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