Aahana Swrup
The Netflix documentary ‘Songs from the Hole” chronicles the life of James Jacobs through his visual album created on the other side of prison walls. The incarcerated musician received his sentence as a teenager after he killed another boy on April 16, 2004. Three days later, he underwent a personal tragedy of his own when his brother, Victor, was killed in a similar act of street violence. Thus, from the day young James entered the prison system as a convict, his journey of grief, redemption, and healing began. In the years that he spent in incarceration, he found a unique salvation in music, putting his life’s story and lessons to self-made beats and rhythms. Today, even outside the prison’s bounds, he continues to chase after this passion and love for music.
James Jacobs Took a Life at the Age of 15
James Jacobs was born in 1989 in a Churgoing family to parents Janine and William Jacobs. Growing up in North Long Beach, California, he was surrounded by two siblings: an older brother named Victor and a younger sister named Renesha. While the eldest Jacobs was a protector and a role model to his younger brother, he was also a frequent bully, whose gang affiliation had an influence on James from a young age. Furthermore, his parents’ divorce in his teen years also contributed to the latter’s inclination toward trouble. Eventually, by the time he turned 15, he himself started running in gang circles, adopting a predisposition for violence. Soon enough, he managed to get his hands on a gun. On April 16, 2004, he had a violent altercation with an older teenager outside of a nightclub in Bellflower, California.
The argument ended with James shooting the other boy, robbing him of his long and fruitful life. Even though the young boy-turned-killer ran from the scene in the aftermath, the cops inevitably caught up to him. Three days after his arrest, Victor faced a similar fate to James’ victim, dying as a result of petty arguments and gun violence. In the court proceedings that followed, the 15-year-old Jacobs received a prison sentence of 40 years to life. The early years of juvenile hall and later incarceration at a California State Prison remained tough for the convict. The grief over his brother’s death and the mounting guilt over his own horrific actions took a heavy toll on him. Consequently, by the age of 20, James became suicidal. Still, a glimmer of hope emerged when a bout of solitary confinement moved the convict to create biographical music. Through rap, he found a way to reflect on his wrongdoings as well as the systemic injustice that he perceived in his time inside prison.
Additionally, James began engaging with rehabilitative prison opportunities like anger management and victim awareness programs. A culmination of these efforts at repentance and self-improvement eventually helped him at a crucial point in his life. After years of friendship with another inmate, Jay, James discovered that the latter was Jamaal Smith, the man reportedly responsible for Victor’s death. Yet, despite the disastrous ways this could have unfolded, the young rapper decided to forgive Smith, in the same way he himself hoped to one day be forgiven for his crime. In a conversation with CNN, James said, “[I forgave Smith] Not only because he is entitled to be redeemed. Not only because I want to go home. But because I want to be something new.”
James Jacobs Wrote His First Album While in Prison
Although James Jacobs began writing music in his 20s, it was really after 25 that he began pursuing music seriously. Led by his inspiration, the rapper submitted to the muse of songwriting whenever it struck, sometimes even writing for days at a time. He also began connecting with other rappers in the prison yard, collaborating with them to hone his own musical talents. Simultaneously, he also worked on his advocacy work, championing the idea of redemption and reinvention for people with similar stories as his. He also appeared on an episode of ‘This Is Life with Lisa Ling,’ a CNN Original Series. Sometime around this, the incarcerated musician’s path crossed with Contessa Gayles.
At the time, Gayles was working on another film, ‘The Feminist on Cellblock Y,’ which brought her in contact with Richie Reseda, a convict in the same facility who was also a budding producer. Inevitably, this led to the introduction of the filmmaker to Reseda’s other colleague, James. As a result, the development of Gayles’ documentary ‘Songs from the Hole’ began. Ultimately, the rapper’s hard work and effort bore some promising fruit. In 2020, California Governor Gavin Newsom made James eligible to seek parole, deeming his rehabilitation process productive. Yet, in the end, this appeal was shot down. Still, the musician refused to give up, holding onto his musical aspirations and dreams of freedom.
James JJ’88 Jacobs Pursues a Musical Career Post His Release in 2022
James Jacobs and his family helmed various efforts at winning the musician’s freedom. His fiancée, Indigo Mateo, a prison abolitionist whom he met during his incarceration, was particularly passionate about their cause. Nonetheless, their resentencing and parole efforts all ultimately failed. It wasn’t until 2022 that the family finally got confirmation of the young rapper’s potential to return home. In 2022, after 18 years in lock-up, James finally came back home, released from his life imprisonment. Since then, his artistic drive and abolitionist passions haven’t dampened in the slightest.
In 2023, James began releasing some of his music, including singles ‘Atlantic’ and ‘Tribalism.’ He also took this time to work with other musicians, like Aneesa Al-Musawwir. The premiere of the documentary directed by Contessa Gayles, first in film festivals and eventually on a streaming platform, further helped spread the musician’s life story. The rapper has also been present in the press junket for the documentary, attending its premieres at the American Film Institute, Urbanworld Film Festival, the SXSW film festival, and more. In October 2024, James, under the stage name JJ’88, performed an intimate live show in Los Angeles.
Since then, James has continued working on the rollout for his documentary/visual album, ‘Songs From the Hole.’ In late 2024, he played multiple shows at prisons and community centers all over the world. Even though all the tracks on the album were written behind bars, its lead single, ‘Here Now,’ was a song the rapper wrote after gaining his freedom. Reportedly, he went on a trip to the Santa Cruz Redwood Mountains, where he built a studio at a cabin and worked on his art.
James Jacobs is Now a Married Man and a Doting Father
James Jacobs’ release allowed him precious time to spend with his family, including mother Janine, father William, step-mom Jackie, sister Renesha, and her son, Naaji. Furthermore, in 2022, he and Indigo also tied the knot, officially transitioning their relationship into a loving marriage. In early 2025, the couple forayed into the exciting world of parenthood with the birth of their daughter, Naima June. Thus, it seems the musician has finally found his happiness in his professional and personal life. Furthermore, James also remains conscious and continuously repentant of his past, never opting to hide it away from the limelight. He spoke about it in a conversation with Hip Hop DX, saying, “I’m honest in my life. I’m honest about taking the life of a young man when I was 15. I’m honest about the pain that I caused his family and my community.” Today, alongside his wife, he continues to fight for his beliefs.
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