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‘Songs From the Hole’ Review: A Poetic Approach Elevates a Familiar Justice System Doc

As robust as streaming, premium cable and PBS have made the documentary marketplace in recent years, you wouldn’t be wrong to feel that there’s a glut of similar stories being told in similar ways. If you’re a documentary about anything cult-related, good luck cutting through an ample amount of clutter.

A desensitized viewership is a bad thing, or at least it can be. There’s no harm if audiences have become numb to stories about different role-players from the championship Lakers and Celtics teams of the ’80s. But if audiences have become numb to stories about the flaws in the prison industrial complex? Well, those are problems we haven’t solved yet.

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Contessa Gayles’ new documentary Songs From the Hole, getting its premiere at SXSW, has a narrative that, conveyed as a dry logline, could be one of any of dozens of documentaries that play the festival circuit before reaching a soul-calloused audience.

Formally, though, this isn’t a film you’ve seen before. Songs From the Hole is an autobiography told in song, a series of deeply personal music videos that double as journal entries, confessions and self-analysis. There’s a poetic audacity that doesn’t quite sustain the film’s entire 106-minute running time, but Gayles has generally found a fresh way to tackle a familiar exploration of the carceral industry, rehabilitation and redemption. It’s eye-opening in a way you may have forgotten your eyes could still be opened.

The film — “documentary” doesn’t feel exactly right, though that’s what this is — introduces viewers to the life and music of James “JJ’88” Jacobs, who also serves as co-writer along with Gayles.

In April 2004, when he was 15, James killed a man. Just three days later, James’ brother Victor was murdered. The two events weren’t directly connected, but they were connected in the tapestry of the neighborhood in which the people concerned lived and the families that were torn apart. James spent his next birthday in prison, followed by the next 18 years. He experienced depression. He spent time in solitary confinement. He encountered the man who killed his brother. He dealt with his own crime and, at some point, he began to write songs as a way of addressing the young man he left behind and the adult he’d become.

Gayles tells James’ story with a foundation of traditional documentary elements, including interviews with James’ father, mother and sister, as well as his fiancée, and conversations/confessions/recollections from James delivered with the tinny audio of a prison telephone system. Most of the film, though, is built around the more polished and heavily produced songs — richie reseda is a producer of the music and a producer on the film — that run the gamut of self-directed anger, harrowing recollection and lyrical meditation.

This is not, it has to be said, an approach that could work for, or be applied to, every incarcerated person or every documentary and, in that, there’s something just a hair disingenuous about Songs From the Hole. That is to say that if JJ’88 were an awful rapper/singer and his songs were over-produced trash, he could still be candid, rehabilitated and worthy of illustrating the idea of restorative justice. We just probably wouldn’t be watching that documentary.

Instead, JJ’88 is really good. His wordplay is exceptional and the songs are varied and catchy. If you aren’t careful, there could be a real confusion of the medium and the message at work here. James’ humanity isn’t validated by the quality of his music, nor is his music validated by the quality of Gayles’ filmmaking, which uses the songs as a far-better-than-average approach to the sort of re-enactments that are a big part of any conventional documentary fatigue. Most of the videos share a dreamlike quality that effectively matches the lyrics and contrasts with James’ direct circumstances.

I frequently found myself comparing the tone here to the short-lived, sometimes spectacular drama David Makes Man, which walked a similar line between romanticizing and eviscerating memory. Sometimes the aspects of James’ story are crushing, while the songs let the sentiments soar.

The film occasionally struggles to affirm its own messaging. It’s revelatory for James and his family to be simultaneously experiencing victimizing and victimization, but I watched the documentary several days ago and I’ve gone back and forth on whether the choice to largely exclude specifics about James’ victim is an act of dehumanization or one of compassion, sparing that victim from being reduced to a supporting character in somebody else’s narrative.

Nor am I sure that Gayles or the documentary find a clear enough articulation for James’ family’s frustration at his difficulties getting paroled. Songs From the Hole fully and passionately makes the case for rehabilitation, redemption and the power of forgiveness, but the systemic critique is fuzzier.

Mostly, though, that’s not what the film’s agenda is. It’s a mission of humanizing somebody who might otherwise get lost in a dehumanizing system, not to expose the dehumanizing system. It has a voice and a style of its own and, in that uniqueness, it cuts through.

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