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Many of the plays of W.B. Yeats and Lady Gregory that were presented in the early years of the Abbey Theatre were allegorical works which promoted the cause of Irish nationalism. This impulse existed as a part of a larger political and literary movement to reject British rule and the idea of British exceptionalism in Ireland at the beginning of the 20th century, and it is one which aligns directly with Franz Fanon’s theory of decolonization. Within the plays Cathleen ni Houlihan, At the Hawk’s Well, and On Baile’s Strand this nationalist impulse is exemplified by young masculine characters who stand in stark contrast to the older generation of male characters in the play. Using Franz Fanon’s theory in conversation with Judith Butler’s theory of gender performativity, I argue that these plays constitute an attempt to redefine the masculine ideal in Ireland through depictions of a generational divide. I further argue that this is the result of anxieties around the process of decolonization, and that they constitute an attempt to shape the masculine ideal towards behavior that would facilitate violent armed resistance. This work exemplifies how the process of decolonization can and has influenced the performance of masculinity, and how it runs the risk of perpetuating patriarchal norms in the postcolonial society.