This article explores the intersection of gender roles, traditional Shona culture, and colonial legacies in Stephen Chifunyise’s play Oh My Grandfather (2018). Set in post-colonial Zimbabwe, the play highlights generational conflicts within the Matanga family, reflecting broader societal struggles. It explores how patriarchal Shona traditions continue to dictate gender dynamics, which are largely oppressive toward women. The article focuses on the roles of Morgan and Dorcas, who navigate between these traditional expectations and modern, Western values, creating what Homi K. Bhabha terms a ‘Third Space’ of cultural hybridity. The article discusses how Chifunyise critiques rigid gender norms while advocating for a balance between preserving cultural heritage and embracing modern ideals, such as gender equality. By highlighting characters like Dorcas and Tandi, who resist oppressive traditions, the play suggests that cultural practices can evolve without perpetuating injustice. Ultimately, Oh My Grandfather provides a nuanced exploration of the complexities of cultural identity in contemporary Zimbabwe, advocating for an integration of tradition and modernity that promotes a more equitable society.