Millicent Dolly May Small CD (6 October 1947 – 5 May 2020) was a Jamaican singer and songwriter, best known for her 1964 recording of “My Boy Lollipop“, which reached number two in both the UK Singles Chart and the US Billboard Hot 100. On her UK records, she was usually credited mononymously as Millie. She was the Caribbean’s first international recording star, and its most successful female performer.

Small was born in Clarendon, Jamaica, the daughter of a sugar plantation overseer. She was one of seven brothers and five sisters. 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. She auditioned for Studio One record producerCoxsone Dodd, who was struck by the similarity of her voice to that of Shirley Goodman of the American duo Shirley and Lee. He paired her with singer Owen Gray, and they made several records together, including “Sugar Plum”, which became a local hit.

When Gray resumed his solo career, Small began recording with another singer, Samuel Augustus “Roy” Panton. Working with producer Roy Robinson, the duo of Roy & Millie had a run of local hits, including “We’ll Meet”. They had further successes working with Dodd, as well with producer Lindon Pottinger, including the local hit “Marie” in 1963; and then with Prince Buster. Her popularity brought her to the attention of Anglo-Jamaican entrepreneur Chris Blackwell, who was convinced of her wider international potential, and became her manager and legal guardian. In late 1963 he took her to Forest Hill, London, where she was given intensive training in dancing and diction.