Popular culture is the culture of everyday lives and we, according to Browne and Brown (2001:3), have seen our popular culture in ourselves. This essay compares the tragic engagements of young Africans with contemporaneous issues relating to culture and popular culture, through the fictional novels of Ken Saro-Wiwa, Sozaboy (1994), and Kopano Matlwa, Coconut (2007). Particular attention is paid to the stumbling blocks Sozaboy’s Mene and Coconut’s Ofilwe Tlou and Fikile Twala encounter with issues