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Famous Jamaicans: "My Boy Lollipop" Singer, Millie Small

Updated: May 9, 2020

Millicent Dolly May Small, popularly known as Millie Small was the first Jamaican singer to expose Jamaican popular music on the international scene with a song which became the first million-selling Jamaican song. Her rendition of “My Boy Lollipop” became the first Jamaican song to make it on the British and American music charts reaching number one in Britain and number two in the United States in 1964.

Early Life

Millie Small was born in Vere, Clarendon on October 6, 1946 and died in the UK on May 5, 2020. She was the daughter of an overseer on a sugar plantation and the youngest of a family of twelve. She was one of the very few female early ska era singers.

In 1960, Small won the popular Vere Johns Opportunity Hour talent contest at the Palladium Theatre in Montego Bay. She got about 10 shillings for her prize. This success led her to team up with Roy Panton, at just twelve and a half years old, to form the duo Roy & Millie, who both recorded the song “We’ll Meet” for producer Clement “Coxsone” Dodd. She also did the song “Sugar Plum” for Coxsone, which was also a duet. Soon after she was heading the Jamaican disc hit parade. Small was paid the sum of £23 for three successful records.

International Success

When, founder of Island Records Label Chris Blackwell was twenty six he heard one of Millie’s local hits. He convinced Sir Coxsone that he could launch Small’s career if she came under his management. Blackwell brought her to England in late 1963 when she was old enough to travel alone. In later years Millie said that “I hadn’t planned on being a star, but I always wanted to be a singer, and I felt like it was my destiny to go to England.”

Chris Blackwell exclaimed that when he brought Millie to London his friends thought he was mad because calypso was the popular music then. Her first recording in London, "Don't You Know", made little impact when released by Fontana Records in late 1963. For her next recording Blackwell recruited guitarist and arranger Ernest Ranglin to oversee the session. Ranglin and his musicians adopted the newly-popular ska style, and his rearrangement of "My Boy Lollipop", a song originally released in the US by teenager Barbie Gaye in late 1956, became immediately successful. She appeared on British TV shows including Top of the Pops, and the single reached number one in the UK Singles Chart, and number two on the US Billboard Hot 100, and in Canada. It also topped the chart in Australia. Initially it sold over 600,000 copies in the United Kingdom, the song has since sold more than seven million copies worldwide.

“My Boy Lollipop” is still regarded as one of the all-time biggest selling reggae or ska discs. Arley Cha who in 2006 was Millie’s producer said that the song still continues to be played every day across the United States, in every State, on CBS FM radio. In the same year the song held the number three spot for the greatest all time hit single for 1964, number one and two were the Beatles and Rolling Stones respectively.

The song reportedly stayed in the Nigerian Top Ten for six years. It had set the pace for later chart toppers in England, Desmond Dekker’s “Israelites” and “Double Barrell” by Dave and Ansel Collins. Although Millie made little success with her follow up song “Sweet William” and others she toured Africa twice in the mid-1960s. This secured her a place in history allowing the wider world to become familiar with Jamaican music.

Millie Small enjoyed popularity and success during the early period of her career. On her first visit to the United States while at the Kennedy International Airport, press photographers, newsmen, magazine editors, radio and television crews were there to meet her. They danced and laughed with her on what was described as one of the warmest and most unusual receptions accorded to a foreign recording artist. Her flight was named The Lollipop Special as she received the world’s largest lollipop. She was idolized by many fans as was evident when the Port Authority police had to restrain an enthusiastic crowd of fans that went wild. Over thirty policemen had to surround Millie when they chanted “Sweet William” and tried to get through the protective barricade just to touch her. This was followed by a hectic schedule with the media, interviews and photo sessions.

In 1964, when Millie Small returned to Jamaica, she was greeted with a massive welcome home greeting party. She was escorted by police motorcycle to greet Prime Minister Sir Alexander Bustamante, and the Governor General of Jamaica. She was feted with ceremonies befitting royal visitors.

Probably the highlight of her success and popularity occurred when she returned to the United States for the New York World’s Fair 1964. The organizers had designated August 12th as Millie Small Day at the fair. Millie was the center of attraction on that day. Music critics hailed Small as the greatest singing sensation since the Beatles.

Small continued to tour and perform in Jamaica, but in 1971 decided to move to Singapore to live. She returned to Britain in 1973, to coincide with the release of another compilation album, Lollipop Reggae. Thereafter, she largely stayed out of the public eye, even when "My Boy Lollipop" was reissued and re-charted in the UK in 1987 at no. 46.

Millie Small had recorded many other songs but, there were only two other hit singles, “Sweet William” and “Bloodshot Eyes”. There was also another popular song called “Oh Henry”.

Later Life

In 1987, during a rare interview with Thames News, it was revealed that Small was destitute and had taken to living in a youth hostel with her toddler daughter.

In November 1987, she made a rare public appearance in Jamaica, to receive the Medal of Appreciation from Prime Minister Edward Seaga. In 2006, she was said to be making new recordings, after some years spent writing, painting, and raising her daughter.

She also insisted, against the denials of Rod Stewart, that it was Stewart who played harmonica on "My Boy Lollipop". She said she remembered the sessions well and recalls Stewart being asked to play. Small also said in 2016 that she had not received any royalties for the single.


On 6 August 2011, the 49th anniversary of the country’s independence, the Governor-General of Jamaica conferred the Order of Distinction in the rank of Commander (CD) upon Millicent (Millie) Dolly May Small, for her contribution to the development of the Jamaican music industry. The award was accepted on her behalf by former Prime Minister Edward Seaga.


“Millie not so ‘small’ anymore.” The Sunday Gleaner 15 October 2006: Teenville Magazine, Issue #2, 1964. Electronic.

Simons, Judith. “Magnificent Millie gets into the Hit Parade.” The Star 28 April 1964: 18. Print.

“When England went mad for Lollipop.” The Sunday Observer 29 March 1998:

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Jacqueline Cameron is a writer with decades of writing experience running the gamut from blogging to reporting. She lives in Kingston, Jamaica and is the chief writer for the Jamaica So Nice Blog. She is a trained engineer and musician and loves to see people transformed through her work.

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