This chapter explores the nature and meanings of masculinities in street life social environments and networks. J. W. Messerschmidt was one of the first scholars to examine the intersections of masculinities and crime at length. While he links crime to issues of power and domination among men of multiple race and class positions, in addressing specific forms of street crime he creates a link between crime and the construction masculinities distinctly connected to street life. The majority of research on street life subcultures is concerned with the relationship between “the streets” and violence, but less attention has been given to relationships between “the streets” and other areas of interest to social scientists. A content analysis of hundreds of rap songs from throughout the 1990s revealed rap music reinforcing specific elements of street culture, namely the use of violence to gain and maintain respect among peers.