Literature as representation has not only been able to capture the people’s imagination of a given epoch but has in itself constituted a historical account that goes deeper than mere representation of historical fact. As such, literature is a good tool for historical representation and examination, which complements historical records. Whereas history deals with hard historical facts, literature deals with fictionalised history inspired by historical events or imagination but in either case shaped by the society it represents. Thus, one can read a historical novel as both a fictional and factual representation of the historical fact. In this regard, the paper argues that the intersection between literature and history is inevitable because fiction uses the creative industry to represent historical events with both history and literature being products of society. Using a historical approach, this paper uses Achebe’s Things Fall Apart, Hussein’s Kinjeketile and Rubadili’s “Stanley Meets Mutesa,” which represents the three key genres—novel, drama and poetry, respectively, to interrogate how history and literature are connected. Achebe’s Things Fall Apart depicts the historical encounter during the advent of colonialism. Hussein’s Kinjeketile portrays the struggle between the colonised and the coloniser in the fictionalised Tanganyika. Rubadili’s “Stanley Meets Mutesa” depicts a cruel encounter between the colonised and the coloniser with the colonised seemingly blind to the machinations of the coloniser. The three literary texts are used to illustrate the historical connection between history and literature.