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MusicJJ’88

JJ’88’s Freedom Dreams

The star of Netflix’s ‘Songs From the Hole’ wrote and recorded his debut album while serving a double life sentence and freed his soul in the process.

By Timmhotep Aku
Photos by Sergio Santos
Artwork by Thanh Nguyen

The lexicons of the traditional Black church in America and the American carceral system have a few words in common. And while words like testify, testimony, and witness are used to help liberate souls in one context, as part of a call-and-response ritual of personal storytelling and affirmations of faith, they are often deployed to condemn people and confine their bodies as punishment in the other. Few people are as familiar with the paradoxical language of churches and court rooms as James “JJ’88” Jacobs, the formerly incarcerated writer, composer, co-producer, and protagonist of Songs From the Hole, a new “documentary visual album” on Netflix.  

Directed by Contessa Gayles (CNN’s The Feminist in Cell Block Y, The Debutantes) and produced by 88’s friend and main musical collaborator, richie reseda, Songs From the Hole is an ambitious film project that accomplishes the Herculean tasks of chronicling an incarcerated man’s life, introducing the world to his music, and making the profound argument that even perpetrators of society’s worst harms are as entitled to humanity and dignity. The film and the accompanying music are 88’s testimony—in the Black church sense.  

“I know I just made a documentary about my life, but my life is still feeling [very] much like a movie, almost like it’s not real,” 88, as he likes to be called, tells me over Google Meet from his home in California. This latest incarnation of himself as free man, artist, and filmmaker is new to him after having been incarcerated for 18 years and only speaking to people outside prison walls via 15-minute timed phone calls and snail-mail letters. “It’s like we’re in The Matrix, a simulation, like at any moment they’ll be like, ‘All right, that was a good test. Mr. Jacobs, please step off the table and come this way.’”  

Before this interview and the dozen or so awards the film has won on the festival circuit, and even before the two-and-a-half-month stretch in a six-foot-by-six-foot solitary confinement cell during which he wrote this music, 88 was simply a Black child in Long Beach, California. With loving parents —including a pastor father—88 and his siblings were raised in the church. A childhood of singing in choir, playing in church bands, and watching his dad deliver sermons from the pulpit laid the groundwork for the artist and orator he is now. “Going to church is the reason why my means of expression is music, as well as cinema, acting, and scripted things like that," he explains. “In church, we had church plays I’d act in. My mom’s side of the family, they all sing and play instruments. My grandmother sang and wrote gospel songs, so the church is my home base.” 

And although the art he makes now is ostensibly secular, it’s created with as much purpose as the music he performed as a kid. “These forms of expression were for [our] entertainment and for the purposes of bearing witness to a particular message or story, so that’s how I make art now. If I make a film, it's gonna bear witness to an experience of an incarcerated person or formerly incarcerated person. If I make a song, it's gonna bear witness to my experience.”

In April 2004, 88 was 15. Drawn to the fraternity of gang affiliation, emulating his older brother, Victor, and motivated by patriarchal pride and a need for acceptance, he shot and killed another young man in a self-described act of “senseless” violence. Three days later, 88 would feel the kind of grief he had caused his victim’s family when his own brother was killed in an unrelated but no less senseless act of violence. 88 was soon arrested, tried, and, in June 2005, sentenced to two life terms for one fateful day: 15 years to life for second-degree murder, plus a 25-to-life enhancement, amounting to a sentence of 40 years to life.    

“I knew music was a vehicle to connect to people, and I knew that it would be less likely that I’m gonna be in immediate conflict with them because of that connection, and I ain’t gotta fight in a place where all we do is fight.”

 JJ’88

While he was raised in the church, 88 came of age in prison, one of the most toxic and dangerous environments possible. Staying mentally and physically intact behind the wall meant taking accountability for the harm he had caused while forgiving himself and committing to changing for the better. “To practice patience with yourself is to practice patience for other people,” he explains. “And in prison, if you don't have patience for other people, you'll crash out. Period. So you have to build the practice of forgiving yourself.” Though prisons are euphemistically called “correctional” facilities and are supposedly sites of rehabilitation, 88's reckoning with himself came despite his prison environment, not because of it. “Accept [your] mistakes,” he says. “Because in prison, you're waking up in a place that's always telling you your mistakes are evidence as to why you aren't valuable.” 

In this seemingly hopeless situation, creativity became his saving grace “I have to manufacture hope,” he says in the film, on a recorded call from prison. “And the way I manufacture hope is by writing music.” Through music, he could express both his dreams of freedom and his frustrations with himself, his situation, and systems of violence and domination. More than an emotional release, his art also allowed him to build relationships with other incarcerated people with whom he may have otherwise had friction. “One of the reasons why I was writing the music in Songs From the Hole was to entertain the homies,” 88 explains. “I knew music was a vehicle to connect to people, and I knew that it would be less likely that I'm gonna be in immediate conflict with them because of that connection, and I ain't gotta fight in a place where all we do is fight.”  

One of the incarcerated homies 88 connected with over music was richie reseda, a producer and artist at Soledad State Prison. Introduced by their mutual friend Talib, 88 and Richie became fast friends and collaborators, with richie in the producer role, helping to flesh out 88’s musical ideas with the makeshift studio set up they put together inside.  

Recording came with great risk. “Making art and sharing it in prison is illegal,” 88 says. “Full stop.” The idea of art as contraband is alien to those of us not incarcerated and reveling in our First Amendment rights, but prisons are meant to be black boxes where the flow of information is tightly controlled. “The people who believe in prison know what will dismantle it. They're not dumb,” 88 says matter-of-factly. “They know if people [who are] incarcerated openly talk about their conditions, they're in trouble. That's why they don't allow you to talk about it. They know if the news [media] actually had free reign to go in and out of prisons and see the conditions, they would be in trouble. So the reason why they're making art illegal, which is the most pure, most honest form of storytelling to me, is because it will expose what's true, and they'll have to address it.”  

richie reseda (left) and JJ’88

Song From the Hole is explicit about a lot: how violence destroys victims, perpetrators, and their families alike; how intentionally soul-crushing the penal system is; and how we are often complicit in our own destruction. What’s left out of the picture is how exactly these “inmates” were able to record a whole album while incarcerated. The omission is deliberate. “I can't even tell you how we recorded this music. It's that illegal. It's homies still doing it! If we would have got caught in the process of doing what we was doing, I probably wouldn't even be here!” 

But miraculously, 88 is here today to give his testimony, after having his sentence commuted by Gov. Gavin Newsom in 2022. Now back home, he’s continued to focus on healing himself and ultimately the world through art and activism. 

“What I now know to be healing, growing up in church, I've always known to be called ‘restoration,’” 88 says. “To be restored, ultimately, to the god [you are] as human beings. So my approach to healing is like restoring myself, my spirit, my mind, my physical body, back to what it naturally is through creation.”  

It’s a lesson he’s not only reminded of through his art, but through becoming a father. “I have a daughter now. She's one, and I'm watching her just become a human being,” he says as a smile creeps onto his face. “I'm watching this living bundle of meat and cartilage become a whole human being. So I believe there is such innocence and such purity in who we are, in our most natural selves, and healing is restoring ourselves as closely back to that as possible. Healing is about restoring and restoring what can be restored.” 

88’s story is extraordinary, but he’s quick to point out that he himself is not exceptional or “one of the good ones.”  

“I'm just a regular nigga who brother got killed and who killed somebody when he was 15,” he states plainly. “And I can see, through that complexity, that the people who hurt me deserve as much love as I think I deserve, because I want to be restored. It's just a way of living.”