Dobby’s career began while he was attending Central Branch School in Kingston, Jamaica. While at Kingston College he composed his first song "Cry A Little Cry" and recorded It with his friends Howard Barrett, Fuzzy Byfield and Dennis Gayle, who were all students in the Delta Stream at Kingston College, hence the name Dobby And The Deltas. Dobby and Chuck Josephs (know as Dobby and Chuck) went on to record a series of hit songs in quick succession namely: Sweeter than Honey, Du Du Wap, Cool School, I Love My Teacher, and Oh Fanny.
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