While originating in the author’s experience as a German and American citizen, the book is not an autobiography. It combines narrative accounts, scholarly literary and art historical commentary, as well as critical political opinions. Focused on readings of German and American literature, art, film and popular culture in the context of the radically changing times, it is a cultural logbook of a shared transatlantic experience (1945 to the 2020s) with democracy at issue. The book speaks for the first time specifically for my unique cohort, ‘Hitler’s war children’ (1939–1945), historically the most Americophile generation ever. At its core tracing the transformations of the German ideal of Bildung (classical education), it is a testimony to a privileged and educated stratum of that age-group.