British Prime Minister Winston Churchill's speeches in the House of Commons from May and June 1940 have now achieved legendary status, but initially they encountered a varied response from politicians, the media, and ordinary citizens. While scholars have previously considered the trajectory of Churchill's reputation as a statesman and leader, this project aims to more narrowly identify key turning points in the immortalization of Churchill's famous speeches. How and when did the the narrative that Churchill's 1940 speeches were universally great and inspiring became established, and what role did Churchill play in immortalizing his own rhetoric? I argue that Allied victory in 1945 facilitated the public's nostalgic embrace of Churchill's "finest hour" rhetoric, demonstrating the critical importance of changing historical context for the later remembrance of a particular historical moment. Over the rest of his lifetime, Churchill's publication of his war memoirs and release of the recorded speeches gave some individuals the false impression that they had heard Churchill's radio broadcasts. Since the turn of the twenty-first century, the reputation of Churchill's speeches has entered a new phase of mythologization with the emergence of Churchill novels and films. Most recently, Brexiteers' arguments for leaving the European Union, framed in "go it alone" language and harkening back to the Dunkirk spirit, further the notion that Churchill's speeches, delivered at a truly extraordinary historical juncture for well-defined purposes, have retroactively acquired a decontextualized canonical status which may be doing as much harm as good.