During the depths of the Great Depression, beer baroness Lady Port-Huntly announces a global competition to determine the “saddest” music in the world. Musicians from across the globe pour into Winnipeg to vie for the whopping $25,000 prize. The Kent family confronts the wretched secrets of their past while locked in the competition for this greatest of prizes. Younger brother Chester, the cynical and failed Broadway producer, is ready to mesmerize all with a little Yankee Doodle razzle-dazzle hanky honker.