Examinations of the relationship of queer sexuality and the hip-hop generation have recently emerged in academia. However, little or no work has been done that explores hip-hop's bisexual, independent poster child, Me'Shell Ndegeocello. Since her debut in 1993, Ndegeocello's relationship to hip-hop has been both a reflection of and influence upon understandings of race, gender, and sexuality for a generation of queer feminists of color. In this paper, I examine how her emergence and popularity mark an important political and ideological moment for queer Black women in the post-civil rights era. Grounded in the works of Patricia Hill Collins, bell hooks, Audre Lorde, and Jewelle Gomez, I examine how media representations of Ndegeocello coupled with her lyrics and music demonstrate the complexities and contradictions of “hip-hop feminism.” In particular, the 1990s represent a movement away from the Reagan/Bush era that characterized not only the teenage years of hip-hop culture, but important cultural and economic advances of the Black community. At the same time, this decade marks the shift to the more “liberal” Clinton administration, where the advances of previous generations began to decline. In this context I ask in what ways does Me'Shell Ndegeocello represent a generation of young queer women who were raised after (and sometimes on) early Black feminist critique? Further, how is her work emblematic of Black feminist understandings of gender and sexuality at the same time that she complicates this same discourse?