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Millie Small (1946–2020), “My Boy Lollipop” singer

by Linnea Crowther

Millie Small was a Jamaican singer who had a hit in 1964 with “My Boy Lollipop,” which is considered to be the first international ska hit.

A trailblazer of ska

Small was just 16 years old when she became a pop star with her recording of “My Boy Lollipop,” featuring her squeaky vocals over a ska beat. She became an early star from Jamaica – her record was the country’s first million-seller. As it topped the charts in the U.K. and went to No. 2 in the U.S., it was the first international ska hit, popularizing the genre. One of the few women recording ska music at the time, Small followed the success of “My Boy Lollipop” with another hit, “Sweet William.” She recorded three albums before stepping away from music in the early 1970s. In later years, Small became a writer and painter, revealing in a 1987 interview with Thames TV that she had been homeless for a time. In 2012, she announced plans to return to making music in Jamaica.

Small on the talent contest that launched her career

“I was 12 years old when I entered a posh talent contest called The Vere John’s Opportunity Hour at the Palladium in Montego Bay on Jamaica’s north coast, where I sang in front of 2,000 people. I don’t remember what I sang, but most of it was with my eyes shut because I was so shy. I won the second prize of 30 shillings and it was the beginning of my new life as a singer.” —from a 2016 interview with Express

What people said about her

Full obituary: New York Post

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