An incarcerated musician struggles for healing and peace as he comes of age in this documentary visual album composed behind bars.

SYNOPSIS 

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. While serving a double-life prison sentence, he searches for healing and peace as he comes of age in this documentary-musical odyssey composed behind bars. 

In a unique creative process director Contessa Gayles (The Feminist on Cellblock Y, The Debutantes) 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 and dreaming that reveal the potential for healing and liberation within us all. 


AWARDS & NOMINATIONS 

FESTIVAL AWARDS 

WINNER — SXSW, Audience Award: Visions, 2024 

WINNER — BlackStar Film Festival, Jury Prize: Best Feature Documentary, 2024

WINNER — Newark Black Film Festival, Jury Prize: Spirit of Paul Robeson Award, 2024

WINNER — Indie Street Film Festival, Jury Prize: Best Feature Documentary, 2024

WINNER — Fist Up Film Festival, Jury Prize: Best Feature Documentary, 2024

WINNER — Sing Sing Film Festival, Jury Prize: Excellence in Criminal Justice Storytelling, 2024

WINNER — Buffalo International Film Festival, Audience Award: Best Feature Documentary, 2024

WINNER — Urbanworld Film Festival, Audience Award: Best Feature, 2024

WINNER — St. Louis Film Festival, Audience Award: Best Feature Documentary, 2024

WINNER — New Orleans Film Festival, Audience Award: Best Feature Documentary, 2024

SPECIAL MENTION — New Orleans Film Festival, Jury Prize: Best Feature Documentary, 2024 

INDUSTRY AWARDS 

NOMINEE — IDA Award: Best Music Documentary, 2024 

WINNER — Cinema Eye Honors: Heterodox Award, 2025


"A deeply affecting experience, both musically and dramatically"

Variety 

"A staggering hip‑hop visual album that also doubles as a cry for humanity and justice"

RogerEbert.com