Songs From the Hole: Music, Memory, and the Work of Healing

Netflix is preparing to release one of the most talked-about documentaries of the year. Songs From the Hole is not just a film, it is a cultural moment that explores violence, forgiveness, and the transformative power of art.

At the center is James “JJ’88” Jacobs, whose life was forever altered at 15 years old. After taking a life and losing his brother’s life three days later, JJ’88 began serving a double-life prison sentence. What unfolds is not a story of despair but a chronicle of transformation. Through narration, lyrical journal entries, and original music, he opens his inner world: the regret, the searching, the dreaming, and the relentless pursuit of healing.

Directed by Contessa Gayles (The Feminist on Cellblock Y), the documentary unfolds as a visual album created in collaboration with JJ’88 and producer-musician richie reseda. It blends nonfiction testimony with imagined memories and dreamlike sequences, all set to music written and performed by JJ’88 himself. The result is a film both raw and poetic, one that asks us to witness a man reckoning with harm he caused and endured while creating art that transforms his pain into possibility.

The film has already captured the attention of critics and audiences alike. Rolling Stone calls it “a firsthand account of the power of restorative justice.” The New York Times describes it as “visually fluid and emotionally complex.” The Guardian praises it as “deeply moving and unconventional.” Its recognition spans major festivals including SXSW, BlackStar, and Cinema Eye Honors, where it has collected both jury prizes and audience awards.

What makes Songs From the Hole resonate beyond accolades is its challenge to how we think about justice. It pushes us to consider what healing looks like for someone who has both inflicted and suffered harm, and what role art can play in breaking cycles of violence. In a cultural moment where conversations about incarceration and community healing are urgent, the film arrives as both meditation and provocation.

The collaboration behind the camera reflects the film’s ethic. Alongside Gayles, JJ’88 serves as co-producer, ensuring his perspective remains central to the storytelling. Together with richie reseda, David Felix Sutcliffe, and executive producers including dream hampton, Regina K. Scully, and Geralyn White Dreyfous, the team ensures the film is told with both intimacy and integrity. Songs From the Hole is about violence, yes, but even more so it is about resilience, imagination, and the possibility of healing in the unlikeliest of places. It is about one man’s songs written from behind prison walls and the chance those songs give us to see ourselves and each other differently. This is not just a documentary to watch. It is a story to carry.