This chapter explores how the novelists Giose Rimanelli and Frank Lentricchia use sexuality to undermine the power of the traditional gangster and turn traditional masculine strengths into weaknesses. These two writers reinvent the gangster figure to function as a criticism of Anglo-American and Italian-American cultures. They are both scholars as well as artists, so they have a long familiarity with irony, which they employ to great effect in their depictions of the gangster figure. In different ways, both authors set up the figure of the gangster not only as a target of cultural criticism, but also as a subject who criticizes the very culture that surrounds him. Thus, the gangster becomes a critic of culture as the author criticizes the culture of the gangster. In this way, both Rimanelli and Lentricchia move the wiseguy closer to the wise man.