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Kayo Takes The Good With The Bad On ‘It Was Fun While It Lasted’

Written by on August 1, 2023

Kayo made a special visit to the Vocalo studios a few days before his show at Schubas Tavern on July 15, sitting down with Bekoe to discuss his debut album It Was Fun While It Lasted. The two also delve into his experiences as a rapper who is Muslim, and explore so much more.

Growing up in many neighborhoods across Chicago’s south side, Kayo is undeniably a child of the city. His deep connection with his hometown is reflected not only in his music but also in the meaningful contributions he makes to his community. An equally prominent aspect of his music and identity is his Muslim faith, which adds another layer of depth to his career as he balances his faith and his artistry.

“You may have to compromise opportunities musically, or you may have to compromise a certain rigidness that you may have as a Muslim,” Kayo told Bekoe. “For example, we’re not supposed to wear earrings [in our specific sector]. And it’s like … clearly, I got earrings in right now …

“As long as you’re kind of aligning with [the five pillars], and, in the words of the messenger, doing unto others as you want done unto you … then it’s like, to me, you good.”

Back in January, Kayo released his debut album, It Was Fun While It Lasted, which featured his lead single “Make It Right,” a collaboration with fellow Chicago artist Morgan Gold. The song gained traction within the Chicago scene, and earned a spot on Vocalo’s on-air rotation for February. Since then, Kayo has continued to impress with two new singles: “I Been,” released on June 2, and “FREE OF CHARGE,” dropped on July 12. Though “FREE OF CHARGE” was written at the time of his album, the single has a different feel entirely and he made the decision to release it separately.

“It was actually the last song for the project, It Was Fun While It Lasted,” Kayo said. “But when we finished it, it clearly didn’t match that project at all. We was like, ‘Nah, this is when we go into rapper-rapper mode.’”

Days before his show at Schubas Tavern for These Days magazine, alongside fellow Chicago artists Khaliyah X, D2X, and Gayun Cannon, Kayo visited the Vocalo studios to sit down with Bekoe. During their conversation, they delved into various topics, including his debut album, moving over 20+ times, the inspiration behind his latest single and tantalizing hints about his next project, which could be coming out very soon.

Bekoe: This is Vocalo Radio 91.1 FM, Chicago’s only NPR music station. I’m your host Bekoe, it is the Windy City Hour and as promised, I got a very special guest with me! He’s bringing a boss, he’s bringing the talent, the brother has it all, man. He goes by the name of Kayo!

Kayo: Love, love, love! It’s good to be here! Good to be here.

B: I’m gonna let these applause ring out, because, long time coming. A long time coming, my brother. Man, you’re here.

K: Yes, sir! At Vocalo, man. The legendary station, man. Come on! Let’s do it. Looking around, seeing all the merch, all the autographs and stuff, this is legendary.

B: It’s missing your merch, as well! But we gon’ get it up there. 

K: I got you. 

B: We gon’ get it up there. How you feeling on this fall type of mood day?

K: Man, this is my favorite type of weather, actually. My favorite weather, by far. I’m mad, because I was leaving the crib and I thought about putting on a hoodie, and I didn’t. I was like, “Nah, it’s summer, it’s probably hot.” In fact, I wanted to wear my merch. We live on Vocalo, of course you should wear your own merch … but then I ended up not, thinking it was gonna be hot. And of course it’s breezy – which I love , but I’m just mad that I didn’t wear my hoodie. 

B: You at least didn’t rain coat, an umbrella? 

K: I didn’t bring nothing! I did go buy a poncho, though, from Dollar Tree this morning. So I got that just in case!

B: You got something, because it is a little misty out. 

K: Yeah, a little bit.

B: I’m thinking this is your merch you wearing, with the blue heart on it.

K: You know what’s interesting? A lot of people do. But this is not. I got this from ASOS, I think. If I’m not mistaken. 

B: Maybe y’all should do a collab. 

K: I know, right? That would be hard. It’s crazy. I wore this, I did a freestyle to Jay Z’s “Anything.” And a lot of the comments – not a lot, but maybe like three comments was like, “Yo, where can I get that shirt?” And you know, mugs be thinking that it’s Southside Blue Hearts, but it’s not. It do look like it.

B: Look, you got taste, man. From fashion to modeling to these bars, man, the music side of things. Before we get into things, you got to let people know a little bit about Kayo, as far as who you are, and where you’re from, my brother.

K: I’m from Chicago, Illinois. Who I am, that’s always a very nuanced answer, because you have Kayo, then you have myself. I would say I’m a rapper, obviously, I’m a Muslim rapper – or I’m a rapper that’s a Muslim, not a Muslim rapper. But I’m a rapper, I’m a Muslim, born and raised in Chicago, moved around like 20 times in my life. So I claim … yeah, a lot of times. So I claim a lot of neighborhoods. You could ask me on any given day, and I would have a different answer. 

B: Different neighborhood? 

K: For sure, different hood. 20 times, well over 20 … 20 is the number that I give now. Once it got, I was in Tinley Park when it hit 19, and then I moved to Florida, which made it 20. Then I moved like six times throughout Florida, and then moved back to Chicago, to 92nd and Wallace, and then moved to Hyde Park, moved downtown. But I stopped there like 19, 20, I stopped counting. 

B: Why so many transitions? 

K: Man, I got the politically correct answer and the real answer. 

B: Give it to us how you want to give it to us.

K: Man, it was a lot. You know parents and stuff, finances, wanted to move around, get better housing, get cheaper housing, or just get a whole new change of scenery. The reason changed a few times. Sometimes we moved because of work, my dad’s job. When my dad started working for the Minister, for Minister Farrakhan, he had to move. We lived in Elgin at the time, that’s where we first moved to Chicago, because obviously, the Nation of Islam is headquartered in Chicago. So that’s when we first moved to the city. We was on the outskirts, but that’s when we first moved to the city of Chicago. And then from there, we started bouncing around a million times, depending on the needs of either him or the minister, whatever the situation may be.

B: Chicago, Kayo was in the building. It’s Vocalo 91.1 FM, I’m your host Bekoe and we’re talking all things. I just heard a keyword: Honorable Minister Farrakhan. 

K: Yes, sir. 

B: What’s that relationship like, because you say your father works for him. Is that current?

K: He stepped down, him and my mom stepped down from their roles around the same time, around, I want to say, 2015 or 16. But the work still extends past that, if that makes sense. For example, right now, I work for Father Pfleger up at St. Sabina, and through him, kinda through him, I work for the minister, if that makes sense … We just saw the minister maybe a month ago.

B: I saw some clips, J. Ivy was out there with you all, G Herbo.

K: Yeah, for his birthday. And he told Father Mike, he was like, “Thank you … for employing me.” So it’s like, if you work for Father Pfleger, you kind of work for the minister, in a way.

B: Hold on, pause. Did you just say, Louis Farrakhan told Father Pfleger he happy that he hired …?

K: Yeah, he was just saying, like, “Thank you.” Because to me, it’s like, he kind of adopts a lot of people. Even if you not his blood relative, if you got the Spirit of God in you and the spirit of just righteousness and the want for justice, he’ll adopt you, in a proxy kind of way. So it’s like, my parents worked for him. So there was a time where I was seeing him frequently. I don’t see him that frequently now. I will see him with my own two eyes probably a few times a year. But see him, like next to him, that’s probably like once a year, if that. But he has a great memory, so he never forgets you. If he sees you, and he sees the work you’re doing, different things like that, he’ll kind of take you in as his own.

B: Now, before we get into this music break, you being a Muslim rapper.

K: Yes, sir. 

B: Or, as you said, a rapper that’s Muslim.

K: Exactly. 

B: Is there like a type of balance you have to find in the midst of things because of their religion, their culture, and the culture of hip-hop itself is very different. 

K: Absolutely. 

B: So is there a balance you have to kind of like find and … what are some of the obstacles that you go through doing what you do?

K: Sometimes you got to, there is a balance, but I will be honest, sometimes you do have to take that L sometimes, so to speak. There are some things that you’re going to have to – I hate this word, because it sounds so scary, but if you look up the definition, it’s not the worst thing in the world. But sometimes you do have to compromise on both sides. You may have to compromise opportunities musically, or you may have to compromise a certain rigidness that you may have as a Muslim.

For example, we’re not supposed to wear earrings. And it’s like … clearly, I got earrings in right now. But that’s our specific sector of Islam, that’s not a national thing. That’s just us. You’re also not supposed to have beards, sometimes I rock my beard. It’s a few different things where it’s like, I’ll just kind of do it for branding. It sounds bad on paper, but to me, it’s like, it ain’t the worst. Our, I guess, modus operandi is freedom, justice and equality. We got the five pillars, which is charity, fasting, and – I’m finna get my membership revoked! Charity, fasting, struggle which his jihad, pilgrimage, and then I’m forgetting the fifth one. But it’s like, as long as you’re kind of aligning with that, and, in the words of the messenger, doing unto others as you want done unto you. In fact, he went as far as to say, there will be no need for any religion if we practice that, then it’s like, to me, you good. So that’s the balance, right there.

B: And before I tap into this live performance you did for WBEZ, my brother, has a Louis Farrakhan ever said anything about your career?

K: Absolutely. Yes. So he is 100% of the reason why I’m still rapping today. There was a scary moment where I definitely wanted to quit, and he told me and a couple of my guys I was rapping with, to our face, as close as you are right now. He said, “Continue rapping, and I pray that Allah makes you a part of the 10,000 Fearless,” which, that’s the people that come behind Jesus when he comes back. That’s just Bible stuff. But, “I pray that Allah makes you a part of the 10,000 Fearless with your raps,” basically. And, in a radio interview, he once said, I wasn’t here for this, but he said, “One rap is worth 1,000 of my lectures.” So yeah, for sure.

B: And with that being said, I mean, what is your connection like with your family?

K: Family. I’m a super family person, but I’m also, I’m weird because I’m kinda to myself. I’m not necessarily anti-social, but I’m not a lovey-dovey person. The only people that get the lovey dovey side of me in my family are my mom and my sister. With my grandmas, I’m not super touchy feely,  with my brother, with my dad. I don’t even get my brother hugs when I see him. We’re not that kind of fam, for whatever reason. While we are are super close, if you saw us just interact in public, you’d be like, “Nah, they not close at all.” But we actually are super, super close. Like if I’m here right now, and I say, “Yo, my car stopped,” and he’s in the furthest suburb you could think of, he would absolutely drive here to grab me. 

B: I see you with your brother, like I see y’all together a lot.

K: All the time! We’re together at least six times a week, like at least six days out of the week, we cross paths for at least an hour out of that day. For sure. No question.

B: Okay, I gotta know. Because you rap and you sing, as well. 

K: Yes, sir. 

B: Your brother sings, does he rap as well?

K: He actually started off rapping.

B: And then switched.

K: Yeah, then switched maybe like a couple years ago. This is new for him, like he’s just now scratching the surface of his voice and stuff. This is very, very brand new for him. And I’m opposite, I was singing first. I was rapping and singing. But he was just rapping, I was rapping and singing. In fact, the very first musical composition I did was a song. I remixed “I’ll Be There” by Jackson Five. 

B: You remember it? 

K: Of course! I’m not gonna do it right now. But of course I remember it, of course … And it’s crazy, because at that time, my voice was really high. And I could hit like every note perfectly well, like perfectly. Even in my mature, like my old raps are for sure wack. I’m not one of the people that think everything I was doing was great. But that was great, no question. 

B: Your voice a little deeper now!

K: Yeah, my joint kinda got the Barry White going now.

B: Do you all give each other feedback or recommendations? Since both of you dabble into the music industry.

K: He could give me some if he wanted to. I don’t give him any, I tell him go elsewhere. Just because I can’t give honest feedback to blood family, unless it’s just awful. If it’s God awful, I’ll be like, “Yeah, nah. I ain’t even gonna let you do this to yourself. I try not to nitpick with him with his music and stuff. Which could be a discredit, or I mean a disservice to him. But I’ll be like, go to Ro [Marsalis], go to Bekoe, go to D-Ro, go to somebody that don’t have the blood ties to. I’m not gonna give you the honest answer. 

B: That’s love, you said, “Go to Bekoe!” Hey now! 

K: For sure go to Bekoe! Come on, now. This is Vocalo! 

B: Look, I appreciate that.

K: You gotta go to the gatekeepers!

B: I don’t know how to take that word. I don’t know if it’s good.

K: I know, yeah, that word do got some kind of …

B: Got some stigma behind it.

K: Yeah, got some steam on it.

B: But if it’s the good part of the gatekeeper, I would greatly take it.

K: There has to be gatekeepers. Even heaven got gates, and that’s the most happiest place in the world. There has to be gatekeepers. If there’s not, then there’s no filter. The gatekeepers are that coffee filter that makes sure that no grounds get into your coffee … There has to be some kind of prep or some kind of buffer to the other side, honestly.

B: That was deep. Ooh. Before we get into this break, man, break down your debut album. We’re talking about gatekeepers, so what was some of the gatekeepers’ feedback on his debut album It Was Fun While It Lasted?

K: Man. Nobody disliked it, bro. I was nervous, because usually when you send something out and nobody dislikes it, it’s kinda scary. Like, “Oh no, y’all lying to me.” But I didn’t hear one negative review while I was making it. From anybody, honestly, like pick a name of the people that you think. Even like, this is my first time linking with … oh my gosh, she’s gonna kill me. I’m blanking on her name. Bree! Bree Specific. My first time linking with her was dropping this project, and I heard, I don’t know, but I heard she’s a harsh critic. Through the grapevine.

B: Women don’t play. 

K: At all. 

B: Women don’t play about their music taste. 

K: I had heard some stories and I’m like, “Ah, nah she’s great.” And she loved it, she didn’t have one bad review. So yeah, nah it’s been great.

B: Let’s talk about the title, too, before we jump into another joint off this album.  It Was Fun While It Lasted can touch so many different topics of things, but for you, what does  It Was Fun While It Lasted mean to you?

K: It means a few things. This is another one that I have a different answer to every time I interview. It’s talking about the music, my musical journey, of just kind of saying the old me all of the negative stuff, all of the bad stuff that I didn’t want to carry into this new phase of my career.  It Was Fun While It Lasted. And then kind of saying to myself, instead of getting hard on myself through situations, you always can just take the good with the bad and just say, “It was fun while it lasted.” Regardless what the negative situation is, in order for something to be negative, there had to had been a positive first. That’s just a fact of life, there’s no way around it. In order for somebody to die, they had to be alive first. There had to be some great thing to have a negative thing. So yeah, “It was fun while it lasted.”

B: So, this came to my mind. What was something that was fun for you that did not last as long as you wanted it to?

K: You know what’s crazy? It was a few things. It was some relationships. At that time, I’m back in a relationship now, at that time I was single. I broke up with my girl like some years, years. And that was probably the number one thing I was saying, “It was fun while it lasted,” to. Also was, I told you all I’m in the nation, I was kinda going out the way … I was kinda MIA I believe is the term, or AWOL is the better term … If you listen to “Running,” the track “Running,” go listen to that when you’re headed home, you can actually hear everything that was going on for no filters. Hear everything that was going on at that time. And that was another thing that was fun while it lasted. Then I got back and I was good but yeah.

B: That’s some in-depth commentary right there! I’m still tripping off the gatekeeper. You said every gate has a keeper.

K: Every gate got a keeper, man. Come on.

B: You know, Kayo, It Was Fun While It Lasted is by far one of my favorite projects that came out. I love it, brother. 

K: Gratitude.

B: The content, the context, the storytelling, you’re something special. I’m happy that we have artists like you right here from the city that’s doing what they do best and putting on, man. So definitely got to just let you know that, give you your flowers on air.

K: Aw, man, got the applause. Thank you. Thank you. I appreciate it.

B: Now, Saturday something’s going down, if I’m not mistaken. You’re hitting the stage.

K: That’s why we’re here! 

B: Exactly. 

K: I forgot, actually, I ain’t gonna hold you.

B: I didn’t! 

K: Let’s talk about it.

B: You were recently featured in These Days, you was profiled in These Days, they featured you. And this Saturday, an event goes down with you. Let the people know.

K: This Saturday we are at Schubas Tavern. Doors open at 7:30 p.m., I’m performing live with three other artists from the These Days artists to watch: myself, D2x, Khaliyah X, and, I know I’m gonna mess her name up, Gayun Cannon. It’s crazy, because she the homie and I tell her I mess her name up all the time. But yeah, we there, doors open at 7:30, and I have, Chicago, I have a very, very special guest coming through, performing a song. If you know me, you should know who he is, but it is not a guest I’ve ever brought out before. So that cancels out a lot of names.

B: I can’t wait to see! I’m there. I’m popping out. I’m there this Saturday. And actually, in an interview with These Days magazine, you said, “I like melodies, but I like rapping more.” 

K: Absolutely. 

B: What do you think you enjoy most about rapping more?

K: I actually just put it in this press release that I did for “Free of Charge,” for the single that just dropped today. When I grew up, you remember when you first heard 50 Cent’sc not even “Many Men,” but “Heat” off the ‘Get rich or die trying’ album, the “Heat” joint? When I grew up, that feeling from hearing it, it wasn’t no kind … Granted, 50 was good at melodies. In fact, one of the best. But that feeling from rappers, hearing people that were just rappers, nothing more, nothing less. I know he’s kind of a joke to say now, but Joe Budden was another one. Hearing that when I was young, I just wanted to be a rapper, bro. Something about having this grit, to you having this kind of this grime, to what you’re saying, just telling the story of the neighborhoods that you grow up in. That’s, to me, that’s the purest form of expression. So yeah, man. That’s rap. That’s rap, for me. I love it.

B: With this debut project coming out – that was this year, right?

K: Yeah, January. January 17.

B: It feels early this year. How has your sound changed since then? Because I know that body of work was probably worked on for some years. 

K: Absolutely. 

B: And now I feel like we, the music – because I got this new joint loaed up.

K: Oh, yeah. If you hear “Free of Charge,” if you hear what you about to play, that’s where the sound is. We was listening to Pusha T every day. Fun fact, this song was actually, “Free of Charge,” the single I just dropped today, was done March 2022. Last March. It was actually the last song for the project, It Was Fun While It Lasted. But when we finished it, it clearly didn’t match that project at all. We was like, “Nah, this is when we go into rapper-rapper mode. Like Pusha T, Ye when he was on his, I forget the name of that album, but you know the one. The new god flow joint click, and this is that … cocaine, kinda. Not cocaine! Oh my god. You can’t say that on the radio. But you know.

B: Cocaine flow, we got that in the system! 

K: Exactly. Yeah, like that -esque kind of sound. So yeah, that’s where we at for this project. 

B: Okay, so then what does free of charge fit on then, my brother? We got a project, we got an album, what’s going on?

K: A Vocalo, exclusive for sure! We working on a project. It actually, for all intents and purposes, is done. The project, the second project, is done. We could drop it in 60 days, and we may. But we could absolutely drop it within the next 60 days and wouldn’t have to stress at all.

B: Is there a title? 

K: Not yet.

B: Not yet? 

K: Not yet. That’s the only reason we haven’t been talking about it, because we don’t have a title nor a cover art for it. Just great music.

B: How many tracks can people expect on this new project?

K: No more than 13, but probably nine. We got four that are great that fit into the project, but we didn’t want more than nine. That was our lucky number this time. We may do an EP first and then do the project. So just know, if you see a four-track EP, the project is coming right behind it.

B: Now, who’s on this project? Any features?

K: No rap features.

B: What? 

K: No rap features yet, and I probably won’t have any, to be completely honest. If I do a rap feature, it’ll be a bucket list kind of joint. No pun intended, but a Saba, Chance, I wouldn’t mind a Vic feature, that’d be great. G Herbo. It’d be one of those ones that I really, really, really want, that I would compromise. But other than that, it definitely won’t be no rap peers on here, for sure. It will be some R&B girls on here, though. For sure. Can’t say those names yet, but yeah.

B: Now, to cap things off, you got to give out your social media handles so people can stay in tune with you.

K: It is @KayoSouthside. It sounds way longer than it actually is. That’s Twitter, IG, TikTok, Snapchat if you happen to use that, Facebook that is everything. It’s also my website. Kayosouthside.com.

B: Why the name Kayo?

K: Ah man, I do not have a bright story. You know how rappers be having rapper stories? It was just the first name that came to mind when I was trying to change my name. And then I looked it up and it meant “beautiful generation” in some language, I can’t remember which. I want to say Japanese. But yeah, it meant “beautiful generation.” I was like, “bet.”

B: Why not?

K: Why not!

B: Hey, well, you bringing some beautiful music to this new beautiful generation we got going on!

Keep up with Kayo on Instagram and Twitter. Stream his music on Spotify below.

Interview and audio production by Bekoe

Video editing by Bekoe, filmed by Rakim Winfert

Photography by Rakim Winfert

Transcription and editing for length and clarity by Morgan Ciocca

Introduction written by Omi Salisbury

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