INTERVIEW: James 'JJ'88' Jacobs, Contessa Gayles & Richie Reseda Talk 'Songs From The Hole,' Prison To Purpose

Summary

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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)

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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.

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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.

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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)

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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

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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.

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Transcript

[Narrator/Host]

This is an iHeart podcast. Guaranteed Human.

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[DJ Envy]

What up y'?

[James 'JJ88' Jacobs]

All?

[DJ Envy]

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[Narrator/Host]

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[DJ Envy]

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[Richie Small]

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[DJ Envy]

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[James 'JJ88' Jacobs]

Com.

[Narrator/Host]

This weekend, one of the homers mentioned he closed on a new crib. While everyone's asking about a housewarming, you're asking the real questions like who is his State Farm agent? See Homeownership is one thing, but the right coverage is the real game changer. It's how you protect your legacy. A State Farm agent can help you with finding the right coverage for your new place and even help you file a claim over the phone, in person, online, or on the app. They're ready to help you, and they don't drop the ball, you know what I mean? Like a good neighbor. State Farm is there.

[James 'JJ88' Jacobs]

Hold up.

[DJ Envy]

Every day I wake up.

[Commercial Announcer (NordicTrack)]

Wake your ass up.

[Charlamagne tha God]

The Breakfast Club.

[Contessa Gales]

Y' all finished or y' all done?

[DJ Envy]

Morning, everybody. It's DJ Envy. Just hilarious. Charlemagne, the God we are the Breakfast Club. Lon Laros is here today. We got some special guests in the building from the documentary on Netflix. Songs from the Hole. We have James Jacobs, JJ88. We have Contessa Gales, and Richie Reseda.

[Richie Small]

Welcome.

[DJ Envy]

How you guys feeling?

[Charlamagne tha God]

It's on Netflix right now, by the way.

[DJ Envy]

Yes. How y' all feeling?

[Richie Small]

Great. Feeling good. Happy to be here.

[DJ Envy]

Now, for people that haven't seen the documentary, break down what the documentary is about.

[James 'JJ88' Jacobs]

Well, it's a documentary visual album. We tell the story of my life. When I was 15, I was incarcerated for second degree murder. And during that time, I spent 18 years in prison. And during that time, I wrote an album. I met him. We produced and recorded that album in prison. And I wrote the visuals. We met Contessa, and it included his film, essentially.

[Charlamagne tha God]

I want to ask you something. You know, at 15, you committed a crime. It was murder. And then three days later, your brother was killed.

[James 'JJ88' Jacobs]

Yeah.

[Charlamagne tha God]

So how did those two events so close together, I guess, shape your sense of identity and a Ultimately give you purpose, I guess?

[James 'JJ88' Jacobs]

Oh, yeah. Well, at first it took me down, like a really dark, like, mental place. And after coming through, like, you know, suicidal ideations and just at first, I just felt like, at first I just felt kind of purposeless. I took a Life, which at 15 is kind of hard to hold, and really recognize the gravity of it. But by the time I was 18 and in prison, I just kind of felt worthless and without hope. And losing my brother within that span was kind of like he was kind of who I was emulating and admiring growing up. So it really devastated me. However, like, through music is like, it kind of gave me a place to talk about it and talk about what me and the homies was just experiencing, what me and my family went through. And so through, I guess through music is where I kind of found purpose in my story and where I could use it.

[Charlamagne tha God]

I want to talk about when you was 15, man. Because you said something that I often feel like with these kids and all of us were kids, at some point, you make a terrible choice, a temporary decision that leads. I mean, a temporary feeling leads to a permanent decision, you know, do you really understand the consequences of your actions at that time?

[James 'JJ88' Jacobs]

I mean, not in the way that I do now. When you 15, you know, I mean, I think when I was a kid, I knew if you shoot someone, they could die. Like, I know that I've seen people die, I've seen violence in my community, but I don't think I knew what it meant for real. Like, the finality of it at 15, I don't think I knew truly at 15, the impact it was having not only on this person, but their family. When there's people that I've got back in touch with since I got home who were there that night and had to witness that, and that night altered their life. And I didn't learn that until I was in my 30s. So at 15, you don't understand the gravity of it, but you do understand that it is serious. 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 Now.

[DJ Envy]

You were charged as an adult, not a child. Why was that?

[James 'JJ88' Jacobs]

Because California is racist.

[Richie Small]

To put it simple.

[DJ Envy]

Yeah. At 15, serving 18 years, it just seems like in any other state, you would have been charged as a child and given a second chance, another opportunity online.

[James 'JJ88' Jacobs]

Nah, they doing it in other states too. They charge kids as adults because they want to take away futures and they have a belief in this punishment system. We live in a culture where revenge is normal. We value it as a culture. Revenge is something that we explore. Me being a perpetrator of murder and having my brother murdered, it's something that I had to face for myself, you know? So the reason why they charge us as adults when we're kids is because they believe in revenge. They believe in retribution. They believe in eye for an eye.

[Narrator/Host]

At 15 years old, when you were standing in front of the judge, not really understanding what's happening in your sentence in the doc, you talk about looking over to your attorney and being like, so when am I going home?

[Contessa Gales]

Yeah, right.

[Narrator/Host]

At that moment, as a kid, what did you need outside of just being locked away behind bars? Like, what could they have given you that would have actually, like, in that moment, helped you reform?

[James 'JJ88' Jacobs]

Do you mean, like, after I've committed murder? Like, what to offer a kid?

[Narrator/Host]

Yeah, like what should be the. You Know, the rehabilitation of a person that is 15 years old that murders a person.

[James 'JJ88' Jacobs]

I don't know what it should be. I can tell you what I did. What helped me was like, just having safe places to talk about it. So I didn't to talk about what I had done. I don't think I needed to necessarily be locked away. Once I committed murder, I knew it was foul. I felt the seriousness of it. It wasn't like I was. I wasn't celebrated by my homies. So I knew that this was not the move to make, but I needed to understand why, and I didn't get that opportunity in court. They don't give you an opportunity to understand why you are in this moment, how serious it is that you have taken a life, and there's no plan to help you mature through it and process it.

[Narrator/Host]

You know, you said you weren't celebrated. You also talk a lot about how you thought, like, you know, this is kind of like a song. Like, we talk about it in songs. The song is over, you know, so you had an idea of what you thought committing a crime would be like, and then you actually found yourself committing.

[Richie Small]

The crime is different.

[James 'JJ88' Jacobs]

Yeah, I mean, that's true for a lot of my homies. We listen to music and this is no, like, condemnation on, like, hip hop and the music we grow up on. I think it's just true that when I listened to music as a kid, when I watched films as a kid and I saw violence, it didn't seem, you know, the film cuts off, and then I see the nigga on the red carpet. Excuse me, I see him on the red carpet. Like, it's regular. You don't really understand that that person in that story didn't come back in real life. And so as a kid, I thought, you know, in 2003, 2004, I was listening to Get Rich or Die Trying. And, like, that was the epitome of being a gangster. And so once I realized after, you know, as a kid, it's not. It ain't just a song. Like, when you go back to your homies, they gonna look at you and they gonna be scared of you. They gonna look at you and they gonna have real fear. Like, what did you just do? The homies ask me what you just do, fool. What did you do? Like, why did you do that? The homie. Everybody I know who had a murder in prison, like, they. None of them got dapped up when they homies found out. Everybody got nah for what they might talk about it in, even, like, they Tell war stories, sure. But it's like, not after it happened. I don't know nobody who got dapped up directly after, like, ooh, we did that. Let's go. Them niggas is in that car quiet.

[Charlamagne tha God]

Dealing with the gravity.

[James 'JJ88' Jacobs]

Smoking, drinking.

[Richie Small]

Yeah.

[James 'JJ88' Jacobs]

Trying to numb out them is seriously quiet. It ain't no game. Like, that's what I came to realize, that you take a life, it ain't fun. It's not honorable to me, especially in the context of just regular street, like, shit.

[Charlamagne tha God]

Contestant Richie, how did y' all connect with James to help him tell his story?

[Contessa Gales]

So what 88 didn't share was that he wrote the music that's in the film in solitary confinement. After he got out of solitary, he transferred to the prison where Richie was at. And that's how they met. He could talk about how they collaborated more on the music. But I met the both of them when I was filming a documentary for cnn. I used to work at cnn. And the last project I did for them was a feature called the Feminists on Cell Block Y. And it was about a group that Richie had co founded in prison and was leading for his fellow incarcerated men, where they're reading feminist literature like bell hooks and, you know, learning about patriarchy and how it shows up in their lives and unlearning it. So Richie was leading that group, and 88 was a participant and a co facilitator of that group. And that was the first time that I heard a little bit of 88's story. And it was the last day of filming. That documentary had nothing to do with the group, but the two of them were in the prison gym, and it was Richie's last day at the prison. He was about to be transferred to finish his sentence somewhere else. And they had the prison rental keyboard, and Richie had the keyboard on a trash can, and 88 was singing and rapping some of those songs that he wrote in solitary. And there was a group of the guys gathered around, and they knew all the lyrics. So you could tell this is something that they've been sharing. And I was just struck by how powerful the music was, how much storytelling there was in 88's lyrics. But I didn't know the context of his story and the relationship between that and the music and how he came to the hole and writing that music in the hole. Fast forward. A year after that film came out, they both approached me about, would you want to work on a visual album using 88's music? You heard some of it. I was like, Sammy, what you got? And I, once I listened to the recordings and really over the course of our development, got to know more about how 88 came to the hole and then writing the music there and then what they were able to do inside producing a whole album. I knew that we had something really special that could really be a testimony, like 88's story is a testimony. And the music is so impactful in being able to hold the narrative and tell his story. So we started collaborating from there and really evolved our relationship from this kind of more traditional space of journalistic. I was the filmmaker, they were the film participants to co collaborators on this project. And it was a true collaboration. 88 was inside the whole time. We were eight months into the edit when he was released. And we managed to figure out how to collaborate across the prison walls through phone calls, through letters, you know, 15 minute phone calls at a time. That's how we met.

[Charlamagne tha God]

I got a two part question for you, 88.

[DJ Envy]

What are you gonna ask Richie how they met? Cause, yeah, I know you asked both of them, but Richie didn't.

[Contessa Gales]

Yeah, Richie could fill in more though.

[Richie Small]

I had met 88 while I was in prison. I had just released an album from prison, so everybody at the prison kind of knew me as a producer. So when 88 got to the yard, the people who knew him from other prisons were like, you gotta meet 88. You gotta meet 88. And, you know, I wasn't. A lot of everybody in prison think they can rap, just like everybody on the streets think they can rap. You know what I'm saying? I wasn't like in a rush to meet him necessarily. I was like, okay. But when I did meet him, we have a homie named Talib who was trying to put together a poetry book. So he was bringing all these artists together and we had met in the law library. And I heard him rap and sing, and I was blown away, honestly. He could both rap and sing very well, which a lot of people can't do. Usually they do one well and then the other they kind of do for fun. And the story he was telling and the position he had on it, it's not an easy thing to make music that doesn't necessarily glorify or judge the streets. And I was like, yo, let's, let's, let's make this album.

[DJ Envy]

Y' all had all the equipment in jail. Y' all were able to have the equipment in jail.

[Richie Small]

Nah, we broke the rules, okay? The way that we made the album was against the rules.

[DJ Envy]

Well, y' all out now.

[Richie Small]

So I said, but I can't tell you, okay, because it's people in who still make music that way. But, yeah, the way we made this album in prison was completely against the rules. The prison was against it in every way. They ran up in my cell, they threatened to send me to the hole for making music, but it was like.

[James 'JJ88' Jacobs]

They denied me at board for making music.

[Charlamagne tha God]

Really.

[James 'JJ88' Jacobs]

I was able to be a part of a collaboration that Richie was eping, and it featured incarcerated artists and free artists. And when I got to board, they named that as, like, a reason why I was a danger to society is that you make music. Wow.

[Richie Small]

Yeah. It's important to point out he had life. He wasn't sentenced to 18 years. He was sentenced to 40 years to double life. So, you know, we didn't know when 88 was coming home. We knew spiritually he was coming home, but we didn't know when he was coming home. So when we finished the album, we were like, you know, typically, you finish, you do an album, then you tour it. And we didn't have that opportunity with him, so we were like, let's do a visual album. And that's kind of how the idea began. Then we approached Contessa, and she built it out to an actual film.

[DJ Envy]

One other question. Is it true that you can't profit off of a crime that was done? Is that true?

[Richie Small]

So in California, the way that the law is written is that basically, you can't take. If you're incarcerated in California, you can't talk about your crime in a way that makes you money, so you can't write a book about it and make money. You can't make music about it or a film or anything and make money. All of that typically has to go to the people who are impacted by. About the crime. And 88's case is unique in that his. He didn't. The album in the film is not about the fact that he harmed somebody, but rather that. That he had committed harm and he had been harmed, that his brother was murdered. So. But we also didn't release it until he got out.

[Charlamagne tha God]

During your time in solitary confinement, 88, like, you turned music into a lifeline, right? Like, what was the moment you realized music was an escape for you? Because I know that probably kept you sane in the hole.

[James 'JJ88' Jacobs]

Yeah. As soon as I got in, as soon as I got locked up, I kn. I grew up with music. I grew up in a church. I grew up singing. I grew up rapping. I started, like, writing in about the seventh grade. So when I got locked up, you don't know what the hell to do. When you're a kid, just in a box kind of. You're just sitting there thinking you're listening different sounds. And suddenly, next to me, the cell next to me is the homie. We call him Johnny West. Jonathan Marquez, he beating on the bed and he rapping, but he rapping radio songs. Some of his, you know, he was rapping some of his stuff, but mostly he was just rapping songs that we all knew. And so I was like, hey, yo. I yelled through the vent like, yo, I could rap too. Like, when we come out, we gonna rap. We get to the day room, he beat on the table. And when I perform, like, these little chicken shit ass, excuse my language. These little, like, you know, raps I wrote in this cell, the kids is kind of like, yo, you hard. And it's like changing the environment. So when I realized, like, oh, I could impact people around me just by occupying our time, they not, like, annoyed, trying to get away from me. They, like, spit that song. I started to do it more, and then I shared it with my father, who is an elder in the church and doesn't listen to hip hop. And he's just like, well, you know, son, music brings people joy. So if you share your gift with them and become their joy, they will protect their joy. And so share your gift with people and you'll see that.

[Charlamagne tha God]

Is that the moment you realize that music can also be your voice?

[DJ Envy]

Yeah.

[James 'JJ88' Jacobs]

I mean, I've always known music was a medium to, like, express myself and use my voice. It was going to come in some oratory fashion for me, my dad being a pastor, my mom being a singer. I knew, like, the power of my voice. I just didn't know the significance of it. Sometimes I still don't, but I didn't know that it could be meaningful to write what's happening in my life to be meaningful, that people would actually value it and care about it. Until I started to see the impact I was having on the yard.

[Charlamagne tha God]

Contesta. There's footage in the doc that shows a time when 88 and his family were still fighting for him to get out of prison. What made you see the value in his story before knowing he'd be freed in there?

[Contessa Gales]

Hmm. The value to me was the music itself. And, you know, I think we can. We can share a little bit. I hope folks go watch the film on Netflix. But the whole story is leading up to the moment where 88 realizes that he's incarcerated with the Person who killed his brother, knowing that and what happened after that. Maybe that's the part I won't say or will, but that there was, like, so much power for healing and transformation if people heard this story to. To understand that, you know, what we were talking about in terms of, like, our culture's obsession and reliance on retribution and punishment and revenge. Like, we can choose something else in our interpersonal relationships and systemically. So that's what drew me to it. But, no, we had no idea that. That 88 would have the opportunities that he had to come home. Like Richie said, He had 40 years to life plus life. And we kind of structured the whole narrative arc of the story around spiritual freedom and, like, internal healing and freedom. And that's. You know, each music video treatment kind of builds on that, healing the younger self. We didn't know that we would have the ending that we would have in the film when we started and once those opportunities started picking up. So we're following his family going to court. What's condensed down in the film was two and a half years of going to court and then commutation from the governor. We had to follow it in real time because it was so. It was relevant to the story, but it really was never a film about. Because I think there's a lot of films about incarceration where it's centered on, does the person get to come home? And do we all get to celebrate at the end if they come home? We wanted to resist that because we really wanted it to feel like everyone watching this had an entry point into their own healing. So to make it about the spiritual journey was more satisfying for me creatively and I think for all of us spiritually. But then, you know, we got the other ending.

[James 'JJ88' Jacobs]

The legal reason why I got home is. Is irrelevant because it's not legality that's gonna get us free for the incarcerated and for us as a people.

[Charlamagne tha God]

Expound on that, brother. Cause I think I like where you're going with this. Expound on that.

[James 'JJ88' Jacobs]

So what I'm saying is we participate in this system. We vote, we pay our taxes, we do the thing, and it's not working. It's not working for nobody. Um, so it's. It's. It's working for the.

[Narrator/Host]

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[DJ Envy]

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[James 'JJ88' Jacobs]

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[James 'JJ88' Jacobs]

That's true. It's working for, you know, some, but it's for, for us the system is.

[Charlamagne tha God]

Working for the people it was designed.

[James 'JJ88' Jacobs]

To work for, right? For us it's a different story. And so it my logic tell me it ain't gonna be that, that get me free.

[Charlamagne tha God]

No, I agree with that. I've been, I've been running that thought in my mind lately. Like, I think that we're just past the point of any political solutions.

[James 'JJ88' Jacobs]

No, you know, we need freedom. Freedom now.

[Richie Small]

Yeah, yeah, yeah, yeah.

[DJ Envy]

I was gonna ask, you know, hold.

[Charlamagne tha God]

On, Richie, Richie, about to say something.

[Richie Small]

I was just gonna quickly say. It's, it's. If you think about it like it's kind of silly to even believe that a system that was also set up by other flawed human beings is perfect and that just by following the rules or voting or just like following the system that someone else set up, that that's all that's needed in, in when our problems are so great. Like actually I think it calls upon us to say, okay, we can look at how this system is an improvement from, you know, the feudal system and kings and queens and serfs and okay, we've improved from there and there is much more improvement that needs to be done if we're gonna live in integrity with each other in the earth.

[DJ Envy]

I wanted to ask, you know, it's hard not to talk about this because you really want people to see it, right? You want people to see the ins and outs of this documentary. But I do want to ask about forgiveness, right. I was talking to Lauren earlier and she was like, certain things I just can't forgive, right? She was like, I can't. Like, you know, my family can, and I can't. And I think Charlamagne knows me. There's certain things I ain't forgiven. It's like. It just is what it is. It's just. How did you find. I would say. I don't even want to say the courage, but how did you break down and be able to forgive somebody, especially the person that you know killed your brother?

[Richie Small]

How?

[DJ Envy]

Like, when did that happen? Was it immediately? Did it take some time? Was it talking to your dad, who's a pastor?

[James 'JJ88' Jacobs]

When, um, when I met him, I had to make a decision. It is not a superpower. It is not an impossibility to, you know, all due respect to the things you say you can't forgive. It's not.

[DJ Envy]

I'm just not there yet. I'll get there one day. I'm just not there yet.

[James 'JJ88' Jacobs]

But truly, it's a matter of choosing it. It's a matter of saying to me what I. This is how I define forgiveness for myself. In that moment, you kill my brother, right? How you get that back?

[Contessa Gales]

How?

[James 'JJ88' Jacobs]

He gone.

[Contessa Gales]

Can't.

[James 'JJ88' Jacobs]

Can't. Gone. What do you owe me now? Because that's what we're talking about in retribution in a retaliatory system. It's like, now you owe me. So this man Jay killed my brother. Now you owe me. What do you owe me? You owe me my brother. What's the value of my brother's life? It ain't even yours. It ain't even your life. For real. Your life is valued differently than my brother's. So I can't just take your life. So now I know you can't pay me back, so what I'm gonna do, be mad my whole life? I know you can't give it back. I know you can't. That's first for forgiveness. I know you can't pay that debt. So forgiveness to me is releasing within myself what I think you owe me because you hurt me. It's just letting go. This idea that you gonna somehow give it back or you gonna somehow realize that you owe it. It has nothing to do with you. It has everything to do with me letting go of what it is. I think you owe me because you did me sour right now. Add to that I did somebody foul. I did a number of somebody's foul throughout my life. And I am not like, that's not my legacy that I want to leave. It's not something that I want to be like. I want to be known for hurting People. Nobody wants to be known for hurting people. And when you hurt someone as seriously as I have, and you want to be accountable for it, then you got to look at all the parts of.

[DJ Envy]

Your life but you are accountable. If that individual wasn't accountable.

[James 'JJ88' Jacobs]

No, no, no. If he wasn't accountable, it don't make no difference. Are you accountable?

[Charlamagne tha God]

Question. Don't you gotta give. You would have to give the person who killed your brother the same grace. You would want the people, the family that you know you killed to give you.

[Contessa Gales]

Right.

[James 'JJ88' Jacobs]

That's true. And I think that was clear for me. But I do not think that that is a requirement for forgiveness, that you have to do an equal harm in order to forgive somebody who has harmed you. Because the truth is we all commit harm daily in some form or another. And I think when for me to forgive, I knew I wanted it in my life. I was trying to be as accountable as I could be growing up in prison. But I knew I wanted forgiveness more than I wanted anything. Because forgiveness symbolized being restored back to my community. It symbolized me being restored back to my value that my grandmother sees when she look at me, you know. But I know the more and more I become accountable, forgiveness isn't something I can ask for. It's not even, I just took everything, or I took a lot from you. And now I'm gonna ask you to give me something else. Like give me grace. That's not something I feel willing to ask for. However, what I can do is plant the seed in the universe. I can plant the seed in my daily walk and in the way I live. And maybe it'll come back. Maybe it'll come to somebody who needs it in my life. But either way. A friend of mine, Chris Wacknick, used to always say, sow a seed from your greatest need. What you need the most, go give it to somebody.

[Charlamagne tha God]

I just wanna stay here for one second. 88. Cause it's such an interesting space. How have you navigated the tension between accountability and self forgiveness.

[James 'JJ88' Jacobs]

Again? Like, what do I owe? Can I pay back what I owe? Even what I think I owe to myself, or I'm faithful in God that He will forgive me and that he has forgiven me. And to me, that's enough. All I have to do is be honest about where I was at when I did whatever I did, where I'm at when I do whatever I do. Being accountable is key. Having integrity to that accountability is the goal. I'm not trying to be like a saint and say everybody should forgive I have the story on how to learn how to forgive. This is like an opportunity for people to discuss if forgiveness is necessary. Do we want a society of forgiveness or do we want one of revenge? So far, we have chosen revenge. Where has it gotten us? My dad stood up in court and looked at Jay, gets sentenced, and he was like, this does nothing for me. This does absolutely. It did absolutely nothing for my family. That that young man got life in prison. Nothing. Nothing. They son was still gone, and they other sons still have 40 years to life plus life. What did that. What could you give my parents besides an opportunity for healing and reconciliation?

[Narrator/Host]

You know, what has the journey been like for your parents? Now the documentary is out and they can kind of look back and watch it. I know in the documentary your mom talked about kind of like the guilt that they felt when everything first happened with you and felt like you were crying out and things of that nature. Like, what is it like now for them being able to see it in a documentary?

[James 'JJ88' Jacobs]

I think. I think they're proud that the three of us have found a way to tell our family story in a way that's like building something and adding value. I guess, when you go through, can sometimes feel like, what is all this for? Why am I. Why am I? Especially for my parents, who, in my opinion, have done all they could do for their children, for their lives, providing a good life for us, and they suffered great loss. So I think now when they see it in the film, they're incredibly proud of us in the way that we've been able to share this story.

[Charlamagne tha God]

Let Contessa answer that.

[Contessa Gales]

Yeah, I actually just talked to 88's mom yesterday, and she was encouraging me that this film is doing what we had hoped it would do out in the world. Like it is healing people. It's allowing people to feel seen and heard that what they went through mattered. And I know that that was their experience. You know, at first they were apprehensive and they were just kind of like, listening to their son be like, oh, we're making this film. But, you know, he's locked up. And me and Richie are on the outside coming to their house and starting to do the interview process and spend all this time with them. And I think they were apprehensive at first, but they came to realize, I think, pretty quickly that their story mattered and that their story would reflect a lot of family stories and help a lot of people heal.

[Charlamagne tha God]

There's a scene in the doc when actors are portraying James family and the family of the Young man that James killed in the courthouse. They're both played by the same actors. Was that intentional?

[Contessa Gales]

It was intentional. That choice was really about that family standing in for all families, no matter what side of harm they find themselves on. Because 88's story is not, unfortunately, unique and that you can experience harm and cause harm in the same turn. And so to choose just one set of actors and to place them in all of the different ways that we place them, they actually. They work as multiple families throughout the course of the film. And that was. That was 88's idea.

[Narrator/Host]

What do you hope that this film does for young men or women that are in it right now? Just trying to survive the way that they know how best.

[James 'JJ88' Jacobs]

Like in. In what?

[Narrator/Host]

In the streets. Like, they. Trying to just day by day, all they know is survival, trying to get through. What do you. If they get a chance to watch this, like, what do you want them to stop in their tracks and think at the end of the documentary?

[James 'JJ88' Jacobs]

I think I would want them to. I hope. I hope that they can see the process that it took to heal. It took Community, it took Richie, it took Contessa, it took my homies in prison that I was around to hold me accountable to who I said I wanted to be. So my advice to them as they watch this film is to think about that and think about who in your life is gonna hold you accountable to who you say you wanna be. Not, you know, and not in a way that's gonna shame you or guilt you back into doing the right thing or being correct, but truly gonna be like, I remember you said you wanted to do X. Like, how is that going and checking in with them and to surround yourself with people who will do that, who will hold you accountable to who you say you want to be that. That's the way. That's the way out of trying to survive.

[Charlamagne tha God]

Richie, why do you put all your. The letters lowercase in your name?

[Richie Small]

Yeah, it's on purpose. I did that. I was inspired by bell hooks to do that. I think it's like English is such a egocentric kind of language. And I liked. I think bell hooks does it from an anti capitalist space. Dream Hampton does it similarly. Dream Hampton is one of our eps and a friend of mine, and I seen she do it.

[Charlamagne tha God]

Dream.

[Richie Small]

Yeah, yeah.

[James 'JJ88' Jacobs]

Shout Out.

[Charlamagne tha God]

Dream is a very. She's a genius. Absolutely.

[Richie Small]

And yeah, so I was just inspired to. To model after people who I feel like kind of mentored me. And I think it has everything to do with what this film is. About, like, we have all committed harm and we have all survived harm. And when we have the kind of. Like this film is not saying everybody has to go forgive. That's quote, unquote, the right thing to do. As much as it's saying, like, what else is possible besides revenge? I don't know. It's just. It's just a let. It takes our ego out of being the center of it.

[Charlamagne tha God]

What else is possible other than revenge? Yeah, I think that that is very hard to explore when you probably are dealing with a lot of your own unhealed trauma and a lot of your own pain and a lot of your own hurt. Like, I think it takes a lot of a person that's already done some work to even know what that is. What is there other than revenge? Because that's what you think, just naturally, automatically.

[Richie Small]

I just think this story is so powerful because it just. And going to the capital letter thing, it's just about humility. Knowing that I committed harm puts me in a position that when someone harms me, I'm like, okay, this doesn't feel good. But this person is not different than me. I'm not better than them. I'm not better than nobody. And therefore, the kind of accountability we're talking about in the film and in our community is not who was wrong and who needs to be punished. It's what happened and what needs to change so that I can show up the way that I want to show up. And when we have our people hold us accountable to that because we need each other. That's the other thing. The system has convinced us we don't need each other. It's convinced us that as long as you have money, you don't need nobody. That's what makes the police even quote, unquote, necessary to begin with, is this idea that we need to be scared with guns to, like, treat each other well. But when we know we need each other back, when we. We. When we know we need each other, we don't need to be scared into treating each other well. And. And when we move from that more humble place, it's not so like, you wronged me, and now I need to wrong you, and I'm the good guy and you're the bad guy. It's like, you wronged me as I feel, or rather, I feel hurt by you, and I know I have hurt other people. And what needs to change so that we're not hurting each other?

[Charlamagne tha God]

Why is it so hard for men to admit that another man just hurt their feelings?

[Richie Small]

I Think men are even more addicted to this system. We're like, more addicted to the ego based system because we're, like, privileged by it. That's why the people who get the most out of it are the ones who are the. The least likely to let go for anything. You know, if there's a fucked up situation, but you kind of benefit from it. You're probably more likely to let it keep going on. And this, this system, this culture, also a key element of it is defensiveness. So it's like the more addicted to it you are, the more defensive you are about it. And I think men, I don't think it's like in our nature to be like that, but I think it's how we're raised to be in this system, for sure.

[Charlamagne tha God]

I also think, you know, when a person forgives, when the aggressor forgives, right? Like the person that can actually do you harm, it's easy to forgive when you in the weaker position, like, okay, I got no choice but to forgive me. He'll beat my ass, right? But when you are the person that could actually do the harm and they forgive that, to me, that's a different, different level.

[Richie Small]

It's like Gandhi said, we don't choose nonviolence because we're scared. If my followers were scared, I would tell them, go fight. We choose nonviolence because we are choosing nonviolence.

[DJ Envy]

We check out songs. Hold on.

[Charlamagne tha God]

Contessa, you and Dream. Why did y'. All. How did you connect with Dream? Because Dream is very intentional about what she decided to do. How did she decide she wanted to be a part of this?

[Contessa Gales]

Dream is actually a mentor of Richie's. So, you know, Richie was the one.

[Richie Small]

She would be hot if we called her a mentor, though. She's a friend. But she has obviously been in this business a lot longer than I have, and I've learned a lot from her.

[James 'JJ88' Jacobs]

Where are you from?

[Charlamagne tha God]

You from Detroit?

[Richie Small]

No, I'm from la. I met Dream while I was in prison through Patrice. Dream and Patrice knew each other. Patrice Colors knew each other for a long time. And then Patrice connected us and we started writing while we were in prison, while she was working on the R. Kelly stuff.

[Charlamagne tha God]

Gotcha.

[Richie Small]

Yeah. So she came on as an EP as one of the first people to EP it. She had saw Contessa's first film, the Feminist, on Cell block Y, which 88 and I are in as well. She was talking about kind of following our. Our work, doing integrity work with other men in the prison. And she was a fan of that film. So when I had approached her and be like, do you want to support this film? She was. She was all for it.

[Charlamagne tha God]

I just got two more questions. Adh. You kept your original prison recorded vocals, right?

[James 'JJ88' Jacobs]

Yeah, yeah.

[Charlamagne tha God]

Why?

[James 'JJ88' Jacobs]

I mean, that was the voice I used. We. We took great risk. We risked our freedom to. To make those recordings. And that was the album Richie and I wanted to release. So we thought it was important.

[Charlamagne tha God]

And you probably couldn't recreate that rawness.

[James 'JJ88' Jacobs]

From your Nah, nah, nah, nah, nah. Yeah, definitely you can't recreate was a moment in time that was like, you know, really spiritual. Really, really a blessed experience for me. One of the few blessed experiences while I was inside to be able to record that music with Richie.

[Richie Small]

And it just shows how incarcerated people are worthwhile. Us in our early 20s in prison making music. Like the fact that that music is now on Netflix and on streamers and on, like, vinyl and being heard all over the world. I'd be looking at our stats on the. On the distributor platform and seeing people are listening to this music in Brazil, and we made it in prison. It's so affirming to me, to us, but also to other people who are in prison right now. Like, you can be whoever you want to be. You don't have to be who they tell you you got to be. Whether that they be the prison system or the streets. You could be who you want to be, not who they tell you.

[Charlamagne tha God]

And Contessa, what do you want people to take away from this story?

[Contessa Gales]

What Richie said. I mean, I saw, like, I saw my brothers when I came into the prison. And I also grew up in church, like, 88. And so we really connected on, like, the music. You know, growing up in the church, listening to gospel music, having that type of a family. And that's why I connected so deeply to. To the music, because it's. It's also so. It's hip hop, but it's so spiritual. And I want people to know that healing is possible and that it can come in different forms. And our film, I think, is an offering in that regard. Like, there's multiple lanes, there's multiple portals, there's multiple entry points into people, people finding their healing. And that's why I made the film.

[DJ Envy]

Has a label ever reached out and said they wanted to sign you or not as of yet.

[James 'JJ88' Jacobs]

A few couple.

[DJ Envy]

You thinking about signing or independent?

[James 'JJ88' Jacobs]

I like being independent. Right now, it's mine.

[DJ Envy]

Do what you want to do, how you want to do it, when you want to do.

[James 'JJ88' Jacobs]

Yeah, but you know, I take a call.

[DJ Envy]

Okay, well, there you have it. Songs from the Hole, the documentary on Netflix right now. Definitely check it out. And we appreciate you guys for joining us.

[James 'JJ88' Jacobs]

Thank you all for having us.

[Charlamagne tha God]

Truly.

[DJ Envy]

James, JJ88 Jacobs, Contessa Gales and Richie Small, R RA thank you so much. Every day I wake up.

[Commercial Announcer (NordicTrack)]

Wake your ass up.

[DJ Envy]

What up, y'?

[James 'JJ88' Jacobs]

All?

[DJ Envy]

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[Commercial Announcer (NordicTrack)]

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[Narrator/Host]

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[Contessa Gales]

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[Narrator/Host]

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[Commercial Announcer (Greenlight)]

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[James 'JJ88' Jacobs]

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[Narrator/Host]

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[James 'JJ88' Jacobs]

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[Contessa Gales]

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[James 'JJ88' Jacobs]

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[Narrator/Host]

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[Contessa Gales]

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[Richie Small]

Classy o'.

[DJ Envy]

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[Contessa Gales]

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[Narrator/Host]

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This is an iHeart podcast. Guaranteed Human.