Beginning with Satan’s dialogue with Jesus, sharply contrasting ideas have permeated human history. Though only a few are actual head-to-head debates, all such clashes provide much food for thought about perennial conceptual differences. In this s/dg we will read or view seven of these “debates” (three, Lincoln/Douglas, Kennedy/Nixon, and Baldwin/Buckley are head-to-head). They cover free will, human nature, miracles, slavery, the role of African Americans in the United States, the 1960 presidential election, and civil disobedience. They involve some of the greatest minds of Western Civilization: St. Augustine, David Hume, Thomas Hobbes, and C. S. Lewis, inter alia.