The British Bulldog and the Little Tramp: Winston Churchill and Charlie Chaplin

On 14 December 1940, as Britain struggled alone against a triumphant Nazi Germany, Winston Churchill briefly set aside his heavy responsibilities to watch with his family and advisers Charlie Chaplin’s new film The Great Dictator. They were at Ditchley Park in Oxfordshire, which was placed at the Prime Minister’s disposal by its owner Ronald Tree MP, on nights when the full moon made Chequers, the PM’s official country house in Buckinghamshire, too inviting a target.

An avid film lover, Churchill naturally enjoyed this pre-release viewing lampooning Hitler, which starred and was directed by an old friend. The Prime Minister laughed throughout, especially the scene where two dictators throw food at each other. After it ended, Churchill returned to composing another secret cable to President Roosevelt.

Hollywood Sojourn

Churchill had met Chaplin more than a decade earlier, during a tour of North America shortly after the Conservatives had been defeated in the 1929 general election. Despite sharp political differences, Churchill and Chaplin had come to admire and appreciate each other’s qualities, and Chaplin had twice been Churchill’s guest at Chartwell.

Accompanying Churchill on his 1929 trip to the United States and Canada were his son Randolph, brother Jack, and nephew Johnny—a foursome which its leader dubbed the “Churchill Troupe.” The troupe was hosted in southern California by newspaper magnate William Randolph Hearst and introduced to the city’s film industry, which Churchill later called “a strange and