This dissertation explores the symbolic structure of the metropolis, probing how neutral spaces may be imbued with meaning to become places, and tracing the processes through which the image of the city can come to be - and carry real consequences. The centrality of the image of the city to a broad array of urban research is established by injecting the question of image into two different research areas: crime and real estate in Washington, DC and the spatial structure of grassroots visual art production in Boston, Massachusetts. By pursuing such widely diverging areas of research, I seek to show the essential linkage between art and crime as they related to the image of the city and general urban processes of definition, distinction, and change. And yet, the research pursued here offers a mixed appraisal of strategies that pin urban prospects to image and image manipulation, from the great crime decline of the past two decades to the rise of the creative economy and application of urban branding campaigns. Across the analyses, I highlight tension between expectations of change and the essentially conservative forces of image. Far from rebranding the city, culture is shown to play a key role in locking in inequalities, undermining revitalization efforts, and generally explaining the reproduction and persistence of place over time, following the logic of the "looking glass neighborhood." Thus, culture is not nearly the tool to revalorize, relabel, and transform place so well depicted in studies nor do the buzz of cultural events shape markets and communities as effectively in "offcenter" cities. Place is not fixed for good, and can be "re-accomplished," albeit through decades-long demographic, cultural, and political processes. / Sociology