Alternative sports have been situated within backlash politics whereby subcultural or marginal representations illustrate a victimized white male. While this may be true of some sports, skateboard media fosters a sustained critique of “whiteness.” To understand the representation of white resistance in skateboarding, we must locate the sport within the larger historical context of white male rebellion found in Jack Kerouac’s On the Road (1957) and Norman Mailer’s White Negro (1957). Similar to these countercultural narratives, skateboard media represents a tension between a death of whiteness (symbolized by co-opting “blackness”) and its inevitable rebirth (through prolific marketing of white skaters). Unlike the Beats, however, the dialectics of white resistance appear in skateboard media through advertisements that are often underscored by parody, which produces its own set of complexities.