By the time Two Trains Running opened at the Yale Repertory Theater in 1990, Wilson had already achieved the status of a prestigious and eminent dramatist. The play itself was generally well-received, was nominated for a Tony Award for Best Play, and was the recipient of an American Theatre Critics' Association Award. Beginning with its 1992 Broadway opening, however, a critical debate raged about how Two Trains Running compared to Wilson's earlier work. As they had his previous play, The Piano Lesson, some critics in the mass media claimed that Wilson was becoming less poetic in his rendition of African American life. Mimi Kramer of the New Yorker suggested that Two Trains Running did not function as eloquently and subtly as Wilson's earlier efforts, and Clive Barnes of the New York Post criticized the play's lack of dramatic elegance.

Other periodicals praised Wilson's efforts; William A. Henry III...