From the earliest elections with popular participation to the present day, American presidential candidates have harnessed music's connotative potential and affective properties in a variety of campaign contexts. But in a corporatized electoral landscape where the fields of politics and popular culture are inextricably intertwined, and every aspect of the candidate's public and private life is subjected to intense scrutiny enabled by the emergence of Web 2.0 technologies, nontraditional texts (such as music) play an increasingly significant role in candidate identity formation. Adding to recent work that explores the aesthetic and social dimensions of newly composed campaign music and its cultural currency, this essay turns a critical lens toward preexisting music and its impact on campaign discourses during Barack Obama's 2008 presidential primary campaign. I investigate three components of Obama's soundscape: 1) his engagement with hip hop—its artists, audiences, and values; 2) the intersections between his professed musical tastes and his complex biography; and 3) the playlists he used at campaign rallies, and the factors that allowed this soundtrack to solidify his own identity as candidate as well as forge alliances with women voters and black voters. Ultimately, cultural and musical analyses reveal how Obama's music strategy allowed him to project a black identity that was both “real” and “respectable.”