Controversy and intrigue greeted Charlie Chaplin's new film, The Great Dictator, when it arrived in Latin American theatres in early 1941. With tear gas, Nazi salutes and anti-Semitic insults, pro-Axis factions from Mexico to Argentina protested against the Hollywood star's ridicule of Adolf Hitler and Benito Mussolini. At an important Good Neighbour moment, the film's tumultuous Latin American circulation and exhibition exposed fault lines in hemispheric solidarity by subverting US efforts to recruit allies in the region and threatened President Roosevelt's support for European intervention at home. Down south, heated public debates over the film trained a harsh light on Latin American leaders’ own anti-democratic impulses and raised questions about constitutionality within unequal societies. This article moves beyond film as text to examine the Chaplin picture as a cultural object and agent that exposed the limits of US imperialism and Latin American resistance strategies more broadly.