Millicent Dolly May Small, CD (born 6 October 1946), is a Jamaican singer-songwriter, best known for her 1964 recording of “My Boy Lollipop.” Small was born in Clarendon, Jamaica, the daughter of a sugar plantation overseer. 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. Wishing to pursue a career as a singer she moved to live with relatives in Love Lane in Kingston. In her teens, she recorded a duet with Owen Gray (“Sugar Plum”) in 1962 and later recorded with Roy Panton for Coxsone Dodd‘s Studio One record label as ‘Roy and Millie’. They had a local hit with “We’ll Meet”.

These hits brought her to the attention of Chris Blackwell who became her manager and legal guardian, who in late 1963 took her to Forest Hill, London, where she was given intensive training in dancing and diction. There she made her fourth recording, an Ernest Ranglin rearrangement of “My Boy Lollipop“, a song originally released by Barbie Gaye in late 1956. Released in March 1964, Small’s version was a massive hit, reaching number two both in the UK Singles Chart and in the US Billboard Hot 100, and number three in Canada. It also topped the chart in Australia. 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. Her later recordings, “Sweet William” and “Bloodshot Eyes”, also charted in the UK, at numbers 30 and 48 respectively, and “Sweet William” also peaked at number 40 in the US, her only other American chart single. “My Boy Lollipop” re-charted in the UK in 1987 at no. 46.