He was described by Sir Winston Churchill as "Scotland's greatest ever ambassador", who "... by his inspiring songs and valiant life, rendered measureless service to the Scottish race and to the British Empire." He became a familiar worldwide figure promoting images like the kilt and the cromach (walking stick) to huge acclaim, especially in America. Among his most popular songs were "Roamin' in the Gloamin", "A Wee Deoch-an-Doris", "The End of the Road" and, a particularly big hit for him, "I Love a Lassie".