Observers will remark that a changing community is “losing its character” and becoming less “authentic” as fixtures of an established era give way to signs of new growth that are not so much foreign as recognizable from a generic “everywhere else.” Chain stores and homogenous architectures are prime offenders. Yet not only do these inauthenticities inspire skepticism among longtime residents, authenticity itself has become a commodity that attracts urban development in the first place. With urban consumers seeking authenticity, “craft” businesses and “artsy” condominiums advertise to elites while even national brands attempt to temper community opposition and appeal to buyers with token nods to local character. This paper explores this paradox of local character and neighborhood change, including critical factors of class and status privilege, by comparing cases in which authenticity is claimed and contested through cultural symbolism in new retail business and other development. Examples in neighborhoods from New York to San Diego include efforts by small businesses, national corporations, and architecture and development firms to appear authentic, as well as the irony of finding authenticity in a countryside replete with Walmarts or downtrodden areas wishful for the symbolism of a single Starbucks.