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Jumbie in the Jukebox is full of Kobo Town frontman Drew Gonsalves’ usual lyrical invention and his band’s musical audacity and infectious grooves. Ghosts jump out of the tracks, from the clanging bells of “Mr. Monday,” about a fallen man who loses his fortune to mental illness, to the groaning trombones of “Joe the Paranoiac,” about a conspiracy theorist who believes his neighbors are terrorist members of sleeper cells. “The War Between Is and Ought” uses scratchy vocals and a traditional santimanitaymelody to tell the tale of two feuding kings, while “The Trial of Henry Marshall,” written in the style of an early kalenda with a call-and-response chant, is about an innoc...

Drew Gonsalves laughs about how he had to leave Trinidad to discover the rich calypso tradition of his birthplace. As a teenager, he was far more interested in rock and heavy metal music than the songs of Roaring Lion or the Mighty Sparrow. The legendary Lord Kitchener even lived up the street from his family home in Diego Martin, a suburb of Port-of-Spain, but he remained unimpressed. “I was very typical of a middle-class Trinidadian boy in that I had a taste for all things foreign,” admits Gonsalves, “which is something that (novelist) V.S. Naipaul wrote so scathingly about in the 1960s. Calypso was always in the air, but I just wasn’t interested.” That all changed when Gonsalves’ mother, ...

On a wintery night at Toronto’s plush Koerner Hall, inside the city’s stately Royal Conservatory of Music, two generations of calypso stars are busy heating up the audience. Onstage in the foreground is the reigning queen, Trinidad & Tobago’s Calypso Rose. Just behind her is the crown prince, Drew Gonsalves, whose Canadian band Kobo Town has opened the show and is now backing the headliner. As the cheeky Rose sings and shimmies through her set to the crowd’s delight, the bearded, bespectacled, guitar-strumming Gonsalves is visibly beaming: he co-wrote and arranged many of the songs Rose is performing, all taken from her award-winning comeback album, Far From Home. And now he and the sept...