An Octoroon is a play written by Branden Jacobs-Jenkins. It is an adaptation of Dion Boucicault's The Octoroon, which premiered in 1859. Jacobs-Jenkins reframes Boucicault's play using its original characters and plot, speaking much of Boucicault's dialogue, and critiques its portrayal of race using Brechtian devices. Jacobs-Jenkins considers An Octoroon and his other works Appropriate and Neighbors linked in the exploration of theatre, genre, and how theatre interacts with questions of identity, along with how these questions (such as "Why do we think of a social issue as something that can be solved?") transform as a part of life. In a 2018 poll by critics of The New York Times, the work was ranked the second-greatest American play of the past 25 years. Characters and casting Jacobs-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 white heir to the Plantation Terrebonne, a photographer M'Closky – an evil white overseer who plots to buy Terrebonne and Zoe Playwright – a characterization of The Octoroons Caucasian author, Dion Boucicault who plays the roles of: Wahnotee – an Indian of ambiguous background, friends with Paul Lafouche – an auctioneer Assistant – Playwright's intern, to be played by an actor of Native American or South Asian descent, 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 Plot The Art of Dramatic Composition: A Prologue 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