In this essay, I explore the use of rap and hip-hop conventions as they have developed within the self-consciously contemporary American Jewish ‘hipster’ scene between c. 1986 and 2006, framed particularly around the way these genres have addressed the discourses of masculinity within Jewish culture. By exploring the works and actions of such artists as Matisyahu and the Hip Hop Hoodíos within the context of both American Jewish masculinity discussions and the historical relationship of Jews with commercial hip-hop performance, I attempt to explore how a population’s attempts at musical ‘change’ act as a crucial part of the religious and ethnic transmission and preservation process. Although outwardly seen as based on mimesis and even novelty, ‘Jewish’ hip hop, I suggest, instils a deep sense of identity into a population often characterised as iconoclastic, dynamic, politically inclusive and culturally mutable. Masculinity therefore serves largely as a vessel for young Jews to fashion a sense of self into a conversation from which they had previously been largely absent: one of several strategies used both to unmoor and to redefine what it means to be a ‘new’ Jew.