When this single by Millie Small became a transatlantic smash (in 1964), I was too young to notice or care. Now I come to the song with a historian’s detached appreciation.
What made this version of “My Boy Lollipop” historic? Well, the teenage singer was from Jamaica. This record was the first international hit by a Jamaican artist.
(The song was originally recorded in 1956 by Barbie Gaye, a white American.)
“My Boy Lollipop” also laid the groundwork for the coming reggae revolution. The music was arranged by guitarist Ernest Ranglin, a now-revered pioneer of both ska and reggae.
The session was produced by Chris Blackwell, founder of Island Records. “My Boy Lollipop” was Blackwell’s first major hit. Within a decade, Blackwell would release breakthrough albums by Bob Marley and the Wailers, thereby re-ordering the universe.
It all started with this.
“I used to go to New York and buy R&B records and then sell them on to the sound systems in Jamaica,” Blackwell recalled. “But I kept tapes of everything I imported, and one of the tracks was ‘My Boy Lollipop.’
“I was playing the tape one night, and when I heard the song again, I knew it was perfect for Millie.”