Chris Blackwell Says Millie Small’s ‘My Boy Lollipop’ Is The “Most Important Song In His Life”

Former Island Records boss Chris Blackwell has pinpointed Millie Small’s Ska single My Boy Lollipop, which she recorded as a teenager, as “the most important song in his life”.

My Boy Lollipop was the first major hit for Chris Blackwell’s Island Records and Jamaica’s first million-selling single.  The song, which went on to sell more than seven million copies worldwide, and is considered one of the three greatest all-time hit singles of 1964, falling just behind the Beatles and Rolling Stones, was what gave the Englishman the impetus to delve deeper into recording.

Blackwell, in an interview with The Guardian, ahead of the release of his new book The Islander: My Life in Music and Beyond today, Blackwell revealed that he had “left for London after Jamaica won its independence in 1962, believing that, as an Englishman, he was on “the wrong side of history”, but that his return to his homeland was at an opportune time as “the British blues boom was just beginning”.

He said that Small’s “distinct, high-pitched voice” had intrigued him on a song he heard back on the island and, while he knew that her unusual voice could serve as a cool hook, he also understood that it could quickly grate.  As a consequence, Blackwell made sure her single, the chirpy My Boy Lollipop, lasted less than two minutes, bucking the expected span of a song, The Guardian noted.

Millie Small was born in Clarendon, and was just 12-years old when she graced a stage for the first time after she won the Vere Johns Opportunity Hour singing contest.  After winning the contest she moved to Lingston to try and make music her full-time career, when she was noticed by Blackwell, who was living in Jamaica at the time.

Blackwell later became her legal guardian and manager, and took her to London in 1963.  A year later, in 1964, he released My Boy Lollipop, which is an Ernest Ranglin rearrangement of the 1956 song “My Boy Lollipop”.

My Boy Lollipop peaked at number two on both the U.S. and U.K. charts, and went on to become one of the top-selling ska hits of all time.   The song is a cover version of My Girl Lollipop, which was written by Robert Spencer of the doo-wop group The Cadillacs, and credited to Spencer, Morris Levy, and Johnny Roberts. It was first recorded in New York by Barbie Gaye in 1956.

Small died in May 2020 from a stroke, and at that time Blackwell, in a statement said that she had opened the door for Jamaican music to the world.

“It became a hit pretty much everywhere in the world. I went with her around the world because each of the territories wanted her to turn up and do TV shows and such, and it was just incredible how she handled it. She was such a really sweet person, very funny, great sense of humour. She was really special,” he had said.

Born Millicent Small in Clarendon, she was the daughter of an overseer on a sugar plantation and was one of the very few female singers in the early ska era in Clarendon.  She was already recording in her teens for Sir Coxsone Dodd’s Studio One label with Roy Panton, as the duo Roy & Millie, when she was discovered by Blackwell.

Small went on to record for Trojan Records after her contract with Island Records had run its course. She released the album Time Will Tell in 1970, but by 1973 Small had “more or less retired from the music industry”.

In 2011, she was given the Order of Distinction for her contributions to Jamaican music.

My Boy Lollipop was used in the first season of Miami Vice on the 1985 episode “Lombard” and also appeared in a few movies among them Riding in Cars with Boys in 2001, The Big Tease in 1999 and Slappy and the Stinkers in 1998.