During the Great Depression in 1933 in Winnipeg, Manitoba, Canada, baroness Helen Port-Huntley (Isabella Rossellini) announces a competition to find the saddest music in the world, as a publicity stunt to promote her company, Muskeg Beer, as Prohibition is about to end in the United States. The prize is $25,000 "Depression-era dollars" and musicians from all over the world pour into Winnipeg to compete. Chester Kent (Mark McKinney), a failing Broadway producer, decides to enter the contest representing America, even though he is Canadian and originally from Winnipeg. An old fortune teller predicts his doom, but Chester mocks this prediction by having his nymphomaniac amnesiac girlfriend Narcissa (Maria de Medeiros) masturbate him. Also entering the contest are Chester's father Fyodor (David Fox), representing Canada, and his brother Roderick (Ross McMillan), representing Serbia as "Gavrilo the Great" (even though he is also Canadian).