A longitudinal content analysis of top-chart hip-hop songs’ lyrics produced between 1980 and 2013 was conducted to investigate the degree and progression of the paradoxical juxtaposition, or postmodern hybridity, of oppositional modernist identities in terms of race/ethnicity, gender, sexual orientation, sexuality, and economic lifestyle, in addition to the longitudinal diversification of artist’s race and gender demographics. Demographically, the percentage of non-African-American artists increased as the percentage of African-American artists decreased. Additionally, the percentage of songs featuring either all male or all female artists decreased, while the percentage of collaboration between male and female artists increased over time. Although hybrid oppositional identities related to race/ethnicity and gender did not increase over time, those of sexual orientation, sexuality, and economic lifestyle increased over time. In addition, materialist identities were related to the hybridity of sexual orientation and sexuality, but not to that of gender and race/ethnicity. Overall, the research found increasing postmodern hybridity within the sexualization of hip-hop songs along with intensified materialism.