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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


In 'Songs From the Hole,' director Contessa Gayles weaves together musical vignettes and the heartbreaking story of James "JJ'88" Jacobs.

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. 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. 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.

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