“Singing About the Dark Times: Alienation and Countercultural Performance in the Long Sixties” examines performances enacted and created during the Long Sixties using the concept of alienation as a tool of theoretical and creative insight. The approach to alienation resonant in counterculture(s) of the Long Sixties—a term used to describe the era of sociocultural transformation spanning from the late 1950s to the early 1970s—was not only interested in the act of “making strange,” but also in the act of making the strangeness of the state and affect of alienation visible within itself. Pulling from theorization foregrounded by Bertolt Brecht, Karl Marx, and Antonin Artaud, among others, the use of the term “alienation” throughout this project integrates its sociopolitical, creative, and affective meanings. Drawing from performance studies, musicology, and Marxist theory, this dissertation considers why artists of the counterculture were drawn toward alienation in their performance practices and tactics, and offers a rereading/relistening of subjects underexamined in current scholarship. Through historical materialist-based close readings of case studies, this dissertation demonstrates how using alienation as a lens increases our understanding of both the immediate and long-term impacts and consequences of this era, as well as foregrounds theoretical terminology that can be used in broader countercultural studies.