Recent popular criminological ethnographies of "the street" deal heavily with men’s underlying aspirations for and constructions of masculinity. However, the presentation of manhood in the street has essentialistic overtones and reduces complex variation among men to overly simplistic and often stereotyped depictions. In this article, I offer a discourse analysis of three well-known criminological ethnographies—Randol Contreras’s The Stickup Kids, Alice Goffman’s On the Run, and Victor Rios’s Punished—with three intentions in mind. First, I introduce the concept of "perilous masculinity" as a version of masculinity that dominates across these ethnographies. Second, I suggest that a more complicated (albeit contradictory) notion of street manhood is possible and can be culled from these works. Third and finally, I point toward and try to exemplify alternative readings of masculinities and street manhood about which future researchers as well as policy makers should be more self-reflexively aware.