January 20, 2009 marked the inauguration of Barack Hussein Obama as the first African-American president of the United States. Political commentators are busy making sense of Obama’s candidacy and election, but not enough attention has been given to how youth have made sense of Obama. As I show in this article, young people—so-called “hip-hoppers” and “millennials”—used their unique sensibilities, technologies, and music to help define and elect the first black, hip-hop president. This article examines “Obama-Hop,” rap music about Barack Obama, and the 2008 presidential election. 1 Rap songs about election year politicswereahighlyvisibleaspectoftheelection(Hamby;NPR).Thisstudy provides the first systematic analysis of the political, racial, and gendered discourse of the Obama-Hop movement. While Obama’s campaign was discussed in the framework of “post-racialism” (Crowley), this study shows how Obama’s black masculinity became a major source of identification for rappers. The paper explores how Obama was depicted, embraced, and defended from scrutiny in hip-hop. Based on the review of ninety-seven Obama-themed mixtapes, I show how music was used in an attempt to energize youth toward voting and embracing Obama’s political messages. The exploration necessarily informs the larger debate over hiphop politics. The “hip-hop wars”—as Rose (2008) labels the persistent controversy overrap—are currentlybeingwagedover thepolitical relevance ofthemusic.Representingagenerationaldivideoverthemeaningofpolitical activism(Boyd), therehasbeenresistancetotheclaimthathip-hopisindeed “political” (Bynoe; McWhorter 2008). Hip-hop academics are increasingly concerned that corporate control and media consolidation are destroying rap’s political significance (Asante; Rose; Powell). This article addresses the debate by considering the political content of digital mixtapes, which are non-commercial compilations of music, news clips, and photos. The proliferation of Obama rap mixes provides evidence that hip-hop continues to be used toward political ends. This paper shows how Obama’s campaign