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.