Millie Small 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.
Millicent Dolly May (Millie) Small (October 6, 1946 – May 5, 2020) was born in Clarendon, Jamaica, the daughter of a sugar plantation overseer and was one of seven brothers and five sisters. Millie’s music career began by winning the Vere Johns Opportunity Hour talent contest, at the age of 12. Wanting to follow a career as a singer, she moved to live with relatives Kingston, Jamaica. She auditioned for Studio One record producer Coxsone Dodd, who put her with singer Owen Gray, one of Jamaica’s ‘Foundation’ singers who has been credited as Jamaica’s first home-grown singing star, and they made several records together, including “Sugar Plum”, which became a hit in Jamaica.
When Owen Gray resumed his solo career, Millie Small began recording with another singer, Samuel Augustus “Roy” Panton and working with producer Roy Robinson, the duo of Roy & Millie had a run of local hits, including “We’ll Meet”.
Millie’s popularity brought her to the attention of Anglo-Jamaican entrepreneur and owner of Island Records Chris Blackwell, who was convinced of her wider international potential. Chris Blackwell became her manager and legal guardian and in 1963 took her to London, where she was given intensive training in dancing and speech.
Millie Small’s first recording in London, “Don’t You Know”, made little impact when released by Fontana Records in late 1963, but for her next recording Chris Blackwell recruited guitarist and arranger Ernest Ranglin to oversee the session.
Ranglin and his musicians adopted the newly-popular ska style, and his rearrangement of “My Boy Lollipop”, which was originally released in the US by teenager Barbie Gaye in late 1956, became immediately successful. Released in March 1964, Millie Small’s version (on which she was credited simply as “Millie”) was a massive hit and reached number two in the UK Singles Chart, in the US Billboard Hot 100, and in Canada. It also topped the chart in Australia. The song has since sold more than seven million copies worldwide.
Millie Small toured in Britain and appeared frequently on British television. Although her next single, “Sweet William”, was less successful, reaching number 30 in the UK, number 40 in the US, and number 22 in Canada, she had become an international celebrity, was given a gold disc in New York, and was driven in an open-top car on her return to Kingston, Jamaica where she performed in several major shows, on one occasion topping the bill over the legendary Otis Redding, Patti LaBelle, and Inez and Charlie Foxx.
Her first album, “More Millie”, contained a varied selection of songs arranged by Ernest Ranglin, and was issued as “My Boy Lollipop”, in the US, with a slightly different selection of tracks. Her early Jamaican recordings were also reissued to take advantage of her popularity.
She appeared on the Beatles TV special “Around the Beatles” in 1964 and in early 1965, she featured in a “Ready, Steady, Go!” special, “Millie in Jamaica”, and soon after embarked on a world tour, with concerts in New Zealand, Australia, Hong Kong, Singapore, Japan, the US, Brazil and Argentina.
Millie Small recorded several duets with Jackie Edwards in 1965, as well as solo material, but sales were disappointing. She also released her second LP record, “Millie Sings Fats Domino”, but it failed to reached the charts. Her eighth single in Britain, a version of Wynonie Harris’ “Bloodshot Eyes”, was her last UK chart success, reaching number 48 in late 1965, but she continued to tour successfully in Australia and Africa. However, her popularity in Britain was dwindling as she spent more time touring abroad. In 1968, after two albums of “The Best of Jackie & Millie”, her recording contracts with Island and Fontana Records ended.
In 1969 the emergence of reggae in the UK prompted Millie Small to return to recording with the single “My Love and I”. She then recorded for the Trojan label, her first single combining a version of Nick Drake‘s “Mayfair” with her own song, the politically-inspired and defiant “Enoch Power”, which was banned on radio but re-established her profile among the British Caribbean community. However, she ended her recording career soon afterwards.
Millie Small continued to tour and perform in Jamaica, but decided to move to Singapore in 1971, before returning to the UK in 1973, to coincide with the release of another compilation album, “Lollipop Reggae”.
During a rare interview with Thames News, in 1987, it was revealed that Millie Small was destitute and had was living in a youth hostel with her young daughter. In November 1987, she made a rare public appearance in Jamaica to receive the Medal of Appreciation from Prime Minister Edward Seaga.
In 2006, she was said to be making new recordings after some years spent writing, painting, and raising her daughter.
On August 6, 2011, the 49th anniversary of Jamaica’s independence, the Governor-General made Millie Small a Commander in the Order of Distinction for her contribution to the Jamaican music industry.
In July 2012, she again stated that she had been recording music and planned to perform in Jamaica for the first time in over 40 years.
After nearly 40 years away from the limelight and refusing most interview requests, Millie Small gave US journalist Tom Graves the first ever in-depth interview for the August 2016 edition of Goldmine. In the interview she discussed her early career and the full impact of “My Boy Lollipop”, she also said in 2016 that she had not received any royalties for the single.
Millie Small died on May 5, 2020, in England, aged 72, reportedly from a stroke.
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