October 6, 2023 marks the 76th birthday of Jamaica’s first international star Millicent Dolly May Small, more popularly known as Millie Small. In 1964, Small had a breakthrough hit with her recording of “My Boy Lollipop.” The track reached the number 2 spot on the British and American charts and marked a turning point for Jamaican music. When Small died in 2020 at the age of 73, the announcement of her death was made by the founder of Island Records, Chris Blackwell, who also produced the song. “My Boy Lollipop” was Small’s only big hit, but it was highly significant in that it exposed Jamaica’s unique sound to the global audience and opened the way for other Jamaican artists like Bob Marley. “My Boy Lollipop” was also the first major success for Blackwell’s Island Records label, which would later release tracks by Marley, Toots and the Maytals, Roxy Music, and U2, among others.
Here are 12 things you may not know about Millie Small, ska’s breakthrough performer.
Clarendon Native
Millie Small was born Millicent Dolly May Small in Clarendon, Jamaica, in 1946.
Daughter of a Sugar Cane Worker
Her father worked in the sugar cane fields.
Small’s Music Career Started at Studio One
After winning second place in a Montego Bay singing contest at age 12, she recorded for Coxsone Dodd’s pioneering Studio One label and recorded hits with fellow singer Roy Panton.
Panton Introduced Small to Chris Blackwell
It was her recording of “We’ll Meet,” a duet with Panton as part of the duo professionally known as “Roy and Millie,” that brought her to the attention of Chris Blackwell.
Global Jamaican Music Ambassador
At the young age of 17, Small became a global ambassador for Jamaican music, traveling to New York to sing at the 1964 World’s Fair chaperoned by Blackwell.
Recorded “My Boy Lollipop” in England
Blackwell also brought Small to England, and it was at his suggestion that she record “My Boy Lollipop” as in the up-tempo ska version arranged by Jamaican guitarist Ernest Ranglin, which featured horns and a blues-harmonica solo said to be played by Rod Stewart (although he later claimed it wasn’t him) in addition to Small’s lively vocals.
First Recorded as R&B
Originally recorded as an R&B shuffle by American singer Barbie Gaye in 1956, Small’s ska version of “My Boy Lollipop” sold six million copies worldwide.
Pop Music Icon
While she made some recordings during the 1960s and went on tour, Small became known as “one of the most elusive performers in pop history,” according to a 2016 feature article in Goldmine magazine.
Small’s Personal Struggles
Small stopped recording after the release of her 1970 album, “Time Will Tell,” and essentially disappeared until she was interviewed on British television in 1987 when she said she had been staying in a hostel with her baby daughter because she had no money.
Grateful for Popularity of Lollipop
Looking back on her “Lollipop” fame with Goldmine magazine, she stated, “I just saw it as a song that had become a hit somewhere, honestly. It seemed so natural. I had the hit, I toured the countries and came back to England, and that was that.”
Lived Mostly in England
Millie Small lived most of her adult life in England.
Jaelee Small Carries Singing Legacy
Her daughter Jaelee Small survives her and is a singer based in London.
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