[2] In a 2018 poll by critics from The New York Times, the work was ranked the second-greatest American play of the past 25 years.
[1] 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.
At the Plantation Terrebonne in Louisiana, Dido and Minnie chat about the arrival of George, and the passing of his uncle, their previous master.
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.
[2] Jacobs-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.
This led Jacobs-Jenkins to see doubles and pairs in Boucicault's play, through relationships between characters e.g. Pete is Paul's grandfather.
[4] By presenting characters in whiteface, blackface, and redface, Jacobs-Jenkins can look at "blackness and how to represent social constructs onstage that are so tied to a specific culture of nation.
[6] An Octoroon had a workshop production at Performance Space 122 from June 19 – July 3, 2010, featuring Travis York, Karl Allen, Chris Manley, Ben Beckley, Gabe Levey, Jake Hart, Margaret Flanagan, Amber Gray, Mary Wiseman, LaToya Lewis, Kim Gainer, and Sasheer Zamata.
[9] Prior to the first performance, Alexis Soloski for 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".
[13] 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 Gray as Zoe.
[15] 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.”[16] 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 New York with Mixed Blood Theatre Company in the fall of 2015.
[19] Dobama Theater in Cleveland Heights, Ohio presented An Octoroon from October 21, 2016 to November 13, 2016, directed by Nathan Motta[20] The first West Coast premiere of An Octoroon was held at the Berkeley Repertory Theatre, directed by Eric Ting with Sydney Morton in the title role.
[22] From May 18 to July 1, 2017 An Octoroon was performed at the Orange Tree Theatre in Richmond, London[23] in a production directed by Ned Bennett and designed by Georgia Lowe.
[26] Artists Repertory Theatre, located in Portland, Oregon, was to stage An Octoroon from September 3 to October 1, 2017.