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SXSW 2024 Interview: Contessa Gayles, James “JJ88” Jacobs and richie reseda on Transcending an Echo Chamber in “Songs From the Hole”

The filmmakers discuss how to break through prison walls with this doc about an incarcerated musician whose songs resonate.

“I have to manufacture hope and the way I manufacture hope is through music,” James “JJ88” Jacobs says in “Songs from the Hole,” having no instruments to play but the sound of his palm on his chest for percussion when he sits incarcerated for a murder he takes full responsibility for when he was 15. From the scratchiness of the audio in which he says this, it’s clear director Contessa Gayles isn’t allowed to speak with him in person, but nonetheless they’ve found a way to get his voice out, with 88 writing lyrics on notebook paper that are ultimately turned into songs that transcend the walls where he’s incarcerated and as it turns out, an ability to bust through barriers isn’t limited to how 88 manages to lay down tracks and get them out to the public when “Songs From the Hole” brings together his family to talk about when they essentially lost two of their sons to gang violence, with 88 arrested for murder and his older brother Victor killed in their native Long Beach only three days apart.

“Songs from the Hole” testifies to the power of art when 88’s music is, if nothing else, a refuge where he can put his incredible creativity to use. But the chance to put pen to paper has offered a chance for reflection and growth that ideally the penal system was designed to facilitate but rarely does and as a narrative emerges of how breaking the law was less a choice than an inevitability given his circumstances, the film becomes a mighty demonstration of that power when Gayles removes any impediments to hearing the incarcerated artist from the physical to abstract, such as preconceptions of what led to his criminal activities, engaging all the senses from listening to 88 perform his music to reading subtitles to immersing one in a purely visual experience at times to share how he continues to endure in prison and how he ended up there in the first place.

Reconciling painful memories with a present where 88 remains everywhere for the family but physically back at home becomes a transcendent experience for those on screen, but even more so off to witness the impact his incarceration has had on every member of his family, from his mother Janine and his father Williams, a pastor, to his sister Reneasha, and you also come to see the impact they’ve had on him, giving him strength in their unwavering support now in spite of the scars that still remain from Janine and William’s devastating divorce. Through a canny mix of recreations that play out with the elegance of the longform Paul Hunter/Hype Williams’ music videos of songs that 88 may have been listening to back in the day as he supplies his own lyrics, the film frees him before that possibility exists in the real world and the opportunity to get to know him on his own terms reveals the issues of a carceral system inclined to lock people up and throw away the key.

Although it might be something of a spoiler to say we spoke to 88 before “Songs from the Hole” is set to take SXSW by storm, surely eliciting one of the most rousing receptions afterwards because of who all will take the stage after its premiere, we were truly honored to talk to the artist, his producing partner richie reseda, who helped forge the bridge for the public to hear his music, and director Gayles about the unique collaboration that will have reverberations beyond sound waves.

Contessa, how did this whole thing come together?

Contessa Gayles: I made a documentary for CNN in 2018 called “The Feminist on Cell Block Y,” and the protagonist of that film was Richie Reseda, who was leading a self-help group in the prison for his fellow incarcerated men that was all about teaching men about toxic masculinity and patriarchy and dismantling that. That is the context in which I got to know Richie and also JJ88, who was a participant and a co-facilitator of that group, so it was in a really a traditional filmmaker/subject kind of relationship and it may be best for Richie to say how we turned into collaborators from there.

richie reseda: Yeah, at the time when we met Contessa, 88 and I were already working on his album that became the centerpiece of “Songs from the Hole.” When we finished it, we knew the story was so much deeper than what could really be grasped through the music alone, especially considering that we were both incarcerated at the time. 88 still had a life sentence and we’d post some music on the internet and helping people hear it didn’t seem to really do the story justice. So we had the idea of doing a visual album. And 88 [said], “Well, what if we ask Contessa to direct it?”

88, what was important to you when you knew this might be a movie?

88: It has always been important to me to reflect what it is that my friends are going through, to capture the feelings of both incarcerated and non-incarcerated folks who are impacted by the system, and I wrote a lot of songs while in solitary confinement during that time, so just being in prison, it inspires you to be a more visual person. Even as I was writing the songs, there were certain visuals that came to me. Part of this is the internal world of me and people like Richie and the people we know, so then deciding to make it a documentary visual album with Contessa and Richie just felt right.

Contessa, what was it like to be able to carry out these visual ideas that lived in the lyrics?

Contessa Gayles: I heard the music first, and I was blown away, understanding 88’s story and knowing what he and his family had gone through on both sides of serious violence and the story that we could tell using his music, which is really reflective of that experience. We really wanted to create something new, but it felt completely organic as [this] project of how do we create this tapestry of interweaving what the music says and does emotionally and what it brings narratively with the other storytelling elements that we had at our disposal [such as] more traditional documentary elements like the narration from James over the prison phone line and the interviews with his family. It wasn’t like we were just making up a new form for the sake of it, but it felt like there was no other way to tell the story without one reinforcing the other.

We ended up taking a total of 10 songs that 88 had written in the whole and really created the narrative spine of the film around the visual representations that we set to that music and those really came from many phone conversations with James, describing everything from his childhood, where he grew up, what the back of the church looked like, and how he felt experiencing being a Black boy in America. It wasn’t hard to [figure out] how do I interpret that cinematically because he speaks very poetically and visually about the imagination [while] being incarcerated. He also wrote all of the original treatments for these musical fiction pieces and then we collaborated from there, rewriting and reworking them into something that could be a full narrative to represent his coming-of-age journey as a 15-year-old being incarcerated into adulthood and the experience of this family, representing the interiority of this artist. That’s how it happened, over 15-minute phone calls at a time, letters back and forth, and just interpreting things that I was learning from him and from his family.

It seemed like forgiveness also becomes a major theme, both for others and yourself. Was that something that could give this shape?

88: I would definitely say yes. Why I started writing this music was influenced by my experience with forgiveness and what I understand about it, being someone who has committed very serious harm in my community. Forgiveness has always been a topic on my heart and particularly, it was something that I thought about and meditated on while I was in the hole, so it feels very pivotal to even tell the story of my family, to tell my story as an artist, to just include talking about the power of forgiveness and the impact that it has and could have.

richie, it seems like you’re in a fascinating position in this movie where you can look at things from a distance because it isn’t exactly your story, but at the same time, it might have parallels to it. What was it like working on this?

richie reseda: I met 88 a year after he went to the hole and a year later, he was transferred to the prison where I was, where I had just completed some music and was looking for the next project that I would produce. So I met this person who had this amazing story and amazing music, and it was truly an honor to be able to work with him and try to bring this story to life.

It took me years, even though we were locked up together, to understand his story, and I think that’s what is so important about the film is that it does a really good job of making those things clear, so artfully and spiritually. Without a solid medium like the film, it’s difficult to even wrap one’s mind around all that took place with these families, and as 88’s friend and somebody who was helping to fight for him to come home, and then to be creating a film and making music about it at the same time, it’s one of the most profound experiences I’ve ever had in my life. When he came home, we took the vocals from prison and then reworked the music with producers and musicians out here, Twin Towers as well as Dylan Wiggins, and that too felt healing in a way. What we were able to do in prison, we were able to do again out here in a way that we never could do inside. And working with Contessa, we were able to bring the story to the world in a way that we never could on our own. All of it was extremely affirming as somebody who spent my late teens and most of my 20s in prison as well.

Contessa, was there anything that happened that changed your ideas of what this could be?

Contessa Gayles: One, the form itself was something that we were figuring out as we were going along. We did have an idea of how we wanted to combine the music with other forms of nonfiction storytelling, but it was really a generative process [where] as I was learning things from 88 and his family, that got incorporated into how we were representing things visually, so it was a lot of just being open to having an initial idea of what something was going to look like, but then listening to what we were recording and what might be incorporated on the nonfiction side to help reinforce what was happening on the fiction side. Everything really worked together and reinforced each other, so it had to be super open in terms of a process.

Then to Richie’s point about what was going on with 88’s freedom journey, that started right as we were beginning to film what we thought was going to be a narrative that was really just centered on telling the story of what happened in the past. But as we were going through production, we didn’t know these opportunities would unfold for 88 to potentially be released from prison early, so that became a part of what we were documenting and while we’re telling a story that’s really centered on spiritual freedom and finding that through the art and the process of healing in other ways — through forgiveness, faith, and relying on family and community —there’s also a physical freedom journey in the film and the two speak to each other, I think, in a really powerful way.

What’s it like getting to this point with the film, about to premiere at SXSW?

Contessa Gayles: I just feel very honored that 88 and his family and Richie all trusted me, not only with the story [which] I really took on as a responsibility to handle with as much care and nuance as possible, but also just 88 and Richie trusting me with the music and having faith in me as an artist to help execute this and manifest their vision. The collaboration really brought me to a place that I didn’t even think I could go creatively as an artist, so I’ve really grown from this experience in a way that I didn’t even know was possible.

Richie, what was it like hearing that amazing sound mix for the first time?

richie reseda: It was so amazing. Even just hearing it on those big 5.1 speakers [during] our cast and crew screening, it was honestly emotional to have initially heard this [when we] made this music in prison and the way it sounded then compared to how it sounds now, it’s hard to give it words. It’s like the music, too, is now free and gets to interact with the world, similar to 88 and me. They never intended for 88 to be home and to be free, and they certainly never intended for this music to be out and to be free and to be at this quality, so to hear it on those speakers hit my heart in a similar way as the scene of when we first see 88 step out of prison.

88, what was it like seeing your experience reflected back to you like this and sharing your story with the world like this?

88: Honestly, it’s a dream. I only imagined being here. I only imagined being free and I only imagined the visuals that you see in the film, so it’s surreal to both be free and to have this work presented to the public. It’s beyond anything I could have ever asked for, for real.

“Songs from the Hole” will screen at SXSW on March 9th at 2:45 pm at the Alamo Lamar 6, March 10th at 2:30 pm at Violet Crown Cinema 2 and 3 pm at Violet Crown Cinema 4 and March 12th at 3:15 pm at Violet Crown Cinema 2 and 3:45 pm at Violet Crown Cinema 4.

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