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Millie is the daughter of a sugar plantation overseer. In her teens, she and Roy Panton recorded for Coxsone Dodd's Studio One record label as 'Roy and Millie. They had a minor localhit with "We'll Meet".
In late 1963 she went to Forest Hill, London to make her fourth recording, an Ernest Ranglin rearrangement of "My Boy Lollipop", which had seen original release by Barbie Gaye in late 1956. Released in March 1964, Small's cover was a massive hit, reaching number two both in the UK Singles Chart and in the U.S. Billboard Hot 100. It also topped the chart inAustralia. Initially it sold over 600,000 copies in the United Kingdom. Including singles sales, album usage and compilation inclusions, the song has since sold more than seven million copies worldwide.
"My Boy Lollipop" was doubly significant in British pop music history. It was the first major hit for Island Records (although it was actually released via Fontana Records because Chris Blackwell, Island's owner, did not want to overextend the label's then-meagre resources; in the U.S. the record appeared on the Smash Records subsidiary of Mercury Records), and Small was the first artist to have a hit that was recorded in the bluebeat style. (She was billed as 'The Blue Beat Girl' on the single's label in the U.S.) This was a music genre that had recently emerged from Jamaica, and which, as with ska, was a direct ancestor of reggae.
Millie continued to tour and perform up to the early 1970s.