Kingdom of Denmark
Who & why: the January 1814 Treaty of Kiel forces Denmark, on the losing side of the Napoleonic Wars, to cede Norway to the King of Sweden — but Denmark negotiates hard and keeps its older North Atlantic dependencies, Iceland, the Faroe Islands, and Greenland, carved out of the transfer. The June Constitution of 1849 ends centuries of absolute monarchy and establishes a constitutional, parliamentary system still in force today. German forces invade on 9 April 1940; Denmark capitulates within hours and lives under an unusually "model" occupation — King Christian X remains on the throne and the elected government keeps functioning — until Berlin imposes direct martial law in August 1943 after resistance sabotage escalates. Liberation comes in May 1945. Iceland uses Denmark's own wartime paralysis to hold a 1944 independence referendum, ending their personal union for good; Denmark becomes a founding NATO member in 1949 and joins the EU (then EEC) in 1973, while Greenland and the Faroe Islands are granted home rule in 1979 and 1948 respectively and remain part of the Danish Realm today.
What it represents: the same Dannebrog flown since 1219, minus only the Kalmar Union's interruption — a design old enough, and used continuously enough, that it is widely cited as the oldest state flag still in everyday use anywhere in the world. Remarkably, occupying Germany never replaced it: the Dannebrog kept flying over Denmark for almost the entire war.