This article attempts to trace the themes of alterity and tragicality in Shakespeare’s Macbeth and Fitzgerald’s The Great Gatsby. We offer a parallel study of the two works with an emphasis on the (anti)heroes’ struggles with time and the other human as metaphors of ‘alterity’. We present a thematic reading and argue that as Macbeth is preoccupied with his imaginatively fabricated future (time) and tries to execute anyone (the other) who jeopardises the totality of that ideal space, Gatsby is also preoccupied with his past (time) and tries to retrieve Daisy (the other). Tragedy, we discuss, is basically the ultimate result of these struggles. We suggest that Fitzgerald’s work generally shares the similar theme of alterity with Shakespeare’s Macbeth and somehow modernises the similar tragicality we witness in the latter.