Beyond popularized sororities and toga days, ‘Greek life’ has taken on a more ideological meaning when considering the impacts of the Dionysian and Apollonian spirits on Generation Z in comparison to past generations, namely the Beat Generation. The rambunctious Beat Generation characterized by efforts in free love and sexuality, opposition to capitalism and exploration of communism, socialization of drugs, and racial disparity defined the American 1950s. Notorious writers Allen Ginsberg and Jack Kerouac were only some of the representative figures of the Beat Generation but hold great significance when compared to Generation Z which has shared the Beat Generation’s fervor for the Dionysian spirit - or a sense of nonconformity and chaos among a generally uniform or Apollonian society. As consistent with their representative Greek gods, each of the spirits has contributed much to social change movements in both generations but has maintained balance for the preservation of society. In this paper, I compare the dynamic between Dionysian and Apollonian spirits within the Beat Generation and Generation Z. I remark upon the use of technology in the late 2010s to stimulate the Dionysian spirit within Generation Z as well as the literary attempts of Beat Generation writers to push back against Apollonian society in the 1950s. I ultimately argue that while there are many similarities between the Beat Generation and Generation Z in combatting social conformity, the lack of intentionality behind the Beat Generation social movements establishes their concession of the Dionysian spirit as more authentic although Generation Z’s attempts at leveraging the Dionysian spirit to accomplish change have been more successful