This article traces the transition from Modernist to Postmodernist aesthetics through a comparative reading of F. Scott Fitzgerald’s The Great Gatsby and Angela Carter’s The Magic Toyshop, Heroes and Villains, and Wise Children. Fitzgerald’s novel captures the modernist sense of fragmentation, disillusionment, and the collapse of the American Dream, while Carter’s fiction turns to parody, intertextuality, and the reimagining of patriarchal narratives as postmodern strategies of resistance. By examining narrative technique, character construction, and the treatment of time and space, the study highlights the ways in which both writers mirror the crises of their cultural moments. The discussion ultimately suggests that Fitzgerald’s lament for lost values and Carter’s playful subversion of authority together mark two stages in the ongoing effort of twentieth-century literature to respond to disorder, uncertainty, and change.