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Born in Damascus in 1931 Zakariyyā Tāmir is widely considered one of the most significant figures in the contemporary literary scene of Syria and the wider Middle East. This thesis addresses his literary trajectory and the ways in which representations of masculinity and femininity have changed throughout his career by situating the stylistic and thematic transformations in the context of major historical and political events in Syria and the region. Applying an approach that relates literary transformations to a rapidly changing political context, the research elucidates how the changing configurations of gender roles in Tāmir’s works can be understood in the context of what Kamal Abu- Deeb has described as a process of political and ideological fragmentation affecting the Arab East since the mid-1970s. Dividing Tāmir’s works into two periods (1958-1978 and 1994-2014) to connect them to the different historical conditions in which they appeared, this study examines the significance of masculinity, patriarchy, sexuality and female identity in relation to the collapse of the totalising discourse of modernity. The research scrutinises the ways in which this process has engendered a multiplication of voices and roles in his short stories. Employing Connel’s theory of hegemonic masculinity the study addresses the ways in which the mutually informing nature of masculinities and femininities in Tāmir’s stories channels compliance and/or subversion to patriarchy and patriarchal authoritarianism. In the first part, this dissertation puts into conversation Tāmir’s early works written in the late 1950s and early 1960s and the modernist trend. The organic relationship Arabic literature enjoyed with the project of national liberation is reflected in the fundamentally male-centred nature of the stories, leaving female characters at the margins of a progressive and existentialist struggle for emancipation from authoritarianism, patriarchy, religious tradition and exploitation. While examples from the very early stories show the significant presence of a genuine concern with the sexual dimension of female characters, episodes expressing a more openly political stance also exhibit a tendency to instrumentalise the female body in order to denounce the pervasiveness of the authoritarian state. The second part, devoted to the analysis of Tāmir’s latest works published since his self-imposed exile to the UK, looks at the emergence of prominent female characters openly expressing their sexual desire, simultaneously assessing their subjectivity and acting as decisive actors that shape the male protagonists’ masculinity. The analysis reveals how the works of this period retain a significant political charge, and brings together the appearance of original female characters and the correlated emergence of weak model of masculinity. In addition, stories typified by pessimism, as well as by extensive resorting to elements of Arab popular tradition, serve as illustrations of a peculiar form of Arab postmodernism which has appeared in Tāmir’s stories lately.