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Mad Men (AMC 2007—), a critically acclaimed television series set in the midst of the prosperous New York advertising industry during the early to mid-1960s, often explores the psychological, romantic, and work-related implications of conflicting identities. This project focuses on how Mad Men constructs the workplace and sexual identities of two of its secondary characters, Sal Salvatore, the Italian-American and closeted homosexual Art Director of Mad Men’s fictional advertising agency, and Joan Harris, a white, heterosexual woman who heads the agency’s secretarial pool for most of the series. Both Sal and Joan experience workplace sexual propositioning from important clients during the series, but the outcomes of their individual situations are vastly different. This article compares Sal and Joan’s situations in order to explore how Mad Men considers and values male homosexuality and active female sexuality in the context of both 1960s and contemporary social mores.