The exploration of masculinity within African literature is rich, yet the application of Antonio Gramsci’s theory of cultural hegemony to scrutinize masculinity and power structures in African literature remains underexplored. Despite the pioneering efforts of scholars, such as Ayodabo and Amaefula, the potential of Gramsci’s theory to unveil the intricate layers of masculinities in African literature, particularly within post-colonial contexts, remains untapped. This research adopts a qualitative methodology, employing critical textual analysis to delve into the nuances of masculinity within Tayeb Salih’s Season of Migration to the North. Extending Ayodabo and Amaefula’s methodological approach, the study draws from Antonio Gramsci’s theory of cultural hegemony to uncover the dynamics of power and resistance within the novel, particularly in the portrayal of male characters and the societal norms that shape their identities. The text offers a profound exploration of colonial encounters and masculine hegemonies, revealing the complexities of power dynamics and struggles shaping the lives of its characters. Through the lenses of Mustafa Sa'eed, the unnamed narrator, and resistant women like Hosna Bint Mahmoud, the novel exposes the construction, maintenance, and contestation of dominant power structures. The portrayal of characters as "subaltern" and "traditional intellectuals" highlights the roles of educated elites in perpetuating or challenging hegemonic masculinity, while women’s resistance underscores the significance of gender and sexuality in this discourse. The study concludes that Season of Migration to the North offers a powerful critique of colonial encounters and masculine hegemonies. By situating the characters within the historical and cultural context of postcolonial Sudan, the novel underscores the ongoing legacy of colonialism and the need for social change. It also acknowledges the complexities and limitations of resistance, leaving space for further exploration of themes like intellectual agency, gender politics, and the ongoing struggles for liberation. This research contributes to the growing body of scholarship on masculinity in African literature and demonstrates the potential of Gramscian theory to illuminate the intricacies of power, identity, and resistance within this domain.