Paul Austers New York Trilogy has long been considered a classic postmodern detective tale. But isn’t there more to the story? In this study I investigate how masculinity and fatherhood is portrayed in the first and the third novel of the trilogy, City of Glass and The Locked Room. Using a theoretical framework including R.W. Connells term hegemonic masculinity, Helena Wahlströms the new father and post-nuclear masculinity, and lived embodiment, as explained by J. Björklund et. al., I discuss how the male characters in the novels struggle with their gender identity and their role as fathers. The results of the study show that the men, portrayed in a time of change and uncertainty about gender roles – New York City during the 1980s – continuously act in relation to the hegemonic masculinity and patriarchal systems, whilst also exploring behaviors and characteristics outside the norm.