This chapter explores the historical evolution of civility in European culture, tracing its roots from medieval courtliness to Renaissance and early modern ideals of the courtier and gentleman, and its culmination in the bourgeois sociability of the long nineteenth century. Drawing on Johan Huizinga’s The Autumn of the Middle Ages, which portrays the late medieval period as marked by intense emotions, cruelty, and fragile cultural forms amid decline, the analysis highlights parallels with Norbert Elias’s civilizing process, influenced by contemporary experiences of political collapse under totalitarian threats. The narrative follows the transformation of the knight into the Renaissance courtier—exemplified in Castiglione’s Il Cortegiano and Michelangelo’s David—and the Christian gentleman as envisioned by John Henry Newman, emphasizing non-violence, prudence, and refined taste. Erasmus’s humanist emphasis on inner piety and outward propriety, alongside Gracián’s cultivation of judgement and discretion, bridges courtly artifice to authentic urban politeness. Finally, the chapter examines the rise of the middle classes, whose culture of Bildung, family intimacy, and civic responsibility sustained civility until its erosion by mass society, nationalism, and twentieth-century upheavals, as evoked in nostalgic portraits by John Lukacs and others. Civility emerges as a fragile yet enduring mechanism for taming human passions and fostering social cohesion.