Millie Small, whose hit song My Boy Lollipop sent ska around the world – obituary

Millie Small, who has died aged 73, was a singer whose 1964 hit My Boy Lollipop became the first record to popularise ska music around the world; it reached No 2 in both the UK and US charts and went on to sell more than 6 million copies.

Millicent Dolly May Small was born in Clarendon, Jamaica, the youngest of 12 children, on October 6 1946; her father was an overseer on a sugar plantation. In 1960 she won a talent contest in Montego Bay, and formed a duo, Roy and Millie, with Roy Panton.

They recorded We’ll Meet for the celebrated producer Clement “Sir Coxsone” Dodd. She became a fixture in the Jamaican charts, and when Chris Blackwell heard her sing – he had been brought up in Jamaica and had founded Island Records at the end of the 1950s – he took her to Britain towards the end of 1963.

He chose My Boy Lollipop for her British debut: “I would go to New York now and again and buy records and sell them to the sound system guys in Jamaica,” he recalled. “One of these records was the original version of My Boy Lollipop.”

The song had been an R’n’B hit in the US in 1956, sung by a schoolgirl, Barbie Gaye (who received no royalties for her contribution to the lyrics). Its “shuffle” beat made it ideal for a ska treatment; Blackwell produced, while the arrangement was done by the Jamaican guitarist Ernest Ranglin.

He replaced the saxophone solo of the original with a harmonica, and to this day no one can be quite sure who played it. Urban legend says it was Rod Stewart, and Millie Small had no doubt: as recently as 2016 she insisted that it was him, although the singer has always denied it. Two other candidates were members of the Five Dimensions R’n’B and soul band, Pete Hogman and Jimmy Powell.

Either way, released in May 1964, the record shot into the UK Top 10, and she sang it on the television special Around the Beatles. Its success was replicated around the world, and Blackwell recalled in the Jamaica Observer: “I went with her 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 sweet person.”

When Blackwell took her to the US, the flight was named “the Lollipop Special”, and at the airport she was greeted, Fab Four-style, by a mob of adoring fans. And when she visited Jamaica she received a police escort as she was taken to meet the prime minister, Alexander Bustamante, and the High Commissioner, Alexander Morley.

She continued making records, none of which emulated the success of My Boy Lollipop; the similar-sounding Sweet William was her only other chart hit. She left Island in 1970, and signed for the celebrated reggae label Trojan.

Her first single was a cover of the Nick Drake song Mayfair. On the B-side was Enoch Power, a response to Enoch Powell’s infamous “Rivers of Blood” speech; when she sang it at Wembley during the Caribbean Music Festival it was rapturously received.

She left the music industry, however, and later lived in Singapore and New Zealand before returning to London, where she wrote and painted while bringing up her daughter.

She later recalled that times had sometimes been hard, and she had spent a period sleeping rough – but, she said, “I didn’t worry because I knew what I was doing. I saw how the other half live. It’s something I chose to do.”

Her fame endured, and in 2011 she received the Jamaican Order of Distinction, while the following year My Boy Lollipop was played during the opening ceremony of the Olympic Games in London.

Millie Small is survived by her daughter, the singer and songwriter Jaelee Small.

Millie Small, born October 6 1946, died May 5 2020