Our presentation examines the impact of two legendary characters who lived and traversed the Bajan landscape and whose lives are closely intertwined with our past, present and future cultural heritage. Ossie Moore and King Dyal were flamboyant characters who emerged in the 1940s for different reasons, but they were from the soil that birthed the fathers of the Bajan nation—Grantly Adams and Errol Barrow. Throughout Barbadian history, many memorable characters and unique actors have entertained us with their personalities, using society as their stage. The persons highlighted in this presentation are in no way celebrities; they were not wealthy or held high-ranking positions. However, they have left their mark on our daily lives. According to the A to Z of Barbados Heritage, the lives of Ossie Moore and King Dyal are not just historical facts but part of a rich storytelling legacy that stems from the African tradition. Storytellers, through their language full of imagery and symbolism, not only preserve our past but also entertain us by acting out the roles of various characters in the stories. Storytelling and practices of orality are fundamental components of Caribbean cultures and a vibrant tapestry of regional and national identities. Folk characters like Anansi, Compere Lapin, La Diablesse, the Soucouyant, and many more are remembered and retold in the Caribbean and its diasporas through a rich oral storytelling tradition. Storytelling has persisted as a means of connection and entertainment in the Caribbean and as a ‘methodological [tool] for unsettling colonialities in the twenty-first century’. (Clarke and Mullings, 2022). Our literature review and analysis of their impact on Bajan society transcends lived years and national boundaries into contemporary periods. Bajans and Caribbean peoples in the diaspora are now aware of the legacy of both characters.