Songs From the Hole

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Film Synopsis

A documentary visual album, Songs From the Hole follows James “JJ’88” Jacobs through a musical opus of hip-hop and soul, inspired by his innermost struggles as both a person who has committed and experienced violent harm. The film interweaves the collective storytelling of its non-fiction participants with imagined representations of memories, dreams and spiritual dialogues set to its protagonist and co-creator’s original music.

Alongside the film’s collective retelling of the past, we see JJ’88 and his family learn that after 18 years in prison, he’s receiving a rare recommendation from the state for a resentencing hearing, and soon after, a commutation from the governor to appear before the parole board – both opportunities that could turn his double life sentence into the possibility of coming home.


May 21, 2024

Good Shepherd Services

Brooklyn, NY

Apr 30, 2024

University of California Santa Barbara Multicultural Center & Underground Scholars

Santa Barbara, CA

Apr 27, 2024

Black Prisoners’ Caucus, Collective Justice & Creative Justice

Seattle, WA

Apr 26, 2024

Seattle Black Film Festival

Seattle, WA

Apr 24, 2024

Your Move MKE

Milwaukee, WI

Apr 23, 2024

Racine Correctional Institution

Sturtevant, WI

Apr 18, 2024 - Apr 22, 2024

Milwaukee Film Festival

Milwaukee, WI

Mar 9, 2024 - Mar 12, 2024

SXSW Film Festival

Austin, TX

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Director, Producer, Writer, Cinematographer, Editor: Contessa Gayles
Producer, Music Producer & Music EP: richie reseda
Producer: David Felix Sutcliffe
Writer & CoProducer, Music Writer, Music Performer & Music EP: JJ’88
Cinematographer: Michelle Kwong
Editors: Rafe Scobey-Thal, Princess A. Hairston
Music Producers: Twiin Towers, Dylan Patrice Wiggins
Music Executive Producer: Rahael Asfaw


Devonte Hoy
Myles Vincent
Africa Uhura
Jovon Times
Ernest Walker
Ryleigh Leggett
Kellie Evans


Victor Benjamin
William Jacobs Jr.
Janine Jacobs
Reneasha Jacobs
Jacqueline Williams
Naaji Pruitt
Lauren “Indigo Mateo” Jacobs

Impact Campaign

JJ’88’s story resonates with too many young  people who are impacted by the legal system. The US incarcerates more young people than any other country in the world, and each year 250,000 kids below the age of 18 are tried and prosecuted in adult courts. Songs From the Hole illuminates how the model of retribution as justice is a centerpiece of both illicit street culture and of our legal system of incarceration, both founded upon a similar belief that violent punishment is the necessary answer to harm. There is a profound lack of media focusing on the transformative justice resources and skills that are essential to interrupt cycles of violence and incarceration that are devastating young people of color.

A critical priority area for Represent Justice is to address the legal system’s impact on young people, and through powerful storytelling, highlight alternatives to incarceration that don’t rely on jails and courts, but instead treat root causes with individual and community investments. The Songs From the Hole impact campaign focuses on bringing the film to audiences impacted by incarceration and in communities disproportionately impacted by violence, and connecting viewers with tools for healing and transformation.