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Both Death of a Salesman and The Subject Was Roses are set in the post-war 1940s and present middle-aged homemakers in crisis. They each include representations of a generation of women who were caught in a fading American family dream from the perspectives of the late 1940s and the mid-1960s in America. Often the female wife character has been approached by playwrights and academics as a supporting role who is a housewife residing in the private space defined by family. She is often shown as a mentally unbalanced entity or the cause of a husband’s failure. Focusing on the private space of the housewife in Arthur Miller’s Death of a Salesman(1949) and in Frank Gilroy’s The Subject Was Roses(1964), this article compares the wife characters from the two plays that were written fifteen years apart to demonstrate a cultural continuance of the exclusion of women from opportunities to obtain the American Dream through their own efforts and an emerging societal transition in the 1960s to the awakening awareness of a woman’s possibilities of personal achievement.