Kehlani is the first featured guest in Live From The Hole, a new Question Culture series built around conversations between artists and incarcerated people. The premiere, released October 12 on Question Culture’s YouTube channel, was filmed at the California Institution for Women—the prison where Kehlani’s mother was once held.
That personal connection gives the opening episode a clear focus: motherhood, forgiveness and the lasting harm that incarceration can create across generations. Rather than treating prison as a distant backdrop, the series brings guests into facilities connected to their own lives and asks them to speak with people currently living behind the walls.
Kehlani and her manager, David Ali, are executive producers on the project. In a statement accompanying the release, Kehlani described the prison system as a force that has shaped her life and the lives around her, and called for a world defined by second chances and long, safe lives.
“There isn’t anything closer to home for me in many ways,” Kehlani said. “The prison system orchestrated my life, and its impact on the world continues to shape me and everyone around.”
A series built from Songs From The Hole
Live From The Hole extends the work of Songs From The Hole, the documentary and visual album created around music by rapper James “JJ’88” Jacobs. Jacobs and producer richie reseda host the new series, and both have experienced incarceration themselves.
The earlier film began with music Jacobs wrote in prison, including songs written while he was in solitary confinement. A visual album is a project that pairs music with an interconnected moving-image work, rather than presenting songs only as separate audio releases. Here, those songs became the foundation for a broader documentary story.
Director Contessa Gayles joined Jacobs and reseda while they were developing the album. The documentary was constructed around 10 songs, interviews with family members, and exchanges with Jacobs conducted through letters and 15-minute phone calls. The form matters: it reflects the practical limits that incarceration places on communication, while also showing how creative work can carry a conversation beyond those constraints.
Songs From The Hole follows Jacobs as he takes responsibility for a killing he committed at age 15. It also follows his family’s grief after his brother was killed in a separate act of violence. That combination of accountability and bereavement is central to the new series’ approach. It does not frame healing as simple absolution or a tidy narrative resolution. Instead, the conversations are positioned around the difficult overlap of harm, responsibility, family separation and the possibility of change.
The original film is streaming on Netflix. Gayles, who edits Live From The Hole, and reseda received a documentary Emmy this year for art direction, set decoration and scenic design on Songs From The Hole.
Why the prison setting is the point
Prison-focused screen projects often rely on observation from outside: interviews after release, expert commentary, archival reporting or dramatized stories. Live From The Hole takes a more direct route by staging its exchanges inside prisons and connecting each artist to a place that is personally significant to them.
For Kehlani, the California Institution for Women is not merely a location chosen for a program format. It is tied to her mother’s incarceration, which makes the episode’s discussion of motherhood especially consequential. The premise recognizes that incarceration affects more than the person serving a sentence. Children, parents, siblings and partners can all live with disrupted family roles, interrupted contact and inherited emotional burdens.
The episode’s emphasis on forgiveness should also be understood alongside its emphasis on accountability. Those terms are often flattened into opposites in public discussion: accountability can be misrepresented as only punishment, while forgiveness can be misrepresented as ignoring the harm done. The story behind Songs From The Hole presents a more demanding framework, one where acknowledging violence and grieving its consequences are both necessary parts of healing.
That makes the program’s stated focus unusually specific. It is not simply a celebrity visit, a performance special or a general discussion about incarceration. Its guests are asked to meet incarcerated participants in a setting tied to their own history, with family impact and repair at the center of the exchange.
From prison-made music to workshops and a public series
Reseda described Songs From The Hole as a tool for making revenge “a thing of the past” in both streets and courts. He said the project was made in prison, later toured through more than 30 prisons, and has been accompanied by healing workshops across the country.
That history explains the transition to Live From The Hole. The new series is presented as a way for incarcerated communities to see and participate in the workshop-oriented conversations that have grown around the earlier project. In practical terms, it moves the focus from one person’s music and documentary account toward an ongoing format that can include a range of artists and incarcerated participants.
Jacobs and reseda’s roles are especially significant because they are not outside commentators brought in to interpret incarceration at a distance. Their prior incarceration informs the work’s perspective, while Kehlani’s connection gives the debut installment its own family-centered lens. The resulting structure puts multiple kinds of lived experience in the room: an artist whose family was affected by imprisonment, hosts who were formerly incarcerated, and women currently living in prison.
richie reseda co-directed the premiere with formerly incarcerated filmmaker Antwan “Banks” Williams. Gayles serves as editor on the series, continuing her creative involvement from the documentary that inspired it.
What comes next
Question Culture has indicated that more Live From The Hole episodes will bring in other artists. No next guest was named with the launch of Kehlani’s episode, so the scope, timing and subjects of later installments remain unannounced.
The premiere nonetheless establishes the core model: personal history leads the conversation, people inside prison are participants rather than an abstract subject, and difficult subjects are addressed through the linked ideas of harm, grief, accountability and healing. For viewers interested in music-led storytelling that reaches beyond performance, the series begins with an unusually intimate and clearly defined mission.
Music and screen projects can take many forms, from televised performances to competition formats. This one sits closer to documentary conversation and community work—an approach that makes it distinct from the music-industry headlines surrounding figures such as Boosie Badazz and Lil Wayne’s proposed Verzuz matchup. Live From The Hole is not structured around winning, catalog comparisons or spectacle. Its first episode is structured around listening in a place whose consequences extend well beyond its gates.
