This play within a play, written by African-American playwright Branden Jacobs-Jenkins and directed by Peter Hinton, goes beyond entertainment to challenge audiences. Jacobs-Jenkins bases his story on master of melodrama Dion Boucicault’s 1859 production The Octoroon about a plantation owner who falls in love with a woman of mixed heritage.

In Boucicault’s time, with people of colour barred from the stage, white actors in blackface played characters of African descent. Today, that practice is deemed highly offensive, but Jacobs-Jenkins successfully flips the script, placing a Black man in whiteface, a white man in redface, and an Indigenous man in blackface.

An Octoroon feels blatantly absurd, but then again so is institutionalized racism and slavery. With that underlying premise, the show goes on with a play so memorable, it sits on your psyche, ruminating and revealing itself, at times abruptly, even days after you’ve seen it.

“We are very careful in rehearsal of the play that we didn’t take the painting of the face lightly,” says actor André Sills. “For me, going into whiteface gives me the opportunity to let people see what I see when I see racism.”

Sills stars in An Octoroon as BJJ, the namesake character of Jacobs-Jenkins who wrote himself into the drama. The original playwright Boucicault would act in his own plays and Jacobs-Jenkins wanted to pay homage and have his own voice represented.

In BJJ’s epic and angry opening monologue, where he treats performance as a form of therapy, he explains that in his attempt to re-imagine Boucicault’s original, white actors refused to represent the white characters claiming the story was too melodramatic.

“It's the racist nature that underlines the world of plantation life that was scaring those white males away,” says Sills. They used “the cover of melodrama to stay away from the play.”

To fill the vacant roles, BJJ dons whiteface to play two slave owners—George and M’Closky—eventually acting in both roles at once. Interestingly, notes Sills, George, the protagonist, says the n-word far more times than the villain, M’Closky. This contrast, and many other parts of this play, will leave audiences questioning who the real heroes in this story are if there are any at all.

“It’s meant to shock, to provoke, to shake you up...It forces people to have the conversation of racial injustice or basically the way we treat people,” says Sills. “The original play was written in 1859, but it’s very apparent as to why it still needs to be staged now in 2017.”

In the main storyline, George inherits the plantation Terrebonne in Louisiana from Judge Peyton and falls in love with Zoe (Vanessa Sears), Peyton’s biological daughter by an enslaved woman. Zoe is an octoroon, meaning one-eighth Black, making it illegal for her and George to marry as an interracial couple. They face bigger problems when due to Judge Peyton’s financial mismanagement, George stands to lose both his land and Zoe, who legally belongs to the estate.

M’Closky, out to possess Zoe, sabotages George’s chances to save the Peyton plantation. Though owning another person is abuse in itself, M’Closky is known especially for his violent control, and Zoe and the plantation’s enslaved residents go to lengths to avoid falling into his grasp.

Lisa Berry and Kiera Sangster own the stage as the two witty and worried housemaids, Dido and Minnie, respectively. Their modern speech, a contrast to typical slave narratives, is an intentional reminder that neither the playwright nor the audience actually knows how slaves spoke.

Expect more of the unexpected in this performance, from significant profanity to a killer soundtrack. “Strange Fruit”, a mournful song about lynching, first made famous by Billie Holiday, will hit you the hardest. Yet, it is tracks of modern-day, black musical successes like Beyoncé, Rihanna, Drake and Lil Jon and the East Side Boyz that stand in starkest contrast to the racism and oppression of plantation life the play portrays—but perhaps that’s the point.

“We need to be reminded of the power of theatre,” says Sills. Though the original play looks back at plantation life in the South, he adds, “this version is challenging the lenses in which we see the world.”

An Octoroon feels infinitely complex, and is the kind of play you’ll be talking about for years. The conversations that this play will spark are a prime example of how a writer can start a story, but it’s up to the audience to finish it.

“This is something everybody should see because it’s a theatrical spectacle of a play,” says Sills. “Whatever you can do to wake people up, to examine themselves, will only help the world get a little better.”

An Octoroon is playing at the Shaw Festival in Niagara-on-the-Lake until October 14.