The twentieth century saw the development of numerous subcultures which shaped the mainstream culture around them through the diffusion of subcultural fashions, music, and literature into the establishment. In the twenty-first century, the postmodern hipster has emerged as a new subculture with distinctive tastes that have shaped dominant Western consumption choices. This dissertation takes a look at some of the twentieth century subcultures that created the foundations for this most recent group before exploring the position of the postmodern hipster in 2018. Building on the work of both scholarly social scientists and popular culture writers who have studied the hipster, I point out some of their key characteristics, such as cultural omnivorism, irony, and bricolage, as elements that make them prime audience members for what I call Alternative Shakespeare companies. The second half of the dissertation offers a case study of one such Alternative Shakespeare company, the New York Shakespeare Exchange (NYSX), who have built a donor base largely made up of individuals between the ages of 25 and 50. By examining NYSX’s mainstage production history, I establish their approach to Shakespeare and mixture of reverence for the text with irreverence for traditional performance methods. Then, their auxiliary performances—the ShakesBEER Pub Crawl, The Sonnet Project, and the Intersections program—are analyzed as further examples of how Shakespeare’s works can be produced in ways that are attractive to the postmodern hipster. By transforming the established, high cultural position of Shakespeare’s works and transgressing against traditional methods of their production, NYSX creates a new kind of cultural capital for the plays that aligns with the kind of entertainments that the postmodern hipster seeks out. Such a model of subversion, while still respecting the integrity of the language, could be employed by other Shakespeare companies to appeal to the hipster, creating future donors and supporters by keeping Shakespeare hip.