Popular American commercial rap is believed to (re)produce cultural narratives of masculinity. Yet, there is no knowledge about the relationship between consumption of idealized masculinity in rap and young (Black) men’s senses of masculine selves. This study aims to explore how sixteen American and Dutch Black adolescent men perceive ideals of masculine behavior, physical appearance, and mate desirability in commercial rap. Grounded in social comparison theory, it furthermore aims to understand whether these young men compare themselves to these ideals, and if so, how this informs their self-evaluations. A (hybrid) comparative thematic analysis of interviews with eight U.S. and eight Dutch adolescents revealed three masculinity ideals to be present in rap and congruent with the majority of the respondents’ own ideals. First, it is appropriate for young men to be ‘playas’ and view (young) women as either (sexually) freaky girls or wifey material. Second, attractive men look wealthy, and, third, desirable men financially provide for their partners. The participants who endorsed these ideals and, subsequently, compared themselves to them, reported positive self-evaluations and emotions, which were believed to translate into their own behavior, appearance, and desirability. Interestingly, although the participants came from different cultural contexts, systematic differences in perception, attitude, social comparison and self-evaluation were not found. Suggestions for future research are provided and implications for intervention programs are discussed.