The Cadillacs and is usually credited to Spencer, Morris Levy and Johnny Roberts. It was first recorded in New York in 1956 by Barbie Gaye. A later version, recorded in 1964 by Jamaican teenager Millie Small, with a very similar rhythm, became one of the top-selling ska songs of all time.
The song caught the attention of one of Levy's partners, alleged mobster and music mogul Gaetano Vadtola (Corky). Vastola had recently discovered 14-year-old singer Barbie Gaye after hearing her sing on a street corner in Coney Island, Brooklyn. Vastola was so impressed that he immediately took her to meet New York radio DJ Alan Freed. Gaye sang a few songs for them and Freed was equally impressed. Vastola became Barbie Gaye's manager and within days, he acquired the sheet music and lyrics for ‘My Girl Lollypop’ from Levy. He gave them to Gaye, with no specific instructions except to change the gender of the subject of the song and be ready to perform it by the following week. Barbie Gaye changed the song's title to ‘My Boy Lollypop and rewrote parts of the original song.
When it came time to record, Gaye cut school and took the subway to a recording studio in Midtown Manhattan. The song was recorded in a relatively new style of R&B called ‘Shuffle’. The four musicians, including the white teenage girl, went into the studio and recorded the song in one take. Over the next few years, the sound grew in popularity and evolved into ‘ska’, Jamaica’s first indigenous popular music style. Ska has developed subgenres such as 2-Tone and Third Wave. The Third Wave has influenced several new Jamaican music genres; most notably ‘Rocksteady’ and ‘reggae.
Gaye's recording was released as a single by Darl Records in late 1956. It was heavily played by Alan Freed. Listener requests increased the song’s popularity. Gaye received no royalties from radio play because her manager routinely counterfeited his artist's music to keep all the profits, the record's sales data is difficult to determine.]
In a 2010 interview, Island Records founder, Chris Blackwell, tell how he came to use ‘My Boy Lollipop’ for Millie’s second British single.
Blackwell had purchased the original record in 1959 and found the copy in his archives in 1963. He went on to produce Millie Small’s remake, changing the spelling of the title of the song to read "Lollipop" instead of "Lollypop.” It was recorded in a rhythmically similar shuffle/ska style and in 1964 it became her breakthrough blockbuster hit in the United Kingdom, reaching Number 2. The song also went to Number 1 in the Republic of Ireland and Number 2 in the United States It is considered to be the first commercially successful international ska song, Small's version of ‘My Boy Lollipop’ sold over six million records worldwide and helped to launch ‘Island Records’ into mainstream popular music. It remains one of the best-selling reggae/ska hits of all time.
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I emigrated to Canada in late 1964 and whilst there, I naturally kept an eye on songs which were popular in both America and Great Britain. Although the Beatles were the world’s newest band sweeping Great Britain and America, the sound of Millie singing this song was so refreshing, so unusually ska (which I was later to learn after I became a fan of reggae). It was a sound that I was never to forget.
I dedicate today’s song to my gay friends Stephen and Michael from Queensbury and Steven from Manchester way.
Love and peace Bill xxx