Episode 101

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Published on:

24th Nov 2025

*DOCNYC - Songs From The Hole - Director Contessa Gayles

At 15, he took a life. Three days later, his brother’s life was taken. A moving chronicle of forgiveness, family, and the transformative power of art, SONGS FROM THE HOLE weaves music and mixed-media storytelling into an innovative documentary visual album. Through clear-eyed narration and lyrical journal entries, incarcerated musician James “JJ’88” Jacobs reveals his innermost struggles as a person who has both committed and experienced violent harm. In a unique creative process, our guest, director Contessa Gayles collaborated with protagonist/writer JJ’88 and producer/music producer Richie Reseda to interweave the collective storytelling of the film’s non-fiction participants, with imagined memories, dreams and spiritual dialogues set to JJ’88’s original music. The result is a powerful mix of truth-telling, healing and liberation that is possible within us all. SONGS FROM THE HOLE it won the 2024 SXSW Audience Award in the Visions category. Director Contessa Gayles (The Feminist on Cellblock Y, The Debutantes) joins us for a fascinating conversation on being open to a very creative way of telling this complex story. 

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About the Podcast

Cinemafile
Cinemafile showcases the very best in independent, documentary and foreign films through our conversations with the more than 2,000 filmmakers who made them. Through Cinemafile we will do our best to bring the most interesting and accomplished filmmakers from around the world to your attention.

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Michael Kaspar

Mike Kaspar is a life-long film fan who has worked as a projectionist at an art house theatre, college radio station general manager as well as a radio show host and producer for over 18 years.