Contessa Gayles
Filmmaker and producer who worked on the Songs from the Hole documentary, contributing to the film's narrative structure and storytelling about incarceration and transformation.
Best podcasts with Contessa Gayles
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Dec 1, 2025 • 1h 42min
FULL SHOW: Ray J Arrested on Thanksgiving, Kandi Burruss Addresses Spending Holiday with Ex + TJames 'JJ'88' Jacobs, Contessa Gayles & Richie Reseda Interview
TJames 'JJ88' Jacobs, a formerly incarcerated musician, and Contessa Gayles, a talented filmmaker, join to discuss their impactful documentary, Songs from the Hole. They share how creating music in prison became a lifeline for TJames, reflecting on the healing power of art. The conversation dives into the challenges of rehabilitation within the prison system and the legal restrictions on profiting from art created by incarcerated individuals. Their journey highlights the transformative nature of storytelling and music in overcoming past traumas.
Dec 1, 2025 • 39min
INTERVIEW: James 'JJ'88' Jacobs, Contessa Gayles & Richie Reseda Talk 'Songs From The Hole,' Prison To Purpose
James 'JJ'88' Jacobs, a formerly incarcerated musician, shares his transformative journey through music in prison. He discusses the impact of youth trauma and the criminal justice system on his life. Contessa Gayles, co-director of the visual album, highlights the healing power of storytelling. Richie Reseda offers insights into the challenges of creating music in prison and the importance of humility in their work. Together, they explore themes of accountability, forgiveness, and the potential for personal redemption.
