CHANCE THE RAPPER Talks Chicago, Mixtapes and Mentors

Summary

The Adam Friedland Show

Episode: CHANCE THE RAPPER Talks Chicago, Mixtapes and Mentors

Date: October 31, 2025
Guest: Chance the Rapper

---

Episode Overview

In this engaging episode, Adam Friedland welcomes Grammy-winning Chicago artist Chance the Rapper for an expansive discussion on Chicago, the politics of art, mixtape culture, mentors, personal philosophies, and the complexity of fame. The conversation blends humor and insight, drawing out Chance’s personal journey from the South Side to international stardom, and exploring the shifting nature of music, celebrity, and social engagement.

---

Key Discussion Points and Insights

1. Growing Up in Chicago (06:46–11:45)

• Chance’s Background:
  • Grew up on 79th street, same as G Herbo.
  • Emphasizes similarity with peers: "We're both from 79th. I've known Herb for a really, really long time." [09:00]
  • On giving back: both he and his peers are involved in community projects, mental health, youth mentorship.
• Family and Political Influence:
  • Deeply political upbringing, with his dad working for Obama, Harold Washington, and Rahm Emanuel.
    • "He worked for Obama. He worked for Harold Washington. He worked for Rahm Emanuel." [09:41]
  • Grandmother’s activism propelled the family into community work, reflecting the “Chicago’s super politically active space” [09:59].

---

2. School, Socialization, and the Greatness of Bullying (14:21–18:45)

• Chance on His Education:
  • Attended magnet and selective enrollment schools that fostered creativity: “The influence of school...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.” [15:25]
  • Discovered Jewish Student Union for pizza and community (“…there’s a dude named Mr. Katz. He orders a whole fucking pizza for me.” [19:22]).
  • Young Chicago Authors afterschool program (“We write poetry and we’re radical. That’s the kids I grew up around.” [20:36])
• On Bullying, Social Skills, and Personality:
  • Adam's comedic riff on the necessity of adversity: “Apparently they’re trying to take bullying away. These kids are going to become sociopaths. You develop a personality by being terrified, right?” [18:06]
  • Chance agrees with the role hardship plays: “No facts…That’s what we’re built on.” [18:06, 18:28]

---

3. Mixtapes, Artistic Freedom, and Identity (20:04–28:12)

• First Mixtape and Early Creativity:
  • “My first mixtape was called 10 Day. It was about a suspension from high school for weed.” [14:21]
  • Describes the seriousness of early work, even before fame: “We already believed that we were rappers.” [20:04]
• The Evolution of ‘Mixtape’ v. ‘Album’:
  • Chance mulls over how the culture perceives mixtapes as less “real”: “I’m like a... linguist. My whole thing is attributing power to words…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.” [26:52–27:19]
  • Personal definition: “Its existence outside of the market while having an influence on the market.” [27:31]
• Influences:
  • References to Chicago’s grassroots style—out the trunk distribution, shout-outs to MC Hammer, Memphis mixtape culture.

---

4. Mentors: Dave Chappelle, Brother Mike, and Community (22:45–34:03)

• Chappelle as Mentor:
  • “You know, Chappelle is my mentor.” [22:55]
  • Describes Chappelle’s lessons about self-determination and control over one’s career:
    • "One of the most important things that you have is self-determination and being able to define who you are and what you’re gonna do.” [23:08]
    • On making records: “Albums…are yearbook photos… not the photo of you as a human.” [25:04–25:55]
• Brother Mike Hawkins:
  • Pivotal figure in Chicago’s music community.
  • “He was a rapper, poet, revolutionary mentor…a lot of the people that people fuck with from Chicago, out of my era…Vic Mensa. NoName. Mick Jenkins. Lucky…” [32:39]
  • After school rapping scene described as a “cohort,” a “scene” that blew up. [34:10]

---

5. Chicago, Music Lineage, and Cultural Appropriation (35:08–39:33)

• On Local and Global Influence:
  • The importance of Chicago’s blues, jazz, house, and rap scenes.
  • “All music…as time goes on, it’s like we continue to do shows like this… there’s such a rich history of black people making something raw…and then us stealing it, popularizing it…” [37:04]
• European Reception of Chicago Music:
  • “Germany and...Poland…they have a greater appreciation, I feel, like. And knowledge of the history of something.” [38:18]
• Footwork, DJ Rashad, and Subcultural Transmission:
  • “We all grew up footworking…it’s such a small subculture… But I met, like, 10 with thick accents that could footwork better than a random person that grew up in Chicago because of the reverence they pay overseas…” [39:01]

---

6. Navigating Fame, Fan Relationships & Personal Life (40:45–57:47)

• ‘Comeback’ and Artist-Fan Relationships:
  • On relation to fans: “My fans are really, really invested in, like, me as a person...I get stories that like me up...music genuinely saved their life.” [40:45–42:10]
  • The blurred boundary between personal life and public perception: “When you publish something...people don’t have to open the book to like, know what everything’s about...they just have to see it on the shelf…” [54:53]
• Chance on Celebrity Intimacy and Internet Culture:
  • Talks about how media frames celebrity narratives, politicizes every detail, and fosters parasocial attachments.
  • Reflects on public reactions to his divorce and how celebrity culture differs from previous generations:
    • “Everything is politicized, even if we’re not talking about politics. But that’s the way the media works.” [57:17]
    • “There was a distance between the artist and then the audience. And... the Internet has blurred that line.” [57:47–58:09]
• Quote on Sharing Personal Life:
  • “That’s a big part of being a rapper is being open about your public life...being open to criticizing, to analyze the real world as well as your own vulnerabilities.” [56:04]

---

7. The New Album ‘Starline’, Black Entrepreneurship & Artistic Innovation (59:11–64:43)

• Physical Album Innovation – NFC-Enabled CDs:
  • “What I did with this project was…create a physical handoff…This has NFC technology...you could just tap your phone straight to it…a link will pop…take you to the album.” [59:11–60:09]
  • Adam is genuinely impressed: “You invented a new thing.” [60:12]
• Lead Single “Tree” and Album Themes:
  • Discusses the single “Tree” and its focus: “The song itself is about my mom, how we grew up with these certain taboos around weed...the inequities in the cannabis industry. How niggas go to jail but other people make billions...there’s a larger conversation…about ownership in agriculture, black farmers, access to produce, access to fresh foods and access to the monies that those things make.” [62:32]
• ‘Starline’ as a Concept:
  • “The whole album…called Starline…named after the Black Starline, which was started by Marcus Garvey...the first ever black-owned shipping and trading company.” [62:32]
  • Album aims to highlight “black entrepreneurship, black self-determination.”

---

Notable Quotes & Memorable Moments

• On Being Yourself:

  "What good artistry should do is make you want to be yourself." (Chance, 46:05)

• On Chappelle’s Philosophy:

  “Albums...are yearbook photos...not the photo of you as a human.” (Chance, quoting Chappelle, 25:04)

• On Mixtape Culture:

  "To me...it's existence outside of the market while having an influence on the market." (Chance, 27:31)

• On Precariousness of Fame:

  “Media can be strong enough to push you in a direction where you feel like you’re not in control anymore. Even though you’re literally taking control.” (Chance, 24:22)

• On Social Media Era Celebrity:

  “Everything is politicized, even if we're not talking about politics. But that's the way the media works.” (Chance, 57:17)

• On Innovation:

  “First person ever...You invented a new thing.” (Adam, 60:12)

---

Timestamps for Important Segments

• Chicago Upbringing & Family: 06:46–11:45
• School, Socializing, Bullying: 14:21–18:45
• Mixtapes & Artistic Formation: 20:04–28:12
• Mentorship, Chappelle, Brother Mike: 22:45–34:03
• Chicago Music & Cultural Appropriation: 35:08–39:33
• Navigating Fame & Fan Intimacy: 40:45–57:47
• Album ‘Starline’, Black Business, NFC CDs: 59:11–64:43

---

By-the-Minute Highlights

• 20:04 – Chance shares how his seriousness about rap began in high school mixtape days.
• 23:08 – On what Chappelle taught him: self-determination and owning your story.
• 25:04 – “Albums are yearbook photos...not the photo of you as a human.” [Quoting Chappelle]
• 27:31 – On what makes something a mixtape versus an album.
• 32:39 – Honoring Brother Mike as a “revolutionary mentor” for Chicago’s scene.
• 40:45 – Reflections on ‘comeback,’ his break between albums, and meaning of artistic return.
• 46:05 – On the value of any artist making you want to be yourself.
• 60:12 – Presentation of NFC-enabled album—tech meets physical memento.
• 62:32 – Description of “Tree” and the political/economic structures underlying album ‘Starline.’

---

Closing

Chance wraps with details about his innovative release (“Starline”), themes of black self-determination and entrepreneurship, and a nod towards Chicago’s past and future. The conversation is insightful, riddled with humor and candor, and laced with stories about creative kinship, music’s social impact, and surviving—and thriving—in the shifting world of fame.

Final plug:

“Make sure you get my album, Starline. It comes out August 15, the same day as Spike Lee and Denzel Washington’s new movie that I’m going to see the premiere of right now.” (Chance, 65:28)

---

For fans of hip hop, Chicago culture, and the modern complexity of fame, this episode offers laughter, depth, and realness—just like the music that made Chance a household name.

Transcript

[A]

You were with someone for 22 years.

[B]

Who?

[A]

Your ex partner, your ex wife, or you knew her for 22 years?

[B]

Yeah, we grew up in Chicago together, so I've known her for, like, most of my life. Yeah.

[A]

Are you single gentlemen now or.

[B]

Yeah.

[A]

Have you considered doing. Doing what? 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?

[B]

That is hilarious.

[A]

Hello and welcome to the Adam Friedland Show. Guys, I'm Adam Friedland. Before we get started, as always, I gotta 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 AdamFriedland Show. Check it out. It's good. It's cool. My guest this week is Chicago artist Chance 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 round the world. Months later, tensions have remained high between Vlad and G Herbo, who have 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.

[B]

Hello?

[A]

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. Whatever the. Whatever the misunderstanding was. Do you guys ever dj or is it just screen name?

[B]

Well, I had a long history of DJing before Vlad TV started.

[A]

Well, I'm getting married this year and perhaps. 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.

[B]

I'll show up to that.

[A]

Okay. Well, sir, Sir, I. I feel. I feel like my conscience is cleared and have it. Have a great day, I think, I guess. 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 Roe Roe Sparks are a 2 in 1 prescription treatment for guys who need a secret weapon. 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 Rose Sparks dissolve, they work in 15 minutes on average. They give you the boost to last longer, and they can give you bigger, longer erections. And sparks stay active in your system for up to 36 hours. So you can go back to back round after round and be ready the morning after. Folks, I've been pretty busy on the show, you know, I haven't had a lot of time to have sex, you know, but once that starts up again, I think in the quarter 3, 20, 29, having a big boner is the way I want to be doing it. And doesn't it sound great that there's a product that works as fast as 15 minutes and it lasts up to 36 hours. And it lasts up to 36 hours, which I can assure you is not how long I last.

[B]

With a woman.

[A]

Best part is it's done 100% online, so there's no awkward conversation with in person providers. If approved, treatment ships directly to your door. If prescribed, new sexual health patients get $15 off your first order of Sparks. On a recurring plan, connect with a provider at Ro Co Tafs to find out if prescription roast sparks are right for you. That's Ro co Tafs for $15 off your first order. And ladies and gentlemen, our next guest is a Grammy award winning, multi platinum diamond certified, I believe. Yeah, Diamond. That's even better than platinum, guys. Diamond certified recording artist, ladies and gentlemen, Chance the Rapper, everyone. Thanks for coming. Thanks for coming, sir.

[B]

Oh, thanks for having me.

[A]

Thanks for coming, sir. Appreciate it. And so I just had Shasta be standing. I just had. No, no, sit down, please. I had Herb on the show and I paid tribute by giving him a bottle of 1942.

[B]

Have you had that before? 1942?

[A]

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 Kaza Azul.

[B]

I'm familiar.

[A]

Do you know this one?

[B]

It's got the ding.

[A]

I see it on, like, Real Housewives kind of shows vibes. Yeah. Like a rich lady who's about to cheat. Yeah, yeah. She like the pool boy. So 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 5. But we're gonna be having this. What is. It's ceramic. So let's do it. You want to do a l'? Chaim?

[B]

Yeah.

[A]

What we do is we drink the bottle.

[B]

Yeah, you just. Oh, you.

[A]

You do grace?

[B]

It's sort of. Yeah, sort of. Same thing. So just tap the bottle.

[A]

Do you want me to do the Jewish stuff?

[B]

That was it. That was the Jewish bang.

[A]

No, no, I mean the Jewish prayer on tequila. Yeah. 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.

[B]

That was more like. That's like some kid I know. Blessing the bottle. That actually has.

[A]

I don't know, 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?

[B]

That's a good question. I think you do.

[A]

You do. I think in Judaism too, for, like, for different. This is the most boring conversation. Let's go.

[B]

Let's have a look each other's faiths.

[A]

I don't have. I don't. I don't faith. I don't faith. You faith you're a God fearing gentleman.

[B]

Amen. Yeah, for sure.

[A]

Amen. But we found out today. This is really blowing my mind. You were in the Jewish Student Union?

[B]

I was in the jsu.

[A]

Why?

[B]

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?

[A]

Yeah.

[B]

You feel me? Like, Like, I was on lit mag. You know what lit mag is?

[A]

You got good grades?

[B]

I didn't get good grades, but I was into things. So I would be into something and. And I would go into. I would just go and, like, join. And lit mag was like all of the. The, like, quirky writer folks at my school.

[A]

Yeah. Girls were there. Were there, like, the class. The glasses girls. Indie girls.

[B]

I would like the indies the indie girls. I was into the indies.

[A]

The indie girls.

[B]

24 girls.

[A]

Here we go. The bisexual lighting. The purple. Sorry. Okay. Thank you for coming on.

[B]

Thank you.

[A]

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 going outside boys.

[B]

It would seem that way. That's not the truth. We're from the same hood. We're both from 79th. I've known herb for a really, really long time.

[A]

He's a great guy.

[B]

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.

[A]

Yeah.

[B]

And we talk, like, once a week. That's my dude.

[A]

Let's get to, like, your upbringing, your family and stuff like that. Like, your father was involved in politics. Both of your parents were?

[B]

Yeah, yeah, my mom a little bit, but my dad, yes, for sure.

[A]

He worked for. He worked for.

[B]

He worked for Obama. He worked for Harold Washington. He worked for Rahm Emanuel. So my dad, really. I guess I gotta 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.

[A]

In Chicago.

[B]

In Chicago. And so, you know, Chicago's super politically active space. This is where Fred Hampton is organizing the Black Panthers, where Stokely 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. For Barack, too. And so that's your boy Barry.

[A]

Barry.

[B]

That's not my boy. But, you know, you met.

[A]

You've met the Goat before.

[B]

I met the. I met the Goat before for sure.

[A]

Really? What's his. What's the energy? Like, what's What's.

[B]

He's just like. He is on TV.

[A]

No, he's not.

[B]

Yeah.

[A]

As a guy.

[B]

100%. Yeah.

[A]

He's like.

[B]

Or maybe he's just like. He is.

[A]

He says, let me be clear to you. Yeah. And he does this.

[B]

He does the really. I don't got the Brock impression.

[A]

What do you think he's up to these days? He's got to be so bored.

[B]

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, you're.

[A]

Best friends with Obama.

[B]

Yeah. That's what people. That's what. That's what I feel like. That's the. No, I'm. I'm honored that they gave me like, they gave me some. Some shout outs in the past. I got a humanitarian award that.

[A]

Did you make one of his best of lists of for the year?

[B]

I was on a playlist once.

[A]

Yeah. That's nepotism. Your dad. It could have been.

[B]

People know people, you know what I'm saying? Like, that was really what I got into the industry for was like to.

[A]

Get to know Obama to get on the playlist.

[B]

You know what I'm saying?

[A]

Obama playlist of the year. Yeah. Yeah. What else did he have on that March Madness?

[B]

I think he did have.

[A]

No, he did it.

[B]

I feel like he did have.

[A]

No, he did it.

[B]

Maybe not March Madison.

[A]

He has like smart stuff on it.

[B]

No, he doesn't have dumb.

[A]

He doesn't. I'm on so many drugs.

[B]

Like, wink, wink on there.

[A]

He's a wink, wink. He has like, I cheated on you, but it's only. Cause I'm depressed. The narrative of future is the best. Yeah. Because you still feel bad for him. He's like, yeah, he's a pussy. I'm so sad. That's why I had to get so much pussy. It's great.

[B]

So much is hilarious.

[A]

He's like, I just. It's because I'm so. Cause I feel so lonely. And you're like, you buy it too.

[B]

Can I vape on your show? Is that a thing? I feel like this is more.

[A]

You hit.

[B]

We're drinking, dude.

[A]

To have some more. Yeah, of course, dude. Are there a lot of rape rapper. Are there a lot of rapper vapors? Vape. I did. Are there a lot of vape Rap Vapor rappers.

[B]

Vapor rappers.

[A]

You hit Jewel. That's old stuff.

[B]

Yeah, I'm definitely. I'm like, 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.

[A]

It made me so addicted. But now I started Upper Deckies.

[B]

Here's the problem. And this is gonna. This is gonna lose us all our tobacco sponsors.

[A]

But the.

[B]

I don't have the issue. I'm joking. The issue is that, like, think about this. Because you used to smoke cigarettes, I'm guessing. Yeah, so.

[A]

Which are cool. They look sick.

[B]

They look way cooler. Faster death. The thing is, like, with cigarettes, it's fine. Going to, like, like weaning yourself off, you know, you get, like, the patch. You know what I'm saying? Or 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 hella people quit smoking cigarettes, but this doesn't buy. This has the unlimited. This is just a cart of cart.

[A]

You could do it in bed. I did it in bed. My girlfriend would be like, you disgust me. It's the least sex. No. It's like, you're not like Humphrey Bogart for hitting a jewel.

[B]

I get that reference.

[A]

No. Girl's 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 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?

[B]

I thought you were going to go in a different direction. What I would say is like, I thought you were going to say. So my first mixtape was called 10 Day. It was about a suspension from high school. For weed.

[A]

For piffin.

[B]

For weed? Yeah. For piffin.

[A]

I got suspended too, but I. Smoking weed. No, for. 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 ass ratted on me to the school.

[B]

This story took 10 left turns. Like, I thought you was going to get in trouble.

[A]

Six things I've never. I don't.

[B]

You said you forged your family report card and your dad told on you to your school.

[A]

He went to the dean who looked like A mole. This guy looked like a mole.

[B]

That is crazy.

[A]

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.

[B]

Yeah, I think I was. Yeah, I was 18. I started at the end of my high school, senior year of high school, and put it out, I think when I was 19.

[A]

Yeah.

[B]

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.

[A]

They're losers.

[B]

Yeah.

[A]

Let's be honest. Teachers are losers.

[B]

So. So just let the record show. I don't. I don't think they are.

[A]

I mean, some of these guys we had.

[B]

Oh, yeah, sorry. No, my bad.

[A]

Yeah, yeah.

[B]

My teachers was losers in general back in the day. Back in the. I'm talking back in the day. I'm talking in 1943, 1944, in antiquity. I'm talking about, like, Stone Age. I'm talking about. I love saying. I'm talking about it. And you elevate. Sounds like a song to me.

[A]

Go ahead. This is a track right now.

[B]

I was gonna say, like Aristotle. Okay.

[A]

Pedophile. Yeah.

[B]

Okay, so let's. So let's. Let's twist. Let's make a pivot. Okay, let's go.

[A]

He was a teacher, though, right?

[B]

Yeah, that's what I was gonna say. Okay, let's go. Talus of Miletus. Right. What used to happen was one person would teach one person. Right. So you get that one on one education. 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 sit all day with an adult who just got a divorce. And so 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.

[A]

Whatever. It's. Come on, dude.

[B]

The point that I'm making, though, is, like, it's. I think the issues with teachers are that they're overwhelmed and they're human beings. So when they're. You know what I'm saying, Getting fucking. Fucking Markers thrown at them and TikTok challenged all over. Like, at a certain point they, like, they check out. And I think that, you know, back in the day, Post Stone Age, pre1941, there was a lot more, you know, like, direct education or at least like, sizable.

[A]

To just be with one adult guy wearing a fucking toga. That'd be annoying.

[B]

No, that would be whack.

[A]

I would want girls to be there and kind of try to have a girl mentor.

[B]

Girls could teach you too.

[A]

No, but you're like, but you can't. I mean, I guess what I'm saying is like, a school socializes you, right? Like, yeah. The fun part about school is that you're terrified to get beat. Like, get called gay when you're in sixth grade, you're trying to survive and it makes you a regular human being. Right.

[B]

No facts.

[A]

Apparently they're trying to take bullying away. These kids are going to become sociopaths. You develop a personality by being terrified. Right? That's.

[B]

No, I mean, bullying away is really funny.

[A]

That's what I. I'm going to send my kids.

[B]

They're trying to take bullying out of the schools.

[A]

I did read that you have to bring bullying back because that's really where you're.

[B]

That's what we're built on.

[A]

I need through like, like, Darwinism to find something to survive. You're like, I'm gonna get really good at rap. And I was like, I. I'm like, gonna. I. I have to do something.

[B]

Better be funny.

[A]

I have to be funny.

[B]

Facts. I fucking feel you.

[A]

Right? So, like, if you send your kids to one of these goddamn $60,000 a year schools where they're told that they're amazing, they're gonna be fucking sociopaths.

[B]

Facts.

[A]

You have to tell them that they suck. And the teacher has to be a loser going through a divorce.

[B]

Yes. That's how we got here.

[A]

That's. Sorry, that's my rant on schools. No, but like, you were also in writers programs and stuff like that.

[B]

Yeah, right after school. Like the fucking Jewish Student Alliance. Jewish Student alliance was more for the pizza. There was a. There was a Jewish pizza. No, dude, in this day and age, you can't just.

[A]

Just act like you didn't do it.

[B]

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. 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 and get pizza. They would. They would talk about a lot of stuff. Israel, I can't. I don't know what they were talking about. I don't know what they were talking about. But what I'm saying is that you.

[A]

Just like Jewish girls.

[B]

You like Jewish girls.

[A]

Big ones with it. Big ones with a skinny waist. I want to ask 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?

[B]

Is that 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, going to 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 acid rapping and combat. 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.

[A]

Yeah.

[B]

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. Yeah, we're like the kids wearing keffiyehs and being, like, vocal and being like, we write poetry and we're radical. That's the kids that I grew up around. 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? It was a very, very diverse group of people that were in the after school shit that I was in, rapping and stuff as a young age. But everybody took it super serious.

[A]

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.

[B]

Believe in this.

[A]

Yeah, yeah, I believe in this. I feel like I think A lot about, like, with music. Like, it's like for like, Nas made Illmatic 17, right?

[B]

Yeah.

[A]

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.

[B]

Like, you know what I think it is? And.

[A]

No, you're right.

[B]

It is a freedom in that you don't have certain knowledge that you, you know, think of as. As fact or like a. 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 might not work out. You know, and not in a not as. And like, how I just did it. You know what I'm saying? As this gesture. Like, oh, this 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, I'm saying no real responsibilities. I haven't tasted the success yet.

[A]

So stand up is the opposite, you know, that you don't like most. Most great standups get great, like, after 40. Like, it's very rare.

[B]

I've heard that before.

[A]

It's very rare for a young person to be like. Like Chappelle was a phenom.

[B]

Yeah. Like, he was a child probably, like, 14.

[A]

Yeah. Yeah. I started stand up in D.C. where he started standing up.

[B]

You know, Chappelle is my mentor.

[A]

He's your.

[B]

He's your Aristotle mentor. Yep.

[A]

He's your. Your.

[B]

The toga man.

[A]

He's your toga man. He's your number one.

[B]

Yeah.

[A]

What has he taught you?

[B]

A lot of things. A lot of, like, jokes that, like, if I repeat him, I'll get canceled. But, like, he's very.

[A]

But say it's a quote. Yeah.

[B]

All right. So Dave Chappelle was talking about. No, I'm just joking. No, but, like, he's like. I met him in 20, I think 14. 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 the 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. I was just at his 50th last year in New York. Like, I. 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 gonna 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 38, so. Okay, so you remember when he was my friend? I called him, though.

[A]

I remember when he went to Durban.

[B]

But they didn't call it going to Durban. They called it going to Africa. And there's a sensation.

[A]

People said he was on crack.

[B]

They said he was on crack.

[A]

And. Yeah.

[B]

Even though he's a devout Muslim and never smoked crack.

[A]

Well, beyond that, he was the funniest guy in the world, but he. But he did. It's a very brave thing.

[B]

And that's what I'm saying is sometimes you make a decision or a. 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.

[A]

Yeah. Yeah.

[B]

Even though you're literally taking control.

[A]

Hollywood likes to do that to black people and. Yeah.

[B]

And people, period.

[A]

Kind of, you know, I think black guys.

[B]

I appreciate you saying that.

[A]

I mean, I don't know if.

[B]

But you're probably right.

[A]

I mean, it's like, 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.

[B]

He talked to me like, he talks in 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.

[A]

Go to the classic, take your ball and go home.

[B]

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. They're going to wait till you come back and ball out like Jordan wearing a 4 or 5. And that same spot's going to 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. But he said a bunch of things. He said this thing about that I always quote about the yearbook photo. 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 eighth grade. It's where you're at in eighth grade.

[A]

I was busted.

[B]

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 your 38 year old self, your 48 year old throughout your life, you can look back and people can get all these pictures of you at different times.

[A]

Yeah. What's the distinction? As someone that came up through mixtapes, what's the distinction there? Because for me, I understood when I was younger there was the drought and the dedication and those were just. You could tell Lil Wayne was just like taking people's beats and then just doing the songs better for beats is.

[B]

What they call it.

[A]

And. But like, it seems like, you know, if you're reading this, it's too late. It just, to me, that just registers as an album. Like acid rap just kind of in my mind, registers as an out. Like, I don't understand what the distinction is in people's mind.

[B]

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 reevaluating the power of words or removing power from certain words. And so the, the whole mixtape thing was like a.

[A]

Is it. I'm just fucking around?

[B]

No, but that's how the world perceives it. Because it's not commercial.

[A]

But the right.

[B]

The thing is that it's. It's hella work. It's hella love.

[A]

You want to Grammy?

[B]

Yeah. It's crazy. It is.

[A]

What is like, I don't understand, like what makes 56 Nights of Mixtape and what makes Dirty Sprite 2 an album?

[B]

It's his 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 niggas. I know all the. The radio DJs. I know all these people and I'm gonna make this.

[A]

You're doing out the trump.

[B]

I'm moving it out. Exactly. So that's the mixtape vibe. DJ Paul style, you know so much.

[A]

I love, I love music.

[B]

Shout out to MC Hammer. Like niggas don't really talk about it but MC Hammer and Masterpiece a little bit later. Yeah, they. They really like started that out the trunk vibe. Like Memphis multi multi state like movements of that shit.

[A]

The Memphis stuff that those DJ Paul like mixtapes like little flies of like that is the cool. It's some of 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.

[B]

No facts. Yeah, it's freeing.

[A]

Folks. If you know me, you know I love to work out. And a lot of people have been messaging me asking for what my secret is. And this is what it is. It's momentous creatine, muscle performance and cognitive function. Sorry, I use it every day. And it's not just for building muscle. It's become a daily essential for strength, focus, recovery, aging and cognitive performance. Imagine being really strong and really smart. These bite sized lemon lime chews make consistency effortless. You just chew and then you fucking go. Each chew delivers exactly one gram of Creapure creatine monon. Each chew delivers exactly one gram of CreapurE creatine monohydrate, which is the gold standard single source from Germany and NSF certified for sport, which means it's independently tested for purity, safety and label accuracy. Trusted by Olympic athletes, pro sports teams and elite military operators, Momentous spent years testing until they created the first chewable that actually meets the Momentous standard. Uncompromising science, meticulous sourcing and real transparency. No artificial sweeteners, no fillers. Just science backed, clinically proven performance in a portable, craveable format. Whether you're training, working or traveling, this is performance without pause. Made to support your body and your brain every single day. Unlike generic brands, Momentous doesn't follow trends. They perfect the fundamentals. And this is creatine done right. So right now, Momentous is offering our listeners up to 35% off your first order with the promo code TAFS. Go to livemomentous.com and use promo code TAFS for up to 35% off your first Order. That's livemomentous.com promo code TAFS. We've all dealt with headaches. Try to make progress with our finances. This could be overdraft fees, missed payments, or wishing you had ways to save more. Chime editor says that every dollar counts. That's why when you set up direct deposit through Chime, you get access to fee free features like free overdraft coverage, getting paid up to two days early with direct deposit and more. Learn [e-mail] Tafs Guys, Chime is banking done right. You can open a checking account with no monthly fees and no maintenance fees. And you get paid up to two days early when you set up direct deposit. That comes in handy, folks. With qualified direct deposits, you're eligible for free overdraft up to $200 on debit card purchases and cash withdrawals. To date, Chime has spotted members over $30 billion. Opened a checking account with no monthly fees and no maintenance fees. Not to mention access to over 47,000 fee free ATMs, which is more than the top three national banks combined. When I think back to who I was as a younger man, I remember that money was a stressful thing. And when you're stressed about money, you're stressed about it 24 7, which is much like the 247 customer support, which would have come in handy. Listen, I did some things that I'm not proud of, but had I had Chime, I probably wouldn't have had to because I would have gotten paid two days early. So work on your financial goals through CHIME today. Open an account in 2 [e-mail] tafs that's chime.com tafs Chime feels like progress. So Chappelle's your mentor. Do you have a mentor in rap?

[B]

My mentor passed away. So my mentor was a dude and I'm so glad I get to see.

[A]

Him on your show.

[B]

No, my mentor is this dude named Mike Hawkins and we called him Brother Mike.

[A]

He was a rapper.

[B]

He's a rapper, poet, revolutionary mentor in Chicago. Yeah, and a lot of the people that people fuck with from Chicago, out of my era. Vic Mensa. No name. Mick Jenkins. Lucky. Exactly. Nico. I'm missing, I'm missing a lot of people.

[A]

Was Juice in your. In your.

[B]

Yeah, yeah, yeah. Juice. Juice didn't go to the same after school program, I think. 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.

[A]

He like emo.

[B]

He kind of, he invented that.

[A]

No There was emo before it, but it was emo, right?

[B]

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, his. His.

[A]

Yeah.

[B]

And definitely the highest streaming 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. 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.

[A]

You were the good kids.

[B]

We were.

[A]

You and Vic and. And Felix Biederman. You guys were the good kids to you for show.

[B]

I think the point is, like, there is a. A value in, like, having a. A cohort, like a group of niggas that are all trying to do the same thing.

[A]

A scene.

[B]

Yeah, a scene that, like, that blew up. I'll take a little.

[A]

Who else is in your scene? Wilco.

[B]

Shout out to Wilco. They're a little bit older, but. But Wilco's from Chicago band. You know what I'm saying?

[A]

Incredible band.

[B]

Do you think you're. Do you think your fan base knows Wilco?

[A]

Oh, yeah.

[B]

Shout out to Wilco. Shout out to Jeff Tweedy. You feel me, dude?

[A]

Yeah. You like John Prime? That's another Chicago.

[B]

I feel like I know that name.

[A]

He's like. He made, like, country music. You have to go now.

[B]

No, he's a guitarist, right? He's a guitar.

[A]

He's like. Yeah, it's like country folk, but he's from Chicago. Yeah, he's a. He's a God. He died. He died from COVID Damn.

[B]

Yeah, unfortunately, that's when I might have heard him. I feel like I heard that name recently.

[A]

Yeah. Yeah.

[B]

I'm just checking.

[A]

How much were you exposed to? Like, like, like old blues. Like. Like Chicago is such a mus. Music city. It's like, so rich in. In history. I'm reading the. The Keith Richards autobiography right now.

[B]

And like, they signed in Chicago, didn't they?

[A]

Well, they like, 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 get. They, like, had to write to Chess Records to get Muddy Waters records sent to England.

[B]

Yeah.

[A]

And they had this music that no one else in their country had heard, basically.

[B]

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, a 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, you know, what we think of as, like, the vanguard of rock were all, like, influenced by, like, Chicago records finally coming out of, like I said, Chess Records.

[A]

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.

[B]

They went on tour with.

[A]

Fuck with this.

[B]

Like, they were opening up for Little Richard and for Muddy Waters and, like, literally singing their songs like that. And they. I think they don't get that because they were always open about where their influence was coming from.

[A]

They loved it. They loved it. Lil Richard took the Beatles on tour. He's a God, that guy.

[B]

100%. 100%.

[A]

Tutti Frutti is a song about butt size.

[B]

The architect. That's what he is. The architect of rock and roll, man.

[A]

You know, that song is. It's Tutti Frutti. Big booty.

[B]

I did know that.

[A]

I saw, like, a psychopath gay guy. That was just unreal. Musician. Yeah. Unbelievable guy. I love Little Richard. He influenced, like, Bob Dylan, too.

[B]

Everybody. He's the architect of rock and roll. That's the, like, the deep thing about, like, all music. And as time goes on, it's like we continue to do shows like this where we can have conversations. It's like there's such a rich history of black people making something raw and then us stealing it, popularizing it. We can call it whatever you want.

[A]

Call it, but, like, especially gay black guys, too.

[B]

They will.

[A]

Chicago House. Chicago House is like, literally.

[B]

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.

[A]

Yeah, it's amazing. Like, techno comes from Detroit and house comes from Chicago, and then it's. It was exported to Europe, and they don't understand that. I feel like when you go to, like, Germany, you go to, like, a, Like, Like a fucking. Like. 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. But they're, like, consuming something that they don't realize kind of what it.

[B]

What's funny, though, is I will say, like, Germany and like, fucking Poland, and I think 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.

[A]

Germany loves their history.

[B]

We met 10, like, multinationals from, like, Korea and Germany and all these other places that were footworkers. You probably don't know what footwork.

[A]

Yes, I do.

[B]

Okay, so, like, think about how small of a. Like, you're like, most people. My fans don't know what footwork.

[A]

I know, but can you do it?

[B]

I can. I won't.

[A]

Today I showed Herb a video of Derrick Rose doing it in high school. Have you seen that video?

[B]

We've all seen that video.

[A]

Yeah. Oh, my God. He's. He could have been a dancer.

[B]

No, we all. 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. I'm telling you, I met, like, 10 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 music. That was my guy. That was my guy.

[A]

Yeah. No, I, I. That music is incredible. Yeah, yeah.

[B]

Rest in peace. DJ Rashad. That was my big brother. That was another one of my mentors.

[A]

You. You knew him well?

[B]

Very well. My first tour ever was with me and DJ Ra Shot.

[A]

Have you ever. Do you make music as well?

[B]

Have you ever producing?

[A]

Yeah, yeah.

[B]

I'm not that good at juke music like that. Like, I got the same, like, two rhythms when it comes to making that, but, like, other rhythms for show.

[A]

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.

[B]

Yeah, I'm certain.

[A]

But being so good at chilling that you. That you can be a, like a super producer.

[B]

Yeah.

[A]

That's the coolest kind of guy you could be.

[B]

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.

[A]

We have to go to the studio right now.

[B]

I'll get the guitar.

[A]

Get the guitar, get the guitar. No, yeah. I want to. I want to talk to you about, like, kind of your path because it's. It's interesting because you. 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 it's. What does the term comeback mean to you in the context of your new album?

[B]

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 and. Yeah, you like the fans. I do.

[A]

They can be annoying, though.

[B]

What's weird is, like, my fans, like, usually we talked about the whole thing about trading cards, 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 person. And so when I meet them, like, I get stories that like 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 they're so. But they're like. It's like, I think there's a. A value in being outside when you're me in that, like the. 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 expected. And the stories, they'd be like, you want to sit and listen to it?

[A]

Really? Yeah. People have said that to me that they were like, I was depressed and suicidal, but the Cometown podcast got me through it. I was like, you should go to therapy or. Or listen to a. I was gonna.

[B]

Tell you when I first saw you. I'm like, man, what's that? Cometown.

[A]

Oh, you know, Cometown.

[B]

I was gonna tell you I was gonna kill myself.

[A]

No, Shut up, dude. Really? What? From what?

[B]

No, I'm just joking. I'm just joking. It's not funny to joke about killing yourself, but he gave me hell.

[A]

It's funny you could say it.

[B]

Yeah.

[A]

How's you. You had a mentorship with. With Kanye as well?

[B]

Yeah, yeah.

[A]

I mean, like, when I was in 11th grade, like, college Dropout came out. It was.

[B]

That's so crazy. I think that's a compliment.

[A]

He was the best.

[B]

I think you're younger than me. I know you already told me that.

[A]

You'Re older than me, but I look young.

[B]

You look young.

[A]

Yeah. Yeah.

[B]

When College Dropout came out, I was in fourth grade. That was the first hip hop album I ever had.

[A]

I. I had. No. Well, I had Ready to Die. I liked Biggie before that. No, no. Actually, no. No. Fifth grade.

[B]

Do you remember when I died?

[A]

No. It was on the news.

[B]

I was like, I was not watching the fucking news.

[A]

I didn't watch the Sesame Street.

[B]

No, no.

[A]

I. I remember, like, Harlem World.

[B]

I remember, like, that's post Biggie. That's towards the end of Biggie's career.

[A]

I remember life after death. Fifth grade, I was sick. I was home from school sick. And I watched Jerry Springer and then Maury, 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, Eminem.

[B]

When we was in sixth grade, Mace had a comeback, and he had a song called welcome Back, and that was hard, bro.

[A]

He also found God and breathe stuff Shake. Yeah.

[B]

Breathe step, shake. Let it go. That's how I learned how to Harlem shake. Dude, you got the second.

[A]

No, I'm from Las Vegas, Nevada.

[B]

I didn't know that.

[A]

Yeah, yeah, you got the second wave, Mace. I got the.

[B]

Yeah, you got the first. You got the OG. That's what I was just thinking. It's like you were already a formed hip hop fan by the time you got to know.

[A]

I wasn't. Well, well, the other thing is the Jew, the boys my age.

[B]

What are you stuttering about?

[A]

We love. We love rap. Yeah, yeah, yeah, yeah.

[B]

But for me, I'm saying, like, the.

[A]

White boy is our age.

[B]

Imagine your introduction to, like, you said your introduction was Mace. And like, Mace Loki has a lot of similarities to ye to me. And they worked together before Kanye did the welcome Back Mace album.

[A]

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.

[B]

It's like, yay.

[A]

Crazy to me is, yay. Are you guys in touch these days? Is he all right?

[B]

You know what's so crazy is people ask me that, like, I'm his therapist. Like, I don't know. I'm. I mean, like, I'm sure that he's. 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, I, like, I haven't, like, I have not texted him recently. That's the, that's the point.

[A]

Yeah, yeah. You. You want to tell him I'm chill. Some of them are okay.

[B]

I'll try. And I'm just joking.

[A]

No, I gotta say this. Like, the anti Semitism is 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 Semitism.

[B]

Definitely two separate things.

[A]

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 is mad at us. I didn't get. I got you.

[B]

So you went to your dad?

[A]

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, it was like, you could be a nerd also kind of be good at music. But no, I adore. I mean, he's my favorite musician.

[B]

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 an 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 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 Ye, if it was Stevie Wonder, if it was whatever the fuck it was, like, yeah, you fall in love with the idea of somebody being themselves. And I think he was. He's always, like, unapologetically gonna 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.

[A]

I don't think he was that wild early on. He was talking about, like, when it would come out that he was at college and stuff and that he wanted to drop out of art school and stuff.

[B]

I wrote my college essay when I thought I was gonna go to college. I wrote it, like, from the perspective of, like. I was like, this is. I'm never gonna 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.

[A]

Went to a magnet school.

[B]

Yeah, yeah, yeah. And then when. 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. Of the school system.

[A]

Yeah.

[B]

Or neighborhoods to go to a school that has, like, you know, that's for smart kids. Right?

[A]

Yeah.

[B]

And then I went to magnet school, too. Vibes.

[A]

Yeah. It was embarrassing.

[B]

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. Your parents don't have to pay, but you get a good education. And I went to. 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 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.

[A]

It's fine. You went to a school that inspired you to be an artist.

[B]

To be an artist.

[A]

Yeah. Kanye went to art school, too. He dropped out and stuff like that. For me, it's like, you know what it was? I'll tell you my age again. When the Harry Potter books were coming.

[B]

Up, growing up, I remember that he.

[A]

Was one year older than me, and I feel like each year he went back to Hogwarts. I was like, now I'm that. And it's like. Yeah. When he wanted to, like, he wanted to clap Cho Chang. I was feeling that kind of way. Yeah. You know, like, he wanted to take down Cho Chang. Yeah. Why am I.

[B]

Why is that name so why.

[A]

Why am I talk. I mean, Harry Potter is so racist in retrospect. Yeah, yeah, they. They asked.

[B]

But I'm a huge, huge Harry Potter fan.

[A]

Yeah, me too.

[B]

Myself on a lot of my projects. Harry Potter, the Boy who Lived.

[A]

Oh, really?

[B]

Yes.

[A]

Who's the Voldemort in your life? King Von. No, I'm just kidding.

[B]

I'm kidding, I'm kidding. I'm kidding, I'm kidding, I'm kidding.

[A]

Were those guys nice to you? Even though you got. 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. Look, cuz, I was a nerd too, right? And like the. I used to.

[B]

Cuz I like that you.

[A]

Cuz I like. I like weed. And that's how I got the cool kids to like this. The kids that were being bad.

[B]

What's the word for, like, you like wood. Like you vibe with somebody, but I can't even think of a word.

[A]

Thrilling.

[B]

It's like, incredible to be around. What do you mean? Resonate?

[A]

Yeah.

[B]

I'm a friendly guy.

[A]

You feel.

[B]

I feel like you. But what I was gonna say is, like, the way that Chicago operates, we all gotta. We all gotta see each other. We all got to work together. So, like.

[A]

So they wanted you to get good grades. They were like, I'm proud of you for getting good grades.

[B]

It's not like California. I think what you're referencing is like, when niggas be like, this a. This a good nigga. He's gonna go to the NFL like Kendrick.

[A]

Stay out the streets like Kendrick. Right?

[B]

I hear what you say is like.

[A]

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. They were just boys.

[B]

I was just talking about that.

[A]

They were in 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? Their 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.

[B]

Yeah, it was. I think it's like, come on, you.

[A]

Could be real about this.

[B]

Yeah. No, I mean, they're also younger than me.

[A]

Are they younger?

[B]

They're younger than me.

[A]

That makes it even scarier.

[B]

By like two years.

[A]

That makes it scarier too, because, you know, the younger kids have less of a moral compass, to be honest.

[B]

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 Louie both blew up out of Chicago around the same time. 2011, 2012, like 14, 15 years old. Louie's older than us, 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 Chicago.

[A]

The Vice one is really cringe.

[B]

Vice one is crazy.

[A]

The Vice one is racism.

[B]

The Vice one is like most of those documents. We're here at.

[A]

Oh, 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.

[B]

It's all racism.

[A]

Well, no, but then it just. He was like. There was an interview with him last year and he's like, yeah, just had to get out of Chicago. He's like, now I live in la. You know, he's just. He was like on a lot of drugs, I think, as a kid. Probably. Yeah.

[B]

You know, it's also environment, like, you.

[A]

Gotta realize, like, he just seems so. Like he's doing great.

[B]

Vegas, right?

[A]

Yeah. Las Vegas.

[B]

Vegas is super different from New York. And even though it's close, I'm sure it's super different from la. And when I say la, I mean like in terms of Hollywood, like in terms of how many opportunities there are. It's like Orange county camera. Well, I feel like Las Vegas is happening. 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 Keefe, if, like there was somebody that was so, you know, transcendent.

[A]

Jimmy Kimmel.

[B]

It's like a. Jimmy Kimmel's from Vegas.

[A]

Yeah, he is. Crazy places to be from. Greg Maddox. Who else is from Vegas? Panic at the Disco. The Killers.

[B]

CSI Las Vegas.

[A]

CSI Las Vegas shouts out CSI Las Vegas. They were kind of the King Vaughn of my childhood.

[B]

I think there's a. 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 gonna be the New thing that white folks were scared of and the. And that popularity grew so many careers and. 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 la. So I think, well, for a long.

[A]

Time it was only New York and la. That. Atlanta.

[B]

Atlanta for a long time.

[A]

A little bit. Houston.

[B]

Yeah.

[A]

And then, yeah, everybody has their regional.

[B]

You know, points in time.

[A]

It was just Common, basically. And then Kanye.

[B]

Kanye Common, I feel like. And then, you know, you, you. Yeah.

[A]

You were with someone for 22 years. Who your ex partner, your ex wife, or you knew her for 22 years.

[B]

We grew up in Chicago together, so I've known her for, like, most of my life. Yeah.

[A]

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, 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, do you think that people are so wrapped up in. In your shit because they thought of you as like, he's the good, happy, go, go, lucky guy.

[B]

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 publish the COVID 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.

[A]

Yeah.

[B]

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 know, I'm a rapper.

[A]

Do you regret being so open about your personal life?

[B]

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.

[A]

It's a little bit annoying, right? Like, you're going through a personal experience and then people have opinions on, like, yeah, your personal life experience.

[B]

Annoying when you don't like the opinions, but, like, when they're good opinions. Don't you like it? Like, when somebody's.

[A]

I don't care what a stranger thinks about my.

[B]

You guys turn the camera.

[A]

Girlfriend.

[B]

Don't care.

[A]

No, Like.

[B]

Yeah, no, no. But I'm just making a point. I was just joking.

[A]

We gotta wrap.

[B]

Sorry for saying that. I was just making. I was making a point. I want to go.

[A]

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.

[B]

He's, you know, didn't make March Madness. But, like, people.

[A]

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, had. Were like, felt betrayed or something because it was relationship goals. It's like, get a fucking life. Like, it's like the future doesn't get that, right? Because it's like the assumption is it has to get pussy.

[B]

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 hot or cold on either side. And so everything is politicized, even if we're not talking about politics. But that's the way the media works.

[A]

It's bad for society. Society, though. No one would, like. No one was like, facts. No one, like, there was the Beatles 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.

[B]

Internet early Yeah, probably the Internet has.

[A]

The Internet has blurred that line.

[B]

Like, remember when, like, women couldn't wear skirts past their knees on tv? Like, remember when like people.

[A]

I don't remember that.

[B]

Well, there was a time when, like, it was controversial to have a black person on TV 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.

[A]

Are you single gentlemen now? Or have you considered doing. Doing what? 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?

[B]

That is hilarious.

[A]

So you've traveled a lot, right? You. You said that. I've seen other interviews with you. Like Ghana was a heavy influence. Tell us about, like the. This is. This is the cd.

[B]

So this is the cd, right?

[A]

Yeah.

[B]

And people don't typically have CD plays in them. 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 used to 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 books. More importantly, I wanted to give them something that was functional. So this has NFC technology. I'm sure you know what NFCs are.

[A]

But National Football Conference. That's incorrect.

[B]

So what NFC is, 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 pop in 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.

[A]

You're the first person ever.

[B]

First person?

[A]

Really?

[B]

Yeah.

[A]

You invented a new thing. It's like when two iPhones touch and then you.

[B]

It's the same technology. Like when you use like your intimate.

[A]

When you do, when you touch another person's eye and you feed and it's.

[B]

Like a hot girl thing happens. It vibrates and stuff.

[A]

There's a vibrate. You're like, are we fucking right now? It's a little bit like that.

[B]

Facts.

[A]

So what do you like? Your first single is. Is called Tree, right?

[B]

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 weed. You know, like how we, how weed is represented when it comes to hip hop artists 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 a separation there. But it's also mainly about the inequities in the cannabis industry. How niggas go to jail, but other people make billions. There's a overar. Oh, 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. So this whole album, it's called Starline. It's named after the black Starline, which was started by Marcus garvey in the 20s. He started the first ever black owned shipping and trading company. Owned these big ass ocean liners that would send beans, coffee, all types of stuff for other companies to South America and Central America.

[A]

Did he print off that?

[B]

He, he did. He had a.

[A]

He had a place called Dirk Has a trucking company.

[B]

Jerk does have a. So all of this is in line. There's. 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.

[A]

Art from Acid Rapid coloring book. Yeah, yeah.

[B]

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 background.

[A]

Aurora Borealis.

[B]

Aurora Borealis, also known as the northern lights, if you're not a nerd.

[A]

Have you ever seen it?

[B]

I've never been there.

[A]

You got to go to Iceland. We gotta go to Iceland boys trip.

[B]

Dude, I like the way you said it the first time. Iceland.

[A]

Iceland. But last trip, I think weed should go back to illegal. Personally. It's not cool anymore.

[B]

Now, no facts.

[A]

There's too much. We walk around New York, it's just like these. And the dispensaries, the aesthetics, they don't have good. They don't have like. Like. Like cool. Like they look gross.

[B]

It's a government scam.

[A]

I think it is, actually.

[B]

It's a government scam. Remember when they legalized. I keep saying remember. Like, you were there. I'm just saying, like, remember in history.

[A]

I remember all of it.

[B]

The end of prohibition. Yeah. Same vibes.

[A]

They did that because the great commercial.

[B]

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. Okay.

[A]

Really? I think us boys were making a little bit of money, too.

[B]

Hey, man, get in where you fit in.

[A]

You know, I think us boys used to print a little bit off that.

[B]

Us boys, too.

[A]

I mean, but it must have made, like, hitting beer so cool when it was illegal.

[B]

Well, you could also go blind because it's somebody's uncle making moonshine. So regulation isn't bad, but also you don't know who's regulating.

[A]

I think that's an anti. Anti.

[B]

That's anti woke.

[A]

That's the anti beer. That's the anti beer propaganda.

[B]

Big beer.

[A]

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

[B]

Maybe a little bit. Did you make her upset last time?

[A]

No, no. We were just. Her was like, I could go all day. He's like, no, we're staying.

[B]

No, yeah, we're late to. We got to go to this.

[A]

Where do you have to go?

[B]

We're going to this premiere. Look. No, but this is real. Because you're 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, Starline. It comes out August 15, the same day as Spike Lee and Denzel Washington's new movie that I'm going to see the premiere of right now.

[A]

You're gonna go right now?

[B]

Yeah, we gotta. That's why we're late.

[A]

You got plus one?

[B]

I don't have.

[A]

Come on, bro.

[B]

I had a plus one, but I already gave it to Taren. So.

[A]

Really, you're better friends? Yeah, I guess so. But enjoy, dude. I'm a big fan of Denzel Washington. Actually, he's one of my favorite actors. I'm going to name my first son Denzel Freeland.

[B]

Let me write all this down so I can tell him when I.

[A]

My guy.

[B]

Appreciate you, man. That was fun, man.