Songs from the Hole — A Musical Approach to Collaborative Filmmaking & Healing

Buffalo Int'l Film Festival
5 min readOct 5, 2024

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Interview w/ Director Contessa Gayles by Dorian Griffin.

At 15, he took a life. Three days later, his brother’s life was taken. A documentary visual album, SONGS FROM THE HOLE follows James “JJ’88” Jacobs through a musical opus of Hip-Hop and Soul, inspired by his innermost struggles as both a person who has committed and experienced violent harm, as he serves a double-life prison sentence.

The film interweaves the collective storytelling of its non-fiction participants with imagined representations of memories, dreams and spiritual dialogues set to its protagonist/writer’s original music.

DG: How do you first meet James “JJ’88” Jacobs? What inspired you to make this film?

CG: I was invited into a collaboration by 88 and our producer richie reseda. After 88 wrote the music that our film is centered around in solitary confinement, he was transferred to another prison where he met richie, and together, they collaborated on producing music for 88’s lyrics. Fast forward a few years — I met 88 and richie in 2017, as I was directing a documentary called The Feminist on Cellblock Y for CNN. That film follows a program for incarcerated men that was led by richie reseda while he was incarcerated. 88 was a participant and co-facilitator in that group, which is where I first heard a bit of his story, as he shared it with the other guys in the group. The last day of filming, outside of documenting the activities of that group, 88 and richie were in the prison gym and had the prison rental keyboard set up on an upside down trash can and 88 was performing his music while richie was on the keys. That was the first time I heard the music and experienced what a talented performer 88 was and the amazing storytelling in his lyrics. Unbeknownst to the three of us, that was the seeds being planted for our future collaboration on Songs from the Hole.

DG: Credited as a writer, producer, and music composer, and with his life story being the dramatic source for the documentary/album, what did the collaborative process look like working with James? As the director, what was the role that you played in bringing his life and art to the screen? And what was the process of working with richie reseda like?

CG: The music pre-dated the film, so that was our starting point and anchor creatively. Building a story and cinematic world around that music was a five year process. We started with some original music video treatments 88 hand wrote and sent us in the mail, and over time, re-wrote and co-wrote together across snail mail, and tons of phone calls, 15-minutes at a time (prison time limits on phone calls) to create a single, unfolding narrative across the songs and those musical fiction segments. As the director I worked with our actors, our amazing Director of Photography Michelle Kwong, my fellow editors Princess A. Hairston and Rafe Scobey-Thal, producers richie reseda and David Felix Sutcliffe, and the entire team to manifest this vision.

Working with richie, we evolved our relationship from filmmaker and film participant as we first were in relation to each other, to collaborators producing this film together, and most importantly, close friends. Making this film was real heart work, and was centered on love and care for community, which richie exemplifies in all of his work — as a creative, a thought leader and cultural organizer — and as a person. I learned so much from him and he challenged me to grow in many ways. And I know he learned a lot from me too!

Working with 88 and richie was the collaboration of a lifetime. They are both incredibly talented artists and managed to create art in the most oppressive environment imaginable. Their artistry, and their faith and trust in me, pushed me in every way to level up my own artistry and make sure I did their music and writing justice, and that I presented 88 and his family’s story with authenticity and care. I’m very proud of what we created together.

DG: In addition to the visual album structuring your film, it’s a unique artistic endeavor to create a film which defies dramatic narrative conventions and inhabits a hybrid space so effortlessly between fiction or nonfiction. What made you decide to tell James’s story in this way?

CG: It felt like the only way to tell the story of the music and 88 and his family’s story and do justice to both. The music, and the conditions and context of its creation, was central to 88’s experience of healing and transformation while incarcerated. We thought expansively, without much of a blueprint or precedent for form, and it took a lot of just trying things and experimenting and unbridling our imaginations to manifest this vision for a new form that was an amalgamation of different genres.

DG: What (if any) Black independent and experimental works of art were sources of inspiration for this project?

CG: There are a ton of references to Black artists and art in this film. Many more than I can name, but to name a few; Kendrick Lamar, photographer Carrie Mae Weems, Kahlil Joseph.

DG: I don’t purport to know anything about the experience of incarceration personally, but I think there’s something about being a thinker or artist, someone who spends most of their time in the “solitary” world of their imagination, that has always made prisons of unique interest to me. If we look at movies as Roger Ebert did, as empathy engines, it would seem the moral and artistic responsibility of those with a platform to communicate the stories and experiences of incarcerated people. With that being said, do you yourself feel any sort of (political) imperatives with your work, whether around prisons or other significant social issues?

CG: Absolutely. I tell stories to help Black and Brown people heal and get free — mentally, emotionally, spiritually. I make films to help us decolonize our minds and imaginations and bring us closer to our collective liberation.

DG: What are you hoping that audiences take away from Songs from the Hole?

CG: That the answer to harm and violence should not be more harm and violence, whether that’s within our communities on an interpersonal level, or at the state level with incarceration. There are alternatives, as we see in the film, to punishment, revenge and retribution. That healing, transformation and accountability are possible in the context of community care.

Songs from the Hole screens on Sunday October 13 at 7:15 PM at North Park Theatre. Director Contessa Gayles in attendance.

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Buffalo Int'l Film Festival
Buffalo Int'l Film Festival

Written by Buffalo Int'l Film Festival

Buffalo International Film Festival (est. 2006) champions regional, national, and international films that push the limits of independent cinema.

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