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‘Songs From the Hole’ Review: From Murder to Anguished Reckoning

August 14, 2025
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‘Songs From the Hole’ Review: From Murder to Anguished Reckoning
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The hole James Jacobs was sent to at 25 shouldn’t be seen as a portal. And yet, Jacobs, ostensibly serving a life sentence for murder, embraced that possibility when he began writing music in solitary confinement. By then he’d been in prison 10 years. Visually fluid and emotionally complex, the nonfiction hybrid “Songs From the Hole,” directed by Contessa Gayles, offers viewers their own portal: into James’s anguished reckoning, but also into bedeviling questions about crime, punishment and forgiveness.

At 15, Jacobs killed a young man in Long Beach, Calif. In voice-over, James admits that at the time he “had made up my mind to be the hardest” member of the gang. Three days later, Jacobs’s brother, Victor, was murdered.

Jacobs’s father, a preacher, recounts how agonizing it was to read the police report of James’s crime. And, in a telling example of just how contradictory we humans can be: As devastating as James’s sentencing had been for her, Jacobs’s mother recalls that when Victor’s killer was sentenced to life she “was not satisfied.”

The film mixes interviews with evocatively filmed recreations (Myles Lassiter is especially notable playing young James). Those “visual album” moments accompany songs Jacobs — a.k.a. “JJ’88”— penned: “Letter to the Homies,” “Most Hunted” and the animation-accompanied “Steel Grave,” among them.

About that last one, James (Devonte Hoy) raps the first two stanzas to his father. Sitting on the other side of a glass partition, his dad offers what he sees as missing: Hope.

Corny? Hardly. Gayles has crafted a film that refuses to tidy the conflicted feelings its subjects share — or those feelings it stirs in us.

Songs From the Hole

Not rated. Running time: 1 hour 46 minutes. Watch on Netflix.

The post ‘Songs From the Hole’ Review: From Murder to Anguished Reckoning appeared first on New York Times.

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