Bessie Head (1937-86) was born in Pietermaritzburg, South Africa, to a white mother and Black father during a time when interracial union was illegal in South Africa. Head was an active protestor of South African apartheid. The political environment eventually became so dangerous for her that she fled the country and moved to Botswana, where she lived for the rest of her life. Despite her personal history, Head chose not to focus exclusively on the politics of apartheid in her writing; her work mainly centers around women’s experiences of patriarchy, paying special attention to the intersections of sexist and racist oppression. “The Prisoner Who Wore Glasses” is one of her only stories centered around a male protagonist. Although the story is outside of her usual setting and narrative structure, she does explore the psychological effects of racism and discrimination through Brille’s internal conflict.

Head’s novels and short stories are situated in a period of transitional African literature. Before the 1960s, African literature largely centered around domestic narratives. However, in the 1970s and onward, the literary themes shifted toward narratives surrounding political and social structures. Head’s novels and short stories are a mixture of these domestic and political genres.