This dissertation is an investigation of the marketing and advertising initiatives of two Canadian distillers Hiram Walker and Seagram in the United States from 1950 until 1969. The study contributes to the field of alcohol studies as it explores the divergent meanings alcoholic beverage advertisements conveyed about drinking in relation to constructs of gender, race and class. This dissertation demonstrates that while Seagram and Hiram Walker’s advertising campaigns and marketing efforts targeted white, middle class men, they disseminated competing and contradictory messages about masculinity and normative alcohol consumption to reach consumers with varied interests. The dissertation argues that despite the existence of an established heterosocial cocktail culture in the 1950s, the majority of Seagram and Hiram Walker’s whisky advertisements presented drinking as a homosocial activity. During the 1950s and 1960s, Hiram Walker and Seagram tried to increase market share by advertising to women and African American consumers in novel ways. This dissertation compares and contrasts the distillers’ advertisements directed at white men, women and African American consumers. As well, it adds to the history of advertising as it explores how the distilleries tried to influence consumers’ purchasing decisions, tap into their desires, expand market share and increase sales at a time when competition was intensifying.