Podcast Summary: The Breakfast Club — INTERVIEW: James 'JJ88' Jacobs, Contessa Gayles & Richie Reseda Talk 'Songs From The Hole,' Prison To Purpose

Original Air Date: December 1, 2025
Hosts: DJ Envy, Jess Hilarious, Charlamagne Tha God
Guests: James 'JJ88' Jacobs, Contessa Gayles, Richie Reseda
Podcast: The Breakfast Club (iHeartPodcasts)

Episode Overview

This deeply reflective episode revolves around the Netflix documentary Songs from the Hole, charting James 'JJ88' Jacobs’ journey from incarceration at age 15 for second-degree murder to his transformation through music, healing, and accountability. Joining him are filmmaker Contessa Gayles and co-collaborator Richie Reseda, discussing prison, restorative justice, the making of the visual album, and the broader meaning of forgiveness, purpose, and community.

Key Discussion Points and Insights

1. Background: From Prison to Purpose (03:23–06:35)

• JJ88’s Story:

  • At 15, incarcerated for second-degree murder; lost his brother to murder three days later.
  • Served 18 years, much in solitary confinement, where he began writing music representing his and others' experiences.
  • Music and creative expression became a lifeline and a means to find purpose from tragedy.
  • “Through music is where I kind of found purpose in my story…” (05:13, JJ88)

• Discussion on Youth and Crime:

  • Hosts challenge the notion of adult sentencing for juveniles.
  • JJ88 highlights the “culture of revenge” and the justice system's retribution focus.
  • “They charge kids as adults because they want to take away futures and have a belief in this punishment system. We live in a culture where revenge is normal.” (06:52, JJ88)

2. The Realities and Impact of Crime — Maturity and Remorse (05:32–06:35)

• Understanding the Gravity:
  • As teens, the full consequences of violent acts aren’t always grasped, impacting not just the victim, but everyone present, including the perpetrator's future self.
  • “At 15, you don’t understand the gravity… The older I got, the more mature I became, the more I understood how serious it is, which is why we made this film for real.” (06:35, JJ88)

3. Rehabilitation, Media Influence, and Misconceptions (07:56–11:11)

• Rehabilitation Needs:
  • Lack of forums to understand or process the impact of one's actions.
  • Music and candid spaces, not isolation, offered healing and understanding.
  • “Once I committed murder, I knew it was foul… but I needed to understand why.” (08:07, JJ88)
• Media’s Influence:
  • Discusses how pop culture and music glamorize violence without showing its irreversible consequences.
  • “The film cuts off and then I see the [actor] on the red carpet... You don’t really understand that person in the story didn’t come back in real life.” (09:13, JJ88)

4. Building the Documentary: Creative Collaboration Against the Odds (11:11–16:41)

• Meeting and Making Music:

  • JJ88 wrote songs in solitary; connected with Richie Reseda in prison to produce an album—despite prison prohibitions.
  • “The way we made this album in prison was completely against the rules… They threatened to send me to the hole for making music.” (15:29, Richie Reseda)
  • Contessa discovered their story while filming Feminist on Cell Block Y.

• Unique Barriers:

  • California law restricts profiting from stories about one's crime. The team only released the album after JJ88’s release.

5. Spiritual and Narrative Arc: Beyond Legal Freedom (19:50–22:09)

• Healing as Narrative:
  • The film’s emphasis is on “spiritual freedom and internal healing and freedom,” not simply legal release.
  • “We wanted [the film] to feel like everyone watching this had an entry point into their own healing.” (20:01, Contessa Gales)

6. Insights on the System: Resistance to True Change (22:09–26:38)

• Limits of Legalism:

  • JJ88 asserts legal changes alone cannot free the incarcerated; the current justice system is fundamentally flawed.
  • “It’s not legality that’s gonna get us free…It’s not working for nobody except the people who set it up.” (22:13, JJ88)

• Necessity of Community and Personal Transformation:

  • Reseda stresses the need for radical change beyond political reform.

7. Forgiveness, Restoration, and Accountability (27:25–33:41)

• On Forgiveness:

  • JJ88 describes meeting his brother’s killer in prison and choosing forgiveness out of necessity for self-healing, not out of obligation.
  • “Forgiveness to me is releasing within myself what I think you owe me because you hurt me. It has nothing to do with you.” (28:42, JJ88)
  • “A friend of mine…used to always say, sow a seed from your greatest need. What you need the most, go give it to somebody.” (32:05, JJ88)

• Accountability vs. Revenge:

  • The system offers only retribution (“revenge”); JJ88 and co. advocate for a paradigm of healing and personal accountability.

8. Family, Collective Healing, and Representation (33:41–36:11)

• Family Journey:
  • Both JJ88 and Contessa affirm that telling their story has helped their family process guilt, grief, and, ultimately, pride.
  • “[The film] is healing people. It’s allowing people to feel seen and heard, that what they went through mattered.” (34:37, Contessa Gales)
  • The film intentionally uses the same actors for both families involved in the crime, symbolizing the shared pain and the complex roles of victim/perpetrator.

9. Key Takeaways for At-Risk Youth and the Power of Community (36:19–37:30)

• Advice for Youth:
  • Importance of community and being held accountable to one’s own best self.
  • “Think about who in your life is gonna hold you accountable to who you say you want to be…That’s the way out of trying to survive.” (36:35, JJ88)

10. Humility, Language, and the Ego (37:30–41:05)

• Lowercase Letters in Names:
  • Richie is inspired by bell hooks and Dream Hampton, using lowercase as a gesture of humility and opposition to ego-based systems.
  • “English is such an egocentric language… The film is about humility, knowing that I committed harm puts me in a position [of empathy]…” (37:35–38:38, Richie)

11. Final Reflections: Healing, Possibility, and Freedom (43:17–44:42)

• Empowerment for Incarcerated People:
  • “You can be whoever you want to be… You don’t have to be who they tell you you gotta be…” (43:17, Richie)
• Healing Is Possible:
  • “Our film is an offering… there’s multiple lanes, multiple entry points into people finding their healing.” (43:55, Contessa)
• Independence vs. Signing with a Label:
  • JJ88 prefers independence for now, valuing creative autonomy.

Notable Quotes & Memorable Moments

• “They charge kids as adults because they want to take away futures and ... believe in this punishment system. We live in a culture where revenge is normal.”
  — James 'JJ88' Jacobs (06:52)

• “At 15, you don’t understand the gravity… I didn’t learn that until I was in my 30s.”
  — James 'JJ88' Jacobs (05:32)

• “Forgiveness to me is releasing within myself what I think you owe me because you hurt me. It has nothing to do with you.”
  — James 'JJ88' Jacobs (28:42)

• “Sow a seed from your greatest need. What you need the most, go give it to somebody.”
  — James 'JJ88' Jacobs, quoting Chris Wacknick (32:05)

• “You can be whoever you want to be… You don’t have to be who they tell you you gotta be.”
  — Richie Reseda (43:17)

• “Our film… is allowing people to feel seen and heard, that what they went through mattered.”
  — Contessa Gayles (34:37)

Key Timestamps

• 03:23 — JJ88 summarizes the documentary’s story: life, prison, music, collaboration
• 06:35 — On being charged as an adult, the role of revenge in justice
• 08:07 — What rehabilitation should offer young offenders
• 09:13 — Influence of pop culture in perceptions of violence
• 15:29 — Making music in prison against the rules
• 19:50 — Contessa on structuring the narrative and centering healing
• 22:09 — JJ88 and Richie discuss the limits of legal/political solutions
• 28:42 — JJ88 defines forgiveness, accountability, and healing
• 33:58 — The impact of storytelling on families and the broader community
• 36:35 — JJ88’s advice to at-risk youth: find accountable community
• 43:17 — Richie: “You can be whoever you want to be...”
• 43:55 — Contessa’s final word on healing and the film’s purpose

Conclusion

The episode is a powerful meditation on transformation, healing after harm, and the potential for art and community to provide meaning even under the harshest circumstances. Through candid conversations about violence, forgiveness, accountability, and the creation of Songs from the Hole, the guests and hosts invite listeners to reconsider punitive systems and instead embrace collective healing and spiritual freedom.

Watch the documentary 'Songs from the Hole' on Netflix to experience the full story firsthand.