5 Great Calypso Music Compilations

Calypso at Dirty Jim's is a soundtrack to a movie of the same name. Dirty Jim's is a legendary post-war nightclub in Port of Spain, Trinidad's capital where, according to lore, the first use of a swizzle stick in a cocktail took place. It also happened to be the best calypso club on the island, and was full every night with locals and tourists of all colors and economic backgrounds. This club, and the musical scene that it inspired, is the theme of the movie, and the soundtrack, which includes cuts from Calypso Rose, Lord Superior, and The Mighty Terror, among others, is a great representation of that era.

This album is a collection of sixteen of the biggest and best Carnival anthems from two of calypso's most legendary artists: Lord Kitchener and the Mighty Sparrow. Most of these songs were Carnival "roadmarches" (an honorable title -- a roadmarch is a song that's selected to be played at the judging stands during the major Carnival parades), including Mighty Sparrow's "Jean and Dinah" (1956), "Obeah Wedding" (1966), and "Sa Sa Yeah" (1969), as well as Lord Kitchener's "Mama Dis is Mas" (1964), "My Pussin" (1965), and "Mas in Madison Square Gardens" (1971).

Calypsos are, of course, fun party songs, but they're not just written to entertain -- they also illuminate. Sometimes this takes the form of commentary on social issues, including gender and race relations. Often, though, they touch on political and current events issues of the day. This can be as simple as the lampooning of politicians via outright statements or hilarious double entendres, or as complicated as long, involved allegories, usually with a humorous touch. 1936-1941 was a tumultuous political time in Trinidad -- there were major labor riots in 1937, World War II broke out in 1939 (remember that Trinidad was still a British colony at this point), and there was a suffrage movement afoot throughout the time period (universal adult suffrage was granted in 1946). Songs on this album touch on all of those points and more, making it both historically important and musically tantalizing.

This is another solid collection of Calypsos slightly earlier than the one just above. The 1920s were really the formative decade for calypso, as the elements that would make up the genre really fused and then popularized throughout those years, but the 1930s are when the genre hit its stride and became something really magnificent (and ultimately influential -- Jamaican music as we know it would not exist, and thus American urban music would also be completely different were it not for calypsos, as would any number of other genres around the world). This collection, from the venerable folkloric label Arhoolie Records, highlights that golden era, with songs from Attila the Hun, Roaring Lion, Lord Executor and more, and again, is both historically important and a pleasure to listen (and dance) to.

This collection of calypsos is from the later 1940s, mostly, and includes a number of songs that would later become inter-island and international hits and standards, including several that would enter the repertoire of famous calypso-folk troubadour Harry Belafonte. Among the songs on this compilation are Calypso Mama's "Don't Touch Me Tomato," Mighty Panther's "Big Bamboo," Blind Blake's "Brown Skin Gal / Mary Ann," and Calypso Eddie's "Matilda." This album might contain the most sing-along-friendly set of songs on this list, and it's just a great listening album, to boot.