The 1920’s and 30’s saw the advent of the automotive era in America as Henry Ford’s vision of production and technological progress was fully realized. But the pleasure of automobility was initially afforded to a select few, and so the automobile revealed a growing chasm between social classes. Additionally, the automobile contributed to a transformation of the social ideology of gender as more and more women spent time in cars as passengers and as drivers. And while some viewed this ideological shift as a welcome change, many Americans worried about the negative implications of women in cars. Representations of automobiles in American literature reveal this juxtaposition between positive and negative reactions, and this thesis explores the cultural impetus behind this duality, as well as the manifestations of this duality in F. Scott Fitzgerald’s The Great Gatsby, James M. Cain’s Double Indemnity, and John Steinbeck’s The Grapes of Wrath.