"The Loving Pauper," as he has been affectionately nicknamed, Dobby Dobson began singing as part of the Deltas while at the Kingston College in Jamaica. They recorded "Cry A Little Cry" for the Tip Top label, but split shortly afterwards. Dobson recorded the solo side "Seems To Me I’m Losing You" for Coxsone Dodd, before releasing the enduring "Loving Pauper" for Duke Reid. Nevertheless, Dobson maintained his jobs as a salesman and proofreader, before establishing a fruitful partnership in 1971 with Rupie Edwards. Their single, "That Wonderful Sound," sold in excess of 40,000 copies and was followed by the international hit, "Endlessly." While his singles enjoyed success, albums like WONDERFUL SOUND and SWEET DREAMS failed to scale the charts, and Dobson began working as a producer, enjoying success with the Meditations’ WAKE UP.