'What you gonna do once you free? You just gonna walk up in somebody house and be like,"Hey. I'm a slave. Help me?"' Judge Peyton is dead, and his plantation Terrebonne is in financial ruins. Peyton's handsome nephew George arrives as heir apparent, and quickly falls in love with Zoe, a beautiful 'octoroon'. But the dastardly M'Closky has other plans - for both Terrebonne and Zoe. Branden Jacobs-Jenkins' exhilarating play, An Octoroon, draws on Dion Boucicault's 1859 melodrama The Octoroon to explore issues about race and identity in America today. The play won an OBIE Award when it was first seen in New York in 2014, and had its European premiere at the Orange Tree Theatre, Richmond, in 2017. It transferred to the National Theatre, London, in 2018.

An Octoroon won Branden Jacobs-Jenkins the Most Promising Playwright Award at the Evening Standard Awards in 2017. He was also named Most Promising Playwright at the Critics' Circle Awards in 2018 for his plays Gloria and An Octoroon.