Working with producer Roy Robinson, the duo of Roy & Millie had a run of local hits, including "We'll Meet". When Gray resumed his solo career, Small began recording with another singer, Samuel Augustus "Roy" Panton. He paired her with singer Owen Gray, and they made several records together, including "Sugar Plum", which became a local hit. She auditioned for Studio One record producer Coxsone Dodd, who was struck by the similarity of her voice to that of Shirley Goodman of the American duo Shirley and Lee. Wishing to pursue a career as a singer, she moved to live with relatives in Love Lane in Kingston. Like many Jamaican singers of the era, her career began by winning the Vere Johns Opportunity Hour talent contest, which she won at the age of twelve. She was one of seven brothers and five sisters. Small was born in Clarendon, Jamaica, the daughter of a sugar plantation overseer.
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