Shepard's plays of the late 1960s demonstrate an abrupt change in the tone and style of his writing, which suggests not merely a continuation of the maturing process apparent in La Turista, but a radical revision in his whole approach. He continued, in the main, to write one-act pieces for Off-Off-Broadway venues, and further developed his concern with the individual self's crisis of survival and definition in a frightening, unstable world. Yet the influence of jazz gave way to that of rock music, while the influence of abstract expressionism was transplanted somewhat by that of pop art. Hollywood movies also became a central source of inspiration. In these plays, stage action, character, and language itself are dominated less by solipsistic fantasy than by a newfound interest in the external world, as Shepard began manipulating and parodying the fragmented discourses of popular culture.

In effect, these changes indicate a significant shift beyond the self-absorbed, primarily modernist sensibility of the early work. While preserving the tendency toward stylization and self-reflexivity, there is simultaneously, and paradoxically, the introduction in these pieces of a more or less explicit critique of the “real world” (a real world which remains impossible to define or depict uncomplicatedly: there is no pretense here at the illusion of naive realism). In particular, these plays explore the artifice and superficiality of contemporary life: the gnawing, indefinable fear felt by the tricksters is replaced by a more overt sense of disillusionment and oppression, as Shepard's characters lash out helplessly against their environments.