From the 1960s to the 1990s, the corrupt building contractor was a stock-villain of Bombay cinema. He was, this article argues, emblematic of crony capitalism prior to the liberalization of the Indian economy. This filmic role was, however, foreshadowed by his depiction as cynical accomplice and profiteer of British rule in fiction of the early and mid-twentieth century. Furthermore, the figure’s ultimate origins lie in colonial literature, in which he is often identified as a threat to the British civilian community that nourished itself with the ideal of its disinterested civilizing mission. This article traces the genealogy of the contractor-as-villain in fiction and film, demonstrating a continuity of themes, and persistence of concerns, across the work of Rudyard Kipling, Flora Annie Steel, Premchand, R. K. Narayan, and Mahasweta Devi. Using historical sources to contextualize these texts, it will also suggest possible explanations for the ubiquity of contractors in the Indian economy.