Africa as a continent was subjected to aggressive colonization in the late 1800s when European education systems, Christianity, and governance structures disrupted African societies, creating conflicts between Western and indigenous beliefs of Africa. This struggle led to the ambivalence of African identity among the educated Africans in the early 20th century, allowing them to stand between the crossroads of modernity and indigenous traditions. In the poetry collections, Song of Lawino & Song of Ocol, Okot p’Bitek tries to portray the tension through the character of Ocol. The Nigerian playwright Wole Soyinka tries to invoke a similarly delusional modern man through the character of Lakunle in his play The Lion and the Jewel. These two characters can be considered as an embodiment of the African intellectual shaped by colonial education and caught in the contradictions of the post-independence era. This paper tries to explore the tension between Eurocentric ideals and indigenous beliefs in Song of Lawino & Song of Ocol by Okot p’Bitek and The Lion and the Jewel by Wole Soyinka through the characters of Ocol and Lakunle. It further tries to examine how African writers critique the incomplete process of decolonization and reveals the enduring psychological and cultural struggles faced by postcolonial societies in redefining themselves beyond colonial frameworks.