Responding to and provoked by an America colored by stark political division, tense racial conflict, and the powerful urban narrative of hip hop culture, Hamilton: An American Musical, created by composer/lyricist Lin-Manuel Miranda, became the subject of a cultural focus unprecedented in the reception history of an American work of art. Hamilton premièred at a critical time during the Obama presidency, and it squarely confronts the issues lying at the heart of our democracy. Hamilton caught the attention of millions of Americans with little prior interest in Broadway musicals, hip hop, or the performing arts in general, and it stimulated important and timely conversations about race, representation, and American identity. Hamilton asks pressing questions: Who speaks for America? How does the character and biographical narrative of this founding father suggest a new, updated conversation about American history? How do the political sensitivities of audiences determine the commercial and artistic success of a stage work? How does the rap genre operate in conveying Hamilton’s historical content in dramatic terms? How do representations of minorities in popular culture affect the wider perception of the sociopolitical order? To what degree is it possible for the historically-rooted genre of musical theater – often viewed as benign musical pablum for middle-class whites – to advance a public conversation about race and representation in the twenty-first-century? This dissertation first considers these questions through the historical lens of racial depiction in American musical theater, situating Hamilton within a lineage of commercially successful musicals that have used the Broadway stage subversively as a place to challenge the social and racial order. It documents Hamilton’s genesis and the collaborative process of adapting Ron Chernow’s acclaimed biography, then examines Hamilton’s music, its relationship to text and musico-historical resonances, and constructs a theory of Lin-Manuel Miranda’s hip hop-infused compositional style. Finally, it examines Hamilton’s reception, contemporary political dimensions, and essential ties to the administrations of Barack Obama and Donald Trump, exploring what are often contentious criticisms of the work within the academic and online worlds.