In the 25-plus years since his death, Tupac Shakur’s legacy has been reimagined as one of a fighter of social injustice and revolutionary whose discography ushered in an era of more “conscious” rap. The consensus scholarly and popular re-imagining of Shakur’s legacy as that of a progressive social justice advocate in the nearly 30 years since his death downplays or altogether overlooks his occasional alignment with conservative ideas. But this reimagining also ignores a longer history of Black music and conservative values. This essay examines Tupac’s complicated relationship with conservative thought and how his musings on the Black family mirrored the laments of conservative intellectuals like George Schuyler, Albert Murray, Stanley Crouch, Walter E. Williams, and Shelby Steele, as well as political figures such as Keyes, Armstrong Williams, and JC Watts. The authors also argue that looking at the legacies of rappers such as Tupac Shakur from purely a left/right perspective doesn’t properly account for the extent to which hip-hop culture has always been in conversation with the gamut of political discourses in the United States over the past 50 years.