This paper presents a comparative analysis of Ananse-like characters in Ghanaian and Caribbean drama. Ananse, the spider trickster in west Africa and the hero of countless folktales, has a strong pervasive influence in the two regions even after years of liberation. This paper analyses the manifestation of some postcolonial aspects and their correlation with the trickster-inspired characters to investigate the extent to which they match the trickster traits in two Ghanaian and two Caribbean plays. It also studies how the Ananse-characters reflect the social, economic and political environment in the two regions in the postcolonial era. The paper adopts a comparative approach that promises a fruitful way to articulate the significance of the trickster theme in resisting or adapting to the postcolonial impact. It integrates this comparative approach with the bricoleur methodology that is described by Denzin and Lincoln as a methodology that is better able to address the “value-laden nature of inquiry" and likewise “how social experience is created and given meaning" (8). Both techniques are used to investigate the occurrence of trickster characters in the four different plays. The study shows the significance of the trickster characters in challenging the awareness of the audience who could face illusion in case they did not realize the deception. The paper concludes with pinpointing the impact of the trickster characters in stressing the postcolonial aspects such as exploitation, corruption, hypocrisy, and hybridity as well as highlighting how they benefit of being trick-players in dealing with such postcolonial issues.