Song style originating in Trinidad and Tobago, the result of the interaction in the mid-1700s between the praise songs of enslaved West African griots (oral historians) and the musical cultures of their French, Spanish, and English colonial masters. With the emancipation of Trinidadian blacks in 1834, calypso became associated with the 'masquerade' festival that evolved in the 20th century into the world-renowned, pre-Lenten Carnival. It in turn has been the model for similar festivals elsewhere in the world, including Caribana in Toronto and Carifête (originally Carifiesta) in Montreal, that have extended the calypso season from February through August and its circuit to Canada, the USA, and England.

Calypso songs, typically of a topical and often satirical nature, are composed and recorded anew annually. Calypsonians (singers) perform to the accompaniment of brass and rhythm sections. Calypso, which is characterized by bright, syncopated, quick-shuffle rhythms and the spirit of bacchanalian brio, is also played in instrumental form by steelbands. Each year Carnival, and Caribana in turn, identifies its most popular performer in the Calypso Monarch competition and awards the most popular song in its parade the distinction of Road March.

Calypso was supplanted in the 1980s as both a style and term by the disco-inflected variant known as soca (a neologism of 'soul calypso'). By then musicians from other eastern Caribbean nations had joined those from Trinidad and Tobago in developing the music's traditions, and two - Arrow (from Montserrat) and David Rudder (from Trinidad) - had aligned themselves successfully with the burgeoning 'world beat' movement in a way that transcended calypso's seasonal cycle.

Calypso was recorded as early as 1914 by Victor and Decca and has had among its leading figures over the years Attila the Hun, Wilmoth Houdini, Lord Invader, Lord Kitchener, Mighty Sparrow, Spoiler, Duke, and Shorty. It was first heard widely in North America as recorded by such US artists as the Andrews Sisters (whose version of Lord Invader's 'Rum and Coca Cola' was a million-seller in 1945) and Harry Belafonte, and was transplanted to Canada in particular by successive waves of Antillean students and emigrants who established Caribbean communities in Toronto, Montreal, and Ottawa in the late 1950s and early 1960s (see Caribbean Music in Canada). The Trinidadian calypsonian Lord Caresser, for example, was heard in these early years on the CBC radio's French network and International Service during a sojourn in Montreal.

With the rise of many West Indian clubs (eg, We Place, Club Trinidad, and Club Karib in Toronto) and of Caribana and Carifête, the first Canadian calypso careers blossomed. The Tradewinds, a quartet formed in 1967 in Toronto by the Guyanese-born singer Dave Martins, have been Canada's most successful calypso-based group, recording some 20 albums and such hits as 'Ride on Baje,' 'Honeymooning Couple,' and 'Come Back Again' for RCA, Penny and other labels, and touring in North America and the West Indies. The Tradewinds were active until 1984 in Canada and thereafter in the Cayman Islands.

The efforts of the Calypso Association of Canada, established in 1980, and the stimulus offered by the introduction of a Juno Award for reggae/calypso in 1985 notwithstanding, calypso and soca have remained sporadic and semi-professional activities that have given rise to a handful of self-produced and self-distributed, Toronto-based recording artists. Most notable among them are Arch Bastien (who in 1967 was the first solo calypsonian to record in Canada), Jayson (Jayson Perez, whose album Soldiers We All Are received the Juno for 1990, the first calypso recording to be so-honored), Bread (Herman Lowes), Elsworth James, Smokey (Cleive Henry), and Lord Protector (Mike Legerton, twice a finalist during the late 1980s in Trinidad's Calypso Monarch contest).

Other bands or bandleaders to record calypso, beginning in 1967 and for the most part in Toronto and Montreal, have included The Legends, Afropan, Trinbyrds, Syl McIntosh, Tony Woodruffe, Flambeau, the Relatives, Auswald James, and Ian Jones. Canadian calypsonians on record in those cities include Ted Toppin, Lord Cosmos, Vibrater, Young Beginner, Ivan Harry, Pan Man Pat (Pat McNeilly), Skel, Shadrock, and Johnny Baptiste. The Dominican-born, Calgary-based Evvo (Hubert Peter), who released two albums during the 1980s, is unique as a Canadian calypsonian not associated with a city that has a summer calypso festival.

The Toronto percussionist Dick Smith was the leader 1972-86 of the popular Syncona which employed Caribbean musicians to play a potpourri of styles that included calypso-derived forms like 'spouge,' 'cadence,' and 'zouk,' as well as reggae and salsa. Joe R. Brown, bassist 1967-81 of the Tradewinds, has been an important international figure in soca: he wrote 'Discolypso' in 1979 for the US singer Ralph MacDonald and, while working 1983-9 in Trinidad, produced recordings by David Rudder and others, and composed a Road March for Carnival.

In turn, the Trinidadian composer Dennis Stevenson, who is credited with four Road Marches, moved in the early 1980s to Hamilton, Ont, where he has produced soca recordings for his own Mahogany label. Other Caribbean performers appear each year at Caribana and Carifête, inevitably overshadowing their Canadian counterparts in the public eye. Both Caribbean and Canadian calypsonians, however, are disadvantaged by the seasonal disposability and quickly-dated, parochial thrust of the calypso repertoire and by their resulting inability to establish a year-round commercial infrastructure for their music.