Pirandello is one of the most famous and important cultural figures of Italian modernism, and his work is deeply invested in responding to the rapidly changing forces of modernization. This chapter examines his complex relationship with modernity through a comparison to the Italian avant-garde movement of Futurism: Where the Futurists were focused on using their cultural production to usher in and intensify processes of technological modernization, Pirandello’s stance is more complex and ambivalent. The chapter thus traces their responses to a shared set of cultural conditions, spanning from a shared rejection of scientific materialism and positivism to engagement with new models of sociology, psychology, and philosophy, and finally considers their divergent views of cinema and the promise of technology to transform the future.