The year 2019 marks the quadricentennial of a momentous event in American history: the arrival of “20 and odd” enslaved Africans in 1619 at Point Comfort, Virginia Colony. This event and its attendant histories would alter the course and character of not only the United States, but also the modern world. The Legacy of 1619: The 2019 Callaloo Conference is an occasion to commemorate this world-historical event and moreover bring to bear the great advances made in African Diaspora literary, visual, and cultural studies to understand the significance of 1619 and its continued reverberations; to raise questions that remain particularly germane in our present: How do the political, economic, and cultural circumstances of Virginia Colony in 1619 speak to us in twenty-first century America? And the voices of those “20 and odd” Africans, what might they say to us now? From the vantage point of 1619, and our own time four centuries later, how do we envision another calculus of being in the world? The Legacy of 1619: The 2019 Callaloo Conference provides a timely occasion to engage and extend these questions.