Anticipation is a basic human condition central to the formation of experience and expectation. This thesis investigates the presence of anticipation within specific continental philosophical traditions and key art histories of the 20th and 21st century. The first chapter focuses on the development of anticipation within particular philosophical traditions and asks what it means to treat anticipation historically and thus open to repetition. It does so by positioning the idea of anticipation within theorizations of the modern, the postmodern, and the contemporary. The second essay argues that Marcel Duchamp’s painting Coffee Mill (1911) develops, perhaps for the first time, an anticipatory logic central to the artist’s oeuvre and legacy. The final essay investigates Duchamp’s legacy using two Cuban case studies of contemporary Cuban art: the practices of artist Flavio Garciandía in the 1970s and Sandra Ceballos’ art space (Espacio Aglutinador) since the 1990s.