Abstract The Lion and the Jewel offered a strong template for the discussion of ideological shifts and cultural critique in which the crisis thereof has culminated into the richness of the controversy of the dramatic conversation and debate of the play. This was done with a view at critically examining the shifts in ideals and cultural beliefs from both the indigenous African cultural perspective and that of the Western modernization. This study, therefore, took a cursory but brief historical leap into the idealization for the liberation and decolonization of the African continent that took its shape ideologically in the first half of the 20th century started by its key pioneers and intellectual founders like Edward Wilmont Blyden (1832-1912), W.E.B. Du Bois and others. The creation of a level playground for the African culture to ideologically clash with that of the Western modernization in the play was a deliberate attempt at critically assessing both cultural values from an empirical prism before drawing one’s conclusion for the decolonization agenda of African nationalism of the 19th and early 20th century that was meant to agitate for a unified African identity. Using a postcolonial theory for this study whilst adopting a qualitative approach method, (Jasper, J.M. 2010) argued it that pragmatism means rethinking action, meaning and emotion while feminism is to mean the investigation of cultural processes and micro-level interactions between oppressor and the oppressed in which gender is based on cultural processes such as the internalization of dominant ideas than into class or race and ethnicity. The deep concern and the finding of this study was that the assertion for the sexual preference and Baroka’s will to overpower that of Lakunle over Sidi, was something that must creditably be given to the social movement of resistance, pragmatism and feminist struggle once mentioned by Jasper. Keywords: Ideological Shifts, Cultural Critique, feminism, de-yorubanization, and self-determination