10 Ultimate Ska Anthems
3. Millie Small – “My Boy Lollipop”
Originally written as “My Girl Lollipop” in 1956 by American doo-wop singer-songwriter Robert Spencer, the renamed “My Boy Lollipop” was first recorded as a shuffle number by 14 year old Barbie Gaye.
It wasn’t until 1964, however, that it became a hit, when Jamaican teenager Millie Small was presented the song by Island Record founder Chris Blackwell. Although rhythmically similar to the original, Small’s version, with her cutesy, high-pitched vocals, and the recording’s joyful, distinctly ska sound, became Jamaica’s first major international hit, reaching the top ten in the UK, US, and Australia, and opening the doors for other Jamaican talent.
Recorded in London, “My Boy Lollipop” was arranged by Jamaican musician Ernest Ranglin, with musical backing provided by the British band The Five Dimensions. Featuring the prominent use of trumpet and sax, the song also includes an unusual, yet rousing harmonica solo, which helped the tune stand out from other Jamaican songs of the time.
Initially marketed as a novelty pop song, “My Boy Lollipop” has become one of ska music’s most enduring hits, thanks to Small’s frequent television appearances and extensive worldwide touring throughout the sixties.