In World War II the Allies and Axis deployed propaganda in myriad forms, among which cinema was especially important in arousing patriotism and boosting morale. Britain and Germany made propaganda films from Hitler’s rise to power in 1933 to the war’s end in 1945, most commonly documentaries, historical films, and after 1939, fictional films about the ongoing conflict. Curiously, the historical films included several about fifteenth and sixteenth century England. In The Private Life of Henry VIII (1933), director Alexander Korda—an admirer of Winston Churchill and opponent of appeasement—emphasizes the need for a strong navy to defend Tudor England against the ‘German’ Charles V. The same theme appears with Philip II of Spain as an analog for Hitler in Arthur B. Wood’s Drake of England (1935), William Howard’s Fire Over England (1937), parts of which reappear in the propaganda film The Lion Has Wings (1939), and the pro-British American film The Sea Hawk (1940). Meanwhile, two German films little known to present-day English language viewers turned the tables with English villains. In Gustav Ucicky’s Das Mädchen Johanna (Joan of Arc, 1935), Joan is the female embodiment of Hitler and wages heroic warfare against the English. In Carl Froelich’s Das Herz der Königin (The Heart of a Queen, 1940), Elizabeth I is an analog for an imperialistic Churchill and Mary, Queen of Scots an avatar of German virtues. Finally, to boost British morale on D-Day at Churchill’s behest, Laurence Olivier directed a masterly film version of William Shakespeare’s Henry V (1944), edited to emphasize the king’s virtues and courage, as in the St. Crispin’s Day speech with its “We few, we proud, we band of brothers”. This essay examines the aesthetic appeal, the historical accuracy, and the presentist propaganda in such films.