Millie Small

My Boy Lollipop

The ever-so-talented Millicent Dolly May Small, more famously known as ‘Millie Small’, was born on October 6, 1946 in Clarendon, Jamaica. She is known for her rendition of the hit song ‘My Boy Lollipop’ which has sold over six million records worldwide and helped launch Island Records into mainstream popularity and remains one of the best-selling reggae hits of all time.

Millie’s career began after she won the Vere Johns Opportunity Hour talent contest at the age of twelve. Wanting to further pursue her career as a singer, she moved in with relatives in Love Lane in Kingston to be closer to the music scene. In her teens, she recorded a duet of the song ‘Sugar Plum’ with Owen Gray in 1962 and would later record with the ska hit ‘We’ll Meet’ with Roy Panton.

These hits caught the attention of Island Records founder, Chris Blackwell, who would end up becoming her manager and legal guardian. In late 1963, Blackwell took Millie to Forest Hill, London, where she was given intensive training in dancing and diction. It was there where she would make her fourth and quite possibly most popular recording of an Ernest Ranglin rearrangement of ‘My Boy Lollipop’, a song originally released by Barbie Gaye in late 1956 (originally titled ‘My Boy Lollypop’).

Blackwell, along with his associate, Chris Peers, were attempting to find songs for Millie to record when they came across ‘My Boy Lollypop’ and found it to be the perfect fit for Millie’s range and style.

Ernest Ranglin, along with arranging the song, played guitar on the recording with the saxophone solo from the original version being replaced by a harmonica solo.

Released in March 1964, Small’s version was a smash hit, reaching number two both in the UK Singles Chart and the US Billboard Hot 100, and number three in Canada before topping the charts in Australia. The popularity of Small’s rendition lead to her performing the song live on the well-revered and watched Australian programme Bandstand as well as the 1964 Beatles television special Around The Beatles.

Her later recordings, ‘Sweet William’ and ‘Bloodshot Eyes’, would also become hits in the UK, charting in at numbers 30 and 48 respectively, with “Sweet William” peaking at number 40 in the US. The success of Small’s music career would lead her to touring well into the 70s.

‘My Boy Lollipop’ also saw resurgence in popularity the UK in 1987 and was featured on the smash-hit television programme Miami Vice. Small’s rendition of “My Boy Lollipop” is considered to be the first commercially successful international ska song and has since sold more than seven million copies worldwide.

On 6 August 2011, the 49th anniversary of Jamaica’s independence, the Governor-General created Small a Commander in the Order of Distinction for her contribution to the Jamaican music industry.