SONGS FROM THE HOLE has been nominated for four News & Documentary Emmy® Awards

Outstanding Arts & Culture Documentary

Outstanding Writing - Documentary

Outstanding Music Composition - Documentary

Outstanding Art Direction - Documentary

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 accountability 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 accountability as he comes of age in this documentary visual album composed behind bars.


AWARDS & NOMINATIONS 

INDUSTRY AWARDS

NOMINEE — News & Documentary Emmy Awards: Outstanding Arts & Culture Documentary, 2026

NOMINEE — News & Documentary Emmy Awards: Outstanding Writing - Documentary, 2026

NOMINEE — News & Documentary Emmy Awards: Outstanding Music Composition - Documentary, 2026

NOMINEE — News & Documentary Emmy Awards: Outstanding Art Direction - Documentary, 2026

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 - Outstanding Impact Campaign, 2026

WINNER — Cinema Eye Honors: Heterodox Award, 2025

NOMINEE — IDA Award: Best Music Documentary, 2024

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 

"A deeply affecting experience,

both musically and dramatically"

Variety 

"A staggering hip‑hop visual album

that also doubles as a cry for humanity"

RogerEbert.com 

“Eye-opening in a way you may have forgotten

your eyes could still be opened”

The Hollywood Reporter

“Visually fluid and emotionally Complex”

The New York Times

“A culture-shifting film”

Complex