There is an aversion within the field of Appalachian Studies to addressing the cultural formulations of the Appalachian/hillbilly/mountaineer as an icon of aggressive resistance. The aversion is understandable, as for far too long images of the irrationally and savagely violent mountaineer were integral to the most gross popular culture stereotypes of Appalachia. Media consumers often take pleasure or comfort in these images, which usually occur in a reactionary context with the hillbilly as either a type of nationally necessary savage OR as an unregenerate barbarian against whom a national civilization will triumph and benefit by the struggle. I bookend my study with two artifacts of Appalachian representation, linked in specific subject matter, but separated by twenty years. The 1991 West Virginia Public Television-produced documentary film The Dancing Outlaw quickly became an underground cult classic—an object of both absurdist delight and cultural identification within the punk subculture, particularly among those with both a punk sensibility and personal connections to the Appalachian region (birth, upbringing, residency, ancestry). In 2009, MTV and the resources of its wildly popular Jackass franchise revisited the locale and family featured in this earlier documentary and produced the sophisticated and polished film The Wild, Wonderful Whites of West Virginia. The core purpose of this project, however, is to examine why Appalachia and/or the hillbilly, as constructed within and across these subcultures, possessed such appeal during this historical moment. My hypothesis is that such appeal lies primarily (but not exclusively) in the negative characteristics of the region and its inhabitants that are represented throughout a variety of subcultural texts: documentary film, art house cinema, niche regional literature, and independent zine publishing and early blogging. For both those identifying themselves as Appalachians/hillbillies (or some related variation thereof) and those “playing” as Appalachians/hillbillies, these images become statements of resistance and survival to challenge the national mass culture and the political ideologies supporting it.