This song helped develop the styles of Reggae and Ska. It was the first and one of the few international Ska hits. To this day, it remains one of the best-selling hits with a Reggae or Ska influence.
After she recorded a couple of songs for a label in her native Jamaica, Small (while still a teenager) was discovered by The A&R man Robert Blackwell and was brought (along with Ernest Ranglin) to England by him in late 1963 to record this; she was 17 at the time. Blackwell, along with his brother Chris, was a successful music producer who contributed to the development of Reggae and Ska music and helped Reggae obtain international recognition. This song was the first to help his Jamaican label, Island, make millions.
Contrary to legend, the harmonica player was not Rod Stewart but Pete Hogman of The Pete Hogman Blues Band and Hoggie & The Sharpetones. Hogman told us: “The backing for ‘My Boy Lollypop’ was recorded live in the studio. I played harmonica and Ernest Ranglin played a black Gibson. Several people have claimed to have played the harmonica break but I can promise you it was me, and it was all recorded in London. By the way, Rod Stewart has never claimed to have played that solo, in fact he has said it was me in the Bob Marley life story Catch A Fire.”
This song was originally an R&B hit in late 1956 for an American singer named Barbie Gaye. Small’s version was a bigger, international hit that crossed over to Pop and Ska music.
Jamaican Ernest Ranglin played the guitar on this. Famous for his session work at Studio One (the “Motown of Jamaica”) in Kingston, he soon became one of the primary pioneers of Caribbean music.

In a scene from the 1997 film Spice World, the Spice Girls and 2 young female fans sing along to Small’s version of this song while the Girls take the 2 fans on a boat ride.
Although this song missed the #1 spot on the national charts in both the US and the UK, it managed to reach #1 in Ireland. (thanks, Jerro – New Alexandria, PA, for above 3)