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In the mid-1940s, Caresser, one of the top Trinidadian calypsonians, settled in Montreal and increased Canadian audiences' familiarity with the calypso tradition. During the 1956-57 U.S. calypso craze, Lord Superior and other Trinidadian calypsonians performed in Toronto, Montreal and other Canadian cities. Trinidadian Johnny Cayonne composed "calypsoperas" during the mid-1960s and became the founding director of the Black Theatre Workshop in Montreal.
Montreal also hosted the Trinidadian steelband Tripoli and the calypsonians Bomber and Young Killer at Expo 67. During this period, Toronto's Caribbean community grew and developed Caribana, a massive Carnival held every July. The festival includes calypso tents, steelbands and masqueraders.