Songs from the Hole

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Songs from the Hole

2024

1h 46m

Documentary

Drama

Music

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88%

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8 Reviews

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Fewer than 50 Ratings

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 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, Founder Girls) 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.

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Lisa Kennedy

New York Times

Visually fluid and emotionally complex, the nonfiction hybrid Songs From the Hole, directed by Contessa Gayles, offers viewers their own portal: into James’s anguished reckoning, but also into bedeviling questions about crime, punishment and forgiveness.

Aug 14, 2025

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Daniel Fienberg

The Hollywood Reporter

A fresh and lyrical take on the genre.

Mar 14, 2024

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Todd Gilchrist

Variety

Co-writer and director Contessa Gayles combines nakedly vulnerable reflections from James "JJ'88" Jacobs with poetic recreations for a deeply affecting experience, both musically and dramatically.

Mar 13, 2024

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Brooke Obie

Black Girl Watching

Part documentary, part visual album, Songs from the Hole is a gorgeous meditation on healing toxic masculinity and breaking generational cycles. It’s thoughtful, it’s searing, it’s painful, and, just like abolition itself, well worth the effort.

Aug 24, 2025

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Jennifer Green

Common Sense Media

This creative documentary weaves together an array of storytelling methods to recount musician JJ'88's gripping but difficult journey of violence, despair, and redemption.

Aug 19, 2025

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Carla Renata

The Curvy Film Critic

Songs From The Hole simultaneously teaches the lesson of how music not only entertains, but literally can save lives and how faith is only as powerfully strong as you allow it to become.

Apr 27, 2024

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Audience Member

This is a must see doc about faith, choices and true wonder of reflection

Rated 5 out of 5 stars

08/17/25

Full Review

S S

Refreshingly original film both inspiring and moving while highlighting all the problems with the US justice system and all the terrible, frustrating & complex reasons 15 year old's like James end up there in the first place. It's a horrible mess. James epitomizes the importance of hope, growth and forgiveness. He is lucky to have such an amazingly supportive family.

Rated 5 out of 5 stars

08/14/25

Full Review

Debra B

Captivating, redemptive, heartbreaking, uplifting, despairing, hopeful. What a roller coaster of emotions and through it all, I pray for James Jacob's victim family. I pray healing and forgiveness has come for them so that they may be free.

Rated 5 out of 5 stars

08/14/25

Full Review

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Contessa Gayles

Director

Kellie Evans

Actor

Devonte Hoy

Actor

Myles Lassiter

Actor

Contessa Gayles

Writer

JJ'88

Screenwriter

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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 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, Founder Girls) 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.

Director: Contessa Gayles
Producer: Contessa Gayles, richie reseda, David Felix Sutcliffe
Screenwriter: Contessa Gayles, JJ'88, Contessa Gayles
Distributor: Netflix
Production Co: Impact Partners, Cocomotion Pictures, Artemis Rising Foundation
Genre: Documentary, Drama, Music
Original Language: English
Release Date (Streaming): Aug 13, 2025
Runtime: 1h 46m

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