'Songs from the Hole': The story behind JJ'88's documentary and visual album

NPR | By Kara Frame

Published March 12, 2026 at 5:30 AM CDT

Actors gaze up to the sky during JJ'88's "ROOT" in the hip-hop artist and former inmate's documentary and visual album Songs from the Hole. Before the song starts, protagonist and producer James "JJ'88" Jacobs describes meditating on his and others' redemption while incarcerated and in solitary confinement. — Actors gaze up to the sky during JJ'88's "ROOT" in the hip-hop artist and former inmate's documentary and visual album *Songs from the Hole.* Before the song starts, protagonist and producer James "JJ'88" Jacobs describes meditating on his and others' redemption while incarcerated and in solitary confinement.

"'I'm dangerous,' they said."

Through tears over the phone, James Jacobs, the hip-hop artist who goes by the stage name of JJ'88, tells his father that the hearing to reduce his sentence was denied. In April 2004, a 15-year-old Jacobs shot and killed an 18-year-old at a party in Bellflower, Calif. At the time he received the letter rejecting his request for a resentencing in 2020, he had lived more years in prison than outside of it.

"They don't believe me. They don't believe who I am," he continues. "They said that all the work that I'm doing, my art and my advocacy work … they said that it's not real. They say I am a clear and present threat to the community."

In 2020, Jacobs was denied a hearing to reduce his prison sentence. His father, pictured here, grapples with the news while trying to comfort his son.

As his father tries to comfort him, an automated voice cuts in: "You have 60 seconds remaining."

Filmmaker and director Contessa Gayles was in the room with Jacobs' father as he received that call.

"I remember, too, after that moment, obviously being incredibly concerned for you and your well-being," Gayles tells Jacobs during an interview with NPR, "but I hesitated, for a long time, to ask you if you wanted to continue with the film. … I just was too afraid for your answer."

The pair had been working with Jacobs' producer on a documentary and visual album together. But he said he did want to continue.

"I've seen hard moments in film before, I've seen hard moments talked about in music — really hard moments — and this was one of the hardest moments in my life," Jacobs says. "I love [Shakespeare's] Titus Andronicus — it's a tragic story, and I remember reading that and I was, like, 'this is art too' — it doesn't always have to be this fairytale Disney ending that I was used to, as a kid and as a fan of films. Some stories end in, 'this guy found spiritual enlightenment but died in prison.' That's the wisdom of the world, I guess. That's the wisdom of our universe. I couldn't argue with it, so I was comfortable [with continuing the film]."

Actor Miles Lassiter, as "kid James," wears antlers in Songs from the Hole. Jacobs says it's the image he's asked about most often. "These antlers, along with being [for the song] 'Most Hunted,' are very gun-hunting, violent-culture — the experience, as a Black man, was that [Black men] were being hunted like deer, like buck in this country. And early references of Black men in this country — we were called Bucks. And so I thought — we [Jacobs and Gayles] thought — it was fitting ... that this character represented the coming-of-age through antlers and the symbolism of being hunted with antlers on his head." — Actor Miles Lassiter, as "kid James," wears antlers in *Songs from the Hole*. Jacobs says it's the image he's asked about most often. "These antlers, along with being [for the song] 'Most Hunted,' are very gun-hunting, violent-culture — the experience, as a Black man, was that [Black men] were being hunted like deer, like buck in this country. And early references of Black men in this country — we were called Bucks. And so I thought — we [Jacobs and Gayles] thought — it was fitting ... that this character represented the coming-of-age through antlers and the symbolism of being hunted with antlers on his head."

Songs from the Hole follows Jacobs' story as he reflects on his coming-of-age within California's state prison system, finds healing in an unlikely place and contemplates forgiveness. After meeting and befriending Gayles when she was on assignment for CNN at California's Correctional Training Facility, commonly known as Soledad State Prison, in 2017, Jacobs and his producer, Richie Reseda, reached out with an ambitious idea: to direct and bring to life the visual album that Jacobs had written entirely from solitary confinement. The request reached Gayles at an important moment of her career: when she was ready to pursue independent filmmaking.

Gayles says she was inspired, during the making of Songs from the Hole, by the 2014 film Boyhood. "I was just thinking about representations that we have of white childhood and the plethora that exists of those depictions, and that often, with storytelling around Black people — Black young people — it's very limited in scope. And so I was just meditating on, '[Richard] Linklater spent 12 years making [Boyhood] about white childhood,' and I was just saying in my head, 'we deserve to have as much space to be as indulgent and wide-ranging with how we tell the stories of Black childhood.'" — Gayles says she was inspired, during the making of *Songs from the Hole*, by the 2014 film *Boyhood*. "I was just thinking about representations that we have of white childhood and the plethora that exists of those depictions, and that often, with storytelling around Black people — Black young people — it's very limited in scope. And so I was just meditating on, '[Richard] Linklater spent 12 years making [*Boyhood*] about white childhood,' and I was just saying in my head, 'we deserve to have as much space to be as indulgent and wide-ranging with how we tell the stories of Black childhood.'"

Reneasha Jacobs holds a photograph of her and James' older brother, Victor Benjamin. Benjamin was shot and killed on April 19, 2004.

Actors reenact a memory from Jacobs' childhood in Songs from the Hole. In the film, Jacobs says, "Memories are crucial in maintaining your sanity in prison. I remember — maybe accurately or inaccurately — but I remember things from my childhood and relive them, sitting on that bunk, and it reminds me that I was a person and I am a person before being incarcerated." — Actors reenact a memory from Jacobs' childhood in *Songs from the Hole*. In the film, Jacobs says, "Memories are crucial in maintaining your sanity in prison. I remember — maybe accurately or inaccurately — but I remember things from my childhood and relive them, sitting on that bunk, and it reminds me that I was a person and I am a person before being incarcerated."

Actor Myles Lassiter portrays a young Jacobs lying in the bed of a pickup truck, holding a toy gun, during the song, "Most Hunted." Jacobs says the visual was important to him because "in the song itself, I mentioned ... a couple of references to 'Friday,' one of them being during the hook, 'the government launched four drones. Still, I need a Glock to walk Smoke home. I'm not a man with it. I'm a man without it.' And those lines kind of hint toward quotes from the film 'Friday,' which is where Craig [played by Ice Cube] is in the room with his father. He just discovered that his father just discovered that he owns a gun. And [his dad] says, 'Back in my day, we would use these [referencing his fists]. Are you a man or are you not?' And [Craig] says, 'I'm a man without it. I'm a man without this gun.' And I knew when I first saw that, that I was like, 'I'm a man without a gun, but in this world, they don't see a man unless I have a gun.'"

Throughout its production, the visual album quickly evolved into a documentary, heavily inspired by Beyoncé's Lemonade. Where Beyoncé added poetic interludes between songs, in Songs from the Hole, the audience learns about Jacobs' story and how his music spiritually liberates him while simultaneously being among the reasons officials cited for not considering his request for resentencing.

Gayles uses messages Jacobs wrote while in solitary to portray his vision for the album. When asked about the decision, Galyes says, "We really made use of 88's handwriting because it was so much a part of his process." She said she also felt "it would be more impactful to have the audience experience 88 in a similar manner to his loved ones ... which is primarily over phone calls and letters."

Reneasha Jacobs, James' older sister, holds an old photograph of herself and her two brothers from when they were kids. James shot and killed someone on April 16, 2004. Three days later, their older brother was murdered.

The film relies heavily on Jacobs' letters and recorded phone calls, through which he, Gayles and Reseda talk about the album's production. The letters consist of scripts, shot lists and lyrics. Through the calls, Jacobs serves as the film's narrator, speaking about his life and the symbolism of the imagery he'd dreamt up in solitary. The film explores cultural themes that touch on Black boyhood, familial relationships, growing up in the church, crime, forgiveness and redemption.

Actor Devonte Hoy depicts Jacobs forgiving the man who murdered his brother. In the film, Jacobs says, "Tears start coming down my face. And I said, 'Man, you killed my brother.' And the first thing out of his mouth was, 'I'm sorry for what I took from you, bro.' ... And I just told him, 'Man, I forgive you. If you want my forgiveness, you have it.' And I got up and left."

Jacobs was released in 2022, after serving 18 years in prison.

Now, with the film streaming on Netflix and the team holding screenings in prisons across the country, Jacobs says he hopes the parole board commissioners who kept him locked up think differently about him if they see the film.

"If only you understood me, you'd see my humanity," he says in the film.

"I would absolutely love to show this film to the commissioners that told me I was a danger to society," he told NPR. "I would love it. I can't wait to catch word that they watched it so that I can see — let's talk again; I don't even have to go to board, but I would love to talk to you now."

Hoy depicts an older Jacobs talking to his father through glass during a visitation. In the film, Jacobs says he had just finished writing two verses of his song "Steel Grave," and rapped both verses over the phone for his dad. When he finished, Jacobs says his father asked him, "What happens to the character? You just described he was in this dark world. Does he ever come out?"

Songs from the Hole is currently streaming on Netflix. Find more of JJ'88's work at linktr.ee/jj_eightyeight and on Instagram, at @jj_eightyeight, and more of Contessa's work on her website, ContessaGayles.com, or on Instagram, at @contessagayles.