The Netflix Documentary ‘Songs From the Hole’ Will Make You Rethink Our Prison System

Music, more than a product or anything else, is a sacred act. That’s the prevailing premise of director Contessa Gayles’ award-winning Songs From The Hole, a 90-minute documentary on Netflix that highlights Long Beach native, artist and activist James “JJ’88” Jacobs’ evolution from a wayward 15-year-old who committed a murder into a beacon of what he calls the “utility of nonviolence, art to tell stories, and being vulnerable.” In the documentary, which won 10 awards on the 2024 film festival circuit, Gayles expertly weaves jailhouse phone calls with JJ’88 with a visual album that he crafted in prison, as well as a harrowing fly-on-the-wall chronicle of how his family supported him throughout his incarceration and repeated attempts at freedom. 

JJ’88 was freed from prison in 2022 after 18 years. But before he was physically liberated, he was spiritually liberated by a chance encounter with the man who killed his brother. The documentary is a glimpse of the practicality and necessity of restorative justice that shares themes with Gayles’ 2018 CNN documentary The Feminist on Cellblock Y, about then-incarcerated producer Richie Reseda starting a prison feminist group (Reseda is a co-producer on Songs From The Hole and made the beats that JJ’88 rapped over). According to Gayle and JJ’88, who spoke on the doc at a screening in July in New York City, it was made over several years, and began while he was still incarcerated, which presented logistical issues (JJ’88 came home eight months into the editing process). JJ’88 had written the treatment for the visual album after being inspired by Beyoncé’s Lemonade and self-titled albums, bonding together songs he wrote while in solitary confinement, and recorded with Reseda’s help. 

Gayle said she completed about one music video per month, then weaved them into the rest of the footage. There was initially consideration of visually demarcating the music videos from the raw documentary footage with different aspect ratios, but she decided that everything should remain uniform. It was the right choice; the seamless visual presentation allowed her to keep things lively while JJ’88 is talking, alternating old photos and video of the Jacobs family with familiar conceits from the visual album, which, derived from his life experience, centers young Black men, mothers, and the justice system. There are repeated appearances from an adolescent and incarcerated man playing JJ’88, and another male who portraying his brother Victor, who was killed three days after JJ’88 fatally shot a man in what he admits was a “senseless” act of trying to bolster his street reputation. Recurring scenes of children dancing cue to the inner child that Jacobs, and too many other Black men, lose to the streets. 

The layered videos and songs feel unmistakably inspired by the artistry of a Kendrick Lamar or Vince Staples, often culling themes of faith, morality, family, and violence. During a song lamenting “crime waves,” two boys jump in the ocean, drowning as JJ’88 raps about the treachery of the Long Beach streets. JJ’88, a representation of incarcerated people, returns from the water a man in prison blues, while Victor, symbolizing men prematurely lost to violence, is still a child. They both walk up to a maternal figure on the sands. 

And Gayles does a great job of leading up to each video with resonant quotes from JJ’88’s support system: his mother Janine, father William, stepmother Jackie, sister Reneasha, and wife Indigo. During one juncture, William, a preacher, talks about how he maintains his faith that JJ’88 will come home from his life sentence. The documentary then shows a video of him delivering a sermon, bellowing, “I have a little praise song that I wanna sing,” which seamlessly slips into JJ’88’s reflective “wake up.” The song is bookended with another clip of his father asking, “Have you ever been in jail? A spiritual jail?”

The documentary does a good job of highlighting a support system that many men in JJ’88’s former position, doing life in jail, don’t have. There are warm moments, such as him singing with his wife Indigo, joking about getting older with his mother and sister, and celebrating with them when state officials co-sign his deservedness for early release. They’re also there for him in his low moments, such as when his father consoles him after a parole denial. The documentary fleshes out his relationship with each family member and lays out the stakes in a way that the viewer is just as crushed as William when the jail call cuts off before he can give his full farewell. 

During the conversation, JJ’88 tearfully laments, “they don’t believe me,” to his father, telling him that the parole board used his appearance on a music project called Defund The Sheriff against him. The moment was yet another glimpse of the justice system scapegoating hip-hop for its own agenda; in this case, it kept JJ’88 incarcerated. The documentary highlights hip-hop as a tool that helped JJ’88 parse his feelings and rehabilitate, the buzzword that prison advocates claim the system exists for. But to the state, during that particular parole meeting, his music was merely a threat. As a music writer, I’ve become accustomed to how artists have historically marketed authenticity and clamored for listeners to believe their lyrics connote real-life violence. But we see JJ’88, who actually lived the treachery of the streets  — and learned the error of it — desperate to shed any negative connotation of his art. When he wants to be believed as a productive human being, while his music peers want to be believed as living their raps, it makes you rethink what believability is worth from people who can’t see your humanity.  

The documentary is a strong case for the benefits of restorative justice. During one scene, Indigo notes that she was a victim of sexual assault and was “retraumatized” by the criminal process. While she was looking for “closure, justice, healing, validation,” she realized the system wasn’t apt to offer that, dishing one of the documentary’s strongest lines: “The system is not prioritizing me, it’s prioritizing punishment, and my healing could never be found in someone else’s punishment.” 

Early in the documentary, JJ’88 meets a man named “J” while in prison, and has a powerful discussion with him about regretting being in jail for murder, but also realizing that, as JJ’88 says later, “my shortcomings don’t diminish my good.” He admits that “J” embracing his humanity helped him do the same, leading him to confront the “grief, cowardice, shame, and heartache” he faced after committing a murder. Society essentially asks the accused to deny their actions to attempt to beat a case or avoid public scrutiny, but it was only through JJ’88’s admission and reflection on his darkness that he was able to heal and forgive himself. And when he shows mercy to “J,” real name Jamaal Smith, after realizing he killed his brother, he acknowledged his ability to forgive his brother’s killer as the atonement for his own sins. Who knows what his healing would have looked like without talking to the very man who killed his brother — the circumstance speaks to the possibility of a system where victims can talk with violators, especially ones allowed to interrogate their regret outside the brutality of prison. JJ’88 said he figured his brother’s killer was “another one of us,” speaking to the hordes of men disillusioned by the system. And just like JJ’88 was able to see his humanity in Jamaal, hopefully viewers can see their capacity for forgiveness, reflection, and growth in him. 

While in solitary confinement, JJ’88 admits that he felt called by God and began writing his raps with no expectations of them. It’s refreshing to hear an artist — a pretty good one — say that in our increasingly callous, numbers-obsessed ecosystem. His experience reflects the genesis of music-making, when it was simply a chance for everyday people to express themselves and make sense of our world. When songs were first sung, there was no option to become an unimpeachable celebrity from it, just a chance to vent, or rejoice, or go wherever one’s imagination took them. Songs From The Hole might not make the number-tabulating stan armies back down from mast and live in harmony, but hopefully it will encourage some of us to be more precious with artistry and artists. While few of them have a story as cinematic as JJ’88’s, who is pursuing a career as a professional musician, they all deserve consideration as people just like us who decided to share with the world.