The Adam Friedland Show (Cumtown) - CHANCE THE RAPPER Talks Chicago, Mixtapes and Mentors

Episode Date: October 31, 2025

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You were with someone for 22 years? Who? Your ex-partner, your ex-wife? Or you knew her for 22 years? Yeah, we grew up in Chicago together, so I've known her for most of my life, yeah. Are you single gentleman now, or have you considered doing what the god did? You get like a girl that looks a little bit like the last one and then make her be naked? What?

That is hilarious. Hello, my kind of favorite show, oh, my Adam Friedland show, oh, and Adam Friedland show, guys. I'm Adam Friedland. Before we get started, as always, I got to thank our members for supporting the show. We couldn't do it without you. If you'd like to join the Friedland Family Foundation, you could do so by clicking the join button on YouTube or clicking the link in the description below. You'll get early access to all of our episodes and your name in the credits if you join at the second or third tiers. Also, we have a Patreon. If you prefer to support the show through Patreon, there's a link in the description below. Finally, last piece of housekeeping.

We have merch, the Adam Friedland. Show. Check it out. It's good. It's cool. My guest this week is Chicago Artist's Chanced the Rapper. Now, of course, famously, the last time I welcomed a Chicago artist, it sparked a firestorm of controversy in the world of rap. Me and my guest, G. Herbo had some criticisms for journalist DJ Vlad, who responded in kind with a direct message. Some called it a shot heard around the world.

Months later, tensions have remained high between Vlad and G. who've been trading blows on social media. In that time, I've kept myself. I've kept my head down and I've done some reflection. And I'm ready to move on from this maelstrom. In fact, I have a potential gig for DJ Vlad if he's willing to hear me out. And what it is? So I finally decided to respond to the direct message

and he was open to further dialogue. So with that, let's give him a call. Hello? Hello, sir, it's Adam. What's up, Adam? I just wanted to parlay with you real quick and just kind of squash this, whatever the, whatever the misunderstanding was.

Do you guys ever DJed, or is it just a screen name? Well, I had a long history of DJ. before Vlad TV started. Well, I'm getting married this year, and perhaps, yeah. Yeah. Oh, and she's lovely. I was just perhaps, I would want you to be part of the greatest day of my entire life. Yeah, sure. I'll show up to that.

Okay. Well, sir, sir, I feel like my conscience is cleared, and have a great day, I guess. Oh, good news. Okay, live long and prosper. Bye. See you. He bought it. Folks, in this crazy world we live in, we don't need any more beef, we need peace.

And if two sworn enemies like DJ Vlad and myself could see eye to eye, you know, let that be a lesson to all warring peoples around the world. And so with that, please enjoy my interview with Chance the rapper. This episode is sponsored by Ro. Roe Sparks are a two-in-one prescription treatment for guys who need a secret weapon. It's the new wave. They hit the bloodstream faster because they dissolve right under the tongue. So no more waiting to perform after Roe Sparks dissolve.

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Diamond! That's even better than platinum, guys. Diamond-certified recording artists, ladies and gentlemen, chance to rapper, everyone. Thanks for that. Thanks for coming, sir. Oh, thanks for having me, yeah. I appreciate you. And so I, I, I just had...

Should I still be standing out? No, no, sit down, please. I had herb on the show. Yes. And I paid tribute by giving him a bottle of 1942. Have you had that before? I have. But the liquor store, I think I bought the last one,

because it was like last week. So they said this one's good. It's called Casa Azul. I'm familiar. Do you know this one? It's got the ding. I see it on like Real Housewives kind of show. vibes yeah like a like a rich lady who's about to cheat yeah yeah she like a with like a

the pool boy so we're gonna we're gonna we're gonna stress out you have the same you got you have the same publicist yeah yeah yeah so you're gonna get stressed out again you have a hard out at five but we're gonna be having this what is this ceramic mm-hmm yeah let's do it the you want to do lehayim yeah what we do we bless the bottle so let's it yeah you just oh you uh you do grace it's sort of yeah Yeah, sort of the same thing. So just tap the bottle? Do you want me to do the Jewish style?

There you go bow. That was it? That was the Jewish style? Bang. No, no, I mean the Jewish prayer on tequila? Yeah. Do you say, do you have to say grace before every meal if you're a devout Christian? Or just like, if it's a drink, you have to say grace or if it's like a fool?

That was more like, that's like some kid weird shit. When a blessing the bottle, that actually has a good Christianity. No, I don't think that, I didn't think of that as religious. But like if it's a snack, do you have to say grace? you have to say grace that's a good question i think you do you do i think in judaism too for like for different this is the most boring conversation let's go let's uh let's have a let's have faith i don't have i don't you know i don't faith i don't faith you're a god-fearing gentleman amen yeah amen but we've found out today this is really blowing my mind in you were in the jewish

student union i was in the jsu why because i have like a ton of Jewish friends that like were really into the same shit that I was into when I was in high school I went to like a really like smoking bud smoking bud yeah I mean like like I was on lit mag you know what lit mag you got good grades I didn't get good grades but I was into things so I would be into something uh-huh and and I would go into I would just go and like join and lit mag um was like all of the the like quirky writer folks at at my school. Yeah, girls.

Were there, were there, like, the glasses girls. Indie girls. I would like the Indies. The Indie girls. I was into the Indie girls. The Indie girls. The 824 girls. Here we go.

The bisexual lighting. The purple light. Sorry. OK. Thank you for coming on. Thank you, guys. Yeah, it's interesting, because we just had Herb on the show.

And it's like, you're of the same generation. But I feel like you're like the good kid side of Chicago and they were the they were the going outside boys it would seem that way yeah that's not the truth we're from the same hood we both from 79th I'm known herb for a really really long he's a great guy he's an amazing dude and you know the hood the hood is the hood you know what I'm saying it's really just about what you do for the hood and herb does for the hood like he has a school he like works with mental health facilities he's got like kids that he mentors

Like, me and him are very, very similar. And we talk, like, once a week, that's my dude. Let's get to, like, your upbringing, your family, and stuff like that. Like, your father was involved in politics. Both your parents were? Yeah, yeah, yeah. My mom a little bit, but my dad, yes, for sure.

He worked for, he worked for... He worked for Obama. He worked for Harold Washington. He worked for Rahm Emanuel. He, so my dad, really, I guess I got to start with my grandmother. My grandmother was very, like, politically active. And at a young age, and she had all her kids young, like my dad and my aunties young.

In Chicago? In Chicago. And so, you know, Chicago's super politically active space. This is where Fray Hampton is organizing the Black Panthers, where Stokey Carmichael and all these people are gathering and having. So she was like really swept up into that stuff. And so she would volunteer her kids for certain things. And then Harold Washington, first black mayor of Chicago.

And like, I think the first, it might have been the first black mayor of a major of a metropolitan city. And so she got them all to sign up for that. And that kind of got my dad into politics. And then I think from there, he just always stayed like, you know, it still has like this grassroots thing of like, you know, he was my black club president, like, my dad was very like, on some like activism shit, but he worked, he did also work for, uh, for Barack too. And so that's your boy, Barry, Barry.

That's not my boy, but you know what I'm saying? You've met the goat before? I met the, I met the goat before for show. Really? What's his, what's the energy like? what's what's uh he's just like he has on TV written no he's not yeah as a guy 100% yeah he's like let me he's just like he says let me be clear to you yeah he does this he does the really I don't got the Brock impression what do you think he's up to these days he's

got to be so bored I don't know I don't really talk to him so I don't think of him as like a person like I think of like listen your best friends with Obama yeah that's what people That's what I feel like that's the no I'm I'm I'm honored that they gave me like they gave me some some shoutouts in the past I got a humanitarian award that you make one of his best of lists of for the year I was on a playlist once yeah you're that's nepotism your dad it could have been people know people you know I'm saying like that was really what I got into the industry for it was like to get it to know Obama to get on the playlist you know about Obama playlist of the year yeah

yeah what else did he have on that March Madness I think he did have no he He didn't. No, he did it. No, he did it. Maybe not marshmallow. No, he has like, he has like smart stuff on it. No, he doesn't have dumb, he doesn't have, I'm on so many drugs. Like, wink, wink, wink on there, you know what I mean? He's a wink, wink, wink. He has like, I cheated on you, but it's only because I'm depressed. The narrative of future as the, is the best. Yeah. Because you still feel bad for him. He's like, I'm so sad.

That's why I had to get so much, so much pussy. It's great. So much is hilarious. He's like, I just, it's because I feel so lonely. And you're like, you buy it too. Can I have vape on your show? Is that a thing? I feel like this is more. You hit V?

We're drinking. Dude, to have some more. Yeah, of course, dude. Are there a lot of rape, rap, rapper. Are there a lot of rapper vapors? Right, because vape. I didn't. Are there a lot of vapor wrappers?

Vapor rappers? Uh. You hit Jewel. That's old school style. Yeah, no. I'm definitely, I'm like, so. So I don't know. I need to be a part of the class action lawsuit because I am thoroughly addicted to these.

And I am like, just so I could watch this back later, you are addicted to these. It got me so into. It made me so addicted. But now I started upper deckies. Here's a problem. And this is going to lose us all our tobacco sponsors. But the issue, I'm joking. The issue is that like, think about this.

Because you used to smoke cigarettes, I'm guessing. Yeah. Which are cool. They look sick. They look way cooler. Faster death. The thing is, like, with cigarettes. It's fine.

Going to, like, weaning yourself off, you know, you get, like, the patch. You know what I'm saying? Where you get the gum. And there's, like, a regimented schedule for how you get off of it, where it's like, okay, to do this much today, then you do this much the next week. Does it work? I'm sure. Hell of people quite smoking cigarettes.

But this doesn't have a, this has the unlimited. This is just a cartridge. You could do it in bed. I did it in bed. That's what I'm saying. My girlfriend would be like, you disgust me. It's the least second. You know, it's like, you're not like Humphrey Bogart for him.

a jewel. I get that reference. No girls like I've wanted to like I want to ride him like a bike because she sees him with a geek bar. You know, it's not a sexy thing. You, no, sorry. Okay. Let's let's get into like one thing I found interesting about you is that it came kind of out of your education. Like your career kind of like it seems like the schools that you went to kind of fostered you becoming an artist. Is that correct? I thought you were going to go on a different direction. What I would say is like, I thought you're going to say, so my first mixtape was called 10 day. It was about a suspension from high school. For weed, for piffing. Yeah, for piffin. I got suspended too, but I. Smoking wheat? No, for, uh, I told my dad

if, if I wanted to go to like this like this teen summer program, I told my dad I get straight A's and I got six A's and two B's and I forged my report card and my dad fucking bitch ass ratted on me to the school. Best story took 10 left time. Like, I, I, I, I, I thought you was going to get in trouble six things ago. I've never, I don't forget. You said, you forged your family report card and your dad told on you till your school. He went to the dean who looked like a mole.

This guy looked like a mole. That shit is crazy. I got called in. I got, and I said to, when I got in trouble, I said, I was like, I'm lying to my parents. And I'm not really lying to the school. So you got in trouble. And then you wrote your first mixtape, 18 years old.

Yeah, I think I was, yeah, I was 18. I started on at the end of my high school, senior year of high school. and put it out, I think, when I was 19. Yeah. And yeah, like, the influence of school and me feeling so dissociated from, like, the building or the idea of work

or the idea of these adults being teachers and not just being regular niggas that hated us. They're losers. Let's be honest, teachers are losers. So just let the record show. I don't, I think you're losers, you know what I mean? Some of these guys we had, poof. Oh yeah, sorry, no, my bad.

Yeah, yeah. My teachers was losers. They were losers. They were losers. Back in the day. Back in the, I'm talking back in the day. I'm talking in... Uh-huh.

In antiquity. Okay. I'm talking about, like, fucking... Stone Age. I'm talking about... I love saying I'm talking about... And you... Adelibbitt sounds like a song to me.

Go ahead. This is a track right now. I was gonna say like Aristotle. Okay. Pedophile, yeah. Okay. So let's twist. Let's make a pivot.

Okay. Let's go... He was a teacher, though, right? Yeah, that's what I was going to say. Let's go Talas of Miletus, right? What used to happen was one person would teach one person, right? So you get that one-on-one education. A mentor.

Typically, it's your father, but yes, or you go to a mentor who's a philosopher, and they teach you one-on-one what the game is. And now we have a standardized education where we send 30 random kids into a room that it all day with an adult who just got a divorce yeah and so they had they owe nothing to this child they don't think that you know and it's not this child it's 30 childs and next year they'll have another 30 child so it's like and I should be saying children but you gave me child whatever it's come on dude the point that I'm making though is like it's a I think the issues with teachers

are that they're overwhelmed and they're human beings so when they're you know I'm saying getting fucking fucking Markers thrown at them and TikTok challenged all over like they at a certain point they'd like they check out and I think that You know back in the day Post Stone Age pre 1941. There was a lot more You know like direct education or at least like more sizable to just be with one adult guy wearing a fucking toga That'd be annoying. No, that would be whack. I would be like girls to be there and kind of try to be funny You can't have a girl mentor girls could teach you too. No, but you're like but you can't I mean I guess I guess I

What I'm saying is, is, like, a school socializes you, right? Like, the fun part about school is that you're, like, you're terrified to get beat, like, get called gay when you're in sixth grade. Like, you're trying to survive, and it makes you a regular human being, right? No fact. Apparently, they're trying to take bullying away. And I'm like, these kids are going to become sociopaths. You develop a personality by being terrified, right? That's how, no, I mean it.

Take bullying away. It's really funny. That's what I'm going to send my kids They're trying to take bullying out of the schools They did read that You have to bring bullying back Because that's really where you're like That's what we're built on

I need through like a like Darwinism To find something to survive You're like I'm gonna get really good at rap And I was like I'm I'm like gonna I have to do something That'd be funny I have to be funny facts I fucking feel you right So like if you send your kids to one of these goddamn $60,000

dollar a year of schools where they're told that they're amazing they're gonna be fucking does sociopaths facts you have to tell them that they suck and the teacher has to be a loser going through a divorce yes that's how we got here that's sorry that's my rant on schools no but like you were also in writers programs and stuff like that yeah right they should do after school like the fucking um jewish student alliance dude jewish alliance was more for the pizza there was a there was a what Jewish pizza no dude in this day and age you can't just just act like you didn't do it yeah I'm like when you go to JSU you get like

there's a dude named mr. Katz he orders a whole fucking pizza um and I say whole fucking pizza I mean a whole fucking pizza for me he orders like 10 pizzas for everybody and then I would come in there we would get pizza um they would they would talk about a lot of stuff Israel I can't I don't know what they were talking I don't know what they were talking I don't know what I'm saying is that you're just like Jewish girls I'm You like big ones with the skinny ways. I want to ask you a question about like your first mixtapes, like the first three, like, is there a freedom

in like making art when you're so young? Because you're like not afraid of like being corny? I think you still have, for the kids that I know, the kids that I grew up with, like, we were all like, we already believed that we were rappers. We weren't like gonna grow up and become rappers. Like we were already taking everything that we did super seriously.

So I don't think that there was ever a point where I had, I damn near had more pressure on me when I was making ASA rap and coming, but I never really thought about it. As a young person. Yeah, because you believe that your existence and your identity is so based on this thing that you, that you at least felt like you were when you were in the comfort of like, I go to fucking school every day.

Like, my mom gives me lunch money. Like, versus being 19, being outside, like, having to figure out a way to pay for stuff. You, like, you take it. even more seriously. But yeah, all the way back when I was in the after school programs, I was doing like fucking, what is it called? It was called Young Chicago Authors. You get like prompts and like, imagine all these kids getting up and they're doing poems about like real fucking trauma and fucking redlining. And like we're all like, we're those kids. Like,

but all the way back in 2010, 2009, we're like the kids wearing cofias and being like vocal and being like, we write poetry and we like, we're radical. Like that's the kids that I grew up. And then some kids also that grew up like Lucky and Mick Jenkins and certain people that came out of Chicago that like you know what I'm saying like it was a very very diverse like group of people that were in the like after school shit that I was in rapping and stuff as a young age but everybody took it super serious right because there's such a there's like a kind of a sweet naivety about being a kid where you're like I'm a real rapper I believe in this yeah yeah I believe in this I feel like I think a lot about like with music like it's like for like

gnaz made illmatic yeah 17 right yeah you know and it must be like there's a freedom in expressing yourself as a young person that might like you know what's like you're not afraid of like maybe i'm gonna fuck up something or something like you know what i think it is and no you're right it is a freedom in that you don't have certain knowledge that you you you know think of as as fact or like uh or a restrictions or boundaries about what you put out or what you say or how you say it or when you drop it when you're a kid because there's this little thing in the back of your head that's like you know this shit might not work out you know and not and not as and like how i just did you know what i'm saying as this gesture like oh this

shit might not work out so i'm gonna do what i'm gonna do but like i don't got kids i don't got you know what i'm saying no real responsibilities i haven't tasted the success yet so stand-ups the opposite you know that you know like most most great stand-ups get great like after 40 like it's very rare I've heard that before it's very rare for a young person to be like like Chappelle was a phenom

yeah at like he was a child at like 14 yeah yeah I started standing up in DC where he started stand up

you know Chappelle's my mentor he's your he's your Aristotle yep he's your the toga man he's your toga man

he's your number one yeah what has he taught you a lot of things a lot of like jokes that like if I repeat him I'll get canceled but like he's very very

No, but say it's a quote. Yeah. All right, so Dave Schill was talking about, no, I'm just joking. No, but he's like, I met him in 2014. He had a show before he did the Netflix deal in Chicago. And we bought tickets. He invited me backstage, me and like my whole team. And we stayed there, like, smoking cigarettes and joking around a piano for like,

till like five in the morning. And we stayed connected through that. He was at my wedding. He was like, you know, knows my kids. Like, this is, I was just at his 50th last year in New York. Like, this is like somebody that I really, really look up to. But what he taught me and what I think really shines through in the album is that, like, one of the most important things that you have is self-determination and being able to define who you are and what you're going to do.

And, like, we don't always talk about it because it was so long ago. How old are you, by the way? I'm 32. I'm 38. So, okay, so we, so do you remember when they blackballed him, though? I remember when he went to Durbin. Like. And, but they didn't call it going to Durban.

They called it going to Africa. And there's a sensational. People said he was on crack. And they said he was on crack. Even though he's a devout Muslim and never smoked crack. Well, beyond that, he was the funniest guy in the world. But he did make a decision. And that's what I'm saying is.

Sometimes you make a decision or a left turn, and media can be strong enough to push you in a direction where you feel like you're not in control anymore. Yeah, even though you're literally taking control. Hollywood likes to do that to black people. Yeah, and people period, kind of. No, no, I think black guys. I appreciate you saying that. I mean, I don't know if it's kind of, yeah, yeah. But you're probably right.

I mean, it's, yeah. I mean, he's talked about it before, too. Did he give you that type of advice? He's like, if shit gets too hot, just, like, take time to yourself. He talked to me, like, he talked to metaphors, and I don't want to butcher it, but he talked about this thing about taking your ball and going home. And the metaphor was about, like, you go to the court. The classic, take your ball and go home.

You go to the court, you play. Everybody wants to play with you and use your basketball, and then when they start playing by weird rules and hacking and fouling you and doing all that shit you take your ball and you go home because they could find another ball but is it going to be the same ball hell no I don't they're gonna wait till you come back and ball out like Jordan wearing a four or five and that same spot's gonna be there for you but you have to be strong enough to walk off and take your ball that was one of the things he told me in 2019 that like so but he said a bunch of things he said

this thing about that always quote about the yearbook photos so he says like albums, whether it's a, you know, music album or comedy album, these albums are yearbook photos. They're not the photo of you as a human, even though as an artist, you want to do that. You want to create. It's like where I'm at, eighth grade. It's where you're at in eighth grade. I was busted. But it's important to take that yearbook photo because that's what you are. You're a documentarian. Your whole power is your voice and being able to say this thing happens. So you have to take those yearbook photos so that, you know, you're a 38-year-old. self, you're 48, you're, throughout your life, you can look back and people can get all

these pictures of you at different times. Yeah, what is, what's the distinction as someone that came up through mixtapes? Yeah. What's the distinction there? Because like for me, I understood, like, when I was younger, like, there was like the drought and the dedication and those were just like, you could tell little Wayne was just like taking people's beats and then just doing the songs better, right? Jacking for beats is what they call it. And, but like, it seems like, you know, if you're reading this is too late, it just, to me, that just registers as an album, like, Asset Rap just kind of, in my mind, registers as an album.

Like, I don't understand what the distinction is in people's minds. I'm like a, what do they call it? Not an etymologist, but a linguist. So, like, my whole thing is, like, attributing power to words and, like, or, like, re-evaluating the power of words or removing power from certain words. And so, um, the, the whole mixtape thing was like a... Is it, I'm just fucking around? No, but that's how the world perceives it because it's not commercial. But the, the thing is that it's, it's hella work, it's hell of love, put into it.

Yeah, off of a mixtape. It is crazy. It is crazy. Like, I don't understand, like, what makes 56 nights a mixtape and what makes Dirty Sprite to an album? It says existence. To me. At the time when I was growing up when I was putting out my first mixtapes, it's existence outside of the market while having an influence on the market.

So albums are already within the commercial landscape of like there's a system, there's labels that press records and have control over radio time and all these other things. And then there's, you know, then there's the culture separate from that where I might burn 50 CDs and I know all the gas station, I know all the radio DJs, I know all these people, I'm gonna make this music. You do it out the trunk. I'm moving it out. Exactly.

So that's the mixtape vibe. DJ Paul style. You know so much. I love, I love music. Shout out to MC Hammer. Like, Noges don't really talk about it, but MC Hammer and ask for P. A little bit later. Yeah.

They really, like, started that out-the-trunk vibe. The Memphis? Multistate, like, movements of that shit. The Memphis stuff, those DJ Paul, like, like, Little Flies, like, that is the cool, it's some of the coolest music in the coolest music in the world. It sounds like it's coming out of hell because the production is so bad. It sounds like it's like coming out of the depths of hell. It's some of the coolest music I've ever listened to. No facts. Yeah. It's freeing. Folks, if you know me,

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Open an account in two minutes at chime.com slash T-A-F-S. That's chime.com slash T-A-F-S. Chime feels like progress. So Chappelle's your mentor. Do you have a mentor in rap? My mentor passed away. So my mentor was due. And I'm so glad I get to say this on your show.

No. My mentor is this dude name Mike Hawkins, and we called him Brother Mike. He was a rapper? He's a rapper, poet, revolutionary, mentor in Chicago. And a lot of the people that people fuck with from Chicago out of my era. Vic Mensa, no name, Mick Jenkins, Lucky X. Nico, I'm missing a lot of people. Was juice in your scene?

Yeah. Yeah, juice didn't code the same. after school program I think he I don't think he went to you media because he's from he's from south suburbs so he like came up he's a little bit younger than me he like emo he kind of to me invented that he invented that no there was emo before it but it was emo right emo I'm saying like emo in the culture like in terms of like he's like I think one of the highest selling artist all time like is his yeah and definitely the highest stream of artist all time yeah so his music, and that's not posthumously, that's like during his lifetime, he's a, you know,

he's a genius in his own right. And I got to spend a little bit of time with him before he passed a couple of times and just like got to pick his brain about that whole era. And he was aware of like, like we thought of it as an after school program, but but niggas outside of that shit looked at us like a super group. You know, I'm sure you've heard of, have you ever heard of Saba or pivot or like, like all of these people came from this little like, We used to go to this after-school program and literally just be kids rapping. You were the good kids.

You and Vic and Felix Beaterman, you guys were the good kids in Chicago. To you, for sure. I think the point is, like, there is a value in, like, having a cohort, like a group of niggas that all trying to do the same thing. A scene. Yeah, a scene that, like, that blew up. I'll take a little bit more of it. Who else is in your scene?

Wilco? Shout out to Wilco. They're a little bit older, but Wilco's from Chicago, band. You know what I'm saying? Incredible band. Do you think your fan base knows Wilco? Oh, yeah. Shout out to Wilco, shout out to Jeff Tweedy. You feel me? Dude, yeah, you like John Prime? That's another Chicago guy.

I feel like I know that name. I'm like it right now. He made like country music. You have to go now? No, he's a guitarist, right? He's a guitarist. He's like, yeah, it's like country folk, but he's from Chicago. Yeah, he's a god. He died, he died from COVID. Damn. Yeah, unfortunately.

Maybe that's when I might have heard him. I feel like I heard that name recently. Yeah, yeah. I'm just like in my... How much were you exposed to like, like, old blues? Like, Chicago is such a music city. It's like so rich in history. I'm reading the Keith Richards' autobiography right now.

And like... They signed in Chicago, didn't they? Well, they like, being the coolest guy, I guess, when they were like young men was like having the best records and they literally they couldn't they like had to write to chess records to get muddy waters records sent to england yeah and they like had this music that no one else in their country had heard basically yeah well you know the invention of like celebrity as a musician is all kind of based off of like trade embargoes opening up and being like okay we can move music and media as like an export from america and so people

that had never been to these other countries started becoming famous off of that and famously a lot of the you know like what we think of as like the vanguard of rock were all like influenced by like Chicago records finally coming out of like you said chess records. They are the

they're the goat swagged out white boy they never even got the cultural appropriation like accusations the stones. Yeah. They were just doing it black but they went on to her with like we fuck with this like they were opening up for a little Richard and for Muddy Waters and like literally singing their songs like they and they I think they don't get that because they were always open about

where their influence they loved it yeah they loved it little Richard took the Beatles on tour he's a god that guy 100% 100% Tudy Fruity is a song about but the architect that's what he is the architect the rock and roll man you know that song is it's Tudy Fudy Big Booty I did know that yeah he was a psychopath gay guy that was just an unreal musician yeah unbelievable guy I love Richard he influenced like Bob Dylan too everybody he's the architect of rock and roll that's the like the deep thing about like all music and and as time goes on is like we continue to do shows

like this where we can have conversations it's like I love you know such a rich history of black people making something raw and then us stealing it well popularizing it yeah what everyone call it but like especially gay black guys too. They'll be, watch out. Chicago House is like literally, I didn't know that it was started by gay people, but I wouldn't be surprised because Chicago as like a culturally rich city, like we have always been progressive and always been like on the forefront of like music getting introduced.

So like a lot of the, like you said, deep house, jungle, all that shit comes from house music in Chicago and that comes from the club scene or like the basement party scene. Yeah, it's amazing. Like techno comes from Detroit and House comes from. Chicago and then it was export to Europe and they don't understand that I feel like when you go to like Germany you go to like a like a like a fucking like it sounds like it sounds like the matrix it doesn't sound like there's no like there's no like black there's no soul in it it's super different and it's just like they they're

like consuming something that they don't realize kind of what it was funny though is I will say like Germany and like fucking Poland and I think it's they have a greater appreciation I feel like and knowledge of the history of something. So just yesterday, we was in High Park in Chicago. Germany loves their history, yeah. We met 10, like, multinationals from, like, Korea and Germany and all these other places

that were footworkers. You probably don't know what footworking are. Okay, so, like, think about how small of a, like most people, my fans, don't know what footworking on. I know it for them. But. Can you do it? I can.

I won't today. I showed Herb a video of Derek Rose doing it in high school. Have you seen that video? We've all seen that video. Yeah. Oh, my God. He could have been a dancer. No, we all grew up footworking, but it's such a small subculture of a subculture of a

city in America that the idea that I'm telling you, I met like 10 motherfuckers with thick accents that could footwork better than like a random person that grew up in Chicago because of the influence and the reverence that they pay overseas to, you know, DJ Rashad. That was my guy. That was my guy. Yeah. No, I, I, uh, that music is incredible. Yeah.

Yeah, rest in peace, DJ Rashad. That was my big brother. That was another one of my mentors. You, you knew him well? Very well. My first tour ever was with me and DJ Rashad. Have you ever, do you make music as well? Have you ever, like producing?

Yeah, yeah, yeah. I'm not that good at juke music like that. Like, I got the same, like, two rhythms when it comes making that, but like other rhythms for show. It's cool how they, I don't think it, I don't fully actually buy it, but when they say Rick Rubin doesn't know any of the buttons. He's just vibes. He has to know the buttons after all these years. Yeah, I'm certain. But being so good at chilling that you can be like a super producer,

that's the coolest kind of guy you can be. Not for sure. It is about vibes. It is about who you got in the room in the studio. Like somebody can throw a vibe off or like set the... Dude, we have to go to the studio right now. Do you just set the vibes? Get the guitar.

Get the guitar. No. Yeah, I want to talk to you about like kind of your past. because it's interesting because you got so successful, so young, right? And now you're 32, right? And like, I think that, like, yeah, like, does this feel, like, what is the term comeback mean to you in the context of your new album? That's a good question.

I feel like I guess it just means coming back to the fans. It's been six years since I dropped a project. Yeah. Do you like the fans? I do. They can be annoying, though. What's weird is, like, my fans. Like, my fans, like usually, we talk about the whole thing about trading cards and about the, you know, devaluing the human part of people that we consider to be celebrities or famous or whatever.

But what's weird about my fans is like because it was so grassroots and like me literally hand-to-handing mixtapes and like selling merch and doing small shows and growing over time, my fans are really like, my fans are really, really invested in like me as a lot. person and so when I meet them like I get stories that like fuck me up like stories about how music genuinely saved their life they were in a dark place or you know I got divorced when they got divorced or I got married when they got married or I had this when they had this and like they should go to therapy probably they're telling me their story no but they like it's like I think a there's a a value in being outside when you're me in that that, like, the type of, like, fan that I have is so at random, it's so, like, so many

demographics, so many different, like, kinds of people that, like, I never expect it. And the stories, they'd be like, you want to sit and listen to it. Really? Yeah. People have said that to me that they were, like, I was depressed and suicidal, but the Comtown podcast got me through it. I was like, you should go to therapy. No.

Or listen to a, the coloring book. CTP, I was going to tell you, when I first saw you, I'm like, man. What's that? Come town. Oh, you know, Comtown? I was going to tell you I was going to fucking kill myself. No, shut up, dude. Really?

What? From what? No, I'm just joking. It's not funny to joke about killing yourself, but he gave me hell to clean. It's funny. You can say it. Yeah. How's, you had a mentorship with Kanye as well?

Yeah, yeah. I mean, like, when I was in 11th grade, like, college dropout came out. That's so crazy. I think, and this is a compliment? He was the best. I think you're younger than me. I know you already told me that you're old than me, I look young.

You look young. Yeah, yeah. When college dropout came out, I was in fourth grade. That was the first hip hop out of my ever had. I had, no, well, I had ready to die. I liked Biggie before that. You are moving in the fifth grade. Do you remember when Biggie died?

No, it was on the news. I was not watching the fucking news. I didn't. I was watching Sesame Street. No, no, I remember Mace. I remember like Harlem World. I remember like. That's post Biggie.

That's towards the end of Biggie's career. I remember life after death. Fifth grade, I was sick. I was home from school sick, and I watched Jerry Springer, and then Mori, and then I watched MTV, and then I heard Feel So Good by Mace, and it became my favorite song in fifth grade. That's ill. And then middle school M&M. When we was in sixth grade, Mace had a comeback, and he had a song called Welcome Back, and that was our shit, bro.

He also found God. And breathe, step, shake. Yeah. Breathe, step, shake. Let it go. That's how I had a Harlem shake. Shout out to MIS. Are you from New York?

No, I'm from Las Vegas. I didn't know that. Yeah, yeah. You got the second wave, Mace. I got the... Yeah, you got the first. You got the O.G. That's what I was just saying.

You were already a formed hip-hop fan by the time you got to Kanye. Well, the other thing is the juke, the boys my age. What are you stuttering on? We love... We love rap. Yeah, yeah, yeah. But for me, I'm saying like... The white boys are age.

Imagine your introduction to, like, you say that your introduction was Mace. And like, Mace, low-key has a lot of similarities to... too yay to me and they worked together before. Kanye did the Welcome Back Mace album. Well he, that's the other thing about Kanye that I don't think people say enough is that he could potentially be the best producer of all time as well. It's like, it's yeah, man. It's crazy to me.

It's yay. Are you guys in touch these days? Is he all right? You know what's so crazy is people ask me that? Like I'm his therapist. Like I don't know. I mean like I'm sure that he's fine. I think he just did like a sold-out show in Korea or something like that.

huge show in Korea, but I, like, I haven't, like, I have not texting him recently. That's the point. Yeah, yeah, yeah. You want to tell them I'm chill? Some of them are okay? I'll try and... No, I'm the show. No, I got to say this. Like, the anti-Semitism has talked about a lot nowadays is really annoying for me because it's like, a lot of the time it's just people criticizing Israel, and it's like, it's just a bad faith argument and not what anti-Semitism is.

It's like you criticize a genocide. That's not anti-seman. Definitely two separate things. But the first time, I didn't feel it growing up ever, but when Kanye said, I want the Jewish kids that love me to ask their dads why Ye's mad at us, I didn't get, I got my. So you went to your dad? I got my feelings hurt. I was like, but I love you.

He's, I mean, he's so important to, like, boys my age when we were in high school because he was the first like he was like he went he worked at the gap and stuff yeah he wasn't he wasn't like uh it was like you could be a nerd also kind of be good at music but uh no i adore i mean he's my favorite musician i think like what good artistry should do is make you want to be yourself like i think anybody that ever fell in love with the artist they were like damn it's also it's obviously like oh this person's talented their voice sounds good and shit like that but like i feel like most people for fall in love, like, when it gets past a superficial phase, they fall in love with, like,

artistry and, like, well-written songs and songs that feel like it speaks to them, and they're like, damn, this person is being themselves. And I think, like, no matter who that person was for you, if it was yay, if it was Stevie Wonder, if it was whatever the fuck it was, like, you fall in love with the idea of somebody being themselves. And I think he was, he's always, like, unapologetically going to say the wildest shit that comes to his brain. And I think that, like, for a lot of people, when we were younger, it was like, it felt like empowering. I don't think he was that wild early on. He was talking about, like, he was at college and stuff, and that he wanted to drop out

of art school and something. I wrote my college essay when I was, when I thought I was going to go to college, I wrote it, like, from the perspective of, like, I was like, this is, I'm never going to go to college. I wrote a college essay, that's a repressed memory. I wrote a college essay because I went to a college prep school. So in Chicago, you go to public school for grammar school, and then... You went to a magnet school. Yeah, yeah, yeah, yeah.

And then when you go to, when you go to, and so magnet school is a public school that basically pulls kids from black and brown neighborhoods or different parts of the, from the, of the school system. Yeah. Or neighborhoods to go to a school that has like, you know, that's for smart kids, right? Yeah, yeah, yeah. I went to a magnet school, too. Vives, you feel? It was embarrassing. And then when you go to high school, you could do this thing called selective enrollment.

where you can test if your school is, like, a good school. You could test into, like, another good school where you don't have to, your parents don't have to pay, but you get a good education. And I went to Jones and was, like, exposed to a lot of shit that I wasn't typically exposed to, and it was like a very artsy school. And I guess, like, in that time, like, I learned a lot about,

I think I lost my train of thought. I feel like I forgot what you had asked me. It's fine. You went to a school that inspired you to be an artist. To be an artist. Yeah, Kanye went to art school too, and he dropped out. Yeah, there's plenty of famous. For me, it's like, you know what it was? I'll tell you my age again, when the Harry Potter books were coming up, growing up.

I remember that. He was one year older than me, and I feel like each year he went back to Hogwarts. I was like, now I'm that age. And it's like, yeah, when he wanted to, like, he wanted to clap Cho Chang, I was feeling that kind of way at school. Yeah, you know, like, he wanted to take down Chochang. Yeah. Yeah. Why is that name so fucked up, though?

Why am I talking? I mean, Harry Potter is so racist in retrospect. Yeah. Yeah. Yeah. They ask. But I'm a huge, huge Harry Potter fan. Yeah, me too.

I call myself on a lot of my projects. Harry Potter? The boy who lived. Oh, really? Yes. Who's the Voldemort in your life? Um. King Vaughn.

No, I'm just kidding. I'm kidding. Chill, chill, chill. I'm kidding. I'm kidding. Chill, chill, chill. I'm kidding. Were those guys nice to you even though you got good, you went to a good, got good grades

and stuff? I would imagine it would be a little bit like, I don't want them to think that I'm a nerd. I just be chilling. Look, because I was a nerd too, right? And like the, I used to, because I liked weed. I appreciate that you, because I like, I liked weed. And that's how I got the cool kids to, like, the kids that were being bad. What's the word for like you, like, you vibe with somebody,

but I can't even think of the word. thrilling it's like incredible to be around with what uh what do you mean resonate yeah I'm a friendly guy yeah you feel I feel like you but what I was gonna say is like the way that Chicago operates we all got to you we all got to see each other we all got to work together so like so they wanted you to get good grades they're like I'm proud of you for getting good grades it's not like California I think what you represent is like one niggas be like this a this a good nigga he's gonna go to the NFL like

Kendrick like kind of the streets like Kendrick right I hear what you're saying is like when I first saw the don't like video I was like it was scary to me because there was no girls in it and there were no there were just boys I was just talking about that they were an empty apartment there was no hose like rap was always about trying to get a lot of

girls right and I'm like these kids just have guns and they have their own apartment whose apartment is that they're children and they I if they and they're your age demographic too and you and Vic must have just been like a little bit butterflies, no?

Before you met the lads? Yeah, it was, I think it's like I was afforded. You could be real about this. Yeah, no, I mean, they're also younger than me. Oh, they're younger than me? That makes it even scarier. By like two years.

That makes it scarier, too. Because you know the younger kids have less of a moral compass. To be honest, they got on before us. Like, if I'm being super real, if it wasn't for Keith, of course. Von was later, but Keith,

Dirk is kind of my same. generation and not generation we all like close in age but like he was like that second wave but like keith and king louis both blew up out of chicago around the same time 2011 2012 like 14 15 years old louis's older than us but but keith yeah younger than me and around that same time was when mtv started coming to chicago to do documentaries like a documentary series on chicago the vice one is really cringe vice one is crazy i'm not in the vice one is racism the Right's one is like... Most of those documentaries are racism.

We're here at O. Block. Where the child murders are happening. Yeah. Like, I saw an interview recently with Sosa where he's like... Like, when we were consuming it from the outside, I was like, people... I think people said that he was autistic, and that's why he's so good at hooks. That's called racism. Well, no, but then it just...

He was like... There was an interview with him last year, and he's like, yeah, I just had to get out of Chicago. He's like, now I live in L.A., you know, he's just, he was, like, on a lot of drugs, I think, as a kid, probably. Yeah, and it's also environment. Like, you got to realize, like. He just seems so annoyed. Where you said he's doing great. Vegas, right?

Yeah, Las Vegas is super different from New York, and even though it's close, I'm sure, super different from L.A. When I, and when I say L.A., I mean, like, in terms of Hollywood, like, in terms of how many opportunities there are to be on camera. Well, I feel like Las Vegas has happened, and I'm not saying it's not a big city. It's just like Chicago. it's a big city but it's not a media export so like you so imagine when like if Vegas had a Keith if like there was somebody that was so you know Jimmy Kimmel Jimmy Kimmel it's like a Jimmy Kimmel's from Vegas yeah yeah yeah crazy place great Greg Maddox who else is from Vegas a panic at the

Disco the killers CSI Las Vegas shouts out CSI Las Vegas they were kind of the King Vaughn of my childhood I think there's a, there's a, there's a time period that happened where Chicago became the epicenter of like, of hip-hop music and what was going to be the new thing that white folks was scared of. And the, and that popularity grew so many careers and really created a scene in Chicago that like, you know, I think like put us at the forefront of music for a long time. And even to this day, like, I think Chicago slang, Chicago artists, like, still have a great influence. But it's not New York. It's not L.A. So I think...

Well, for a long time, it was only New York and L.A., that Atlanta for a long time. A little bit Houston. Yeah. And then, yeah. Everybody has their regional, you know, points in time. It was just common, basically. And then Kanya. Kanye, common. I feel like... And then, you know, you, you were with someone for 22 years. who your ex partner your ex-wife or you knew her for 22 years yeah we grew up in Chicago together so I've known her for like most of my life yeah so in doing the research for this like I saw like the way people are so wrapped up in like you're

like it has to be a product of celebrity that people are like I thought this was relationship goals but that you know like that people are like so invested in it in a certain way and the first thought I had was like going back to that future point Right? Future is like You think that people are so wrapped up in your shit because they thought

of you as like he's the good happy go lucky guy And I think that's super possible I think like there's an outside Like when you put out When you publish something You publish the work

But you also just published the cover Right? So it's like people don't have to open the book To like know what everything's about They just have to see it on the shelf And that metaphor I'm just saying like If I'm a celebrity like everybody that watches that interview doesn't necessarily do a deep dive into my music they're just introduced to me in this video and so I think like with celebrity and with like personal lives being shared I think that there's people that don't have a full context of anything other than maybe something that they've read or like something that I've put out there about how long we've known each other or you know what the relationship feels like yeah versus like people that are my fans know like I was you know I got

married like four years after I had already had my kid like I've known this person for a long time we've been in and out of things but we have like a you know really really strong relationship and I think that when I was very public about being married to her and being happy about getting married and being you regret do you regret being so open about your personal life no I'm a rapper like that's a that's a big part of being a rapper is being open about your public life and being I'm sorry about your personal life and being open to criticizing to analyze the real world

as well as your own vulnerabilities. It's a little bit of annoying, right? Like, you're going through a personal experience and then people have opinions on like your personal life. It's only annoying when you don't like the opinions, but like when they're good opinions, don't you like it? No, I don't care what a stranger thinks of my, my, you guys turn the cameras on since the niggas don't care?

No, no, I'm just kidding. I'm kidding. I'm kidding. No, no, I'm just, but I'm just making a point. I was just joking. We got a rap. Sorry for saying that. I was just making, I was making a point. I wasn't, we should have read soon, but I want to go,

I want to get back to the point I made about Future, right? Like, no one's team Russell Wilson. Everyone's like, yeah, future he's got, he's, you know, he's, he's, he didn't make March Madness, but like, people love Russell Wilson. What I'm saying is, like, people are like, what I found was like, and I didn't know about this because I don't, like, consume this type of media, but, like, the response to your divorce is like that people were, like,

were, were, like, felt betrayed or something because it was relationship goals. And it's like, get a fucking life. Like, it's like, I mean, future doesn't get that, right? Because it's like, the assumption is, is like, he has to get pussy. I was making this point earlier. Like, everything that we see, like, celebrities are the flagship of conversation. We push product, right?

So when any headline that you get from a blog or from a shade room or anything, it's pushing a story, but it's also pushing a specific moral boundary where people have to feel you know hot or cold on either side and so everything is politicized even if we're not about politics that's just but that's the way the media works it's bad for society though no one would like no one was like facts no one like there was the beetles or like Elvis Presley no one would like felt like personally betrayed by their personal lives like that there was a there was a distance between the the artist and then the audience and I think for sure probably the internet early yeah probably the

The internet has blurred that line. Remember when, like, women couldn't wear skirts past their knees on TV? Like, remember when, like, people couldn't be. I don't remember that. Well, there was a time when, like, it was controversial to have a black person on TV on sharing the same set as a white person. So I'm saying, like, through media, as it's, as society and culture has revolutionized, there's been more and more, like, a close relationship to TV, and it's grown as society becomes cooler with things that used to be taboo. Are you single gentleman now?

Yeah. Have you considered doing what the god did? You get like a girl that looks a little bit like the last one and then make her be naked? What? That is hilarious. So you've traveled a lot, right? You said that I've seen other interviews with you. Like Ghana was a heavy influence.

Super, yeah. Tell us about, like, the, this is the CD? So this is the CD, right? Yeah. And people don't typically have CD playroom. I'm sure you probably don't. So what I did with this project was in an attempt to create a physical handoff between me and my fans, because that's what people, you still really like, is like, I could get something that I own forever that I got from this artist that I love.

Something physical. I gave them some physical, but more importantly, I wanted to. to give them something that was functional. So this has NFC technology. I'm sure you know what NFCs are. National Football Conference. That's incorrect. So what NFC is, it's a near field communication.

So what you could do with this CD is you could just tap your phone straight to it without like using a QR code or anything and a link will populate and come down and it'll take you to the album so you can Bluetooth it straight from your phone. So at any point, like if you keep your CD, you could play it on any speaker. You're the first person ever? First person. Really?

Yeah, yeah. You invented a new thing? It's like when two iPhones touch and then you. It's the same technology. Like when you use like your, when you tap to pay. Yeah. When you do, when you touch another person's, you, a sweet.

And you feel and it's like a hot girl's. Thing happens, it vibrates and stuff. There's a vibrate, and you're like, are we fucking right now? It's a little bit like that. Facts. So what do you, like, your first single is, is called tree. Right? My first song is called Tree. So it was a record that took a long time to put out that I love dearly and I feel like is a good thesis for the project. It's not, it doesn't

cover all the topics of the project. But the song itself is about, you know, my mom, my, you know, how we grew up with these certain taboos around wheat, you know, like how weed is represented it when it comes to hip hop artist and black culture versus how we look at it as a financial like yeah exactly like a you know so there's a there's there's a separation there but it's also mainly uh about the inequities in the cannabis industry um how niggas go to jail but other people make billions is there's a there's a there's a over our i'm sorry there's an overarching disparity when it comes to ownership in agriculture, black farmers, access to produce, access to fresh foods, and access to the monies that those things make.

And there's a microcosm of that is in the cannabis industry, but there's like, there's a larger conversation that I'm having that has a lot of connection to sharecropping and to slavery and just the way that capitalism was allowed to go crazy in this country. This whole album, it's called Star Line. It's named after the Black Star Line, which was started by Marcus Garvey in the 20s. He started the first ever black-owned shipping and trading company. He owned these big-ass ocean liners that would send beans, coffee, all types of stuff for other companies to South America and Central America. Did he print off that?

He did. He did a place called... Dirk has a trucking company. Dirk does have a... So all of this is in line. There's a lot of actual trucking companies that are named Starline because that's typically like a freighting company name. And the point of this project is to kind of like for the first time, I think, at the forefront of hip hop highlight black entrepreneurship, black self-determination. And I think just shining.

Like, I feel like that's what you see this. So this was painted by Brandon Bro. It's the same art from Chicago. Same artist. Same artist. Same artist. Yeah. And what he really focuses on is the composition, which is always typically the same with like

the portraiture in the center. But he's very really focused on like the fucking. That's the Aurora Borealis. Aurora Borealis. Also known as the Northern Lights, if you're not a nerd. Have you ever seen it? I've never been there. You got to go to Iceland or something.

We gotta go Iceland. Boys trip, dude. I like the way you said it the first time. Ice trip. Iceland. But Ladd's trip. I think we should go back to illegal personally. It's not cool anymore now.

No fact. It's too much we. You walk around New York, it's just like these, the dispensaries, the aesthetics. They don't have good, they don't have like cool, like they look gross. It's a government scam. I think it is, actually. It's a government scam. Remember when they legal?

legalized. I keep saying remember like you were there. I'm just saying like remember in history. I remember all of it. The end of prohibition. Yeah. Same vibes. They did that because of the great depression. They did it because of the commercialization of alcohol and how much they could, you know, viably make off of, you know, not allowing gangsters or black folks to be the only people making money off of liquor. Really? I think us boys were making a little bit of money too. Hey man. Get in where you fit in, you know. I think us boys used to print a little bit off of that. Us boys, too. I mean, but it must have made it, like, hitting beer so cool when it was illegal. You could also go blind because it's somebody's uncle

making moonshine. So, the regulation isn't bad, but also you don't know who's regulating. I think that's an anti, anti- That's anti-beer. That's the anti-beer propaganda, dude. Big beer?

Yeah. Beating off does not make you blind. Uncle's moonshine does not make you blind. Anyway. Chance, we have to go. Adam Friedem. Once again, she's upset. me? Are you upset at me?

Maybe a little bit. Did you make her upset last time? No, no. We were just... This my home girl. Herb was like, I could go all day. He's like, no, we're staying. I was like, I can't.

No, yeah, we're late to, we gotta go to this premiere. Where do you have to go? We're going to this premiere. Shit is huge. Is green mean that it's on? Is this our cam? It's not live, so you can edit, however. But basically, hey, make sure you get my album, Star Line.

It comes out August 15th, the same day as Spike Lee and Denzel Washington's new movie, I'm going to see the premiere of right now. You're gonna go right now? Yeah, we gotta, that's what we're late. You got a plus one? I don't have, come on, bro. I had a plus one, but I already gave it to Taryn, so.

Really? Oh, you're better friends with it. Yeah, I guess so. But, enjoy it, dude. I'm a big fan of Denzel Washington, actually. He's one of my favorite actors. I'm gonna name my first son, Denzel Freeland. Let me write all this down so I could tell him on us.

My guy. I appreciate you, man. Thank you so much, man. I appreciate it. I appreciate it. Thank you. Thank you.