This thesis explores the era in which shopping centers reached the zenith of its growth and pop cultural relevancy in the United States in the late twentieth century. By tracing the shopping center from its inception as an enclosure that served the needs of the developing and sprawling suburbs to the entertainment complexes that came to define them in the late twentieth century, it can be argued that malls turned away from serving their communities in favor of promoting a type of conspicuous consumption. This thesis also explores the parallel rise of the so-called “teenager,” a demographic that was named to complement the commercial culture that came to define them. This thesis focuses on self-described mallrats in the late twentieth century, and particularly how the two phenomena—mall culture and youth culture—dovetailed under an increasingly deregulated neoliberal regime. This thesis, therefore, delves into the implications of a generation that came of age within the windowless walls of the shopping mall.