Two-act play with music. An adventure story, a political satire, a pop-art “smash up,” this play with music points up the dehumanizing effects of technology on American culture, circa 1970. A sophisticated Air Force computer in the form of a huge snake escapes in the Mojave Desert, becoming the focus of a multitude of forces – black militants, a hapless young tourist couple, the military establishment that tries to recapture the sidewinder – against a backdrop of Hopi Indian magic and mysticism.

First production was staged at the Repertory Theater at Lincoln Center, New York, on March 12, 1970. The music was written and performed by the Holy Modal Rounders. It was directed by Michael Schultz.

The play was originally scheduled to have its premiere at the Yale Repertory Theater on January 23, 1969. Because of a protest by some of the black drama students, Shepard withdrew the play. Among their objections were the portrayal of the black militants in the play as stereotypes of blacks, reminiscent of Stepin Fetchit or Amos 'n' Andy. There were depicted as people unable to formulate and carry out plans they had made, but forced to rely on whites. The Yale administration said they remained convinced that the play was completely harmless on the black question by any objective standards.  Shepard, however, declined to have his play become a social issue. He contended that the main problem was one of bitterness between the black students and the faculty.

Playbill (1970):
The play was staged with dazzling surrealism and the story involved a deadly military device which was a large mechanical rattlesnake. There was a lot of violence and loud rock music onstage.

Clive Barnes, NY Times (March 13, 1970):
The difficulty of the play is in the writing. The symbolic progression, while clearly charting the progress to atomic holocaust, is altogether too symbolic. It seems as though Mr. Shepard has been so busy making his points that he has almost forgotten to write his play... As a result, I feel that he has written, and indeed very cleverly conceived, a rather bad play about a rather good subject... Mr. Shepard has envisaged his play as a series of progressive vignettes, split with complementary musical interludes. Those interludes are provided by, and for that matter performed by, the Holy Modal Rounders. The music is bland, a kind of country and Wester rock-pop, unlikely to offend any, but also likely to inspire few. They perform their music with more fervor than might have been expected, yet it is dry.

Clive Barnes, NY Times (April 2, 1970):
"Sidewinder", to be honest, does have a kind of idiot, metaphorical story to guide it, but it is one that only Hans Christian Anderson could love. They do represent, with a series of humorous and explosive images, a pretty emotionally colored view of our America.

Contemporary Theater Review: Of all Shepard's plays, Operation Sidewinder is perhaps the most representative of Shepard's "imperalist nostalgia" and of an archetypal search for the authentic and for spiritual origins in a modern and material world of technology and media-generated simulacra. Nowhere else in his dramatic writings does Shepard so transparently attempt to acclaim the spiritual lifestyle of Native American culture as vastly superior to the high-tech, militarized and industralized world of the modern white man. And nowhere else does Shepard go through such pains to "authentically" re-create and represent Native American legend and ritual ceremony.