This essay explores how the contemporary drag king deconstructs and appropriates the iconography of the classical Hollywood western to reimagine the cowboy figure through subcultural drag performance. Through a combination of interviews and textual, ideological, and genre analyses, this case study illustrates how one drag king in the Washington, DC drag scene, King Molasses, responds to the western’s prescriptive and normative constructions of gender and race by naming them and transforming them into new sites of resistance. Dragging the cinematic cowboy troubles the western’s thematic binary oppositions between the individual and society, the masculine and feminine, as well as the cowboy archetype’s rigid racial construction. The drag king’s embodiment of the Hollywood cowboy renders visible the erasures inherent in the American frontier mythology of this figure, and simultaneously infuses these symbols with new meanings in the context of drag performance to create new subcultural voices and subjectivities.