Club Shay Shay – G Herbo Part 1 (October 8, 2025)
Main Theme & Purpose This episode of Club Shay Shay, hosted by NFL Hall of Famer Shannon Sharpe, features platinum-selling rapper and Chicago native G Herbo. The conversation dives deep into Herbo’s journey from Chicago’s East Side to hip-hop stardom, exploring his childhood, the intersections of sports and rap culture, surviving street violence, processing loss and trauma, community impact, and his growth both as an artist and as a man. The discussion is candid and emotional, giving listeners rare insight into the realities of growing up amid violence, success, and personal evolution.
Episode Breakdown
1. Marriage and Openness (00:00–00:12)
- G Herbo expresses excitement about marrying his partner:
- “I get on one knee right now. Ready to go home and propose.” — G Herbo (00:07)
- Sets a tone of vulnerability and authenticity for the conversation.
2. Origins and Childhood in Chicago (01:12–04:48)
- Herbo details his background as “Lil Herb,” growing up on the rough East Side of Chicago.
- “Lil Herb is a kid from the east side... one of the most poverty struck and dangerous neighborhoods in Chicago, who just had a dream… but was knee deep in the midst of the fire.” — G Herbo (01:37)
- Fondest memories revolve around playing basketball at local parks; memories tinged with loss:
- “A lot of those people who I shared those memories with, not here no more.” — G Herbo (03:01)
- Early dreams of being a basketball player; compares his style to Nick Van Exel:
- “I used to be able to get to wherever spot, like, so ‘Nick the Quick.’” — G Herbo (05:13)
3. Sports vs Rap — Parallel Dreams (04:48–09:11)
- Herbo admits he never played football; basketball was his first love.
- Discusses the special place Derrick Rose holds in Chicago culture, even more so than Michael Jordan for some:
- “D. Rose, homegrown… He just gave us so much hope in Chicago.” — G Herbo (06:21)
- Explores mutual admiration between athletes and rappers:
- “They got more money than us, but we having more fun.” — G Herbo (08:34)
- Addresses how music motivates athletes and how many rappers once dreamed of pro sports.
4. Hoop Dreams and Rap Stardom (09:11–10:55)
- Hypothetical: would Herbo trade rap stardom for NBA success?
- “No… I feel like I’m living in my purpose now… The greatest feeling that I get from this is when people tell me, ‘You changed my life, bro.’” — G Herbo (09:22)
5. Rappers on the Court (10:00–11:45)
- Herbo claims basketball victories over Drake and 21 Savage:
- “We beat they ass like four, five times in a row. For sure.” — G Herbo (10:55)
- Notes that games among rappers are heavy on competition and trash talk, but usually just for fun, unless money is involved.
6. Chris Brown’s Entertainer Status (11:45–14:13)
- Sharpe asks if Chris Brown is the closest artist to Michael Jackson.
- “There’s nobody closer... Chris Brown. Right. Honestly, like, for real.” — G Herbo (12:13)
- Herbo describes Brown’s energy on stage and work ethic as “mind blowing… It’s just what he do.”
- Cites Breezy, Juice WRLD, Future, Meek Mill, and Young Thug as the most naturally gifted artists he’s worked with.
7. Herbo’s Creative Process (15:12–17:46)
- Breaks down his studio approach:
- Describes blending Jay-Z’s introspection and Lil Wayne’s freestyle spontaneity.
- “I haven’t wrote no song in probably four, five years… I just be in there vibing and off the top of my head…” — G Herbo (16:00)
- Likes chaos and conversation in the studio; finds inspiration from people around him.
8. Artistic Evolution, Pressure, and Authenticity (17:46–21:13)
- Describes changing his style after advice from his best friend—stopped overthinking rhymes and started trusting intuition.
- “Now I really just don’t care… this is my art.” — G Herbo (20:13)
- Gained confidence to not worry about audience or peer opinions when creating.
9. Guest Verses, Rapper Etiquette, and Studio Politics (22:55–24:55)
- Discusses the competitiveness in collaboration:
- “Don’t send me no blank song… I feel like I gotta at least hear your verse to give me some type of direction.” — G Herbo (23:01)
- Who gets to go last/first often depends on who has the hardest verse.
10. Street Life, Gun Violence, and Surviving Chicago (25:02–36:10)
- Herbo details daily life and trauma on the East Side:
- Early exposure to guns at school, violence, and death from as young as fifth grade:
- “Lost some of my first friends…sixth grade… that’s when I started seeing people get killed.” — G Herbo (27:08)
- Realized how traumatic his childhood was only after traveling to other cities:
- “I thought it was normal because everybody was doing that.” — G Herbo (25:54)
- Early exposure to guns at school, violence, and death from as young as fifth grade:
- Dropping out at 16 because he couldn’t safely attend school, then gaining fame locally before rising nationally.
- Early survival strategies—never letting family ride with him for their safety; moving his mother far from the neighborhood as soon as he could.
- Early gun acquisition:
- “I bought my first gun when I was like 14.” — G Herbo (34:42)
- The escalation from fistfights to firearm use due to the risk of retaliation.
11. The Day He Was Shot (36:10–42:59)
- Candid retelling of being shot at 16 during a block shooting that injured nine people:
- “I got shot in the foot… nine of us got hit. That shit was on newspaper.” — G Herbo (41:17)
- Admits to returning to the streets immediately after, despite being wounded:
- “I got shot. I probably went out there the next day or the day after with a boot on my leg, just outside…” — G Herbo (42:16)
- Reveals ongoing desensitization to violence and its normalization.
12. Navigating Loss, Trauma, and Survival Guilt (43:44–44:55, 60:35–70:11)
- Recounts losing friends and the impact of survivor’s guilt:
- “I felt like I was responsible for his death for a long time… I ain't used to drink at all…but I fell into alcoholism. Crazy. Like, I was down in a whole fifth a day, like by myself every single day.” — G Herbo (62:53, 68:43)
- The death of a close friend (shot at a barbershop) as a major turning point; struggled with thoughts of retaliation, depression.
- Conversation with bereaved friend’s grandmother gave him difficult clarity and encouragement:
- “She looked at me and said, yeah, my grandson died because of you… but you better not fuck your life up. You better be the best you could be.” — G Herbo (69:25)
13. Reflections on King Von, Violence, and Change (45:32–54:16)
- Talks about King Von, high school days, and the reality behind notorious street reputations.
- Grapples with the difficulty of leaving street life even after achieving fame:
- “When that shit in you, it’s in you…” — G Herbo (49:58)
- “Took me years and years to just be like, shit ain’t worth it.” — G Herbo (50:45)
- Emphasizes it can take time to adjust and react differently to disrespect.
- Admits to being in situations where walking away was the hardest part—but a sign of personal growth:
- “That’s one of the hardest things to do, to walk away for real.” — G Herbo (52:21)
14. Trauma, Insomnia, and Mental Health (58:37–60:18)
- Herbo shares how chronic hypervigilance and trauma from his upbringing affects his sleep and emotional health:
- “It be hard for me. Like, my girl be waking me up sometimes… I got bad insomnia. I be up all night.” — G Herbo (59:08)
- Has sought therapy; credits community work and family for helping manage his pain, but admits that “it don’t really help, for real, for real.”
Notable Quotes & Memorable Moments
- “Jordan is the biggest of the biggest… But coming from Chicago, D. Rose, homegrown… He gave us so much hope.” — G Herbo (06:05)
- “I never put my mom in the car… I would rather just wait all day until somebody pick me up before I desperately tell my mama to drop me off somewhere.” — G Herbo (44:00)
- “My parents always like, trusted me enough to just make good decisions. Like, although I was in the streets… they trusted me to never bring it back to my house.” — G Herbo (45:04)
- “You live by the gun, you die by the gun… But just seeing it, like, you know what I’m saying? I feel like it just… He had so much more life… more shit to do.” — G Herbo on King Von (48:20)
- “I could my life up. I could go to jail or possibly die, anything. Like, people really want you to stoop down to their level a lot.” — G Herbo (57:06)
- “I never really could enjoy [success] for real. Because I always wanted to share it with [my friend]. He ain’t here.” — G Herbo (67:50)
- “That’s growth... I never was that person…” — G Herbo, reflecting on not retaliating in a tense situation (52:21)
Timestamps for Key Segments
- Early Life & Dreams: 01:37–05:08
- Derrick Rose Conversation: 05:33–07:42
- Rappers x Basketball Stories: 09:11–11:45
- Chris Brown vs. Michael Jackson Debate: 11:45–13:13
- Herbo’s Recording Process: 15:12–17:46
- Street Trauma & Gun Culture: 25:02–36:10
- The Day Herbo Was Shot: 36:10–42:59
- King Von & Cycle of Violence: 45:32–54:16
- Mental Health & Insomnia: 58:37–60:18
- Processing Loss, Grief, Survival Guilt: 60:35–70:11
Tone & Style
Authentic, candid, and conversational. Shannon Sharpe brings empathy and humor, while G Herbo’s responses are unflinching, raw, at times emotional, and deeply reflective of his environment and journey.
End note:
This episode provides powerful insight into cycles of violence, trauma, and transformation, illustrating why G Herbo is seen as both a voice for the voiceless and an advocate for healing in Chicago. For further continuity, listeners are encouraged to check out Part 2 of the conversation.