Tracing a thread from the fictionalized pre-colonial to the post-independence period, this paper analyzes the representation of houseboying by locating it at the intersection of gender, race, and class. Reading the representation of domestic service against a backcloth of a discourse that constructs the houseboy as a primitive being, the paper analyzes houseboying as a process of civilization; a form of power relations; and a site where social inequalities and social differences are produced; contested; negotiated; and renegotiated. Since houseboying requires servile postures and is stereotypically based on reversal of gender roles, the question this paper asks is how does the houseboy acquire them given that his background is portrayed to be patriarchal per se where even boys are groomed to be prospective paterfamilias? In analyzing the portrayal of how the houseboy’s masculinity is compromised and how he deals with the resultant societal stigma associated with his work, the paper also examines how, ironically, the houseboys are portrayed to be complacent in sustaining and occasionally enforcing the asymmetrical master-servant relationship. It argues that the houseboy’s ‘slavish’ posture is only situational—a performance and a strategic adaptation to the demands of domestic service.