Today marks 58 years since Millie Small’s version of “My Boy Lollipop” reached #2 on the Billboard Hot 100 chart. The song entered the Hot 100 on May 23 1964. It was Chris Blackwell’s moment of clarity that gave him credibility and started him off on a remarkable career in the music industry.
It was a time when the blues movement had captured the hearts of fans in both the U.S. and the U.K.
Small’s My Boy Lollipop was Blackwell’s first major hit selling over 7 million copies.
The Island Records founder told The Guardian that Small’s recording is “the most important song in my life”.
The original “My Boy Lollipop” was “My Girl Lollypop“) written in the mid-1950s by Robert Spencer of the doo-wop group The Cadillacs. It was first recorded in New York in 1956 by Barbie Gaye.
In a 2010 interview, Island Records’ founder, Chris Blackwell, told how he came to use “My Boy Lollipop” for Millie’s second British single:
I would go to New York now and again and buy records and sell them to the sound system guys in Jamaica. One of these records was the original version of ‘My Boy Lollipop’. But I’d make a copy of each one on a reel-to-reel tape, it was before cassettes, and when I brought Millie over to England I sat down trying to work out if we can find a song for her and I found this tape which had the original version of ‘My Boy Lollipop’ and I said, ‘that’s the song we should do’, so it was really really lucky that I found the tape
Blackwell’s memoir, The Islander: My Life In Music And Beyond is available June 7.
