Jenkins recommends the play be performed with 8 or 9 actors, with male characters played using blackface/whiteface/redface, and female characters portrayed by actresses that match the characters' race.BJJ - a black playwright who plays the characters:
George - the heir to the Plantation Terrebonne, a photographer
M’Closky - a neighbor who plots to buy Terrebonne and Zoe
Playwright - a characterization of The Octoroon's author, Dion Boucicault who plays the roles of:
Wahnotee - an Indian of ambiguous background, friends with Paul
Lafouche - an auctioneer
Assistant - Playwright's intern who plays the roles of:
Pete - an older, loyal slave in charge of the house
Paul - a pickaninny-type young slave
Zoe - the titular octoroon. She is the daughter of George's Uncle and a slave. Zoe grew up in the house, was educated, and has an affection for the slaves, who appreciate her
Dora - a wealthy white woman who sets her eyes on George
Minnie - a house slave
Dido - a slave, friends with Minnie
Grace - a pregnant slave
Br’er Rabbit - a presentation of the Br'er Rabbit character. The actor playing Br'er Rabbit can also double as:
Captain Ratts - the owner of a ship that comes to buy slaves
The play begins with BJJ, in a black box telling the audience a conversation he and his therapist had, to get him excited about playwriting and to overcome depression. BJJ is focused on a play, The Octoroon, but runs into issues staging it because the white actors quit, so he applies whiteface in order to play them himself. Playwright taunts BJJ, and laments how theatre has changed since his death. Then Playwright and Assistant put on redface and blackface paint.
At the Plantation Terrebonne in Louisiana, Dido and Minnie chat about the arrival of George, and the passing of his uncle, their previous master. Pete, George, and Dora acquaint themselves when Zoe enters to meet George. M’Closky announces that Terrebonne is for sale and plots to steal Zoe; because she is an octoroon, she is a piece of property and therefore a part of the estate.
George photographs Dora with his camera while she and Zoe plot to make George marry her. Pete sends Paul to go find a letter that would promise enough money to save Terrebonne. Zoe and George are alone, and George confesses his love for her. Paul—with the mailbags—stops to take a photo of himself with George’s camera. While posing, M’Closky comes from behind and kills Paul to take the letter.
Minnie and Dido realize all the other slaves ran away. Lafouche comes to run the auction of the property and announces Zoe will be sold. George proposes to Dora, but Zoe confesses their love, which turns off Dora. The auction begins and M’Closky aggressively bids on Zoe, winning her.
BJJ stops the action of the play. BJJ, Playwright, and Assistant explain the significance of the fourth act, the sensation scene in melodrama. Wahnotee, accused by the members of Captain Ratts’ ship of killing Paul, is about to be lynched. George defends him and demands a fair trial, while M’Closky reluctantly takes the role of prosecution. Searching him, George finds the letter which resolves the conflict of Terrebonne's future. A plate from George camera is presented, showing both Paul sitting, and M’Closky murdering him is presented and proves M'Closky's guilt. Pete pleads for M’Closky to not be lynched, so George demands that M'Closky be taken away, not revenged by Wahnotee, but M'Closky escapes and sets fire to the boat. Wahnotee murders M’Closky. Assistant announces that the boat explodes.
Zoe heads out to the slave quarters to ask Dido for poison. Zoe calls Dido Mammy, and she puts on a mammy character as they argue. Eventually, Zoe takes the poison and runs off. Minnie comforts Dido and they look forward to their new lives on Captain Ratts’ boat.
Through Brechtian elements such as direct address, Jenkins explores "the idea that you could feel something and then be aware that you’re feeling it".
Jenkins researched Boucicault heavily while working on An Octoroon and found an unfinished essay at the New York Public Library saying that theatre is a place for dramatic illusion—the most believable illusion of suffering—and catharsis. Present in An Octoroon is the illusion of suffering and actual suffering.
Jenkins also cites Peter Brooks' The Melodramatic Imagination as an inspiration for his approach to melodrama. Brooks' idea is that melodrama is about binaries and opposites, where there is always good and bad with no gray area. This led Jenkins to see doubles and pairs in Boucicault's play, through relationships between characters e.g. Paul is Pete's grandfather. Boucicault portrayed Wahnotee, and in his play Jenkins explores the connection between a person and their identity as artist. Jenkins looks at the consequences of putting oneself onstage in their own work, if it is a real self or a fake self, which Jenkins embodied himself in the roles of Br'er Rabbit and Captain Ratts.
The sensation scene of the original play is deconstructed in act four. Following the act three climax: the plot lines must converge, the moral is made clear, and the audience has to be hit with a "theatre trick" which overwhelms the audience with technical elements. Rather than execute this, the actors explain and act out what happens. BJJ clarifies that in the time of play, a photograph was a novel/innovative/contemporary way for the plot to be resolved. In An Octoroon, the projection of a "lynching photograph" is an attempt towards an actual experience of finality. A photograph of a real murdered human contrasts with the original play's use of a photograph for justice.
By presenting characters in whiteface, blackface, and redface, Jenkins can look at "blackness and how to represent social constructs onstage that are so tied to a specific culture of nation." This examination of race as a social construct is also in Appropriate and Neighbors.
Jenkins developed his take on The Octoroon while he was a Dorothy Strelsin Fellow at Soho Rep in the 2009/10 season.
An Octoroon had a workshop production at Performance Space 122 from June 19 - July 3, 2010 featuring Travis York, Karl Allen, Chris Manley, Gabe Levey, Jake Hart, Margaret Flanagan, Amber Gray, Mary Wiseman, LaToya Lewis, Kim Gainer, and Sasheer Zamata. It was originally directed by Gavin Quinn of the Irish theatre company Pan Pan, but Jenkins took over the role several weeks into rehearsals. Prior to the first performance, The Village Voice published an email from cast member Karl Allen who wrote, "the play has transformed from an engaging piece of contemporary theatre directed by Gavin Quinn to a piece of crap that wouldn't hold a candle to some of the community theater I did in high school". Vallejo Gantner, artistic director of PS 122 along with theatre critics Elisabeth Vincentelli and Adam Feldman, argued that although it wasn't unethical to publish the email, it may not have been "nice" to publish it.
Mark Ravenhill staged a workshop production of the play featuring Saycon Sengbloh in April 2012.
An Octoroon premiered Off-Broadway at Soho Rep on April 23, 2014 and closed on June 8. Directed by Sarah Benson, featuring music by César Alvarez (of The Lisps), choreography by David Neumann, set design by Mimi Lien, and lighting design by Matt Frey. The cast featured Chris Myers as BJJ, in triple roles: the black playwright, George Peyton and M'Closky; Danny Wolohan as Dion Boucicault, Zoë Winters as Dora, and Amber Grey as Zoe. Jenkins himself took on the role of Br'er Rabbit and Captain Ratts.
The production was critically acclaimed, winning an Obie Award for best new American play in 2014 (a tie with his previous play, Appropriate). In his review for The New York Times, Ben Brantley called the play “this decade’s most eloquent theatrical statement on race in America today.” The production transferred to Theatre for A New Audience's Polonsky Shakespeare Center in Brooklyn and ran from February 14, 2015 to March 29, 2015.
Nataki Garrett directed the first production of An Octoroon outside of NY with Mixed Blood Theatre Company in the fall of 2015.
Company One Theatre in Boston co-produced the play with ArtsEmerson, directed by Summer L. Williams. The production ran from January 29 - February 27, 2016.
The play was presented at the Wilma Theater in Philadelphia from March 16, 2016 to April 10, 2016, directed by Joanna Settle.
Dobama Theater in Cleveland Heights, Ohio presented An Octoroon from October 21, 2016 to November 13, 2016, directed by Nathan Motta