Playing Underground: An Interview with UNDERGROUND RAILROAD GAME creators Jennifer Kidwell and Scott R. Sheppard

Interview by Woolly Mammoth Literary Director, Kirsten Bowen

As a fifth grader at Hanover Middle School in Hanover, Pennsylvania, Scott R. Sheppard learned about the Civil War and slavery by participating in a live action role playing game called the Underground Railroad Game. Years later, he and co-creator Jennifer Kidwell unpack the effectiveness of that experience, as well as race, history, and the ways we still struggle to teach and talk about both. Kidwell and Sheppard spoke with Woolly’s literary department about the genesis of the play, power dynamics, and the complexity of the Underground Railroad itself.

What inspired the play, and how did you develop it together?

S: In Hanover, which is a small town in South Central Pennsylvania, there’s a lot of reenactment culture and Civil War lore because it’s near Gettysburg. There was a thematic unit for every grade, and for fifth graders it was the Civil War. They decided that it was going to be a live action role playing educational war. One of the games we played was called The Underground Railroad Game, where teachers explained that dolls were going to stand in for fleeing slaves. The teachers split the class into two groups: the Union soldiers and the Confederate soldiers. If you were a Union student then you would earn points for each safe house you were able to safely transport a doll to. And the Confederate students were out to catch you. Years later, the game started to resonate with me in a different way. It revealed a lot of the unknown or latent cultural assumptions, blind spots, and racism about my hometown, in ways that I don’t think they realized. I told this story to Jenn when we were in Pig Iron’s School for Advanced Performance Training. The idea was to use this as a jumping off point to explore dares, games, and the ways in which competition can get us to reveal things about ourselves that we would normally protect, censor, or edit. The reality of a middle school and two teachers became central threads of the piece later on.

J: One really pivotal moment of research for us was when we went to the National Portrait Gallery in Philadelphia and watched a talk given by a federally funded historian/park ranger about the Underground Railroad. This white man was talking about the Underground Railroad and the conditions of slavery but having a very difficult time talking about Black people and just stumbling over his words: “slave…enslaved…Afro-American…Negro…” He never landed on what to call Black people. So instead of us learning anything about the Underground Railroad, we learned what it was like to not be able to speak about a troubled history. It is amazing to me that I would walk out of a talk about the Underground Railroad thinking more about the white guy who was talking about it. We were doing an improv for two of our classmates one day and it was not going well and then we both just started playing around with the hilarity of this man. I think that’s how we jumped to, “Oh let’s be teachers. Let’s teach about this.”

Tell us about the significance of the props in the play.

J: One of the things that really struck me was that these teachers were trying to teach about objectification of body and objectification of labor and race through the use of rag dolls. And I asked, “Your school, let me guess, is predominantly white?” “Yes.” So basically the only black bodies in the building were rag dolls that people were carrying around and using as tokens, which seems like just the worst pedagogy ever. When you can see an object in more than one dimension, so that it signifies more than one thing, we start to understand different facets and different points of view. I think the reuse and re-inscription of the objects was once for utility because of the budget, but also “To you, this is the icon of freedom, to me it’s actually the icon of death.”

Over the course of the play Teacher Caroline and Teacher Stuart become romantic partners. Why did you decide to take their relationship in that direction?

S: With these two teachers there was an impulse of crossing lines and wanting to see how far they could go. That started to be a motor for the way in which these two characters operated. We realized that with every scene in the piece, they’re on different levels of caricatures of themselves. When we wear masks, what kind of games can we play with each other, and what does that free us to express about ourselves that we might not ordinarily if we weren’t wearing a mask?

J: And if you’re going to do a piece dealing with race in America, and you have a white guy and a Black woman, you have to talk about sex. To me that’s just so present, so forward and funny, because we don’t want to talk about sex in a puritanical country like this. We wanted there to be a clear and immediate understanding of what’s at play with what those two bodies stand for.

S: What does love look like, or can love exist, with such a deep power imbalance to start? And how does love potentially allow people to negotiate that power imbalance? Or does that power imbalance preclude love from really ever happening?

J: The power that Scott is referencing really comes out in the performance of those two bodies. That’s what the piece is trying to do, to get at “So this is public and this is private,” or is it? And so what is the power dynamic outside of that public space? Can you actually create an ecology between two people that doesn’t reference the outside world and so isn’t beholden to those vectors of power?

What are your thoughts on the Underground Railroad as a historical icon? Teacher Caroline refers to it “as a silver lining to the dark side of slavery.” Do we tend to forget the origin of these historical icons and why they existed in the first place?

J: People have been asking, “Why is this in the zeitgeist?” Part of the function of the piece is to say that it’s certainly convenient to talk about the entire system of slavery, spend a little time talking about how hard slavery was, and then say, “But there was this really great Underground Railroad and there were a lot of really helpful white people on it.” I think that that’s bound in this: a lack of being able to reckon with the evil, the injustice, the perniciousness of the institution of slavery, and to shed light on this narrative of the white savior. Because as long as that white savior exists, we don’t have to fully deal with it. I think that the nation feels like an adolescent right now, and that’s why people have used the term “woke,” because it’s like, “Wait, wait, I didn’t actually realize that all of the things that I’ve held to be true are A) not true for everybody and B) are wrong.” And there are some people who are like, “I will not look at things like that.” I think that the mythos of the Underground Railroad helps assuage the brutality of actually reckoning with truth for those who need that salve.

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