SONGS FROM THE HOLE has been nominated for TWO NAACP IMAGE awards!

Outstanding Directing in a Feature Documentary - Contessa Gayles: Songs from the Hole

Outstanding Breakthrough Creative (Motion Picture) - Contessa Gayles: Songs from the Hole

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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. 


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

PRIOR
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

NOMINEE — NAACP Image Awards - Outstanding Directing in a Feature Documentary, 2026

NOMINEE — NAACP Image Awards - Outstanding Breakthrough Creative (Motion Picture), 2026

WINNER - SIMA Awards - Legacy Award for Best Impact Campaign, 2026


"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