Contessa Gayles’ Songs from the Hole is a cry for humanity for its central subject, but is presented as a moving visual hip-hop album. It is a documentary based on James JJ’88 Jacobs.
Songs from the Hole review
Film: Songs from the Hole
Cast: Kellie Evans, Devonte Hoy, Myles Lassiter, James “JJ’88” Jacobs, Victor Benjamin, William Jacobs Jr., Janine Jacobs, Reneasha Jacobs, Jacqueline Williams, Naaji Pruitt, Lauren “Indigo Mateo” Jacobs, Jovon Times, Africa Turner, Ernest Walker, Ryleigh Legget
Writer/Director: Contessa Gayles
Rating: 3 stars
Runtime: 107 m
Contessa Gayles’ Songs from the Hole is basically a cry for humanity for its central subject, but is presented as a moving visual hip-hop album. An incarcerated musician struggles for healing and peace as he comes of age in this documentary.
At the age of fifteen, James JJ’88 Jacobs shot and killed a man on the streets of LA and was incarcerated in solitary confinement towards a double-life sentence. He spent that time in “the hole,” left alone in a tiny confined space with literally nothing but his thoughts. His thoughts, penned down over 15 years of confinement in a notebook, spoke about his past, present, and uncertain future in verse and music, and became fodder for a bevy of music producers. These music producers eventually brought them to life outside the walls of his prison.
Jacobs himself co-writes this story with Contessa Gayles and it's a sing-out for justice. The hypnotic blend of music, imagery and personal testimony is quite powerful. Jacobs reflects back on the anger and violence leading to remorse, redemption and healing through his deeply moving original songs. We experience his past trauma, feelings of hopelessness and struggles with a justice system not structured for rehabilitation. We also get to experience Jacobs’ personal growth throughout this process. As he pours his turbulent emotions into song, the visuals bring us into his reflective process.
Gayles’ thoughtfully crafted video sequences are poetic illustrations of Jacobs’ lyrics. The slickly produced music accompanied by hurting, pathos-ridden lyrics (eg, “If the legal system don't give me life, I’ll probably get shot by my own nine”) manages to tug at your heartstrings.
Gayles handles the sequences depicting Jacob’s anger and remorse about the life and youth he sacrificed with elan. Poverty, systemic discrimination, white supremacy may have been reasons for his downfall, but the murder of his brother mere 3 days after the incident gives him cause to pause and rethink about what he has lost and what he could possibly salvage. Jacobs' story is told through archival photos, collect calls from prison, and, largely, through his songs.
Meanwhile, his surviving family — father, who is a pastor, stepmother, sister, and fiancée—pursue attempts to get him released. This documentary crafts its story through the pursuits of his family, the pain he experiences following his circumstances, and the intense, beautiful art he creates. The perceived path to redemption involves musical glory. Gayles visual interpretation showcases the redemptive strength of that creative expression.
Songs from the Hole tries to humanise someone who has committed one of the most irredeemable crimes. As such, this documentary works as a powerful testimony for the cause of judicial reform.
Subscribe today by clicking the link and stay updated with the latest news!" Click here!



