We investigate the social and behavioral characteristics of male adolescents who self-identify as players, focusing particularly on Anderson's claim that this social role is inextricably linked with poverty and minority status. Results indicate that African American respondents, those affiliated with liberal peers and young men who initially report a relatively high number of sexual partners are more likely to resonate with this identity label. Nevertheless, analyses reveal that a number of players within the sample are not disadvantaged African American youth, and there is considerable variability in their attitude and behavior profiles. Findings based on longitudinal analyses indicate that the player identity is a significant predictor of later variations in self-reported sexual behavior, net of traditional predictors, including prior behavior. Yet results of in-depth interviews conducted with a subset of the respondents complicate these quantitative findings, highlighting that young men's perceptions of this identity are not as uniformly positive as Anderson's depiction might lead us to expect.