This essay tracks the transformation of the fictional ship's cabin boy in literary and oral texts from the 16th century to contemporary 21st century renderings. By establishing the presence of the female cabin boy as a maritime archetype, I argue that this elastic figure resists and confirms crucial social commentary in small communities which translates to global concerns of violence, language, and cultural traditions. This essay maps the different ways that the female cabin boy figure preserves oral traditions such as folktales and ballads through texts like T's. Eliot's "Christopher Columbo" and L.A. Meyer's Bloody Jack: Being an Account of the Curious Adventures of Mary "Jacky" Faber, Ship's Boy. By exploring the symbolic nature of the female cabin boy, in her respective community, theoretical lenses such as colonialism, nationalism, and gender studies are recognized as possible means of gauging this figure's primary function.