“A Self-Portrait of Success: The Images of Jewish Masculinity in 1940s America” is a research paper that seeks to define what masculinity and success looked like to Jewish men in the mid-twentieth century. To do so, This paper examines New York Times obituaries throughout the 1940s and analyzes the content that prominent Jewish men had published about themselves. These obituaries represent the fulfillment of the Jewish male aspirations and what they wanted to be known for. Along with this, this paper also explores Arthur Miller’s Death of a Salesman, a 1949 play that narrates the life and death of an “everyman.” While he strives to find success and fame for himself and his family, he fails to achieve the same aspirations as the men in the obituaries. Ultimately, this paper works to add complexity and new dialogue to the understanding of Jewish masculinity and also seeks to generate interest in comparatively working with both nonfiction and fiction primary printed sources.