Island Records founder Chris Blackwell, who originally produced that song, told the Jamaican Observer that she died from a stroke.
Recorded under the name Millie, My Boy Lollipop reached No 2 in the UK and US, with Blackwell remembering: “It became a hit pretty much everywhere in the world … and it was just incredible how she handled it. She was such a sweet person. Very funny, great sense of humour. She was really special.” In a separate statement, Island Records heralded her as “a true original, a wonderful human being”.
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Small was born in 1946 in Jamaica’s Clarendon parish, and began her recording career in her mid-teens, cutting singles for the island’s legendary Studio One label. Blackwell discovered her after her duet with Roy Panton, We’ll Meet, topped Jamaican charts and, with her parents’ permission, became her manager and moved her to the UK. “It felt like I was coming home, that this was where I was meant to be,” she remembered in 2016, having never returned to Jamaica.
She recorded My Boy Lollipop shortly after moving to London, a song originally recorded by New York singer Barbie Gaye in 1956. The “shuffle” style of US R&B used by Gaye had become popular in the Caribbean and mutated into ska; Small’s sweet, charming and high-pitched vocal, combined with the novelty of the unfamiliar new style, made My Boy Lollipop a huge hit. As well as its transatlantic success, it also topped the Australian charts.
In a 2016 interview she claimed that Rod Stewart played harmonica on the song – “I can see him now at the studio, leaning against the wall. Cute little boy. A very nice-mannered guy” – though Stewart has said session player Pete Hogman played it. Small also claimed in 2016 that she had not received any royalties for My Boy Lollipop.
Small had another UK chart placing in 1964 with Sweet William, which reached No 30, though that would be her only other Top 40 hit.
Her recording career ended in 1970, and she moved to Singapore. She reappeared on a London news report in 1987, poor and living in a youth hostel with a young daughter. Speaking in 2016, she said: “I focused on being a mother from 1984, when my daughter was born, and since then I’ve been happy living a quiet life, sleeping and dreaming and meditating.”
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