This dissertation explores the prevalent representation of the bicycle as a liberatory figure in theoretical texts, novels, films, and poetry. Because the bicycle confers unexpected creativity and autonomy, it alters definitions of technology, modernity, and identity. Chapter one recuperates and employs Ivan Illich's concept of conviviality in order to re-examine the inheritance of the project of modernity and question the definition of technology in the twenty-first century bicycle epoch. For Illich, the bicycle epitomized the community-centered creativity that defines the convivial in his 1970s works Tools for Conviviality and Energy and Equity. Chapter two investigates the narrative tradition of the road cycling race, especially the Tour de France as theorized by Roland Barthes. To complicate road cycling at the extreme of end of the trope of suffering, the chapter then reads the reform of a terrorist in Viken Berberian's 2001 novel The Cyclist, using the theoretical work of C. L. R. James and Gayatri Chakrabarty Spivak. The penultimate chapter argues the bicycle is consistently used as an icon of working-class struggle in world cinema, based upon the evidence of twenty-five films that maintain the working-class bicycle icon theme, by comparing and contrasting Vittorio de Sica's 1948 Italian neorealist film Bicycle Thieves and Xiaoshai Wang's Chinese Sixth Generation 2000 film Beijing Bicycle. The final chapter explores the effect of Afro-diasporic history in British Columbia in C. S. Giscombe's long poem Giscome Road. Utilizing the travel writing tradition of cyclotour literature since the 1890s juxtaposed with the critical cartography of James Wood, the last chapter renders the full effect of Giscombe's poem as an experimental, postcolonial, counter-mapping cyclotour text with the surprising capacity of what defines the convivial bicycle. Throughout this study the convivial bicycle is found to exceed straightforward arguments of the bicycle's efficiency and self-apparent low carbon footprint. Beyond the proclaimed contrast with the automobile, the bicycle confers an unexpected creativity and autonomy, providing a fuller understanding of what drives and sustains contemporary bicycle culture in the twenty-first century.