1964 One-Hit Wonder Became a No. 1 Song When the Singer Was Only 16

"My Girl Lollypop" was written by Robert Spencer from The Cadillacs in the 1950s, but it became a hit when sung by Jamaican singer Millie Small in 1964. The song, which was retitled "My Boy Lollipop," reached No. 1 in Ireland and No. 2 in the US and UK, selling millions of copies worldwide. To this day, it is one of the best-selling reggae songs of all time.

Chris Blackwell, the founder of Island Records, called it "the most important song in his life." When talking about how Small came to perform it in a 2009 interview, he said, "When I heard ‘My Boy Lollipop,' I knew it was a hit. I also knew it was way beyond what Island could handle, plus it was much more slick than something that we would put out, so I licensed it to [Dutch Philips Records]. And then that record was indeed a huge hit everywhere in the world. I brought Millie over to England in '63, the record came out in '64, and I went with her on a world tour for six months in '65."

"It became a hit pretty much everywhere in the world," he continued. "I went with her around the world because each of the territories wanted her to turn up and do TV shows and such, and it was just incredible how she handled it. She was such a really sweet person, very funny, great sense of humor. She was really special."

Although no other song was as popular as "My Boy Lollipop," Small released many other songs throughout her career, including "Sweet William" and "What Am I Living For." Small also received the Medal of Appreciation in Jamaica from Prime Minister Edward Seaga in 1987. This award was established to recognize Jamaican citizens who have made significant personal achievements or contributions to the nation.

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In a 2016 interview, Small revealed that she hadn't received any royalties from "My Boy Lollipop." She also stated, "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."

Small died in 2020 at the age of 72.

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This story was originally published July 4, 2026 at 8:49 AM.