part or what energy of Chicago were you really trying to represent with the Rémy Martin Mixtape Museum project? What were you trying to showcase there?

Jay iLLA: I’m just trying to showcase the, I don’t want to say true culture, because everybody has their own definition of what hip hop is. What I’m trying to showcase and then I mentioned this in the Bronx. Me, representing our city, I’m not a part of this culture representing Chi-Raq. That’s not who we are.

So, I am looking to represent that good energy. That Rhymefest, Twone Gabz, may he rest in peace, Common…Like that bridging that gap. Where we like everything. We good dudes. Like that type of energy. That Hyde Park. You know at Rock and Roll McDonald’s, I’m trying to represent that energy. And I think I did that. I think I was successful.

I think the industry here in Chicago can be crabs in a barrel because we don’t get a lot of shine. But when it comes to the forefront, I think our talent really shows. I mean, you got your Lil Durks. But you also got your Chance The Rappers. So, it’s a broad spectrum of what Chicago brings.

CD: Can you talk about Chicago’s contribution to the genre of hip hop? And how has that contribution evolved or changed over the years?

Jay iLLA: Starting out, I never thought that Chicago really got it just due of the contribution that we gave. What I mean by that is, I mentioned Twista earlier and Infamous Syndicate and Do or Die, that style of rap. Like Twista was out before Bone Thugs. And you know that tongue twisting, that rapid fire rap was made popular by [Bone Thugs-N-Harmony’s] “East 1999.” But Twista had like, I think his first song was “Mista Tung Twista.” 

CD: Yeah, I remember the video.

Jay iLLA: Yeah. So, we never really got that just due. To be perfectly honest, even Common had to leave Chicago to get his just due. If you ask a true Chicagoan, their favorite Common album is probably Resurrection, which is a great album. When you think of Resurrection the only song people can think of is “I Used to Love H.E.R. and we never really got our just due until Kanye came. And Kanye started bridging that gap…that “Can I Borrow a Dollar,” like that in the middle, can I get some. That influence that we got from everybody, ‘Ye took that and was able to, with his production, build that bridge and show people like ‘man, like Chicago got a lot of talent’. 

And you could take it to No I.D., pound for pound, probably one of the best producers in the world. He’s produced everything from Common to John Mayer. But you wouldn’t have known that because number one, he’s so low key and Dion just goes about his business. But when he got up paired with Jay Z, then it was like, ‘Oh man, like this guy is incredible’…

I think the industry here in Chicago can be crabs in a barrel because we don’t get a lot of shine. But when it comes to the forefront, I think our talent really shows. I mean, you got your Lil Durks. But you also got your Chance the Rappers. So, it’s a broad spectrum of what Chicago brings.

Jay iLLA Rémy Martin Mixtape Museum mural

CD: Who would you like to give a shout out from Chicago from the DJs that represent the city?

Jay iLLA: Oh man. My mentor, DJ Shaun T. DJ Twilite Tone, was one of my huge influences. One of the very first DJs that I met, DJ Phat Mike. These are all my OGs. DJ Mustafa Rocks, Jamal Smallz, DJ Kwest_On, rest in peace. Joe Kollege. On the younger side, my man Charles Protégé, DJ Kid Clay. Who else? Geez, there’s so many

CD: I don’t mean to put you on the spot like that. 

Jay iLLA: Look, if you good with it, man, I got love for you.

CD: You know, when all is said and done, looking back on your contribution to mixtape culture, to the art form of hip hop. What do you think will be your legacy? What do you hope will be your legacy?

Jay iLLA: I never switched up. And I was just, thoroughly dope. And I never did it for the clout. I did it because it was me. And when I say I never switched up, it was like, I never had to rebrand myself because I portrayed myself as something that I wasn’t. So that’s what I want my legacy to be. When somebody says Jay iLLA, that they be like, ‘man, a really dope DJ, but an even better person’.

This interview has been edited and condensed for clarity.

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