The Italian American man is the result of the interaction of centuries of Italianate masculinities coming into contact with the variety of masculinities that have come to make up the American man. The results of these encounters are more varied and complex than the stereotypical art and media representations of the Latin lover, the brutish bully, and the flashy gangster that have dominated American culture since the early 1920s. Over the years, theories of masculinity have all fallen short of describing the plurality of possiblities of Italian American masculinity, and in fact provide us with nothing more than categories that confine explanations and distort the very realities they try to describe. I offer the following discussion of historical performances of Italian American masculinities in the hopes that they will help us better understand the complexities involved in gender identity and the politics implicit inthe creation and expression of gendered identities. Authors discussed include: John Fante, Mario Puzo, Louisa Ermelino, Robert Ferro, Rachel Guido DeVries, and Annie Lanzlilotto.