Gypsy

Gypsy ranks among T&T’s premier calypsonians, securing the National Extempo Calypso crown every year since 1988 in a contest that demands contestants improvise lyrics spontaneously. His career has traced a volatile path through towering highs and crushing lows. The track “Sinking Ship: SS Trinidad,” drawn from his landmark 1986 album, was widely viewed as the decisive strike that toppled the PNM administration after nearly three decades in office. Even with that achievement, he finished behind David Rudder’s “Bahia Gyal/The Hammer” in the same year’s competition. Resentment lingered, evident in his 1987 calypso “Sing Ram Bam,” which mockingly derided the “inane” lyrics of Rudder’s “Bahia Gyal.” Additional professional reversals compounded the strain, yet he has continued to craft exceptional calypsos annually. Any Gypsy album merits attention.