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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 bandmate, 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.
Buoyed by that success, Dobson now began self-producing his own singles as well as continuing to cut 45s for others. His debut album, Wonderful Sound, arrived in 1977, with 1978's Sweet Dreams following hot on its heels. A split festive set with Ringo, Sweet Christmas, provided holiday cheer. Dreams, incidentally, was not a reggae set; instead, it was filled with lovely ballads, and although Dobson continued having hits during this period in Jamaica, the roots scene passed him by entirely, at least as a vocalist. In the mid-'70s, Dobson was working at Federal Studio, running the auditions for new talent. While there, he discovered the Meditations and produced their earliest singles, as well as 1978's Message from the Meditations and Wake Up albums. Dobson also oversaw Barrington Levy's 1977 recording debut (with the Mighty Multitude), "Fi Me Black Girl." Even after immigrating to the States in 1979, Dobson's career continued apace, with 1982's "Sweetheart" nearly breaking into the British chart. Even so, the singer's output slackened notably during this decade, although live appearances at reggae festivals kept his profile high. The '90s were far more productive, kicked off with Studio One's roundup of oldies Through the Years, with new material arriving on 1994's At Last and 1997's If I Only Had Time set. Released in 2000, VP's Vintage Series roundup featured the Donovan Germaine-produced hit "Words." That same year, the death of Dobson's mother led to a crisis of faith, and the singer was born again. Since then, he's continued to record, but now concentrates exclusively on Christian music.