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Dobby Dobson

One of Jamaica’s most beloved singers, Dobby Dobson has had a long-running career, but his name has been permanently twinned with 1967’s self-penned “I’m a Loving Pauper.” Born in Kingston in 1945, Dobson entered the music industry via the island’s popular talent show circuit. In 1960, he paired up with Chuck Josephs, and under the moniker Chuck & Dobby they cut their debut single, “Cool School,” for Duke Reid. Over the next two years, the pair recorded a steady stream of hits. With the duo’s demise, Dobson joined forces with a group of college friends as the Deltas, cutting “Cry a Little Cry” for Linden Pottinger in 1963, another huge hit for the singer. Several more popular 45s followed that year, all credited to Dobson alone. The following year, the singer was fronting the Sheiks, a band featuring pianist Jackie Mittoo, then in 1965 he linked up with Rupie Edwards and Junior Menz in the Virtues. With the rise of rocksteady, Duke Reid’s Treasure Isle was the place to be, and Dobson cut a clutch of excellent singles there, including “Pauper” and the equally successful “Trouble Jim.” In 1968, though, the singer was back at Studio One, where he cut such hits as “Seems I’m Losing You.” It was his old band mate, Rupie Edwards, however, who would oversee his biggest. Dobson’s 1972 cover of “That Wonderful Sound” was a smash right across the Caribbean, the best-selling single of its time.