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Review: ‘How to Prepare For Prison’ is an intense tearjerker (Includes first-hand account)

If you’ve managed to avoid being arrested for a crime, you’re likely aware of how slow the system is to punish people. From arrest to conviction to sentencing, the process can last for years. If you’re going through that system, however, each and every passing day can seem like torture.

How to Prepare For Prison, directed by Matt Gallagher, is an intimate character study, so to speak. It focuses on three people: Joe, arrested for marijuana production and trafficking despite proclaiming his innocence; Demarco, who assaulted a girl after she tormented him over his homosexuality; and Christy, who stole $950,000 from her boss.

Filmed over three years, it checks in on the three during the most vulnerable time of their lives. There’s a palpable sense of dread that hangs over most of this film; the audience knows that each of these people may eventually spend a significant amount of time in prison. Still, it’s hard not to root for them as they try to cope with their lives being turned upside down.

Despite their transgressions, each subject has a compelling story to sell. Joe, the most stoic of the three, has three kids and a wife who is constantly stressing out about how much his possible jail sentence could upend their family, emotionally and financially. Demarco, a college student, faces a judge in Detroit as his lawyer does his best to secure a favourable deal. Even Christy, who fully admits to her fraud, sees her friends abandon her and her relationships crumble as she awaits a sentence.

Christy’s story brings an interesting side note to the documentary; to prepare for what prison, she hires a prison consultant who coaches her through what she can expect when she’s behind bars. The prison consultant industry could probably be a separate documentary on its own.

There’s also Lee, who served 14 years in prison. He tells his story throughout the film, almost like an apocryphal warning of what Joe, Demarco and Christy can expect.

This is an emotionally charged documentary from start to finish; almost everyone who provides a talking-head interview breaks into tears at some point, and as a viewer it’s hard not to cry along with them. The film is not an indictment of the justice system, but it seems like an imposing and intimidating monolith for the three people awaiting their sentences.

How to Prepare For Prison establishes a real sense of empathy for everyone involved. It’s a must-see if you want to understand the pain an impending prison sentence can inflict not just on the convicted, but on everyone around them.

The documentary will play on April 30 and May 8 at the Hot Docs International Film Festival in Toronto. See Digital Journal’s 2016 festival coverage here.

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