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‘Songs From the Hole’ Review: The Mesmerizing Story of a Rap Album Created Behind Bars That Helped a Convict Find Redemption

Visual albums — a bunch of videos strung together to commemorate the release of new work from a musical artist — typically either feel like shameless promotion or a vanity project. “Songs From the Hole” not only earns the label honestly, but actually takes this co-called next-level artistic endeavor to, well, another level: Chronicling the incarceration of James “JJ’88” Jacobs, who went to jail at age 15 for murder, co-writer and director Contessa Gayles combines nakedly vulnerable reflections from Jacobs with poetic recreations for a deeply affecting experience, both musically and dramatically.

“Songs From the Hole” immediately lays out the landscape of James’ crime and its repercussions: three days after killing a man on the streets of Los Angeles, James’ older brother Victor was murdered, leaving their parents to grieve the death of one child and the imminent incarceration of another. Fifteen years into a 40-years-to-life sentence, James has turned to music to explore his feelings about his circumstances, even as his father, William, mother Janine, sister Reneasha and fiancée Indigo petition for his release — or even a less harsh re-sentencing — from the outside.

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In between, James’ music articulates thoughts, feelings and experiences that he cannot express except via scratchy collect calls made from jail. Gayles enlists a group of actors to portray him and his family, and otherwise dramatize the events portrayed in his songs. The combination feels especially powerful given that he lived many of the stories he tells in his verses and is not merely conjuring his cinematic narratives for the purpose of entertainment. It also makes you forget that he goes virtually unseen for the majority of the film, a challenge for his co-writer and director since he and his journey is the centerpiece of her film.

Yet the connective tissue in this tapestry of crime and punishment, loss and redemption is James’ unexpected honesty about the harm he caused and his attempts to take true responsibility for it. Though his multiple failed efforts to seek a re-sentencing highlight the carceral system’s priority on punitive rather than restorative justice, James identifies the violent, lash-out attitude he embraced as a teenager in a community where gang violence was the norm, and charts a path toward accountability whose challenges are easy to empathize with even if you’ve never committed the kinds of acts that earned him his prison sentence.

By his own admission, James believed as a teenager that the only solution — or way of resolution — for conflict was through violence. But after crossing paths early in his sentence with a fellow incarcerated person named Jay who shows contrition and sincere remorse for his own crimes, he begins to develop a sense of empathy for the family of the person he killed and an earnest desire to turn around a worldview rooted in anger.

While James takes that “long walk” his father tells him will be necessary before God (much less the penal system) decides he can be forgiven, Gayles explores the lives of his remaining family, and how the simultaneous loss of one son to the criminal justice system and another to an act of violence virtually identical to the one he committed has impacted them. Gayles’ understandable sensitivity occasionally elides some details about their lives about which audiences may be curious, including a more specifically rendered portrait of the climate in which James and Victor grew up, outside of the loose timeline he provides about his mother and father’s divorce, a foundational event in his emotional hardening as a teenager. But even absent those clarifications, the film offers an appreciably more complex portrait of Black families in communities dominated by crime than has been shown before, certainly in fictional films, whether or not the devotion and dedication William and Janine show their son was more directly amplified because of his arrest.

Meanwhile, the music holds its own against higher-profile hip-hop contemporaries, and is bolstered by the authenticity of his lived experience. Sounding a bit like North Carolina rapper J. Cole, JJ’88’s songs move skillfully through the life cycle of an inmate’s physical and emotional journey, encapsulating the anger that led to his crime, regret for committing it, and frustration at a legal system that targets people of color in disproportional numbers. In fact, his music is so convincing that it eventually becomes an obstacle for him to obtain his freedom, because the parole board brands it calculated propaganda rather than a sincere expression of his rehabilitation and growth.

Woven between the artistic and procedural threads of the story are numerous twists and turns that will keep audiences on the edge of their seats — revelations that you might not find plausible were his story told as fiction. But the synergy between reality and art is the point on which Gayles’ film pivots, so much so that his written notes about sequences appear on screen to set a scene, and more vividly, establish the amount of time that he had in prison to contemplate how he wanted to tell his story. The result is ultimately deeply moving, even therapeutic, and provides insights about both criminals and the system meant to punish them that haven’t been shown before, at least in this way.

Moreover, it serves as a reminder of the humanity of people who commit acts considered unredeemable. “Songs From the Hole” may have started as a spotlight for art created in an unlikely place, and born from unimaginable circumstances. But like any great song — or album, visual or otherwise — it establishes a connection that makes an audience feel like they’re getting a window into the unique worldview of the artist that ultimately doubles as a mirror forcing them to reflect upon their own.

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