With the emergence of alternative R&B, contemporary R&B and hip hop culture are being confronted with a subgenre that challenges its key characteristics. One of the aspects that typify alternative R&B is the emergence of an alternative masculinity. The aim of this study is to research whether the alternative masculinities represented in alternative R&B resist the hegemonic masculine ideal established within R&B and hip hop culture. To this end, this study conducts a textual analysis of the representations of gender in the work of Frank Ocean and The Weeknd, artists considered representative for alternative R&B. The analysis reveals that Ocean’s work features successful nonnormative masculine identities, whereas The Weeknd refrains to representing postmodern exaggerations of the hegemonic male. Despite divergent representational strategies, both artists do engage in questioning what it means to be a man in R&B and hip hop culture and thereby at least attempt to challenge the supremacy of hegemonic masculinity.