This book offers historical and theoretical readings of Caribbean and African American interaction from the 1700s to the present. By analyzing travel narratives, histories, creative collaborations, and political exchanges, it traces the development of African American/Caribbean dialogue through the lives and works of four key individuals: historian Arthur Schomburg, writer/archivist Zora Neale Hurston, poet Jayne Cortez, and politician Jean-Bertrand Aristide. The book examines how these influential figures have reevaluated popular culture, revised the relationship between intellectuals and everyday people, and transformed practices ranging from librarianship and anthropology to poetry and broadcast journalism. This discourse, the book notes, is not free of contradictions, and misunderstandings arise on both sides. In addition to noting dialogues of unity, the book focuses on instances of intellectual elitism, sexism, color prejudice, imperialism, national chauvinism, and other forms of mutual disdain that continue to limit African American and Caribbean solidarity.