Pop Culture

Exclusive: Netflix's Powerful 'Songs From the Hole' Documentary Shares Trailer

The award-winning film, directed by Contessa Gayles, hits Netflix next month.

Next month, Contessa Gayles’ Songs From the Hole, billed as a documentary-visual album in collaboration with James “JJ’88” Jacobs, will arrive on Netflix following its award-winning festival run. You can check out the doc's official trailer, which just dropped, up top.

But first, we break down everything you need to know about this uniquely powerful story. Keep reading for more.

What is Songs From the Hole about?

Directed by Contessa Gayles, Songs From the Hole, winner of a SXSW Audience Award, focuses on JJ’88, who says in an early look at the film available above that he’s been “thinking about freedom since the day I got locked up when I was 15.” Deeper into the preview, JJ’88 notes the difficulty of acknowledging “the worst thing you’ve ever done.” For him, that’s “the day I took a life.”

In a BlackStar Projects interview last year, Gayles described the film as being “about faith, family, freedom, and the transformative, liberatory healing power of art and imagination.”

As Gayles explained, she made the film in collaboration with JJ’88, who’s not only the story’s protagonist but also a writer and co-producer.

“We use his music that he wrote in solitary confinement and collaborated while he was incarcerated to tell this story,” she added.

How can I hear JJ’88's music?

“Here Now,” the Tairiq Bright and Garfield Bright III-produced first single off JJ'88’s upcoming EP, also titled Songs From the Hole, is out now. Per press notes, all songs featured on the EP were recreated from tracks initially produced and recorded in prison by JJ’88 and richie reseda.

"I was reflecting on my journey when I wrote ‘Here Now,’” JJ’88 said in a statement shared with Complex. “I was in the Santa Cruz redwood forests, a few miles from the prison where I made Songs From the Hole. It’s a declaration of my arrival to the free world and my music dreams.”

When and where can I see the Songs From the Hole documentary?

The documentary is set to launch Aug. 13 on Netflix. That same day, JJ'88’s new EP will hit streaming services. Those in New York also have multiple chances to see the documentary-visual album in a proper theatrical setting, starting with three showings at Firehouse Cinema on July 25.

ComplexCon returns to Las Vegas on October 25–26, 2025, with over 300 brands and live performances by Young Thug, YEAT & Friends, Peso Pluma, Central Cee, Ken Carson, and more. Get your tickets now.

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