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Englewood Boys: A Play on Portraiture

by Ruby C. Berryman

Spalding MFA Playwriting Alumna (2013)

Chicago-based artist Julian Williams painted Englewood Boys, a portrait series, as a response to his interaction with the prison system when his own son was incarcerated at a medium-security facility. Seeing these portraits for the first time, I found a narrative within them and suggested they be exhibited in a prison while I wrote a play about them. I felt the play would ring truer with input from inmates, so I devised a writing project in which the men created monologues based on the portraits. I crafted the play around these monologues.

The Englewood Boys exhibit had been installed at the Northeast Correctional Complex in St. Johnsbury, Vermont, a week and a half before my first visit, to inmate curiosity and skepticism with comments like, “What’s with the shoes?” (The shoes were a portion of the exhibit which gave some indicator to the painted inmate’s walk in life.) The Superintendent, while a huge advocate for the project, remarked that many staff as well as inmates may not consider watercolor portraits of thirteen Black men and their shoes, “art.” Additionally, the inmates’ literacy level tended to be low, and writing monologues would be completely new on many levels. I knew they would balk if it felt like another English class.

The evening of the first meeting, I waited outside for the correctional officer to let me in so he could frisk the pages of my writing exercises, springless Bic pens, and Sharpie highlighters. As my eyes followed the barbed wire that framed the walls of the correctional complex giving way to beautiful mountains in all their fall foliage glory, I wondered how well this idea of writing from portraits would be received, but mostly I hoped that at least some inmates would show up. Finally inside, I greeted the diverse group of nine inmates who had shown up: the visual artist, the songwriter, the rapper, the graffiti artist and the bored. Some were inspired by the talk the painter had given at the artists’ reception the week prior. Some were just looking for something to do.

Having no bestseller to consult on icebreakers for inmates, I set about finding ways to break down barriers between the men and myself. I attended a workshop with teaching artist Genevieve Aichele where I learned techniques that I could modify to use with the inmates. By far the most important one was the talisman exercise. In this exercise each person shares his talisman, an object that has a sacred or personal significance to him. This exercise created bonding where the inmates began to trust each other, which became very important later when they shared their writing. Group exercises were used throughout to build the neighborhood of Englewood and to situate themselves and their characters within it, to connect the characters to each other, to create a continuum of past, present, and future for the Englewood Boys and to keep the inmates from getting restless under the burden of so much writing so quickly.

The 90-minute writing exercises took place over four Tuesdays, not much time to learn how to write a monologue and create a performance piece. To help the inmates generate words on the page from the portraiture, I use the technique of ekphrastic writing that is used in generating poetry from portraiture. Week one, they each created word portraits using a template that I devised for this purpose where complete sentences weren’t necessary, just two to twelve words. Week two, they finished word portraits for their chosen portraits and moved on to word portraits of themselves. Week three was spent crafting the portraits into monologues for each character. Week four was working on performing the monologues. During week four, I was granted two extra 90-minute periods to block and rehearse the piece for a Saturday morning performance for inmates and staff.

On performance day, supporters and naysayers filled the room. The seven inmates (two had been discharged) were seven artists that day. They portrayed the characters we crafted from the Englewood Boys portraits connecting the stories of those men with their own personal ones. Conveying all the violence and oppression of the neighborhood of Englewood on the south side of Chicago, they still left room for hope in their words. I was proud of them for embracing something foreign and by doing so, creating art which extends outside the boundaries of their physical and, for some, mental prisons.

 The Englewood Boys collection will be on exhibit in the upper gallery at the Catamount Arts Center in St. Johnsbury for the month of January. A live performance of Ms. Berryman’s play will take place on January 30. This performance is open to the public. For information on the event, check out


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