Songs From the Hole

James, a prisoner serving a double life sentence, struggles with being both victim and perpetrator of violence, expressed through hip-hop and soul.

2024 | Running Time: 1 Hour 46 minutes | Rating: NR

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/co-creator’s original music.


“Gayles has generally found a fresh way to tackle a familiar exploration of the carceral industry, rehabilitation and redemption. It’s eye-opening in a way you may have forgotten your eyes could still be opened.”