The simplest way to describe An Octoroon is to call it a comedy.

Branden Jacobs-Jenkins' 2014 script is a satirization of an 1859 melodrama, The Octoroon. (Jacobs-Jenkins is black; the original playwright, Dion Boucicault, was white.)

Wearing whiteface, actor Joseph Gibson plays George, a slave owner who's just inherited a bankrupt plantation and who's in love with a woman named Zoe (Alex Ramirez de Cruz). Zoe is in love with him too, but the antebellum South has outlawed their potential marriage because Zoe is one-eighth black. Gibson also plays another slave owner, M'Closky, who's distinguished from George by his handlebar mustache. The skeezy, violent M'Closky is obsessed with Zoe, and is determined to marry her, despite her objections.

Premiering in Portland at Artists Repertory Theatre, An Octoroon is punctuated by absurdities. Whenever Zoe says the line "I'm an octoroon," she drapes the her hand across her forehead. Eventually, M'Closky and George get into a fist fight, which requires Gibson to sling punches at a mustache on a stick that he holds up in front of his face.

And that's just the play within the play. Along with George and M'Closky, Gibson also portrays Jacobs-Jenkins, who starts off the show wearing nothing but a white tank top, underwear and black socks. He tells us that he plays so many characters because the white guys he hired kept quitting. They all refused to play a slave owner who doesn't have a speech about how they don't "want to be racist" but it's "just so hard."

He's interrupted by a stumbling, drunk Boucicault (Michael Mendelson), who covers his face in red makeup while his assistant (John San Nicolas) covers his with black makeup. Boucicault explains his casting method—he decided that his assistant in blackface was a "more convincing" black man than the black men who came to audition. When Boucicault's monologue ends, An Octoroon is constructed before our eyes. Beyoncé's "Formation" blasts over the theater's speakers as the cast cover the stage with cotton that looks like chunks of insulation, and pull out from behind the curtains a large wooden platform, which functions as a porch.

An Octoroon is a dense, complicated play. But you're willing to follow along through all of its meta twists partly due to Gibson, who effortlessly switches from satirical theatrical to utterly candid. An Octoroon requires a big cast, most of whom play multiple characters. Thankfully, Artists Rep has filled every supporting role with highly competent actors. Kailey Rhodes is hilarious as Dora, a plantation heiress vying for George's affection. As Dido and Minnie, two slaves who gossip in modern language, Josie Seid and Andrea Vernae craft a compelling side plot.

An Octoroon always seems like it's one step ahead of you—it constantly wonders aloud about its own limits. Just as the melodrama is about to reach its climax, Gibson as Jacobs-Jenkins pauses the plot to address the audience. He tells us that he struggled to update this part of the play, since its big reveal involves a camera. That would have been surprising in the 1800s, since cameras were a new and exciting technology. Now, it seems cliche. "The theater is no longer an experience of novelty," says Gibson.

If anything, An Octoroon's message is to point out that need for constant questioning. It pushes back against the language we have for discussing race in more ways than just dramatic punctuation of the word "octoroon." It tests our cultural lexicon, too.

An Octoroon doesn't all come together in the end. Instead, it sends you through trap door after trap door, until you slam onto solid ground and confront the tragedy that's been lurking behind all the comedy.

After one particularly chilling scene, the lights in the theater go black. From the darkness comes the voice of San Nicolas: "Anyway, the point was to make you feel something." It's tempting to take his word, but by now, it doesn't feel like things can be explained in a single sentence.

SEE IT: An Octoroon is at Artists Repertory Theatre, 1515 SW Morrison, 503-241-1278, artistsrep.org. 7:30 pm Wednesday-Sunday, 2 pm Sunday, through Oct. 1. $25-$50.