Accounts of African letters have been riven by debates about who owns modernism and revelations about covert CIA sponsorship of African cultural institutions. Rather than relitigating the question of whether modernism in Africa is always (covertly) Euro-modernist, this chapter treats modernism as inherently dialectical. It considers African literary modernism in relation to the modernist aesthetics of Uche Okeke, who illustrated Chinua Achebe’s Things Fall Apart, to the Cold War-era criticism of Es’kia Mphahlele and performed poetry of Atukwei Okai, and to the chimeric category of modernity as figured in Jennifer Nansubuga Makumbi’s Kintu. At the end of the day, untethering modernism from the chimera of modernity may well enable more persuasive analyses of each. The chapter concludes with Yvonne Vera’s fiction to sketch how modernism emerges as a historical discourse and stylistic repertoire that some African writers continue to make part of practices of freedom.