Occasionally, I'll watch a film so stunning -- visually, musically -- and so important, in terms of cultural relevancy and the issues that it raises, I'll know within a few minutes that I'd love for the director to be on the podcast. It's a blessing that my guest today, filmmaker Contessa Gayles, is here to talk about her journey from CNN to making groundbreaking documentaries.

It's not to say that the topics are easy. Making a documentary visual album about an incarcerated musician is an unbelievably daunting task. But Contessa is more than up for it. Go watch SONGS FROM THE HOLE (2024), now streaming on Netflix, and come back and hear my conversation with Contessa Gayles.

In this episode, Contessa and I discuss:

• the artistry of her filmmaking of SONGS FROM THE HOLE;
• how she got started in documentary;
• whether you need to pick up the skillsets of writing, editing, directing, producing -- the whole toolbox -- to be a successful documentary filmmaker;
• which skillset she feels most drawn and the importance of editing in documentary;
• her film, FOUNDER GIRLS (2023) -- an ode to girlhood -- at a historically Black summer camp and how it resonates today;
• her timeline of releasing several films all at once last year, including THE DEBUTANTES (2024) and SONGS FROM THE HOLE;
• why news organizations trust her work;
• what she wants people to feel when watching SONGS FROM THE HOLE and how does she want them to feel afterwards;
• how the film flips the narrative of how prisoners are viewed and whether that was ever an issue for backers of the film;
• how was this film made -- the "creative solutions" to get this film made;
• how she successfully balanced the impact of the crime as part of the film;
• her recommendation for people just starting out in documentary;
• do we have to wait till 2030 for this incredible filmmaker's next project?

Contessa's Indie Film Highlights: AXEL (2025) dir. by Stefani Saintonge; THE IN BETWEEN (2024) dir. by Robie Flores

Memorable Quotes:

"We were really trying with this film to push the boundaries in terms of form and to really create something that folks hadn't experienced before. Not just for the sake of it, but because it felt like that was really the only way to tell this story and do both the story and the music justice."

"There was really an expectation of...it used to be called the Predator, but the producer, shooter, editor where you were really like one man banding," 

"Our stories are focused on our traumas and our struggles and the stories that are more centered around our joy and our freedom are less prioritized."

"I definitely don't go by the book."

"I hope that folks approaching the film are open to seeing something and experiencing something that they haven't before."

"Not wanting the project to stall out, to lose momentum or to just not happen, we had to come up with some creative solutions for how else we could tell the story outside of the kind of more obvious way of doing it."

"How we could possibly interweave 10 music video treatments that are also holding the narrative of the film. Not just like random music videos, but like, we need to build a story through that."

"I'm not super concerned with being prolific so much as I'm concerned with being impactful."

Links:

Follow Contessa On Instagram

Watch SONGS FROM THE HOLE On Netflix

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