This article presents a content analysis of two group interviews with street life–oriented, U.S.-born African men that addresses issues of masculinity. The two group interviews are drawn from a more extensive dissertation data set that includes 371 surveys, 22 individual interviews, and 2 group interviews. The men specifically in the group interviews were asked to listen to and remark on a popular street life–oriented hip-hop song titled “A Gangster and a Gentleman” by Styles P. Findings indicate that for many of these men, masculinities are crafted in the face of inhumane socioeconomic conditions. In fact, findings reveal that their masculinity plays a vital role within their street-life orientation, thus serving a profoundly critical function in the development of street life as a “site of resiliency.”