Best that we not tell you what’s going to happen here. (Ben Arons)

“Underground Railroad Game” owes a lot to an unfortunate time in our past that many people would rather forget: middle school.

The play, which won the 2017 Obie Award for best new American theater work, was inspired by a classroom activity in which co-writer and performer Scott Sheppard’s teachers divided the students into make-believe Union and Confederate soldiers. The former group attempted to slip “escaping slaves” — in the form of dolls — past the latter. Partly from that incredibly awkward and kind of offensive experience from his childhood came “Underground Railroad Game,” which Sheppard wrote and stars in with Jennifer Kidwell.

The two-person show, which opened last week at Woolly Mammoth Theatre, begins with Kidwell and Sheppard playing Hanover Middle School teachers who have the audience partake in a similar doll-smuggling activity. As the play goes on, Kidwell’s black teacher and Sheppard’s white one become romantically involved, raising questions about the intersection of race and sex. Kidwell and Sheppard also take on other roles, including a Confederate soldier and a stereotypical, larger-than-life “Mammy.”

Consequently, the show often becomes … uncomfortable. By the end, “Underground Railroad Game” has forced the audience to recognize and engage with some hard truths — namely, America’s troubled (to put it mildly) track record on race, gender and power.

But, you know, with laughs.

“We really look at comedy in this piece as a kind of tenderizer for the audience,” Sheppard says. “In this day and age, you can be very well-equipped to respond to a piece of art or writing with your politically correct points of view. It’s kind of, ‘I know exactly what I’m supposed to say and supposed to do.’ Humor, for us, is a tool to put us back in the experience of feeling things for the first time.”

“The way laughter is invited in this piece can feel dangerous to people,” Kidwell says. “It can feel offensive to people to have that public release around some of the things that the piece deals with. Offering a nexus of comedy and injustice is its own taboo.”

That doesn’t mean “Underground Railroad Game” uses comedy to entrap you into a spiral of shock or guilt.

“We’re not interested in that gotcha culture, where it’s, ‘Ha-ha, you laughed at that, now you’re a bad person,’” Sheppard says. “It’s actually a bunch of people laughing and then having to further articulate why something is funny. It forces the audience to come up with a more complicated framework for their own laughter, a more complicated understanding of their own laughter.”

“Underground Railroad Game” premiered at Philadelphia’s Fringe Festival in 2015 before moving to Ars Nova, a New York City-based company dedicated to supporting emerging talent. Now, as the show heads out on its first tour, with performances scheduled in Denver and the U.K. this year, more and more audiences may find themselves unexpectedly laughing at America’s original sin and slavery’s echoes in society today.

“Laughter is close to crying,” Sheppard says. “The line between the two is as thin as a tightrope.”

Woolly Mammoth Theatre, 641 D St. NW; through April 29, $20-$89.