Experimental writing challenges familiar ways of the representation of reality through a literary text. This chapter interrogates the notion of experimental writing and considers its place among African literary genres. The chapter then zooms in on experimental writing in African languages, with a case study of two contemporary Swahili writers, Euphrase Kezilahabi (1944–2020) and William Mkufya (1953–). Both writers have interrogated in their writing the nature of African postcolonial reality and considered possibilities of altering that reality, through reparation and reconstruction, but also through a full-fledged recasting and redefinition of the intellectual frameworks that support contemporary African life. Both authors use Swahili, but they load language and style with a multitude of new meanings. In effect, language becomes an abstract and flexible structure capable of thorough transformation to conceive of and express a radically new reality. The same applies to the adoption and adaptation of literary genres. Genres lose their typical literary and ideological determinations. The experimental writing of these authors challenges literary realism in African literature and creates a “novel genre” to articulate texts of a futurist and truly emancipatory African philosophy.